Antibody-photosensitive substance conjugate

Abstract

Provided are: a novel photosensitive substance; an antibody-photosensitive substance conjugate obtained by binding the photosensitive substance and an antibody via a linker; and an antitumor agent containing the antibody-photosensitive substance conjugate. [Solution] An antibody-photosensitive substance conjugate is represented by formula (1). (In formula (1), Ab represents an antibody or an antigen-binding fragment of the antibody, L represents a linker that links Ab and P, Ab is directly bound to L through the amino acid residue or indirectly bound to L through the glycan chain, P represents a monovalent group derived from a photosensitive substance and connected to L, and x represents a number in the range of 1 to 10.)

Description

Antibody-photosensitizer conjugate

[0001] The present invention relates to a novel photosensitizer, an antibody-photosensitizer conjugate in which the photosensitizer is bound to an antibody via a linker, an antitumor agent containing the antibody-photosensitizer conjugate, and the like.

[0002] Photodynamic therapy (PDT) is a localized cancer treatment that utilizes a photochemical reaction caused by light irradiation with a photosensitizer. Unlike conventional physical destructive methods such as laser photocoagulation and vaporization, PDT is capable of selectively treating cancer lesions with low energy and is a minimally invasive treatment that causes minimal damage to normal tissue. When exposed to light, photosensitizers absorb light energy and transition to an excited state (singlet state). When this state returns to the ground state, the resulting energy transfer generates reactive oxygen species, which are thought to cause cell degeneration and necrosis. Currently, PDT has been shown to be effective against lung cancer, esophageal cancer, gastric cancer, cervical cancer, brain tumors, head and neck cancer, and prostate cancer, among other cancers. PDT is a promising cancer treatment for elderly patients, who require minimal invasiveness (Non-Patent Document 1).

[0003] Porfimer sodium was approved as a PDT therapeutic agent in Japan in 1994, and to date, several photosensitizers, such as talaporfin sodium (Non-Patent Document 2), temoporfin (Non-Patent Document 3), verteporfin padeliporfin (Non-Patent Document 4), etc., have been approved as PDT therapeutic agents around the world. Many photosensitizers for PDT have been investigated, including those with a porphyrin skeleton, a chlorin skeleton with one reduced pyrrole ring, a bacteriochlorin skeleton with two opposing reduced pyrrole rings, and a phthalocyanine skeleton, which have chemical structural characteristics that show strong absorption in the visible light region.

[0004] However, these PDT therapeutic agents are small-molecule drugs, and although some of them have tumor-accumulating properties, they have issues with cancer selectivity and are fraught with side effects such as photosensitivity and damage to the irradiated area. Therefore, research into improved PDT therapeutic agents utilizing drug delivery technology is ongoing (Non-Patent Documents 1 and 5). A representative example is cetuximab saratarocan sodium, which is an anti-EGFR antibody cetuximab conjugated with an IR700 dye (Patent Document 1).

[0005] IRDye® 700DX is a dye based on a phthalocyanine skeleton, with a silicon atom at the center of the phthalocyanine ring and two axial ligands with three sulfonic acid groups at the terminals to maintain water solubility. The N-hydroxysuccinimide activated ester (NHS ester) of IRDye® 700DX is generally used to form antibody-IR700 conjugates, and the aforementioned cetuximab saratarocan sodium is synthesized by lysine conjugation of the anti-EGFR antibody cetuximab with the same NHS ester. Cetuximab saratarocan sodium has been approved as a PDT treatment in Japan under the conditional expedited approval system.

[0006] Patent Document 2 describes that a conjugate in which chlorin e6 having a specific structure is linked to the anti-HER2 antibody trastuzumab via a linker can be used for diagnosing breast cancer, but the antitumor effect of the conjugate has not been confirmed at all.

[0007] International Publication No. 2017 / 031367 International Publication No. 2016 / 052971

[0008] Xingshu L. , et al. , Nat. Rev. Clin. Oncol. 657-674, 17(11), 2020. S Wang, et al. , Expert Opin. Pharmacother. 133-140, 11(1), 2010. ArnoW. , et al. , Photochem Photobiol. 356-419, 99(2), 2023. Abdel-Rahmene A. , et al. , Lancet Oncol. 181-191, 18(2), 2017. Naoto S. , et al. , Anticancer Res. 2823-2832, 33(7), 2013.

[0009] The problem to be solved by the present invention is to provide a novel photosensitizer, an antibody-photosensitizer conjugate in which the photosensitizer and an antibody are linked via a linker, an antitumor agent containing the antibody-photosensitizer conjugate, and the like.

[0010] The present inventors conducted extensive research to achieve the above-mentioned object and found that a novel photosensitizer characterized by having a chlorin skeleton exhibits singlet oxygen-mediated cytotoxic activity upon light irradiation. Furthermore, the present inventors discovered that an antibody-photosensitizer conjugate, in which the photosensitizer and an antibody are linked via a linker, is administered to a subject, and after a certain period of time, the conjugate is irradiated with light at the site of accumulation, thereby exhibiting an antitumor effect on tumors expressing an antigen. Furthermore, the present inventors discovered a light irradiation schedule, light irradiation dose, light irradiation intensity, and light irradiation time suitable for the antibody-photosensitizer conjugate to exhibit an antitumor effect, and thus completed the present invention.

[0011] That is, the present invention includes the following inventions: [1] A compound represented by the following formula (1): (wherein, Ab represents an antibody or an antigen-binding fragment of the antibody; L represents a linker linking Ab to P; Ab is directly bound to L via its amino acid residue or indirectly bound to L via its sugar chain; P represents a monovalent group derived from a photosensitizer and linked to L; x represents a number in the range of 1 to 10; and the photosensitizer is represented by the following formula (2): (where R１ , R ３ and R ４ each independently represent a hydrogen atom, a formyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group or an aromatic heterocyclic group, the C1-C6 alkoxycarbonyl group, the C1-C6 alkanoyl group, the mono-C1-C6 aminocarbonyl group, the di-C1-C6 alkylaminocarbonyl group, the mono-C1-C6 alkylamino group, the di-C1-C6 alkylamino group, the C1-C6 alkyl alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the cyclic hydrocarbon group, the aromatic hydrocarbon group or the aromatic heterocyclic group is optionally substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group and an azide group; R ２ Functional groups contained in R ５ and the functional groups contained in R ６ (i) a group selected from the group consisting of functional groups included in R ２ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ａ (R ２ａ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｂ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R２ｂ is a hydrogen atom or a C1-C6 alkyl group) or an optionally substituted amino group, ２ｃ (R ２ｃ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ ), -R ２ｄ -R ２ｅ (R ２ｄ is a C1-C6 alkylene group, and R ２ｅ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH-C(=O)-(CH ２ ) ｐ -OH) or -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｇ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｇ is a hydrogen atom or a C1-C6 alkyl group) or a 5- to 6-membered aromatic heterocyclic group (the 5- to 6-membered aromatic heterocyclic group is -(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ and R ５ is -R ５ａ -R ５ｂ (R ５ａis a C1-C6 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, —X—R (wherein X represents —S—, —O—, —CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, and R ５ｄ is a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C6 alkylene group, and R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, and R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅ is a C1-C6 alkyl group substituted with one or more hydroxy groups; (ii) R ６ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or —NH—, where R is a residue of a monosaccharide), —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, —X—R (wherein X represents —S—, —O—, —CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, and R ５ｄis a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C6 alkylene group, and R ６ｇ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH(R ６ｉ ) (R ６ｈ is a hydrogen atom or a C1-C6 alkyl group, and R ６ｉ represents a hydrogen atom, -C(=O)-(CH ２ ) ｐ -NH ２ or -C(=O)-(CH ２ ) ｐ (iii) R ５ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ- optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or —NH—, where R is a residue of a monosaccharide), —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ｇ -R ５ｈ (R ５ｇ is a C1-C6 alkylene group, and R ５ｈ represents an optionally substituted amino group, and R ６ is -R ６ａ -C(=O)-R ６ｂ (R６ａ is a C1-C6 alkylene group, and R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, and R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅ

[0033] In all of the above formulae, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, q ​​is an integer of 1 to 6, and r is an integer of 0 to 6, or a metal complex thereof, or a pharmaceutically acceptable salt thereof. [2] R １ [3] The antibody-photosensitizer conjugate according to [1], or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein R ３ [4] The antibody-photosensitizer conjugate of [1] or [2], or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein R４ [5] The antibody-photosensitizer conjugate according to any one of [1] to [3], or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein R represents an ethyl group. １ and R ３ represents a methyl group, and R ４ [6] The antibody-photosensitizer conjugate according to any one of [1] to [4], or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein R represents an ethyl group. ２ The functional group contained in R is bonded to L, ２ [7] The antibody-photosensitizer conjugate according to any one of [1] to [5], or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein an amino group, a hydroxyl group, or a thiol group contained in R ２ The functional group contained in R is bonded to L, ２ [8] The antibody-photosensitizer conjugate according to any one of [1] to [6], or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein an amino group or a hydroxy group contained in R ２ The amino group or hydroxy group at the end of R is bonded to L, ２ -CH=CH-C(=O)-R ２ａ (R ２ａ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｂ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｂ is a hydrogen atom or a C1-C3 alkyl group) or an optionally substituted amino group substituted with an amino C1-C3 alkyl group), -CH=N-R ２ｃ (R ２ｃ is -O-(CH ２ CH ２ O) ｍ - (CH ２ )ｎ -NH ２ ), -R ２ｄ -R ２ｅ (R ２ｄ is a C1-C3 alkylene group, and R ２ｅ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH-C(=O)-(CH ２ ) ｐ -OH) or -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｇ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｇ is a hydrogen atom or a C1-C3 alkyl group) or a 5-membered aromatic heterocyclic group (the 5-membered aromatic heterocyclic group is -(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ and R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 6-membered aromatic heterocyclic group, -X-R (wherein X represents -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C3 alkanoyl group, and R ５ｄ is a C1-C3 alkyl group, and the C1-C3 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C3 alkoxy group, and the C1-C3 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ But, -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C3 alkylene group, and R ６ｂ is a C1-C3 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C3 alkyl group, and R ６ｄ represents a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups or —(CH ２ )ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅ [9] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to [7], or a pharmaceutically acceptable salt thereof, wherein R represents a C1-C3 alkyl group substituted with 1 to 3 hydroxy groups, and in all of the above formulae, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, and q is an integer of 1 to 6. ２ The amino group or hydroxy group at the end of R is bonded to L, ２ is expressed by the following formula: and the amino or hydroxy group indicated by the arrow is bonded to L; R ５ is expressed by the following formula: R is a group selected from the group consisting of ６ is expressed by the following formula:

[10] The antibody-photosensitizer conjugate according to any one of [1] to [8], or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein R ２ The amino group at the end of R is bonded to L, ２ But -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ ) and R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, and R ５ｂ represents a 6-membered nitrogen-containing saturated heterocyclic group, and R ６ But, -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C3 alkylene group, and R ６ｂ is -N(R ６ｃ)-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C3 alkyl group, and R ６ｄ represents a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups), and in all of the above formulas, m is an integer of 0 to 10, and n is an integer of 1 to 6. The antibody-photosensitizer conjugate or a metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of [1] to [8].

[11] The antibody-photosensitizer conjugate or a metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of [1] to

[10] , wherein the photosensitizer is represented by the following, and the amino group indicated by the arrow is bonded to L:

[12] The antibody-photosensitizer conjugate or metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of [1] to

[10] , wherein the photosensitizer is selected from the following, and the amino group indicated by the arrow is bound to L:

[13] R ６ The functional group contained in R is bonded to L, ６

[14] The antibody-photosensitizer conjugate according to any one of [1] to [5], or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein an amino group, a hydroxyl group, or a thiol group contained in R ６ The functional group contained in R is bonded to L, ６

[15] The antibody-photosensitizer conjugate according to any one of [1] to [5] and

[13] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein an amino group or a hydroxy group contained in R ６ The amino group or hydroxy group at the end of R is bonded to L, ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ )ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C3 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C3 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C3 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ But, -R ５ａ -R ５ｂ (R ５ａis a C1-C3 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 6-membered aromatic heterocyclic group, -X-R (wherein X represents -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C3 alkanoyl group, and R ５ｄ is a C1-C3 alkyl group, and the C1-C3 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C3 alkoxy group, and the C1-C3 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ But, -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C3 alkylene group, and R ６ｇ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH(R ６ｉ ) (R ６ｈ is a hydrogen atom or a C1-C3 alkyl group, and R ６ｉ represents a hydrogen atom, -C(=O)-(CH ２ ) ｐ -NH ２ or -C(=O)-(CH ２ )ｐ In all of the above formulae, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, q ​​is an integer of 1 to 6, and r is an integer of 0 to 6.

[16] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to [5],

[13] , and

[14] , or a pharmaceutically acceptable salt thereof.

[16] R ６ The amino group or hydroxy group at the end of R is bonded to L, ２ is expressed by the following formula: R is a group selected from the group consisting of ５ is expressed by the following formula: R is a group selected from the group consisting of ６ is expressed by the following formula:

[17] The antibody-photosensitizer conjugate according to any one of [1] to [5] and

[13] to

[15] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein R is a group selected from the group consisting of ６ The amino group or hydroxy group at the end of R is bonded to L, ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ represents a hydrogen atom or a C1-C3 alkyl group, and R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, and R ５ｂ represents a 6-membered nitrogen-containing saturated heterocyclic group, and R ６ But, -R ６ｆ -C(=O)-R ６ｇ (R６ｆ is a C1-C3 alkylene group, and R ６ｇ is -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH ２ (R ６ｈ represents a hydrogen atom or a C1-C3 alkyl group), and in all of the above formulas, m is an integer of 0 to 10, n is an integer of 1 to 6, and r is an integer of 0 to 6. The antibody-photosensitizer conjugate or a metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of [1] to [5] and

[13] to

[15] .

[18] The antibody-photosensitizer conjugate or a metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of [1] to [5] and

[13] to

[17] , wherein the photosensitizer is selected from the following, and the amino group indicated by the arrow is bonded to L:

[19] R ５ The functional group contained in R is bonded to L, ５

[20] The antibody-photosensitizer conjugate according to any one of [1] to [5], or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein an amino group, a hydroxyl group, or a thiol group contained in R ５ The functional group contained in R is bonded to L, ５

[21] The antibody-photosensitizer conjugate according to any one of [1] to [5] and

[19] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein an amino group contained in R ５ The amino group at the end of R is bonded to L, ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ-OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is hydrogen or a C1-C3 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C3 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C3 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ But, -R ５ｇ -R ５ｈ (R ５ｇ is a C1-C3 alkylene group, and R ５ｈrepresents a 6-membered nitrogen-containing saturated heterocyclic group substituted with an amino group or an amino C1-C3 alkyl group, and R ６ But, -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C3 alkylene group, and R ６ｂ is a C1-C3 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is hydrogen or a C1-C3 alkyl group, and R ６ｄ represents a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups or —(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅrepresents a C1-C3 alkyl group substituted with 1 to 3 hydroxy groups), and in all of the above formulas, m is an integer of 0 to 10, n is an integer of 1 to 6, and q is an integer of 1 to 6. The antibody-photosensitizer conjugate or a metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of [1] to [5] and

[19] to

[20] .

[22] The antibody-photosensitizer conjugate or a metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of [1] to [5] and

[19] to

[21] , wherein the photosensitizer is selected from the following, and the amino group indicated by the arrow is bonded to L:

[23] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[22] , wherein m is an integer of 0 to 5, or a pharmaceutically acceptable salt thereof.

[24] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[23] , wherein m is an integer of 0 to 3, or a pharmaceutically acceptable salt thereof.

[25] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[24] , wherein m is 1 or 2, or a pharmaceutically acceptable salt thereof.

[26] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[25] , wherein m is 2, or a pharmaceutically acceptable salt thereof.

[27] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[26] , wherein n is an integer of 1 to 3, or a pharmaceutically acceptable salt thereof.

[28] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[27] , wherein n is 2, or a pharmaceutically acceptable salt thereof.

[29] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[28] , wherein p is 1, or a pharmaceutically acceptable salt thereof.

[30] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[29] , wherein q is an integer of 1 to 4, or a pharmaceutically acceptable salt thereof.

[31] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[30] , wherein q is 3, or a pharmaceutically acceptable salt thereof.

[32] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[31] , wherein r is an integer of 0 to 5, or a pharmaceutically acceptable salt thereof.

[33] The antibody-photosensitizer conjugate or metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of [1] to

[32] , wherein r is an integer of 0 to 3.

[34] The antibody-photosensitizer conjugate or metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of [1] to

[33] , wherein r is 0.

[35] The antibody-photosensitizer conjugate or metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of [1] to

[34] , wherein in the formula (2), the optionally substituted amino group is a di-C1-C6 alkylamino group (the di-C1-C6 alkyl of the di-C1-C6 alkylamino group are each independently optionally substituted with a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkylsulfonyl group, a sulfonyl group, or an amino-C1-C3 alkyl group) or a 3- to 8-membered nitrogen-containing saturated heterocyclic group (the 3- to 8-membered nitrogen-containing saturated heterocyclic group is optionally substituted with a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkylsulfonyl group, a sulfonyl group, or an amino-C1-C3 alkyl group).

[36] The antibody-photosensitizer conjugate or metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of [1] to

[34] , wherein in the formula (2), the optionally substituted amino group is a di-C1-C6 alkylamino group (the di-C1-C6 alkyl of the di-C1-C6 alkylamino group are each independently optionally substituted with a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkylsulfonyl group, a sulfonyl group, or an amino-C1-C3 alkyl group).

[37] The antibody-photosensitizer conjugate or metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of [1] to

[35] , wherein -X-R is a group selected from the group consisting of the following formula:

[38] The antibody-photosensitizer conjugate according to any one of [1] to

[36] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein L is a group selected from the group consisting of: ２ ) n ａ -Lc-Ld-* or -Lb-La-Lp-NH-(aromatic hydrocarbon group)-(CH ２ ) n ａ The antibody-photosensitizer conjugate according to any one of [1] to

[37] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, represented by -Lc-Ld-*: wherein * indicates binding to P; Lb represents a spacer that connects the sugar chains of La and Ab, or a spacer that connects the cysteine ​​residues of La and Ab; La represents a linker in which 0 to 20 groups selected from the following group are linked in any order, and -(CH ２ CH ２ O)-, -(CH ２ )-, -C(=O)-NH-, -C(=O)- and -O-C(=O)-;２ CH ２ O)- and -(CH ２ any hydrogen atom of - may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a cyano group, a nitro group, an amino group, an azide group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; the —NH— of —C(═O)—NH— of La may be substituted by one or more substituents selected from the group consisting of a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; Lp represents a linker consisting of 1 to 10 amino acid residues or is absent; n ａ represents an integer of 0 to 6; Lc represents *-C(=O)-NH-, *-NR ７ - (CH ２ ) n ｂ represents -, -O- or a single bond, where * represents -(CH ２ ) n ａ - indicates bonding to n ｂ represents an integer of 1 to 6, and R ７ represents a hydrogen atom, a C1-C6 alkyl group, -(CH ２ ) n ｃ -COOH or -(CH ２ ) n ｄ represents —OH, and n ｃ represents an integer of 1 to 4, and n ｄ represents an integer of 1 to 6; Ld represents *-CHR ８ - (CH２ )-C(=O)-, *-CH ２ - (CHR ８ )-C(=O)-, *-CHR ８ -C(=O)-, *-CR ８ R ９ - (CH ２ )-C(=O)-, *-CR ８ R ９ -C(=O)-, *-(cyclic hydrocarbon group)-C(=O)-, *-O-C(=O)-, *-NR １０ -C(=O)- or *-C(=O)-, where * indicates bonding to Lc, R ８ and R ９ are each independently a C1-C6 alkyl group, a C3-C7 cyclic hydrocarbon group, or —(CH ２ ) n ｅ -NH ２ , -(CH ２ ) n ｆ -COOH or -(CH ２ ) n ｇ represents —OH, and R １０ represents a hydrogen atom or a C1-C6 alkyl group, n ｅ represents an integer of 0 to 6, and n ｆ represents an integer of 1 to 4, and n ｇ represents an integer of 1 to 4.

[39] L is -Lb-La-Lp-NH-(CH ２ ) n ａ The antibody-photosensitizer conjugate according to any one of [1] to

[38] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, represented by -Lc-Ld-*: wherein * indicates binding to P; Lb represents a spacer that connects the sugar chains of La and Ab, or a spacer that connects the cysteine ​​residues of La and Ab; La represents a linker in which 0 to 20 groups selected from the following group are linked in any order, and -(CH ２ CH ２ O)-, -(CH ２ )-, -C(=O)-NH-, -C(=O)- and -O-C(=O)-; ２ CH ２ O)- and -(CH ２any hydrogen atom of - may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a cyano group, a nitro group, an amino group, an azido group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic aromatic hydrocarbon group, and a heterocyclic group; the —NH— of —C(═O)—NH— of La may be substituted by one or more substituents selected from the group consisting of a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; Lp represents a linker consisting of 1 to 10 amino acid residues or is absent; n ａ represents 1; Lc represents —O—; Ld represents the following formula (* represents bonding to P, and the wavy line represents bonding to Lc):

[40] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[37] , or a pharmaceutically acceptable salt thereof, wherein L is represented by -Lb-La-Lp-*: wherein * represents a bond to P; Lb represents a spacer linking the sugar chains of La and Ab, or a spacer linking the cysteine ​​residues of La and Ab; La represents a linker in which 0 to 20 groups selected from the following group are linked in any order, and -(CH ２ CH ２ O)-, -(CH ２ )-, -C(=O)-NH-, -C(=O)- and -O-C(=O)-;２ CH ２ O)- and -(CH ２ any hydrogen atom of - may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a cyano group, a nitro group, an amino group, an azide group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; The -NH- of -C(=O)-NH- of La may be substituted by one or more substituents selected from the group consisting of a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; Lp represents a linker consisting of 1 to 10 amino acid residues, or is absent.

[41] The antibody-photosensitizer conjugate or a metal complex thereof according to any one of

[38] to

[40] , wherein La represents any one selected from the group consisting of: *-(CH ２ CH ２ O)n １ - (CH ２ ) n ２ -C(=O)-, *-(CH ２ ) n ３ -C(=O)-NH-(CH ２ CH ２ O)n １ - (CH ２ ) n ２ -C(=O)-, *-(CH ２ ) n ４ -O-C(=O)- and *-(CH ２ ) n５ -C(=O)- (where * indicates bonding to Lb, n １ represents an integer of 1 to 20, and n ２ represents an integer from 1 to 12, and n ３ represents an integer of 1 to 6, and n ４ represents an integer from 1 to 10, and n ５ represents an integer of 1 to 10).

[42] La is one of the following: *-(CH ２ CH ２ O)n １ - (CH ２ ) n ２ -C(=O)- or *-(CH ２ ) n ３ -C(=O)-NH-(CH ２ CH ２ O)n １ - (CH ２ ) n ２ -C(=O)- (where * indicates bonding to Lb, n １ represents an integer from 1 to 16, and n ２ represents an integer of 1 to 8, and n ３

[43] The antibody-photosensitizer conjugate according to any one of

[38] to

[41] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein La represents one of the following: *-(CH ２ CH ２ O)n １ - (CH ２ ) n ２ -C(=O)- or *-(CH ２ ) n ３ -C(=O)-NH-(CH ２ CH ２ O)n １ - (CH ２ ) n ２ -C(=O)- (where * indicates bonding to Lb, n １ represents an integer from 1 to 12, and n ２ represents an integer of 1 to 4, and n ３

[44] The antibody-photosensitizer conjugate according to any one of

[38] to

[42] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein La represents one of the following: *-(CH ２CH ２ O)n １ - (CH ２ ) n ２ -C(=O)- or *-(CH ２ ) n ３ -C(=O)-NH-(CH ２ CH ２ O)n １ - (CH ２ ) n ２ -C(=O)- (where * indicates bonding to Lb, n １ represents an integer of 1 to 8, and n ２ represents an integer of 1 to 2, and n ３

[45] The antibody-photosensitizer conjugate according to any one of

[38] to

[43] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein La represents one of the following: *-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-(CH ２ ) n ２ -C(=O)- or *-(CH ２ ) n ３ -C(=O)-NH-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-(CH ２ ) n２ -C(=O)- (where * indicates bonding to Lb, n ２ represents an integer from 1 to 12, and n ３

[46] The antibody-photosensitizer conjugate according to any one of

[38] to

[44] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein La is one of the following: *-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ -C(=O)- or *-CH ２ CH ２ -C(=O)-NH-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ The antibody-photosensitizer conjugate according to any one of

[38] to

[45] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein La represents *-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２P.S. ２ CH ２ P.S. ２ CH ２ P.S. ２ CH ２ P.S. ２ CH ２ P.S. ２ CH ２ P.S. ２ CH ２The antibody-photosensitizer conjugate or metal complex thereof according to any one of

[38] to

[46] , or a pharmaceutically acceptable salt thereof, wherein Lp represents -C(=O)- (where * indicates binding to Lb).

[48] The antibody-photosensitizer conjugate or metal complex thereof according to any one of

[38] to

[47] , or a pharmaceutically acceptable salt thereof, wherein Lp consists of 1 to 8 amino acid residues.

[49] The antibody-photosensitizer conjugate or metal complex thereof according to any one of

[38] to

[48] , or a pharmaceutically acceptable salt thereof, wherein Lp consists of 1 to 6 amino acid residues.

[50] The antibody-photosensitizer conjugate or metal complex thereof according to any one of

[38] to

[49] , or a pharmaceutically acceptable salt thereof, wherein Lp consists of 2 to 4 amino acid residues.

[51] The antibody-photosensitizer conjugate or metal complex thereof according to any one of

[38] to

[50] , or a pharmaceutically acceptable salt thereof, wherein Lp represents an amino acid sequence consisting of at least one amino acid selected from phenylalanine, glycine, valine, lysine, citrulline, serine, glutamic acid, aspartic acid, glutamine, alanine, proline, isoleucine, methionine, leucine, and asparagine.

[52] Lp is one of the following: *-GGVA (SEQ ID NO: 37)-, *-AA-, *-AAN-, *-VA-, *-GGFG (SEQ ID NO: 38)-, *-FG-, *-GGPI (SEQ ID NO: 39)-, *-PI-, *-GGVCit (SEQ ID NO: 40)-, *-VCit-, *-ACit-, *-GGVK (SEQ ID NO: 41)-, *-VK-, *-GGFCit (SEQ ID NO: 42)-, *-FCit-, *-GGFM (SEQ ID NO: 43)-, *-FM-, *-GGLM (SEQ ID NO: 44)-, *-LM-, *-GGICit (SEQ ID NO: 45)- and *-ICit- (where * indicates binding to La). The antibody-photosensitizer conjugate or metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of

[38] to

[51] , which is any one selected from the group consisting of:

[53] The antibody-photosensitizer conjugate or metal complex thereof according to any one of

[38] to

[52] , or a pharmaceutically acceptable salt thereof, wherein Lp represents any one selected from the group consisting of the following: *-AA-, *-AAN-, *-VA-, *-GGFG-, *-VCit-, and *-ACit- (where * indicates binding to La).

[54] The antibody-photosensitizer conjugate or metal complex thereof according to any one of

[38] to

[53] , or a pharmaceutically acceptable salt thereof, wherein Lp represents *-AA- (where * indicates binding to La).

[55] The antibody-photosensitizer conjugate or metal complex thereof according to any one of

[38] to

[54] , or a pharmaceutically acceptable salt thereof, wherein Lp is cleavable in target cells.

[56] Lb is -(succinimide-3-yl-N)-, wherein -(succinimide-3-yl-N)- has the following structural formula: The antibody-photosensitizer conjugate or metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of

[38] to

[55] , wherein * indicates bonding to La, and the wavy line indicates bonding via the formation of a thioether with the side chain of a cysteine ​​residue of the antibody.

[57] L is represented by -Lb-La-Lp-*, wherein * indicates bonding to P, Lp is *-AA- (where * indicates bonding to La), and La is *-(CH ２ CH ２ O) ８ -CH ２ CH ２ represents —C(═O)— (wherein * indicates a bond to Lb), Lb is —(succinimide-3-yl-N)—, where —(succinimide-3-yl-N)— is a compound having the following structural formula:

[58] The antibody-photosensitizer conjugate or metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of

[38] to

[56] , wherein -L-P represents the following formula:

[59] The antibody-photosensitizer conjugate according to [1], or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein -LP is represented by the following formula:

[60] The antibody-photosensitizer conjugate according to [1], or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein -L-P is represented by the following formula:

[61] The antibody-photosensitizer conjugate according to [1], or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein -L-P is represented by the following formula:

[62] The antibody-photosensitizer conjugate according to [1], or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein -LP is represented by the following formula:

[63] The antibody-photosensitizer conjugate according to [1], or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein -LP is represented by the following formula:

[64] The antibody-photosensitizer conjugate according to [1], or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein -LP is represented by the following formula:

[65] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[64] , or a pharmaceutically acceptable salt thereof, wherein x is in the range of 1 to 8.

[66] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[65] , or a pharmaceutically acceptable salt thereof, wherein x is in the range of 3 to 8.

[67] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[66] , or a pharmaceutically acceptable salt thereof, wherein x is in the range of 3.5 to 5.5.

[68] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[67] , or a pharmaceutically acceptable salt thereof, wherein x is in the range of 4 to 5.

[69] The antibody-photosensitizer conjugate or metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of [1] to

[66] , wherein x is in the range of 7 to 8.

[70] The antibody-photosensitizer conjugate or metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of [1] to

[66] and

[69] , wherein x is in the range of 7.5 to 8.

[71] The antibody or antigen-binding fragment of the antibody is anti-EpCAM antibody, anti-TROP2 antibody, anti-HER3 antibody, anti-DLL3 antibody, anti-FAP antibody, anti-CDH11 antibody, anti-A33 antibody, anti-CanAg antibody, anti-CD19 antibody, anti-CD20 antibody. Antibodies, anti-CD22 antibodies, anti-CD25 antibodies, anti-CD30 antibodies, anti-CD33 antibodies, anti-CD56 antibodies, anti-CD70 antibodies, anti-CD98 antibodies, anti-CEA antibodies, anti-Cripto antibodies, anti-EphA2 antibodies, anti-G250 antibodies, anti-MUC 1 antibody, anti-GPNMB antibody, anti-integrin antibody, anti-PSMA antibody, anti-tenascin-C antibody, anti-SLC44A4 antibody, anti-mesothelin antibody, anti-ENPP3 antibody, anti-CD47 antibody, anti-EGFR antibody, anti-GPR20 antibody, or anti-DR5 antibody, or an antigen-binding fragment of said antibody, or a metal complex thereof, or a pharmaceutically acceptable salt thereof.

[72] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[70] , or a pharmaceutically acceptable salt thereof, wherein the antibody or antigen-binding fragment of the antibody is an anti-EpCAM antibody, an anti-TROP2 antibody, an anti-CD25 antibody, or an anti-EGFR antibody, or an antigen-binding fragment of the antibody. [72A] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[70] , or a pharmaceutically acceptable salt thereof, wherein the antibody or antigen-binding fragment of the antibody is an anti-EpCAM antibody.

[73] The antibody-photosensitizer conjugate according to [72A], or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein the anti-EpCAM antibody or antigen-binding fragment of the antibody comprises a CDRH1, CDRH2, and CDRH3, and a CDRL1, CDRL2, and CDRL3 of the following (a) or (b): (a) a CDRH1 consisting of the amino acid sequence set forth in SEQ ID NO: 26, a CDRH2 consisting of the amino acid sequence set forth in SEQ ID NO: 27, and a CDRH3 consisting of the amino acid sequence set forth in SEQ ID NO: 28, a CDRL1 consisting of the amino acid sequence set forth in SEQ ID NO: 30, a CDRL2 consisting of the amino acid sequence of QMS, and a CDRL3 consisting of the amino acid sequence set forth in SEQ ID NO: 31; and (b) a CDRH1 consisting of the amino acid sequence set forth in SEQ ID NO: 26, a CDRH2 consisting of the amino acid sequence set forth in SEQ ID NO: 27, and a CDRH3 consisting of the amino acid sequence set forth in SEQ ID NO: 29, a CDRL1 consisting of the amino acid sequence of SEQ ID NO: 30, a CDRL2 consisting of the amino acid sequence of QMS, and a CDRL3 consisting of the amino acid sequence set forth in SEQ ID NO: 31.

[74] The antibody-photosensitizer conjugate according to [72A] or

[73] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein the anti-EpCAM antibody or antigen-binding fragment of the antibody comprises a heavy chain variable region and a light chain variable region selected from the group consisting of the following (a) to (e): (a) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 in SEQ ID NO: 9 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 in SEQ ID NO: 4, (b) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 in SEQ ID NO: 10 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 in SEQ ID NO: 5, (c) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 in SEQ ID NO: 10 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 in SEQ ID NO: 6, (d) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 12 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 5; and (e) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 15 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 4.

[75] The antibody-photosensitizer conjugate or metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of [72A] to

[74] , wherein the anti-EpCAM antibody or antigen-binding fragment of the antibody comprises a heavy chain and a light chain selected from the group consisting of the following (a) to (e): (a) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 in SEQ ID NO: 9 and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO: 4, (b) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 in SEQ ID NO: 10 and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO: 5, (c) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 in SEQ ID NO: 10 and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO: 6, (d) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 in SEQ ID NO: 12 and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO: 5, and (e) A heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 in SEQ ID NO: 15, and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO: 4.

[76] The antibody-photosensitizer conjugate or a metal complex thereof, or a pharmaceutically acceptable salt thereof, according to any one of [72A] to

[74] , wherein the anti-EpCAM antibody or antigen-binding fragment of the antibody comprises the following heavy chain variable region and light chain variable region: a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 in SEQ ID NO: 12, and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 in SEQ ID NO: 5.

[77] The antibody-photosensitizer conjugate according to any one of [72A] to

[76] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein the anti-EpCAM antibody or antigen-binding fragment of the antibody comprises the following heavy chain and light chain: a heavy chain consisting of the amino acid sequence represented by amino acid numbers 20 to 465 in SEQ ID NO: 12, and a light chain consisting of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO: 5.

[78] The antibody-photosensitizer conjugate according to

[72] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein the anti-TROP2 antibody or antigen-binding fragment of the antibody comprises the following heavy chain variable region and light chain variable region: a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 140 in SEQ ID NO: 16, and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 129 in SEQ ID NO: 17.

[79] The antibody-photosensitizer conjugate according to

[72] or

[78] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein the anti-TROP2 antibody or antigen-binding fragment of the antibody comprises the following heavy chain and light chain: a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 470 in SEQ ID NO: 16, and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 234 in SEQ ID NO: 17.

[80] The antibody-photosensitizer conjugate according to

[72] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein the anti-CD25 antibody or antigen-binding fragment of the antibody comprises the following CDRH1, CDRH2, and CDRH3, and CDRL1, CDRL2, and CDRL3: CDRH1 consisting of the amino acid sequence set forth in SEQ ID NO: 32, CDRH2 consisting of the amino acid sequence set forth in SEQ ID NO: 33, and CDRH3 consisting of the amino acid sequence set forth in SEQ ID NO: 34, and CDRL1 consisting of the amino acid sequence set forth in SEQ ID NO: 35, CDRL2 consisting of the amino acid sequence of FVS, and CDRL3 consisting of the amino acid sequence set forth in SEQ ID NO: 36.

[81] The antibody-photosensitizer conjugate according to

[72] or

[80] , wherein the anti-CD25 antibody or antigen-binding fragment of the antibody comprises the following heavy chain variable region and light chain variable region: a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 133 of SEQ ID NO: 23, and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 21.

[82] The antibody-photosensitizer conjugate or metal complex thereof according to any one of

[72] ,

[80] , and

[81] , or a pharmaceutically acceptable salt thereof, wherein the anti-CD25 antibody or antigen-binding fragment of the antibody comprises the following heavy and light chains: a heavy chain consisting of the amino acid sequence represented by amino acid numbers 20 to 463 in SEQ ID NO: 23, and a light chain consisting of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO: 21.

[83] The antibody-photosensitizer conjugate or metal complex thereof according to

[72] , or a pharmaceutically acceptable salt thereof, wherein the anti-EGFR antibody or antigen-binding fragment of the antibody comprises the following heavy and light chains: a heavy chain consisting of the amino acid sequence represented by amino acid numbers 20 to 468 in SEQ ID NO: 24, and a light chain consisting of the amino acid sequence represented by amino acid numbers 21 to 234 in SEQ ID NO: 25.

[84] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[83] , or a pharmaceutically acceptable salt thereof, wherein the antibody or antigen-binding fragment of the antibody contains a deletion or absence of one or two amino acids at the carboxyl terminus of the heavy chain.

[85] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[84] , or a pharmaceutically acceptable salt thereof, wherein the antibody or antigen-binding fragment of the antibody lacks a lysine residue at the carboxyl terminus of the heavy chain.

[86] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[85] , or a pharmaceutically acceptable salt thereof, wherein the sugar chain of the antibody or antigen-binding fragment of the antibody is a remodeled sugar chain.

[87] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[86] , or a pharmaceutically acceptable salt thereof, wherein the maximum absorption wavelength in the Q band is 600 nm to 800 nm.

[88] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[87] , or a pharmaceutically acceptable salt thereof, having a maximum absorption wavelength in the Q band of 670 nm to 750 nm.

[89] The antibody-photosensitizer conjugate or metal complex thereof according to any one of [1] to

[88] , or a pharmaceutically acceptable salt thereof, having a maximum absorption wavelength in the Q band of 705 nm to 720 nm or 730 nm to 745 nm.

[90] A compound represented by the following formula (1): (wherein Ab represents a humanized anti-EpCAM antibody represented by the following heavy and light chains or an antibody in which the lysine residue at the carboxyl terminal of the heavy chain of the anti-EpCAM antibody has been deleted, wherein the heavy chain consists of the amino acid sequence represented by amino acid numbers 20 to 465 in SEQ ID NO: 12 and the light chain consists of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO: 5; -L-P represents a group represented by the following formula: and x is 7.5 to 8, or 4 to 5, or a metal complex thereof, or a pharmaceutically acceptable salt thereof.

[91] An antibody-photosensitizer conjugate represented by the following formula (1): (wherein Ab represents a humanized anti-EpCAM antibody represented by the following heavy and light chains or an antibody in which the lysine residue at the carboxyl terminal of the heavy chain of the anti-EpCAM antibody has been deleted, wherein the heavy chain consists of the amino acid sequence represented by amino acid numbers 20 to 465 in SEQ ID NO: 12 and the light chain consists of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO: 5; -L-P represents a group represented by the following formula: and x is 7.5 to 8, or 4 to 5, or a metal complex thereof, or a pharmaceutically acceptable salt thereof.

[92] An antibody-photosensitizer conjugate represented by the following formula (1): (wherein Ab represents a humanized anti-EpCAM antibody represented by the following heavy and light chains or an antibody in which the lysine residue at the carboxyl terminal of the heavy chain of the anti-EpCAM antibody has been deleted, wherein the heavy chain consists of the amino acid sequence represented by amino acid numbers 20 to 465 in SEQ ID NO: 12 and the light chain consists of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO: 5; -L-P represents a group represented by the following formula: and x is 7.5 to 8, or 4 to 5, or a metal complex thereof, or a pharmaceutically acceptable salt thereof.

[93] An antibody-photosensitizer conjugate represented by the following formula (1): (wherein Ab represents a humanized anti-EpCAM antibody represented by the following heavy and light chains or an antibody in which the lysine residue at the carboxyl terminal of the heavy chain of the anti-EpCAM antibody has been deleted, wherein the heavy chain consists of the amino acid sequence represented by amino acid numbers 20 to 465 in SEQ ID NO: 12 and the light chain consists of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO: 5; -L-P represents a group represented by the following formula: and x is 7.5 to 8, or 4 to 5), or a metal complex thereof, or a pharmaceutically acceptable salt thereof.

[94] J-La-Lp-NH-(CH ２ ) n ａ -Lc-Ld-P or J-La-Lp-NH-(aromatic hydrocarbon group)-(CH ２ ) n ａ a compound represented by the formula -Lc-Ld-P, a metal complex thereof, or a pharmaceutically acceptable salt thereof; J represents a cyclic structure containing an alkyne structure that reacts with an azide group to form a 1,2,3-triazole ring, or a compound that bonds to the side chain of an amino acid residue of an antibody or an antigen-binding fragment of the antibody, or a halogen atom; La represents a linker in which 0 to 20 groups selected from the following group are linked in any order, and ２ CH ２ O)-, -(CH ２ )-, -C(=O)-NH-, -C(=O)- and -O-C(=O)-; ２ CH ２ O)- and -(CH ２any hydrogen atom of - may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a cyano group, a nitro group, an amino group, an azide group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; the —NH— of —C(═O)—NH— of La may be substituted by one or more substituents selected from the group consisting of a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; Lp represents a linker consisting of 1 to 10 amino acid residues or is absent; n ａ represents an integer of 0 to 6; Lc represents *-C(=O)-NH-, *-NR ７ - (CH ２ ) n ｂ represents -, -O- or a single bond, where * represents -(CH ２ ) n ａ - indicates bonding to n ｂ represents an integer of 1 to 6, and R ７ represents a hydrogen atom, a C1-C6 alkyl group, -(CH ２ ) n ｃ -COOH or -(CH ２ ) n ｄ represents —OH, and n ｃ represents an integer of 1 to 4, and n ｄ represents an integer of 1 to 6; Ld represents *-CHR ８ - (CH ２ )-C(=O)-, *-CH ２ - (CHR ８)-C(=O)-, *-CHR ８ -C(=O)-, *-CR ８ R ９ - (CH ２ )-C(=O)-, *-CR ８ R ９ -C(=O)-, *-(cyclic hydrocarbon group)-C(=O)-, *-O-C(=O)-, *-NR １０ -C(=O)- or *-C(=O)-, where * indicates bonding to Lc, R ８ and R ９ are each independently a C1-C6 alkyl group, a C3-C7 cyclic hydrocarbon group, or —(CH ２ ) n ｅ -NH ２ , -(CH ２ ) n ｆ -COOH or -(CH ２ ) n ｇ represents —OH, and R １０ represents a hydrogen atom or a C1-C6 alkyl group, n ｅ represents an integer of 0 to 6, and n ｆ represents an integer of 1 to 4, and n ｇ represents an integer of 1 to 4; P represents a monovalent group derived from a photosensitizer and linked to Ld, and the photosensitizer is represented by the following formula (2): (where R １ , R ３ and R ４each independently represent a hydrogen atom, a formyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group or an aromatic heterocyclic group, the C1-C6 alkoxycarbonyl group, the C1-C6 alkanoyl group, the mono-C1-C6 aminocarbonyl group, the di-C1-C6 alkylaminocarbonyl group, the mono-C1-C6 alkylamino group, the di-C1-C6 alkylamino group, the C1-C6 alkyl alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the cyclic hydrocarbon group, the aromatic hydrocarbon group or the aromatic heterocyclic group is optionally substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group and an azide group; R ２ Functional groups contained in R ５ and the functional groups contained in R ６ (i) a group selected from the group consisting of functional groups included in R ２ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ａ (R ２ａ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｂ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｂis a hydrogen atom or a C1-C6 alkyl group) or an optionally substituted amino group), -CH=N-R ２ｃ (R ２ｃ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ ), -R ２ｄ -R ２ｅ (R ２ｄ is a C1-C6 alkylene group, and R ２ｅ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH-C(=O)-(CH ２ ) ｐ -OH) or -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｇ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｇ is a hydrogen atom or a C1-C6 alkyl group) or a 5- to 6-membered aromatic heterocyclic group (the 5- to 6-membered aromatic heterocyclic group is -(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ and R ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, and R５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, —X—R (wherein X represents —S—, —O—, —CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, and R ５ｄ is a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C6 alkylene group, and R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２- or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, and R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅ is a C1-C6 alkyl group substituted with one or more hydroxy groups; (ii) R ６ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or —NH—, where R is a residue of a monosaccharide), —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ )ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, —X—R (wherein X represents —S—, —O—, —CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, and R ５ｄis a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C6 alkylene group, and R ６ｇ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH(R ６ｉ ) (R ６ｈ is a hydrogen atom or a C1-C6 alkyl group, and R ６ｉ represents a hydrogen atom, -C(=O)-(CH ２ ) ｐ -NH ２ or -C(=O)-(CH ２ ) ｐ (iii) R ５ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ- optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or —NH—, where R is a residue of a monosaccharide), —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ｇ -R ５ｈ (R ５ｇ is a C1-C6 alkylene group, and R ５ｈ represents an optionally substituted amino group, and R ６ is -R ６ａ -C(=O)-R ６ｂ (R６ａ is a C1-C6 alkylene group, and R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, and R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅ and n is a C1-C6 alkyl group substituted with one or more hydroxy groups; In all of the above formulas, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, q ​​is an integer of 1 to 6, and r is an integer of 0 to 6.

[95] A compound represented by J-La-Lp-P, a metal complex thereof, or a pharmaceutically acceptable salt thereof: J represents a cyclic structure containing an alkyne structure that reacts with an azide group to form a 1,2,3-triazole ring, or a compound that bonds to the side chain of an amino acid residue of an antibody or an antigen-binding fragment of the antibody, or a halogen atom; La represents a linker in which 0 to 20 groups selected from the following group are linked in any order, and -(CH２ CH ２ O)-, -(CH ２ )-, -C(=O)-NH-, -C(=O)- and -O-C(=O)-; ２ CH ２ O)- and -(CH ２ any hydrogen atom of - may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a cyano group, a nitro group, an amino group, an azide group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; The -NH- of -C(=O)-NH- of La may be substituted by one or more substituents selected from the group consisting of a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; Lp represents a linker consisting of 1 to 10 amino acid residues or is absent; P represents a monovalent group derived from a photosensitizer linked to Ld, and the photosensitizer is represented by the following formula (2): (where R １ , R ３ and R ４each independently represent a hydrogen atom, a formyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group or an aromatic heterocyclic group, the C1-C6 alkoxycarbonyl group, the C1-C6 alkanoyl group, the mono-C1-C6 aminocarbonyl group, the di-C1-C6 alkylaminocarbonyl group, the mono-C1-C6 alkylamino group, the di-C1-C6 alkylamino group, the C1-C6 alkyl alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the cyclic hydrocarbon group, the aromatic hydrocarbon group or the aromatic heterocyclic group is optionally substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group and an azide group; R ２ Functional groups contained in R ５ and the functional groups contained in R ６ (i) a group selected from the group consisting of functional groups included in R ２ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ａ (R ２ａ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｂ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｂis a hydrogen atom or a C1-C6 alkyl group) or an optionally substituted amino group), -CH=N-R ２ｃ (R ２ｃ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ ), -R ２ｄ -R ２ｅ (R ２ｄ is a C1-C6 alkylene group, and R ２ｅ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH-C(=O)-(CH ２ ) ｐ -OH) or -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｇ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｇ is a hydrogen atom or a C1-C6 alkyl group) or a 5- to 6-membered aromatic heterocyclic group (the 5- to 6-membered aromatic heterocyclic group is -(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ and R ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, and R５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, —X—R (wherein X represents —S—, —O—, —CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, and R ５ｄ is a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C6 alkylene group, and R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２- or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, and R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅ is a C1-C6 alkyl group substituted with one or more hydroxy groups; (ii) R ６ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or —NH—, where R is a residue of a monosaccharide), —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ )ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, —X—R (wherein X represents —S—, —O—, —CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, and R ５ｄis a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C6 alkylene group, and R ６ｇ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH(R ６ｉ ) (R ６ｈ is a hydrogen atom or a C1-C6 alkyl group, and R ６ｉ represents a hydrogen atom, -C(=O)-(CH ２ ) ｐ -NH ２ or -C(=O)-(CH ２ ) ｐ (iii) R ５ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ- optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or —NH—, where R is a residue of a monosaccharide), —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ｇ -R ５ｈ (R ５ｇ is a C1-C6 alkylene group, and R ５ｈ represents an optionally substituted amino group, and R ６ is -R ６ａ -C(=O)-R ６ｂ (R６ａ is a C1-C6 alkylene group, and R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, and R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅ is a C1-C6 alkyl group substituted with one or more hydroxy groups; In all of the above formulas, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, q ​​is an integer of 1 to 6, and r is an integer of 0 to 6.

[96] A compound in which J is represented by the following formula (in each structural formula, * indicates bonding to La): Or a maleimidyl group represented by the following formula (* indicates that it is bonded to La):

[97] The compound according to

[94] or

[95] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, which is represented by the following formula:

[98] The compound according to any one of

[94] to

[96] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, represented by the following formula:

[99] The compound according to any one of

[94] to

[96] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, represented by the following formula:

[100] The compound according to any one of

[94] to

[96] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, represented by the following formula:

[101] The compound according to any one of

[94] to

[96] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, represented by the following formula:

[102] The compound according to any one of

[94] to

[96] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, represented by the following formula:

[103] The compound according to any one of

[94] to

[96] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, represented by the following formula:

[104] The compound according to any one of

[94] to

[96] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, represented by the following formula (Ia): (where R １ , R ３ and R ４each independently represent a hydrogen atom, a formyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group or an aromatic heterocyclic group, the C1-C6 alkoxycarbonyl group, the C1-C6 alkanoyl group, the mono-C1-C6 aminocarbonyl group, the di-C1-C6 alkylaminocarbonyl group, the mono-C1-C6 alkylamino group, the di-C1-C6 alkylamino group, the C1-C6 alkyl alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the cyclic hydrocarbon group, the aromatic hydrocarbon group or the aromatic heterocyclic group is optionally substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group and an azide group; R ２ , R ５ and R ６ The combinations are selected from the following groups (i) to (iii): Group (i): R ２ is -CH=CH-C(=O)-R ２ａ (R ２ａ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｂ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｂ is a hydrogen atom or a C1-C6 alkyl group) or an optionally substituted amino group), -CH=N-R ２ｃ (R ２ｃis -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ ), -R ２ｄ -R ２ｅ (R ２ｄ is a C1-C6 alkylene group, and R ２ｅ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH-C(=O)-(CH ２ ) ｐ -OH) or -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｇ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｇ is a hydrogen atom or a C1-C6 alkyl group) or a 5- to 6-membered aromatic heterocyclic group (the 5- to 6-membered aromatic heterocyclic group is -(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ and R ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, —X—R (wherein X represents —S—, —O—, —CH ２- or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, and R ５ｄ is a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C6 alkylene group, and R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃis a hydrogen atom or a C1-C6 alkyl group, and R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅ represents a C1-C6 alkyl group substituted with one or more hydroxy groups); Group (ii): R ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or —NH—, where R is a residue of a monosaccharide), —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —N(R ２ｉ )-(CH ２ CH２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, —X—R (wherein X represents —S—, —O—, —CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, and R ５ｄ is a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆrepresents a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C6 alkylene group, and R ６ｇ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH(R ６ｉ ) (R ６ｈ is a hydrogen atom or a C1-C6 alkyl group, and R ６ｉ represents a hydrogen atom, -C(=O)-(CH ２ ) ｐ -NH ２ or -C(=O)-(CH ２ ) ｐ Group (iii): R ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or —NH—, where R is a residue of a monosaccharide), —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ｇ -R ５ｈ (R ５ｇ is a C1-C6 alkylene group, and R ５ｈ represents an optionally substituted amino group, ６ is -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C6 alkylene group, and R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ )ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, and R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅ

[105] R is a C1-C6 alkyl group substituted with one or more hydroxy groups; in all of the above formulas, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, q ​​is an integer of 1 to 6, and r is an integer of 0 to 6), or a metal complex thereof, or a pharmaceutically acceptable salt thereof. １

[106] The compound according to

[104] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein R represents a methyl group. ３

[107] The compound according to

[104] or

[105] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein R represents a methyl group. ４

[108] The compound according to any one of

[104] to

[106] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein R represents an ethyl group. １ and R ３ represents a methyl group, and R ４

[109] The compound according to any one of

[104] to

[107] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein R represents an ethyl group. ２ , R ５ and R ６ is selected from group (i), and R ２ -CH=CH-C(=O)-R ２ａ (R ２ａ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｂ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｂ is a hydrogen atom or a C1-C3 alkyl group) or an optionally substituted amino group substituted with an amino C1-C3 alkyl group), -CH=N-R ２ｃ (R ２ｃ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ ), -R ２ｄ -R ２ｅ (R ２ｄ is a C1-C3 alkylene group, and R ２ｅ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH-C(=O)-(CH ２ ) ｐ -OH) or -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｇ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｇ is a hydrogen atom or a C1-C3 alkyl group) or a 5-membered aromatic heterocyclic group (the 5-membered aromatic heterocyclic group is -(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ and R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 6-membered aromatic heterocyclic group, -X-R (wherein X represents -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C3 alkanoyl group, and R ５ｄ is a C1-C3 alkyl group, and the C1-C3 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C3 alkoxy group, and the C1-C3 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ But, -R６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C3 alkylene group, and R ６ｂ is a C1-C3 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C3 alkyl group, and R ６ｄ represents a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups or —(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅ

[110] R represents a C1-C3 alkyl group substituted with 1 to 3 hydroxy groups, and in all of the above formulae, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, and q is an integer of 1 to 6.

[111] R represents a C1-C3 alkyl group substituted with 1 to 3 hydroxy groups, and in all of the above formulae, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, and q is an integer of 1 to 6.

[112] R represents a C1-C3 alkyl group substituted with 1 to 3 hydroxy groups, and in all of the above formulae, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, and q is an integer of 1 to 6.

[113] R represents a C1-C3 alkyl group substituted with 1 to 3 hydroxy groups, and in all of the above formulae, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, and q is an integer of 1 to 6. ２ , R ５ and R ６ is selected from group (i), and R ２ is expressed by the following formula: R is a group selected from the group consisting of５ is expressed by the following formula: R is a group selected from the group consisting of ６ is expressed by the following formula:

[111] The compound according to any one of

[104] to

[109] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein R is a group selected from the group consisting of ２ , R ５ and R ６ is selected from group (i), and R ２ But -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ ) and R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, and R ５ｂ represents a 6-membered nitrogen-containing saturated heterocyclic group, and R ６ But, -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C3 alkylene group, and R ６ｂ is -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C3 alkyl group, and R ６ｄ represents a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups), and in all of the above formulae, m is an integer of 0 to 10, and n is an integer of 1 to 6. The compound according to any one of

[104] to

[109] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof.

[112] The compound according to any one of

[104] to

[111] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein the compound represented by formula (Ia) is represented by the following:

[113] The compound according to any one of

[104] to

[111] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein the compound represented by formula (Ia) is any one of the following:

[114] R ２ , R ５ and R ６ is selected from group (ii), R ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C3 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R２ｉ is a hydrogen atom or a C1-C3 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C3 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 6-membered aromatic heterocyclic group, -X-R (wherein X represents -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C3 alkanoyl group, and R ５ｄ is a C1-C3 alkyl group, and the C1-C3 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C3 alkoxy group, and the C1-C3 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ But, -R ６ｆ -C(=O)-R ６ｇ (R ６ｆis a C1-C3 alkylene group, and R ６ｇ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH(R ６ｉ ) (R ６ｈ is a hydrogen atom or a C1-C3 alkyl group, and R ６ｉ represents a hydrogen atom, -C(=O)-(CH ２ ) ｐ -NH ２ or -C(=O)-(CH ２ ) ｐ In all of the above formulae, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, q ​​is an integer of 1 to 6, and r is an integer of 0 to 6.

[115] The compound according to any one of

[104] to

[108] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof. ２ , R ５ and R ６ is selected from group (ii), R ２ is expressed by the following formula: R is a group selected from the group consisting of ５ is expressed by the following formula: R is a group selected from the group consisting of ６ is expressed by the following formula:

[116] The compound according to any one of

[104] to

[108] and

[114] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein R is a group selected from the group consisting of ２ , R ５ and R ６ is selected from group (ii), R ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH２ O) ｍ - (CH ２ ) ｎ -OH or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ represents a hydrogen atom or a C1-C3 alkyl group, and R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, and R ５ｂ represents a 6-membered nitrogen-containing saturated heterocyclic group, and R ６ But, -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C3 alkylene group, and R ６ｇ is -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH ２ (R ６ｈ is a hydrogen atom or a C1-C3 alkyl group), and in all of the above formulae, m is an integer of 0 to 10, n is an integer of 1 to 6, and r is an integer of 0 to 6. The compound according to any one of

[104] to

[108] and

[114] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof.

[117] The compound according to any one of

[104] to

[108] and

[114] to

[116] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein the compound represented by formula (Ia) is any one selected from the group consisting of:

[118] R ２ , R ５ and R ６ is selected from group (iii), and R ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O)ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is hydrogen or a C1-C3 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C3 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C3 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２- or -NH-, and R is a residue of a monosaccharide; ５ But, -R ５ｇ -R ５ｈ (R ５ｇ is a C1-C3 alkylene group, and R ５ｈ represents a 6-membered nitrogen-containing saturated heterocyclic group substituted with an amino group or an amino C1-C3 alkyl group, and R ６ But, -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C3 alkylene group, and R ６ｂ is a C1-C3 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is hydrogen or a C1-C3 alkyl group, and R ６ｄ represents a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups or —(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅrepresents a C1-C3 alkyl group substituted with 1 to 3 hydroxy groups), and in all of the above formulae, m is an integer of 0 to 10, n is an integer of 1 to 6, and q is an integer of 1 to 6. The compound according to any one of

[104] to

[108] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof.

[119] The compound according to any one of

[104] to

[108] and

[118] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein the compound represented by formula (Ia) is any one of the following:

[120] The compound according to any one of

[104] to

[119] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein m is an integer of 0 to 5.

[121] The compound according to any one of

[104] to

[120] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein m is an integer of 0 to 3.

[122] The compound according to any one of

[104] to

[121] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein m is 1 or 2.

[123] The compound according to any one of

[104] to

[122] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein m is 2.

[124] The compound according to any one of

[104] to

[123] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein n is an integer of 1 to 3.

[125] The compound according to any one of

[104] to

[124] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein n is 2.

[126] The compound according to any one of

[104] to

[125] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein p is 1.

[127] The compound according to any one of

[104] to

[126] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein q is an integer of 1 to 4.

[128] The compound according to any one of

[104] to

[127] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein q is 3.

[129] The compound according to any one of

[104] to

[128] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein r is an integer of 0 to 5.

[130] The compound according to any one of

[104] to

[129] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein r is an integer of 0 to 3.

[131] The compound according to any one of

[104] to

[130] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein r is 0.

[132] The compound according to any one of

[104] to

[131] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein in the formula (Ia), the optionally substituted amino group is a di-C1-C6 alkylamino group (the di-C1-C6 alkyl of the di-C1-C6 alkylamino group are each independently optionally substituted with a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkylsulfonyl group, a sulfonyl group, or an amino-C1-C3 alkyl group), or a 3- to 8-membered nitrogen-containing saturated heterocyclic group (the 3- to 8-membered nitrogen-containing saturated heterocyclic group is optionally substituted with a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkylsulfonyl group, a sulfonyl group, or an amino-C1-C3 alkyl group).

[133] The compound according to any one of

[104] to

[131] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, wherein in the formula (Ia), the optionally substituted amino group is a di-C1-C6 alkylamino group (the di-C1-C6 alkyl of the di-C1-C6 alkylamino group are each independently optionally substituted with a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkylsulfonyl group, a sulfonyl group, or an amino-C1-C3 alkyl group).

[134] In the formula (Ia), -X-R is a group selected from the group consisting of the following formula:

[135] The compound or metal complex thereof according to any one of

[104] to

[134] , or a pharmaceutically acceptable salt thereof, wherein the maximum absorption wavelength in Q band is 600 nm to 800 nm.

[136] The compound or metal complex thereof according to any one of

[104] to

[135] , or a pharmaceutically acceptable salt thereof, wherein the maximum absorption wavelength in Q band is 640 nm to 780 nm.

[137] The compound or metal complex thereof according to any one of

[104] to

[136] , or a pharmaceutically acceptable salt thereof, wherein the maximum absorption wavelength in Q band is 670 nm to 750 nm.

[138] The compound according to any one of

[104] to

[137] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, having a maximum absorption wavelength in the Q band of 690 to 710 nm or 715 to 735 nm.

[139] A pharmaceutical composition comprising any one selected from the group consisting of the antibody-photosensitizer conjugate according to any one of [1] to

[93] , the compound according to any one of

[104] to

[138] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, and the pharmaceutical composition according to

[139] .

[140] An antitumor agent comprising any one selected from the group consisting of the antibody-photosensitizer conjugate according to any one of [1] to

[93] , the compound according to any one of

[104] to

[138] , or a metal complex thereof, or a pharmaceutically acceptable salt thereof, and the pharmaceutical composition according to

[139] .

[141] The antitumor agent according to

[140] , for use in photodynamic therapy (PDT).

[142] The antitumor agent according to

[140] or

[141] , wherein the tumor to which the antitumor agent is applied is lung cancer, kidney cancer, urothelial cancer, colorectal cancer, prostate cancer, glioblastoma multiforme, ovarian cancer, pancreatic cancer, breast cancer, melanoma, skin cancer, liver cancer, bladder cancer, gastric cancer, esophageal cancer, uterine cancer, testicular cancer, cervical cancer, placental choriocarcinoma, glioblastoma multiforme, brain tumor, head and neck cancer, thyroid cancer, mesothelioma, gastrointestinal stromal tumor (GIST), gallbladder cancer, bile duct cancer, adrenal cancer, squamous cell carcinoma, leukemia, malignant lymphoma, plasmacytoma, myeloma, or sarcoma.

[143] The antitumor agent according to any one of

[140] to

[142] , wherein the tumor to which the antitumor agent is applied is lung cancer, breast cancer, bladder cancer, stomach cancer, bile duct cancer, esophageal cancer, prostate cancer, or head and neck cancer.

[144] The antitumor agent according to any one of

[140] to

[143] , wherein the antitumor agent is used so that the tumor site is irradiated with light after administration to a subject.

[145] The antitumor agent according to

[144] , wherein the tumor site of the subject is irradiated with light at a wavelength of 600 nm to 800 nm.

[146] The antitumor agent according to

[144] or

[145] , wherein the tumor site of the subject is irradiated with light at a wavelength of 640 nm to 780 nm.

[147] The antitumor agent according to any one of

[144] to

[146] , wherein the tumor site of the subject is irradiated with light at a wavelength of 670 nm to 750 nm.

[148] The antitumor agent according to any one of

[144] to

[147] , wherein the tumor site of the subject is irradiated with light at a wavelength of 680 to 700 nm or 720 to 745 nm.

[149] The antitumor agent according to any one of

[144] to

[148] , wherein the antitumor agent is administered once to the subject, and then light irradiation is performed once a day for a total of 1 to 21 times.

[150] The antitumor agent according to any one of

[144] to

[149] , wherein the antitumor agent is administered once to the subject, and then light irradiation is performed once a day for a total of 3 to 21 times, preferably 4 to 21 times.

[151] The antitumor agent according to any one of

[144] to

[150] , wherein the antitumor agent is administered once to the subject, and then light irradiation is performed once a day for a total of 3 to 14 times, preferably 4 to 14 times.

[152] The antitumor agent according to any one of

[144] to

[151] , wherein the antitumor agent is administered once to a subject, followed by once-daily light irradiation a total of 3 to 7 times, preferably 4 to 7 times.

[153] The antitumor agent according to any one of

[144] to

[152] , wherein the antitumor agent is administered once to a subject, followed by once-daily light irradiation a total of 7 times.

[154] The antitumor agent according to any one of

[144] to

[152] , wherein the antitumor agent is administered once to a subject, followed by once-daily light irradiation a total of 3 or 4 times, preferably 4 times.

[155] The antitumor agent according to any one of

[144] to

[154] , wherein the antitumor agent is administered once to a subject, followed by the first light irradiation 1 to 48 hours later.[155A] The antitumor agent according to any one of

[144] to

[154] , wherein the antitumor agent is administered once to a subject, followed by a first light irradiation 1 to 72 hours later.

[156] The antitumor agent according to any one of

[144] to [155A], wherein the antitumor agent is administered once to a subject, followed by a first light irradiation 20 to 28 hours later.

[157] The antitumor agent according to any one of

[144] to

[156] , wherein the antitumor agent is administered once to a subject, followed by a first light irradiation 24 hours later.

[158] The antitumor agent according to any one of

[144] to

[155] , wherein the antitumor agent is administered once to a subject, followed by a first light irradiation 48 hours later.

[159] The antitumor agent according to any one of

[144] to

[158] , wherein the light irradiation is performed every 24 hours.

[160] After an antitumor agent is administered to a subject, the light irradiation dose per irradiation is 2 to 500 J / cm. ２ , preferably 10 to 500 J / cm ２

[161] The antitumor agent according to any one of

[144] to

[159] , wherein the light irradiation dose per irradiation after administration of the antitumor agent to a subject is 50 to 450 J / cm ２

[162] The antitumor agent according to any one of

[144] to

[160] , wherein the light irradiation dose per irradiation after the antitumor agent is administered to a subject is 50 to 300 J / cm ２ The antitumor agent according to any one of

[144] to

[161] , wherein the light irradiation intensity is adjusted so that the irradiation time is 100 seconds to 10 days.

[163] The antitumor agent according to any one of

[144] to

[162] , wherein the light irradiation is performed by adjusting the light irradiation intensity so that the irradiation time is 100 seconds to 10 days.

[164] The antitumor agent according to any one of

[144] to

[163] , wherein the light irradiation intensity is adjusted so that the irradiation time is 384 seconds to 10 days. [164A] The antitumor agent according to any one of

[144] to

[164] , wherein the irradiation time per irradiation is 100 seconds to 1 day.

[165] The irradiation intensity per irradiation after the antitumor agent is administered to the subject is 1000 mW / cm ２

[166] The antitumor agent according to any one of

[144] to

[164] , wherein the irradiation intensity per irradiation after the antitumor agent is administered to a subject is 10 μW / cm or less.２ ~1000mW / cm ２

[167] The antitumor agent according to any one of

[144] to

[165] , wherein the irradiation intensity per irradiation after the antitumor agent is administered to a subject is 60 μW / cm ２ ~800mW / cm ２

[168] The antitumor agent according to any one of

[144] to

[166] , wherein the irradiation intensity per irradiation after the antitumor agent is administered to a subject is 10 mW / cm ２ ~400mW / cm ２

[169] The antitumor agent according to any one of

[144] to

[167] , wherein the irradiation intensity per irradiation after the antitumor agent is administered to a subject is 10 mW / cm ２ ~200mW / cm ２

[170] The antitumor agent according to any one of

[144] to

[168] , wherein the irradiation intensity per irradiation after the antitumor agent is administered to a subject is about 780 mW / cm ２

[171] The antitumor agent according to any one of

[144] to

[167] , wherein the irradiation intensity per irradiation after the antitumor agent is administered to a subject is about 156 mW / cm ２

[172] The antitumor agent according to any one of

[144] to

[169] , wherein the irradiation intensity per irradiation after the antitumor agent is administered to a subject is about 78 mW / cm ２The antitumor agent according to any one of

[144] to

[169] , wherein the antitumor agent is a compound having a structure similar to that described above.

[173] The antitumor agent according to any one of

[144] to

[172] , characterized in that the agent is used to comprise one or more treatment cycles comprising the administration and irradiation.

[174] The antitumor agent according to

[173] , comprising at least three treatment cycles.

[175] The antitumor agent according to

[173] , comprising four or more treatment cycles.

[176] The antitumor agent according to any one of

[173] to

[175] , wherein the administration interval of the antitumor agent is one day to two months.

[177] The antitumor agent according to any one of

[173] to

[175] , wherein the administration interval of the antitumor agent is three days to one month.

[178] The antitumor agent according to any one of

[173] to

[175] , wherein the administration interval of the antitumor agent is five to ten days.

[179] The antitumor agent according to any one of

[144] to

[178] , which is used in combination with an immune checkpoint inhibitor.

[180] The antitumor agent according to

[179] , wherein the immune checkpoint inhibitor is any one or more selected from the group consisting of an anti-PD-1 antibody, an anti-PD-L1 antibody, an anti-CTLA-4 antibody, an anti-TIM-3 antibody, an anti-LAG-3 antibody, an anti-TIGIT antibody, an anti-BTLA antibody, and an anti-VISTA antibody.

[181] The antitumor agent according to

[179] , wherein the immune checkpoint inhibitor is any one or more selected from the group consisting of an anti-PD-1 antibody, an anti-PD-L1 antibody, and an anti-CTLA-4 antibody.

[182] The antitumor agent according to

[179] , wherein the immune checkpoint inhibitor is an anti-PD-1 antibody.

[183] ​​The antitumor agent according to

[179] , wherein the immune checkpoint inhibitor is one or more selected from the group consisting of nivolumab, pembrolizumab, pidilizumab, cemiplimab, toripalimab, dostallimab, atezolizumab, durvalumab, avelumab, ipilimumab, tremelimumab, tiragolumab, leratolimab, LAG525, MAB10, BTLA-8.2, and JNJ-61610588.

[184] The antitumor agent according to any one of

[144] to

[183] , wherein the subject is a human.

[0012] The present invention also encompasses the following inventions: [i] An antibody or an antigen-binding fragment of the antibody, which specifically binds to EpCAM and comprises a CDRH1, CDRH2, and CDRH3, and a CDRL1, CDRL2, and CDRL3 of the following (a) or (b): (a) a CDRH1 consisting of the amino acid sequence set forth in SEQ ID NO: 26, a CDRH2 consisting of the amino acid sequence set forth in SEQ ID NO: 27, and a CDRH3 consisting of the amino acid sequence set forth in SEQ ID NO: 28, a CDRL1 consisting of the amino acid sequence set forth in SEQ ID NO: 30, a CDRL2 consisting of the amino acid sequence of QMS, and a CDRL3 consisting of the amino acid sequence set forth in SEQ ID NO: 31, and (b) a CDRH1 consisting of the amino acid sequence set forth in SEQ ID NO: 26, a CDRH2 consisting of the amino acid sequence set forth in SEQ ID NO: 27, and a CDRH3 consisting of the amino acid sequence set forth in SEQ ID NO: 29, a CDRL1 consisting of the amino acid sequence of SEQ ID NO: 30, a CDRL2 consisting of the amino acid sequence of QMS, and a CDRL3 consisting of the amino acid sequence set forth in SEQ ID NO: 31. [ii] An antibody or antigen-binding fragment of the antibody according to [i], which specifically binds to EpCAM and comprises a heavy chain variable region and a light chain variable region selected from the group consisting of the following (a) to (e): (a) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 9 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 4; (b) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 10 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 5; (c) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 10 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 6; (d) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 12 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 5; (e) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 15, and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 4.[iii] An antibody or antigen-binding fragment of the antibody according to [i] or [ii], which specifically binds to EpCAM and comprises a heavy chain and a light chain selected from the group consisting of the following (a) to (e): (a) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 in SEQ ID NO: 9 and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO: 4, (b) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 in SEQ ID NO: 10 and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO: 5, (c) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 in SEQ ID NO: 10 and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO: 6, (d) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 in SEQ ID NO: 12 and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO: 5, and (e) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 in SEQ ID NO: 15, and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO: 4. [iv] An antibody or antigen-binding fragment of the antibody of any one of [i] to [iii], which specifically binds to EpCAM and comprises the following heavy chain variable region and light chain variable region: a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 in SEQ ID NO: 12, and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 in SEQ ID NO: 5. [v] An antibody or antigen-binding fragment of the antibody of any one of [i] to [iv], which specifically binds to EpCAM and comprises the following heavy chain and light chain: a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 in SEQ ID NO: 12, and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO: 5. [vi] A polynucleotide encoding any one of the antibodies of [i] to [v], or an antigen-binding fragment of the antibody. [vii] An expression vector containing the polynucleotide of [vi]. [viii] A host cell transformed with the expression vector of [vii]. [ix] The host cell of [viii], wherein the host cell is a eukaryotic cell.[x] A method for producing an antibody or an antigen-binding fragment of the antibody, comprising the steps of culturing the host cell of [viii] or [ix] and collecting the antibody of interest from the culture obtained in the step. [xi] An antibody or an antigen-binding fragment of the antibody, obtained by the production method of [x]. [xii] An antibody or an antigen-binding fragment of the antibody of [xi], which contains one or more modifications selected from the group consisting of N-linked glycosylation, O-linked glycosylation, N-terminal processing, C-terminal processing, deamidation, aspartic acid isomerization, methionine oxidation, tryptophan oxidation, addition of a methionine residue to the N-terminus, amidation of a proline residue, and a heavy chain having one or two amino acids deleted at the carboxyl terminus. [xiii] An antibody or an antigen-binding fragment of the antibody of [xii], in which one or two amino acids are deleted at the carboxyl terminus of the heavy chain. [xiv] An antibody or antigen-binding fragment of said antibody according to [xii] or [xiii], in which one amino acid is deleted at the carboxyl termini of both of the two heavy chains. [xv] An antibody or antigen-binding fragment of said antibody according to any one of [xii] to [xiv], in which the proline residue at the carboxyl terminus of the heavy chain is further amidated. [xvi] An antibody-photosensitizer conjugate, in which a photosensitizer is bound to any one of the antibodies according to [i] to [v] and [xii] to [xiv], or an antigen-binding fragment of said antibody. [xvii] A method for producing an antibody-photosensitizer conjugate, comprising the steps of: culturing the host cell according to [viii] or [ix]; recovering the antibody of interest or the antigen-binding fragment of said antibody from the culture obtained in said step; and reacting the antibody or the antigen-binding fragment of said antibody obtained in said step with a photosensitizer linker intermediate compound.

[0013] The present invention provides a novel photosensitizer. When irradiated with light, the photosensitizer exhibits singlet oxygen-mediated cytotoxicity. Furthermore, since the photosensitizer is more water-soluble and less prone to aggregation than conventional photosensitizers, a photosensitizer suitable for producing antibody-photosensitizer conjugates is provided. The present invention also provides a novel antibody-photosensitizer conjugate that exhibits antitumor effects in tumors expressing an antigen. When irradiated with light, the antibody-photosensitizer conjugate of the present invention exhibits singlet oxygen-mediated antitumor effects. In addition, the antibody-photosensitizer conjugate of the present invention exhibits high selectivity against cancer, thereby reducing side effects. Furthermore, since the antibody-photosensitizer conjugate of the present invention exhibits light absorption in the long-wavelength region, it can be used not only for superficial cancers but also for cancers located deep within or that have infiltrated deep within the tumor.

[0014] This figure shows the in vivo antitumor effect of antibody-photosensitizer conjugates (2), (4), and (10) on BALB / c nude mice implanted with human pancreatic cancer cell line CFPAC-1 cells. This figure shows the in vivo antitumor effect of antibody-photosensitizer conjugates (2), (3), (9), (11), and (12) on BALB / c nude mice implanted with human pancreatic cancer cell line CFPAC-1 cells. This figure shows the in vivo antitumor effect of antibody-photosensitizer conjugate (13) on BALB / c nude mice implanted with human pancreatic cancer cell line CFPAC-1 cells. This figure shows the in vivo antitumor effect of antibody-photosensitizer conjugates (14) and (15) on BALB / c nude mice implanted with human pancreatic cancer cell line CFPAC-1 cells. This figure shows the in vivo antitumor effect of antibody-photosensitizer conjugates (17) and (27) on BALB / c nude mice transplanted with human pancreatic cancer cell line CFPAC-1 cells. This figure shows the in vivo antitumor effect of antibody-photosensitizer conjugate (28) on BALB / c nude mice transplanted with human pancreatic cancer cell line CFPAC-1 cells. This figure shows the in vivo antitumor effect of antibody-photosensitizer conjugate (29) on BALB / c nude mice transplanted with human pancreatic cancer cell line CFPAC-1 cells at 150 J / cm ２ (780 mW / cm ２ for 192 seconds), 300 J / cm ２ (780 mW / cm ２ for 384 seconds), 450 J / cm ２ (780 mW / cm ２ This figure shows the in vivo antitumor effect of the antibody-photosensitizer conjugate (29) on BALB / c nude mice implanted with human pancreatic cancer cell line CFPAC-1 cells, when the conjugate was irradiated with a light dose of 150 J / cm for 576 seconds. ２ Light intensity (780 mW / cm ２ for 192 seconds at 156 mW / cm ２ for 960 seconds and 78 mW / cm ２This figure shows the in vivo antitumor effect of the antibody-photosensitizer conjugate (4) on BALB / c nude mice implanted with human pancreatic cancer cell line CFPAC-1 cells at 150 J / cm. ２ (78 mW / cm ２1 shows the in vivo antitumor effect when irradiated once, twice, four times, or seven times with a light dose of 1000 dpi (1920 seconds) at 1000 dpi. The amino acid sequence of W94-Lwt (SEQ ID NO: 4). The amino acid sequence of W94-L01 (SEQ ID NO: 5). The amino acid sequence of W94-L02 (SEQ ID NO: 6). The amino acid sequence of W94-Hwt-LALAPA (SEQ ID NO: 9). The amino acid sequence of W94-H03-LALAPA (SEQ ID NO: 10). The amino acid sequence of W94-H03Nq-LALAPA (SEQ ID NO: 12). The amino acid sequence of W94-Hwt (SEQ ID NO: 15). The amino acid sequence of an anti-TROP2 antibody heavy chain (hTINA1-H1) (SEQ ID NO: 16). The amino acid sequence of an anti-TROP2 antibody light chain (hTINA1-L1) (SEQ ID NO: 17). 1 shows the signal sequence and the amino acid sequence of the cMAb2_hIgG1LALA-PA light chain (SEQ ID NO: 21). 2 shows the signal sequence and the amino acid sequence of the cMAb2_hIgG1LALA-PA heavy chain (SEQ ID NO: 23). 3 shows the amino acid sequence of the full-length cetuximab heavy chain (SEQ ID NO: 24). 4 shows the amino acid sequence of the full-length cetuximab light chain (SEQ ID NO: 25). 5 shows the in vivo antitumor effect of antibody-photosensitizer conjugate (35) on BALB / c nude mice implanted with human pancreatic cancer line CFPAC-1 cells. 6 shows the in vivo antitumor effect of antibody-photosensitizer conjugate (40) on BALB / c nude mice implanted with human pancreatic cancer line CFPAC-1 cells. 1 is a diagram showing the in vivo antitumor effect of antibody-photosensitizer conjugate (45) on BALB / c nude mice implanted with human pancreatic cancer line CFPAC-1 cells. 2 is a diagram showing the in vivo antitumor effect of antibody-photosensitizer conjugate (5) at various doses on BALB / c nude mice implanted with human pancreatic cancer line CFPAC-1 cells under the condition of one irradiation. 3 is a diagram showing the in vivo antitumor effect of antibody-photosensitizer conjugate (5) at various doses on BALB / c nude mice implanted with human pancreatic cancer line CFPAC-1 cells under the condition of four irradiations.This figure shows the in vivo antitumor effect of antibody-photosensitizer conjugate (5) on BALB / c nude mice implanted with human pancreatic cancer cell line CFPAC-1 cells, under conditions of irradiation at various irradiation intensities and the same irradiation time. This figure shows the in vivo antitumor effect of antibody-photosensitizer conjugate (5) on BALB / c nude mice implanted with human pancreatic cancer cell line CFPAC-1 cells, under conditions of irradiation at various irradiation times and the same irradiation intensity. This figure shows the in vivo antitumor effect of antibody-photosensitizer conjugate (5) on BALB / c nude mice implanted with human breast cancer cell line HCC1806 cells. This figure shows the in vivo antitumor effect of antibody-photosensitizer conjugate (5) on BALB / c nude mice implanted with human breast cancer cell line HCC70 cells. This figure shows the in vivo antitumor effect of antibody-photosensitizer conjugate (5) on BALB / c nude mice implanted with human breast cancer cell line SUM149PT cells. This figure shows the in vivo antitumor effect of antibody-photosensitizer conjugate (5) on BALB / c nude mice implanted with human lung cancer cell line NCI-H1975. This figure shows the in vivo antitumor effect of antibody-photosensitizer conjugate (5) on BALB / c nude mice implanted with human lung cancer cell line NCI-H2081. This figure shows the in vivo antitumor effect of antibody-photosensitizer conjugate (5) on NOD-SCID mice implanted with human lung cancer cell line NCI-H211. 1 shows the in vivo antitumor effect of antibody-photosensitizer conjugate (5) on BALB / c nude mice transplanted with an EpCAM antigen-negative cancer cell line. 2 shows the in vivo antitumor effect of single-agent administration of antibody-photosensitizer conjugate (5), single-agent administration of an anti-PD-1 antibody, and combined administration of antibody-photosensitizer conjugate (5) and an anti-PD-1 antibody on C57BL / 6 mice transplanted with the human EpCAM antigen-expressing murine lung cancer line 3LL.

[0015] The present invention relates to a novel photosensitizer that can be used for photodynamic therapy (PDT), an antibody-photosensitizer conjugate in which the photosensitizer is bound to an antibody via a linker, an antitumor agent containing the antibody-photosensitizer conjugate, and the like.

[0016] Photodynamic therapy (PDT) has traditionally been known as a treatment for malignant tumors such as esophageal cancer, lung cancer, and brain tumors. In photodynamic therapy, a photosensitizer is administered to the subject as a drug that accumulates in tumor cells. When the photosensitizer accumulates, the subject is then irradiated with light of a specific wavelength band appropriate for the photosensitizer, causing the photosensitizer to undergo a photochemical reaction and generate reactive oxygen species. In photodynamic therapy, the reactive oxygen species generated by the photochemical reaction of the photosensitizer exert cytotoxic activity on the tumor cells in which the photosensitizer has accumulated.

[0017] In the present invention, the term "photosensitizer" refers to a substance that exerts a pharmacological effect when irradiated with light, and is used to include precursors that produce photosensitizers within cells. Photosensitizers are not particularly limited, but examples include porphyrin, corrin, chlorin, bacteriochlorin, phthalocyanine, bacteriochlorophyll, corphin, corrole, porphycene, and derivatives thereof. In the above, the term "derivative" refers to a substance that is structurally related to the original substance and has the properties of a photosensitizer.

[0018] In the present invention, the terms "cancer," "carcinoma," and "tumor" are synonymous.

[0019] In the present invention, the term "antitumor effect" refers to the suppression of tumor growth or the induction of tumor regression by a drug that directly or indirectly affects tumor cells. For example, a drug can directly damage tumor cells, or the antitumor immunity of tumor cells can be activated by the drug, or the drug delivered to tumor cells can be released extracellularly, activating the antitumor immunity around the tumor cells, thereby reducing the number of tumor cells or causing tumor regression.

[0020] In the present invention, "cytotoxic activity" refers to causing pathological changes in cells in some form, and refers to causing not only direct trauma but also any damage to the structure or function of cells, such as DNA breakage, formation of base dimers, chromosome breakage, damage to the cell division apparatus, and reduced activity of various enzymes.

[0021] In the present invention, "active oxygen" refers to four types of oxygen: singlet oxygen, superoxide anion radical (also called superoxide ion), hydroxyl radical, and hydrogen peroxide (also called peroxide ion).

[0022] In the present invention, "singlet oxygen" refers to a singlet oxygen atom that is located in one of the molecular orbitals π ＊ ２ｐ It is an excited state in which the orbital electrons are occupied in a singlet state, i.e., the total spin quantum number is zero. １ O ２ Singlet oxygen can be generated, for example, by the reaction of a photosensitizer with ground state oxygen.

[0023] In the present invention, the term "cells" also includes various cells derived from individual animals, subcultured cells, primary cultured cells, cell lines, recombinant cells, yeast, microorganisms, and the like.

[0024] In the present invention, the term "tumor site" refers to a site where pathological changes occur due to the presence of tumor cells, or a site where residual, re-grown, or metastasized tumor cells are located after treatment such as surgery, radiation therapy, or anticancer drug therapy.

[0025] In the present invention, examples of the "halogen atom" include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0026] In the present invention, the term "C1-C6 alkyl group" refers to a linear or branched alkyl group having 1 to 6 carbon atoms. Examples of the "C1-C6 alkyl group" include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, an s-butyl group, a t-butyl group, an n-pentyl group, and an n-hexyl group.

[0027] In the present invention, the term "C1-C6 alkoxy group" refers to an alkoxy group having a straight or branched alkyl group having 1 to 6 carbon atoms. Examples of the "C1-C6 alkoxy group" include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an i-butoxy group, an s-butoxy group, an n-pentyloxy group, and an n-hexyloxy group.

[0028] In the present invention, the term "C1-C6 alkoxycarbonyl group" refers to a carbonyl group bonded to an alkoxy group having a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms. Examples of the "C1-C6 alkoxycarbonyl group" include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, an i-butoxycarbonyl group, an s-butoxycarbonyl group, an n-pentyloxycarbonyl group, and an n-hexyloxycarbonyl group.

[0029] In the present invention, the term "C1-C6 alkanoyl group" refers to an alkanoyl group having a straight or branched alkyl group having 1 to 6 carbon atoms. Examples of the "C1-C6 alkanoyl group" include an acetyl group, a propanoyl group, a butanoyl group, a 2-methylpropanoyl group, a pentanoyl group, a 2-methylbutanoyl group, a 3-methylbutanoyl group, a 2,2-dimethylpropanoyl group, and a hexanoyl group.

[0030] In the present invention, the term "aminocarbonyl group" refers to a carbonyl group substituted with an amino group. In the present invention, the term "mono C1-C6 alkylaminocarbonyl group" refers to an -NH bonded to an aminocarbonyl group. ２ In the present invention, the term "di-C1-C6 alkylaminocarbonyl group" refers to a group in which one hydrogen atom of the group is substituted with a C1-C6 alkyl group. ２ are each independently substituted with a C1-C6 alkyl group.

[0031] In the present invention, the term "mono C1-C6 alkylamino group" refers to an amino group (-NH ２In the present invention, the term "di-C1-C6 alkylamino group" refers to an amino group (-NH ２ ) are each independently substituted with a C1-C6 alkyl group.

[0032] In the present invention, the term "C2-C6 alkenyl group" refers to a straight-chain or branched-chain alkenyl group having 2 to 6 carbon atoms. Examples of the "C2-C6 alkenyl group" include a vinyl group, an allyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group (including cis and trans), a 3-butenyl group, a pentenyl group, and a hexenyl group.

[0033] In the present invention, the term "C2-C6 alkynyl group" means a straight-chain or branched-chain alkynyl group having 2 to 6 carbon atoms. Examples of the "C2-C6 alkynyl group" include an ethynyl group, a 1-propynyl group, a propargyl group, a 3-butynyl group, a pentynyl group, and a hexynyl group.

[0034] In the present invention, the term "cyclic hydrocarbon group" refers to a non-aromatic 3- to 8-membered cyclic hydrocarbon group. Examples of the "cyclic hydrocarbon group" include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and groups thereof having an unsaturated bond at any position.

[0035] In the present invention, examples of the "aromatic hydrocarbon group" include a phenyl group, a benzyl group, an indenyl group, a naphthyl group, a fluorenyl group, an anthranyl group, and a phenanthrenyl group.

[0036] In the present invention, examples of an "aromatic heterocyclic group" include a thienyl group, a pyrrolyl group, a pyrazolyl group, a triazolyl group, an oxazolyl group, an oxadiazolyl group, a thiazolyl group, a pyridyl group, a pyrimidyl group, a pyridazyl group, a pyrazinyl group, a quinolyl group, a quinoxalyl group, a benzothiophenyl group, a benzimidazolyl group, a benzotriazolyl group, and a benzofuranyl group. In the present invention, a "nitrogen-containing saturated heterocyclic group" means a saturated heterocyclic group having one or more nitrogen atoms in the ring. Examples of a "nitrogen-containing saturated heterocyclic group" include a morpholino group, a thiomorpholino group, a thiomorpholin-1,1-dioxid-4-yl group, a 3-oxopiperazin-1-yl group, a 4-methylsulfonylpiperazin-1-yl group, a piperidino group, a pyrrolidino group, and a 1,4-oxazepan-4-yl group.

[0037] In the present invention, the term "C1-C6 alkylsulfonyl group" refers to a sulfonyl group having a linear or branched alkyl group having 1 to 6 carbon atoms. Examples of the "C1-C6 alkylsulfonyl group" include a methanesulfonyl group, an ethanesulfonyl group, an n-propanesulfonyl group, an i-propanesulfonyl group, an n-butanesulfonyl group, an i-butanesulfonyl group, an s-butanesulfonyl group, a t-butanesulfonyl group, an n-pentanesulfonyl group, and an n-hexanesulfonyl group.

[0038] In the present invention, "monosaccharide" refers to a monomeric sugar that is not further hydrolyzed, and examples of "monosaccharide" include glucose, galactose, mannose, rhamnose, fucose, etc. "Monosaccharide residue" refers to a monovalent group obtained by removing one hydroxy group from a monosaccharide.

[0039] In the present invention, "optionally substituted" means unsubstituted or substituted with 1 to 5 substituents. "Substituted" means substituted with one or more substituents. Acceptable substituents for the terms "optionally substituted" or "substituted" may be any substituent that is commonly used in the art as a substituent for each group. Furthermore, each group may have one or more identical or different substituents.

[0040] In the present invention, the term "optionally substituted amino group" refers to an unsubstituted amino group or an amino group substituted with 1 to 2 substituents. Examples of the "optionally substituted amino group" include an amino group, a methylamino group, an ethylamino group, a dimethylamino group, a 2-methoxyethyl(methyl)amino group, a bis(2-hydroxyethyl)amino group, a morpholino group, a thiomorpholino group, a thiomorpholin-1,1-dioxid-4-yl group, a 3-oxopiperazin-1-yl group, a 4-methylsulfonylpiperazin-1-yl group, a piperidino group, a pyrrolidino group, a 1,4-oxazepan-4-yl group, a phenylamino group, a benzoylamino group, and an acetylamino group.

[0041] In the structural formula of a compound that may have geometric isomers in the present invention, a wavy line indicates a bond that does not particularly specify a geometric isomer. In the structural formula of a compound in which a sugar forms a cyclic structure in the present invention, a wavy line of a hydroxy group bonded to the 1-position (anomeric position) indicates a bond that does not particularly specify an α-isomer or a β-isomer.

[0042] In the present invention, "several" means 1 to 10, 1 to 9, 1 to 8, 1 to 7, 1 to 6, 1 to 5, 1 to 4, 1 to 3, or 1 or 2.

[0043] Preferred embodiments for carrying out the present invention will be described below. Note that the embodiment described below is an example of a typical embodiment of the present invention, and the scope of the present invention should not be construed as being narrow.

[0044] 1. Photosensitizer The photosensitizer of the present invention is a novel photosensitizer characterized by having a chlorin skeleton. That is, the photosensitizer of the present invention is a compound represented by the following formula (Ia), a metal complex thereof, or a pharmaceutically acceptable salt thereof:

[0045] <1.1 R in Formula (Ia) １ , R ３ and R ４ > In formula (Ia), R １ , R ３ and R ４ each independently represent a hydrogen atom, a formyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group or an aromatic heterocyclic group, The C1-C6 alkoxycarbonyl group, the C1-C6 alkanoyl group, the mono-C1-C6 aminocarbonyl group, the di-C1-C6 alkylaminocarbonyl group, the mono-C1-C6 alkylamino group, the di-C1-C6 alkylamino group, the C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the cyclic hydrocarbon group, the aromatic hydrocarbon group, or the aromatic heterocyclic group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group, and an azide group.

[0046] R １preferably represents a C1-C6 alkyl group, more preferably a C1-C3 alkyl group, and particularly preferably a methyl group. These groups may be substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group, and an azido group.

[0047] R ３ preferably represents a C1-C6 alkyl group, more preferably a C1-C3 alkyl group, and particularly preferably a methyl group. These groups may be substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group, and an azido group.

[0048] R ４ preferably represents a C1-C6 alkyl group, more preferably a C1-C3 alkyl group, and particularly preferably an ethyl group. These groups may be substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group, and an azido group.

[0049] R １ is a C1-C6 alkyl group, and R ３ is a C1-C6 alkyl group, and R ４ is preferably a C1-C6 alkyl group. １ is a C1-C3 alkyl group, and R ３ is a C1-C3 alkyl group, and R ４is more preferably a C1-C3 alkyl group. １ and R ３ is a methyl group, and R ４ is particularly preferably an ethyl group. These groups may be substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group, and an azido group.

[0050] <1.2 R in Formula (Ia) ２ , R ５ and R ６ > R ２ , R ５ and R ６ The combination is selected from the following groups (i) to (iii):

[0051] Group (i) is as follows:

[0052] Group (i): R ２ is -CH=CH-C(=O)-R ２ａ (R ２ａ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｂ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｂ is a hydrogen atom or a C1-C6 alkyl group) or an optionally substituted amino group), -CH=N-R ２ｃ (R ２ｃ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ ), -R２ｄ -R ２ｅ (R ２ｄ is a C1-C6 alkylene group, and R ２ｅ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH-C(=O)-(CH ２ ) ｐ -OH) or -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｇ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｇ is a hydrogen atom or a C1-C6 alkyl group) or a 5- to 6-membered aromatic heterocyclic group (the 5- to 6-membered aromatic heterocyclic group is -(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ and R ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, —X—R (wherein X represents —S—, —O—, —CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ-OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, and R ５ｄ is a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C6 alkylene group, and R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, and R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ-X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅ is a C1-C6 alkyl group substituted with one or more hydroxy groups).

[0053] In all of the above formulas, m is an integer from 0 to 10, n is an integer from 1 to 6, p is an integer from 1 to 3, and q is an integer from 1 to 6.

[0054] In one embodiment of the present invention, R ２ , R ５ and R ６ is selected from group (i), and R ２ -CH=CH-C(=O)-R ２ａ (R ２ａ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｂ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｂ is a hydrogen atom or a C1-C3 alkyl group) or an optionally substituted amino group substituted with an amino C1-C3 alkyl group), -CH=N-R ２ｃ (R ２ｃ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ ), -R ２ｄ -R ２ｅ (R ２ｄ is a C1-C3 alkylene group, and R ２ｅ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH２ or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH-C(=O)-(CH ２ ) ｐ -OH) or -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｇ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｇ is a hydrogen atom or a C1-C3 alkyl group) or a 5-membered aromatic heterocyclic group (the 5-membered aromatic heterocyclic group is -(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ and R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 6-membered aromatic heterocyclic group, -X-R (wherein X represents -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃis a hydrogen atom or a C1-C3 alkanoyl group, and R ５ｄ is a C1-C3 alkyl group, and the C1-C3 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C3 alkoxy group, and the C1-C3 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ But, -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C3 alkylene group, and R ６ｂ is a C1-C3 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C3 alkyl group, and R ６ｄ represents a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups or —(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅis a C1-C3 alkyl group substituted with 1 to 3 hydroxy groups), and in all of the above formulas, m is an integer from 0 to 10, n is an integer from 1 to 6, p is an integer from 1 to 3, and q is an integer from 1 to 6.

[0055] In another embodiment of the present invention, R ２ , R ５ and R ６ is selected from group (i), and R ２ is expressed by the following formula: R is a group selected from the group consisting of ５ is expressed by the following formula: R is a group selected from the group consisting of ６ is expressed by the following formula: is a group selected from the group consisting of:

[0056] In yet another embodiment of the present invention, R ２ , R ５ and R ６ is selected from group (i), and R ２ But -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ ) and R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, and R ５ｂ represents a 6-membered nitrogen-containing saturated heterocyclic group, and R ６ But, -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C3 alkylene group, and R ６ｂ is -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C3 alkyl group, and R ６ｄis a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups), and in all of the above formulas, m is an integer of 0 to 10, and n is an integer of 1 to 6.

[0057] Specific examples of the compound represented by formula (Ia) in group (i) include the compounds represented by the following formula:

[0058] Other specific examples of the compound represented by formula (Ia) in group (i) include the compounds represented by the following formula:

[0059] Group (ii) is as follows:

[0060] Group (ii): R ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or —NH—, where R is a residue of a monosaccharide), —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ )ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, —X—R (wherein X represents —S—, —O—, —CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, and R ５ｄis a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C6 alkylene group, and R ６ｇ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH(R ６ｉ ) (R ６ｈ is a hydrogen atom or a C1-C6 alkyl group, and R ６ｉ represents a hydrogen atom, -C(=O)-(CH ２ ) ｐ -NH ２ or -C(=O)-(CH ２ ) ｐ -OH) is shown.

[0061] In all of the above formulas, m is an integer from 0 to 10, n is an integer from 1 to 6, p is an integer from 1 to 3, q ​​is an integer from 1 to 6, and r is an integer from 0 to 6.

[0062] In one embodiment of the present invention, R ２ , R ５ and R ６ is selected from group (ii), R ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ-OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C3 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C3 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C3 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide;５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 6-membered aromatic heterocyclic group, -X-R (wherein X represents -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C3 alkanoyl group, and R ５ｄ is a C1-C3 alkyl group, and the C1-C3 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C3 alkoxy group, and the C1-C3 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ But, -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C3 alkylene group, and R ６ｇ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH(R ６ｉ ) (R ６ｈ is a hydrogen atom or a C1-C3 alkyl group, and R ６ｉ represents a hydrogen atom, -C(=O)-(CH ２) ｐ -NH ２ or -C(=O)-(CH ２ ) ｐ In all of the above formulas, m is an integer from 0 to 10, n is an integer from 1 to 6, p is an integer from 1 to 3, q ​​is an integer from 1 to 6, and r is an integer from 0 to 6.

[0063] In another embodiment of the present invention, R ２ , R ５ and R ６ is selected from group (ii), R ２ is expressed by the following formula: R is a group selected from the group consisting of ５ is expressed by the following formula: R is a group selected from the group consisting of ６ is expressed by the following formula: is a group selected from the group consisting of:

[0064] In yet another embodiment of the present invention, R ２ , R ５ and R ６ is selected from group (ii), R ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ represents a hydrogen atom or a C1-C3 alkyl group, and R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, and R ５ｂ represents a 6-membered nitrogen-containing saturated heterocyclic group, and R ６ But, -R ６ｆ -C(=O)-R６ｇ (R ６ｆ is a C1-C3 alkylene group, and R ６ｇ is -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH ２ (R ６ｈ is a hydrogen atom or a C1-C3 alkyl group), and in all of the above formulas, m is an integer from 0 to 10, n is an integer from 1 to 6, and r is an integer from 0 to 6.

[0065] Specific examples of the compound of group (ii) represented by formula (Ia) include the compounds represented by the following formulas:

[0066] Group (iii) is as follows:

[0067] Group (iii): R ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２or —NH—, where R is a residue of a monosaccharide), —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ｇ -R ５ｈ (R ５ｇ is a C1-C6 alkylene group, and R ５ｈ represents an optionally substituted amino group, and R ６ is -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C6 alkylene group, and R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, and R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅ is a C1-C6 alkyl group substituted with one or more hydroxy groups).

[0068] In all of the above formulas, m is an integer from 0 to 10, n is an integer from 1 to 6, and q is an integer from 1 to 6.

[0069] In one embodiment of the present invention, R ２ , R ５ and R ６ is selected from group (iii), and R ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ- optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is hydrogen or a C1-C3 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C3 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C3 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ But, -R ５ｇ -R ５ｈ (R ５ｇ is a C1-C3 alkylene group, and R ５ｈ represents a 6-membered nitrogen-containing saturated heterocyclic group substituted with an amino group or an amino C1-C3 alkyl group, and R ６ But, -R ６ａ -C(=O)-R６ｂ (R ６ａ is a C1-C3 alkylene group, and R ６ｂ is a C1-C3 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is hydrogen or a C1-C3 alkyl group, and R ６ｄ represents a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups or —(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅ is a C1-C3 alkyl group substituted with 1 to 3 hydroxy groups), and in all of the above formulas, m is an integer from 0 to 10, n is an integer from 1 to 6, and q is an integer from 1 to 6.

[0070] Specific examples of the compound of group (iii) represented by formula (Ia) include the compounds represented by the following formulas:

[0071] <1.3 m, n, p, q and r in all formulae in formula (Ia)> In all formulae in formula (Ia), m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, q ​​is an integer of 1 to 6, and r is an integer of 0 to 6.

[0072] m is preferably an integer of 0 to 5, more preferably an integer of 0 to 3, even more preferably 1 or 2, and particularly preferably 2. n is preferably an integer of 1 to 3, more preferably 2. p is preferably 1. q is preferably an integer of 1 to 4, more preferably 3. r is preferably an integer of 0 to 5, more preferably an integer of 0 to 3, and even more preferably 0.

[0073] In formula (Ia), the optionally substituted amino group is preferably a di-C1-C6 alkylamino group (the di-C1-C6 alkyl of the di-C1-C6 alkylamino group are each independently optionally substituted with a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkylsulfonyl group, a sulfonyl group, or an amino-C1-C3 alkyl group), or a 3- to 8-membered nitrogen-containing saturated heterocyclic group (the 3- to 8-membered nitrogen-containing saturated heterocyclic group is optionally substituted with a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkylsulfonyl group, a sulfonyl group, or an amino-C1-C3 alkyl group).

[0074] In formula (Ia), specific examples of the optionally substituted amino group include the structures shown below.

[0075] In formula (Ia), specific examples of —X—R include the structures shown below.

[0076] In the present invention, the photosensitizer or metal complex thereof, or a pharmaceutically acceptable salt thereof of the present invention includes hydrates thereof.

[0077] When the photosensitizer or metal complex thereof of the present invention has a basic functional group such as an amino group, it can form a pharmaceutically acceptable acid addition salt, as desired. Examples of such acid addition salts include hydrohalides such as hydrofluoride, hydrochloride, hydrobromide, and hydroiodide; inorganic acid salts such as nitrate, perchlorate, sulfate, and phosphate; lower alkanesulfonates such as methanesulfonate, trifluoromethanesulfonate, and ethanesulfonate; arylsulfonates such as benzenesulfonate and p-toluenesulfonate; organic acid salts such as formate, acetate, trifluoroacetate, malate, fumarate, succinate, citrate, tartrate, oxalate, and maleate; and amino acid salts such as ornithine, glutamate, and aspartate.

[0078] When the photosensitizer or metal complex thereof of the present invention has an acidic group such as a carboxy group, it can form a pharmaceutically acceptable base addition salt, if desired. Examples of such base addition salts include alkali metal salts such as sodium salt, potassium salt, and lithium salt; alkaline earth metal salts such as calcium salt and magnesium salt; inorganic salts such as ammonium salt; and organic amine salts such as dibenzylamine salt, morpholine salt, phenylglycine alkyl ester salt, ethylenediamine salt, N-methylglucamine salt, diethylamine salt, triethylamine salt, cyclohexylamine salt, dicyclohexylamine salt, N,N'-dibenzylethylenediamine salt, diethanolamine salt, N-benzyl-N-(2-phenylethoxy)amine salt, piperazine salt, tetramethylammonium salt, and tris(hydroxymethyl)aminomethane salt.

[0079] The scope of the present invention includes complexes formed by the photosensitizer of the present invention coordinating with a specific metal through the chelating effect, complexes formed by coordinating with phosphorus (P), and pharmaceutically acceptable salts thereof. The metals forming the complexes are not particularly limited, and examples thereof include magnesium (Mg), aluminum (Al), silicon (Si), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), zinc (Zn), molybdenum (Mo), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), and tin (Sn). A preferred embodiment of the present invention is a complex formed by the chlorin skeleton contained in the photosensitizer of the present invention coordinating with a specific metal through the chelating effect, a complex formed by coordinating with phosphorus (P), and pharmaceutically acceptable salts thereof.

[0080] The photosensitizer, its metal complex, or pharmaceutically acceptable salt thereof of the present invention can be used for photodynamic therapy. The photosensitizer, its metal complex, or pharmaceutically acceptable salt thereof of the present invention is believed to act, for example, as follows: The photosensitizer, its metal complex, or pharmaceutically acceptable salt thereof is administered to the target tumor site and then taken up into tumor cells. By irradiating the tumor site with light of a specific wavelength band corresponding to the photosensitizer, its metal complex, or pharmaceutically acceptable salt thereof, the photosensitizer, its metal complex, or pharmaceutically acceptable salt thereof undergoes a photochemical reaction to generate reactive oxygen species. This reactive oxygen species exhibits cytotoxic activity against tumor cells in which the photosensitizer, its metal complex, or pharmaceutically acceptable salt thereof has accumulated. The photosensitizer, its metal complex, or pharmaceutically acceptable salt thereof of the present invention is believed to exert its antitumor effect via this cytotoxic activity.

[0081] The photosensitizer or metal complex thereof, or pharmaceutically acceptable salt thereof of the present invention has a maximum absorption wavelength in the Q band, measured as a methanol solution, of preferably 600 nm to 800 nm, more preferably 640 nm to 780 nm, even more preferably 670 nm to 750 nm, and particularly preferably 690 nm to 710 nm or 715 nm to 735 nm. The photosensitizer or metal complex thereof, or pharmaceutically acceptable salt thereof of the present invention exhibits light absorption in a longer wavelength region than photosensitizers having a phthalocyanine skeleton, and therefore can be applied not only to superficial cancers but also to cancers that are located deep within or have infiltrated deep within the body.

[0082] The maximum absorption wavelength (nm) in the Q band of the photosensitizer of the present invention, its metal complex, or a pharmaceutically acceptable salt thereof can be measured by methods well known to those skilled in the art. For example, it can be determined from the ultraviolet-visible absorption spectrum in the wavelength range of 220 to 800 nm measured with a spectrophotometer using a solution of the photosensitizer of the present invention, its metal complex, or a pharmaceutically acceptable salt thereof dissolved in a good solvent. Porphyrin compounds, including chlorin derivatives, are generally known to have characteristic absorption bands called the Soret band (a region corresponding to wavelengths around 400 nm) and the Q band (a region corresponding to wavelengths of 600 to 800 nm).

[0083] The photosensitizer or metal complex thereof, or a pharmaceutically acceptable salt thereof of the present invention is more water-soluble and less prone to aggregation than conventional photosensitizers, and is therefore suitable for producing antibody-photosensitizer conjugates.

[0084] <2. Antibody-Photosensitizer Conjugate> The photosensitizer or metal complex thereof, or a pharmaceutically acceptable salt thereof of the present invention may be administered directly to a target tissue (e.g., intratumor administration), or may be administered as an antibody-photosensitizer conjugate linked via an optional linker to an antibody capable of recognizing and binding to a target cell (e.g., a tumor cell).

[0085] The antibody-photosensitizer conjugate of the present invention is represented by the following formula (1): In formula (1), Ab represents an antibody or an antigen-binding fragment of the antibody; L represents a linker connecting Ab and P; Ab is directly bound to L via its amino acid residue or indirectly bound to L via its sugar chain; P represents a monovalent group derived from a photosensitizer and connected to L; and x represents a number ranging from 1 to 10.

[0086] The "monovalent group derived from a photosensitizer" is, for example, a group obtained by removing one hydrogen atom from a photosensitizer. Examples of the monovalent group derived from a photosensitizer include a group obtained by removing one hydrogen atom from an amino group contained in a photosensitizer, or a group obtained by removing one hydrogen atom from a hydroxy group contained in a photosensitizer.

[0087] x represents the average number of photosensitizers bound per antibody molecule. In the antibody-photosensitizer conjugates of the present invention, the number of photosensitizers bound per antibody molecule is an important factor affecting their efficacy and safety. Antibody-photosensitizer conjugates are produced by specifying reaction conditions, such as the amounts of reacting raw materials and reagents, so that a certain number of photosensitizers are bound. However, unlike chemical reactions of low-molecular-weight compounds, a mixture containing a different number of bound photosensitizers is typically obtained. The number of photosensitizers bound per antibody molecule can be specified as an average value, i.e., the average number of photosensitizers bound per antibody molecule. The number of photosensitizers bound to an antibody molecule can be controlled, and the average number of photosensitizers bound per antibody can be in the range of 1 to 10, preferably 1 to 8, more preferably 3 to 8, even more preferably 3.5 to 5.5 or 7 to 8, and particularly preferably 4 to 5 or 7.5 to 8. It should be noted that a person skilled in the art would be able to design a reaction for binding a required number of photosensitizers to an antibody based on the description in the Examples of the present application, and obtain an antibody-photosensitizer conjugate in which the number of bound photosensitizers is controlled.

[0088] The antibody-photosensitizer conjugate of the present invention may be a metal complex thereof or a pharmaceutically acceptable salt thereof. Furthermore, the antibody-photosensitizer conjugate, metal complex thereof, or pharmaceutically acceptable salt thereof of the present invention also includes hydrates thereof. The antibody-photosensitizer conjugate, metal complex thereof, or pharmaceutically acceptable salt thereof of the present invention may become a hydrate by absorbing moisture or by adsorbed water being attached thereto when left in the air or when subjected to recrystallization or purification procedures. Such antibody-photosensitizer conjugates, metal complexes thereof, or pharmaceutically acceptable salts thereof containing water are also encompassed by the present invention.

[0089] When the antibody-photosensitizer conjugate of the present invention has a basic group such as an amino group, it can form a pharmacologically acceptable acid addition salt, as desired. Examples of such acid addition salts include hydrohalides such as hydrofluoride, hydrochloride, hydrobromide, and hydroiodide; inorganic acid salts such as nitrate, perchlorate, sulfate, and phosphate; lower alkanesulfonates such as methanesulfonate, trifluoromethanesulfonate, and ethanesulfonate; arylsulfonates such as benzenesulfonate and p-toluenesulfonate; organic acid salts such as formate, acetate, trifluoroacetate, malate, fumarate, succinate, citrate, tartrate, oxalate, and maleate; and amino acid salts such as ornithine, glutamate, and aspartate.

[0090] When the antibody-photosensitizer conjugate of the present invention has an acidic group such as a carboxy group, it can form a pharmaceutically acceptable base addition salt, if desired. Examples of such base addition salts include alkali metal salts such as sodium salt, potassium salt, and lithium salt; alkaline earth metal salts such as calcium salt and magnesium salt; inorganic salts such as ammonium salt; and organic amine salts such as dibenzylamine salt, morpholine salt, phenylglycine alkyl ester salt, ethylenediamine salt, N-methylglucamine salt, diethylamine salt, triethylamine salt, cyclohexylamine salt, dicyclohexylamine salt, N,N'-dibenzylethylenediamine salt, diethanolamine salt, N-benzyl-N-(2-phenylethoxy)amine salt, piperazine salt, tetramethylammonium salt, and tris(hydroxymethyl)aminomethane salt.

[0091] The scope of the present invention includes molecules in which the photosensitizer contained in the antibody-photosensitizer conjugate of the present invention coordinates to a specific metal by chelate effect to form a complex, and molecules in which the photosensitizer coordinates to phosphorus (P) to form a complex. The metal that forms the complex is not particularly limited, and examples include magnesium (Mg), aluminum (Al), silicon (Si), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), zinc (Zn), molybdenum (Mo), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), and tin (Sn). One preferred embodiment of the present invention is a molecule in which the chlorin skeleton of the photosensitizer contained in the antibody-photosensitizer conjugate of the present invention coordinates to a specific metal by chelate effect to form a complex, and a molecule in which the chlorin skeleton coordinates to phosphorus (P) to form a complex.

[0092] <2.1 Photosensitizer in Antibody-Photosensitizer Conjugate> The photosensitizer is represented by the following formula (2).

[0093] <2.1.1 R in formula (2) １ , R ３ and R ４ > In formula (2), R １ , R ３and R ４ are each independently a hydrogen atom, a formyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group (the amino is -NH ２ , mono-C1-C6 alkylamino or di-C1-C6 alkylamino), a cyano group, a nitro group, a mono-C1-C6 alkylamino group, di-C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group or an aromatic heterocyclic group; The C1-C6 alkoxycarbonyl group, the C1-C6 alkanoyl group, the mono-C1-C6 aminocarbonyl group, the di-C1-C6 alkylaminocarbonyl group, the mono-C1-C6 alkylamino group, the di-C1-C6 alkylamino group, the C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the cyclic hydrocarbon group, the aromatic hydrocarbon group, or the aromatic heterocyclic group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group, and an azide group.

[0094] R １ preferably represents a C1-C6 alkyl group, more preferably a C1-C3 alkyl group, and particularly preferably a methyl group. These groups may be substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group, and an azido group.

[0095] R ３preferably represents a C1-C6 alkyl group, more preferably a C1-C3 alkyl group, and particularly preferably a methyl group. These groups may be substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group, and an azido group.

[0096] R ４ preferably represents a C1-C6 alkyl group, more preferably a C1-C3 alkyl group, and particularly preferably an ethyl group. These groups may be substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group, and an azido group.

[0097] R １ is a C1-C6 alkyl group, and R ３ is a C1-C6 alkyl group, and R ４ is preferably a C1-C6 alkyl group. １ is a C1-C3 alkyl group, and R ３ is a C1-C3 alkyl group, and R ４ is more preferably a C1-C3 alkyl group. １ and R ３ is a methyl group, and R ４ is particularly preferably an ethyl group. These groups may be substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group, and an azido group.

[0098] <2.1.2 R in formula (2) ２ , R ５ and R ６ > R ２ Functional groups contained in R ５ and the functional groups contained in R ６ A group selected from the group consisting of functional groups included in

[0099] Below, R ２ The case where the functional group contained in is bonded to L will be described.

[0100] (i) R ２ When the functional group contained in R is bonded to L, ２ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ａ (R ２ａ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｂ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｂ is a hydrogen atom or a C1-C6 alkyl group) or an optionally substituted amino group), -CH=N-R ２ｃ (R ２ｃ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ ), -R ２ｄ -R ２ｅ (R ２ｄ is a C1-C6 alkylene group, and R ２ｅ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -O-(CH ２CH ２ O) ｍ - (CH ２ ) ｎ -NH-C(=O)-(CH ２ ) ｐ -OH) or -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｇ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｇ is a hydrogen atom or a C1-C6 alkyl group) or a 5- to 6-membered aromatic heterocyclic group (the 5- to 6-membered aromatic heterocyclic group is -(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ and R ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, —X—R (wherein X represents —S—, —O—, —CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, and R ５ｄis a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C6 alkylene group, and R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, and R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅ is a C1-C6 alkyl group substituted with one or more hydroxy groups).

[0101] In all of the above formulas, m is an integer from 0 to 10, n is an integer from 1 to 6, p is an integer from 1 to 3, and q is an integer from 1 to 6.

[0102] Preferably, R ２ The functional group contained in R is bonded to L, ２ is bonded to L. The amino group, hydroxy group, or thiol group contained in is bonded to L by forming, for example, —NH—, —O—, or —S—, respectively.

[0103] More preferably, R ２ The functional group contained in R is bonded to L, ２ is bonded to L. The amino group or hydroxy group is bonded to L, for example, by forming —NH— or —O—, respectively.

[0104] In one embodiment of the present invention, R ２ the amino group or hydroxy group at the end of R is bonded to L (the amino group or hydroxy group is bonded to L, for example, by forming —NH— or —O—, respectively), ２ -CH=CH-C(=O)-R ２ａ (R ２ａ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｂ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｂ is a hydrogen atom or a C1-C3 alkyl group) or an optionally substituted amino group substituted with an amino C1-C3 alkyl group), -CH=N-R ２ｃ (R ２ｃ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ-NH ２ ), -R ２ｄ -R ２ｅ (R ２ｄ is a C1-C3 alkylene group, and R ２ｅ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH-C(=O)-(CH ２ ) ｐ -OH) or -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｇ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｇ is a hydrogen atom or a C1-C3 alkyl group) or a 5-membered aromatic heterocyclic group (the 5-membered aromatic heterocyclic group is -(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ and R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 6-membered aromatic heterocyclic group, -X-R (wherein X represents -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ )ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C3 alkanoyl group, and R ５ｄ is a C1-C3 alkyl group, and the C1-C3 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C3 alkoxy group, and the C1-C3 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ But, -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C3 alkylene group, and R ６ｂ is a C1-C3 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C3 alkyl group, and R ６ｄ represents a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups or —(CH ２ ) ｑ-X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅ is a C1-C3 alkyl group substituted with 1 to 3 hydroxy groups), and in all of the above formulas, m is an integer from 0 to 10, n is an integer from 1 to 6, p is an integer from 1 to 3, and q is an integer from 1 to 6.

[0105] In another embodiment of the present invention, R ２ the amino group or hydroxy group at the end of R is bonded to L (the amino group or hydroxy group is bonded to L, for example, by forming —NH— or —O—, respectively), ２ is expressed by the following formula: and the amino or hydroxy group indicated by the arrow is bonded to L; R ５ is expressed by the following formula: R is a group selected from the group consisting of ６ is expressed by the following formula: is a group selected from the group consisting of:

[0106] In yet another embodiment of the present invention, R ２ The amino group at the end of R is bonded to L (the amino group is bonded to L, for example, by forming —NH—), ２ But -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ ) and R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, and R ５ｂ represents a 6-membered nitrogen-containing saturated heterocyclic group, and R ６ But, -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C3 alkylene group, and R６ｂ is -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C3 alkyl group, and R ６ｄ is a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups), and in all of the above formulas, m is an integer of 0 to 10, and n is an integer of 1 to 6.

[0107] R ２ Specific examples of photosensitizers in which the functional group contained in is bonded to L include the compounds shown below: The amino group indicated by the arrow is bonded to L (the amino group is bonded to L, for example, by forming -NH-).

[0108] R ２ Other specific examples of photosensitizers in which the functional group contained in is bonded to L include the compounds shown below: The amino group indicated by the arrow is bonded to L (the amino group is bonded to L, for example, by forming -NH-).

[0109] Below, R ６ The case where the functional group contained in is bonded to L will be described.

[0110] R ６ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ CH ２O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or —NH—, where R is a residue of a monosaccharide), —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, —X—R (wherein X represents —S—, —O—, —CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, and R ５ｄ is a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C6 alkylene group, and R ６ｇ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH(R ６ｉ ) (R ６ｈ is a hydrogen atom or a C1-C6 alkyl group, and R ６ｉ represents a hydrogen atom, -C(=O)-(CH ２ ) ｐ -NH ２ or -C(=O)-(CH ２ ) ｐ -OH) is shown.

[0111] In all of the above formulas, m is an integer from 0 to 10, n is an integer from 1 to 6, p is an integer from 1 to 3, q ​​is an integer from 1 to 6, and r is an integer from 0 to 6.

[0112] Preferably, R６ The functional group contained in R is bonded to L, ６ is bonded to L. The amino group, hydroxy group, or thiol group contained in is bonded to L by forming, for example, —NH—, —O—, or —S—, respectively.

[0113] More preferably, R ６ The functional group contained in R is bonded to L, ６ is bonded to L. The amino group or hydroxy group is bonded to L, for example, by forming —NH— or —O—, respectively.

[0114] In one embodiment of the present invention, R ６ the amino group or hydroxy group at the end of R is bonded to L (the amino group or hydroxy group is bonded to L, for example, by forming —NH— or —O—, respectively), ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C3 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C3 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C3 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, and R ５ｂ represents an optionally substituted amino group, a 6-membered aromatic heterocyclic group, -X-R (wherein X represents -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ ), -N(R ５ｃ )-R ５ｄ (R ５ｃis a hydrogen atom or a C1-C3 alkanoyl group, and R ５ｄ is a C1-C3 alkyl group, and the C1-C3 alkyl group is substituted with one or more optionally substituted amino groups; or —R ５ｆ (R ５ｆ represents a C1-C3 alkoxy group, and the C1-C3 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ But, -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C3 alkylene group, and R ６ｇ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH(R ６ｉ ) (R ６ｈ is a hydrogen atom or a C1-C3 alkyl group, and R ６ｉ represents a hydrogen atom, -C(=O)-(CH ２ ) ｐ -NH ２ or -C(=O)-(CH ２ ) ｐ In all of the above formulas, m is an integer from 0 to 10, n is an integer from 1 to 6, p is an integer from 1 to 3, q ​​is an integer from 1 to 6, and r is an integer from 0 to 6.

[0115] In another embodiment of the present invention, R ６ the amino group or hydroxy group at the end of R is bonded to L (the amino group or hydroxy group is bonded to L, for example, by forming —NH— or —O—, respectively), ２ is expressed by the following formula: R is a group selected from the group consisting of ５ is expressed by the following formula: R is a group selected from the group consisting of６ is expressed by the following formula: and the amino group or hydroxy group indicated by the arrow is bonded to L.

[0116] In yet another embodiment of the present invention, R ６ the amino group or hydroxy group at the end of R is bonded to L (the amino group or hydroxy group is bonded to L, for example, by forming —NH— or —O—, respectively), ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ represents a hydrogen atom or a C1-C3 alkyl group, and R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, and R ５ｂ represents a 6-membered nitrogen-containing saturated heterocyclic group, and R ６ But, -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C3 alkylene group, and R ６ｇ is -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH ２ (R ６ｈ is a hydrogen atom or a C1-C3 alkyl group), and in all of the above formulas, m is an integer from 0 to 10, n is an integer from 1 to 6, and r is an integer from 0 to 6.

[0117] R ６Specific examples of photosensitizers in which the functional group contained in is bonded to L include the compounds shown below: The amino group indicated by the arrow is bonded to L (the amino group is bonded to L, for example, by forming -NH-).

[0118] Below, R ５ The case where the functional group contained in is bonded to L will be described.

[0119] R ５ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or —NH—, where R is a residue of a monosaccharide), —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ｇ -R ５ｈ (R ５ｇ is a C1-C6 alkylene group, and R ５ｈ represents an optionally substituted amino group, and R ６ is -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C6 alkylene group, and R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, and R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅ is a C1-C6 alkyl group substituted with one or more hydroxy groups).

[0120] In all of the above formulas, m is an integer from 0 to 10, n is an integer from 1 to 6, and q is an integer from 1 to 6.

[0121] Preferably, R ５ The functional group contained in R is bonded to L, ５ is bonded to L. The amino group, hydroxy group, or thiol group contained in is bonded to L by forming, for example, —NH—, —O—, or —S—, respectively.

[0122] More preferably, R ５ The functional group contained in R is bonded to L, ５ is bonded to L. The amino group is bonded to L, for example, by forming —NH—.

[0123] In one embodiment of the present invention, R ５ The amino group at the end of R is bonded to L (the amino group is bonded to L, for example, by forming —NH—), ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ-OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is hydrogen or a C1-C3 alkyl group) or —N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C3 alkyl group) or —R ２ｊ -R ２ｋ (R ２ｊ is a C1-C3 alkylene group, and R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ But, -R ５ｇ -R ５ｈ (R ５ｇ is a C1-C3 alkylene group, and R ５ｈrepresents a 6-membered nitrogen-containing saturated heterocyclic group substituted with an amino group or an amino C1-C3 alkyl group, and R ６ But, -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C3 alkylene group, and R ６ｂ is a C1-C3 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ - optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is hydrogen or a C1-C3 alkyl group, and R ６ｄ represents a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups or —(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide, or -R ６ｅ (-R ６ｅ is a C1-C3 alkyl group substituted with 1 to 3 hydroxy groups), and in all of the above formulas, m is an integer from 0 to 10, n is an integer from 1 to 6, and q is an integer from 1 to 6.

[0124] R ５Specific examples of photosensitizers in which the functional group contained in is bonded to L include the compounds shown below: The amino group indicated by the arrow is bonded to L (the amino group is bonded to L, for example, by forming -NH-).

[0125] <2.1.3 m, n, p, q, and r in all formulas in formula (2)> In all formulas in formula (2), m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, q ​​is an integer of 1 to 6, and r is an integer of 0 to 6.

[0126] m is preferably an integer of 0 to 5, more preferably an integer of 0 to 3, even more preferably 1 or 2, and particularly preferably 2. n is preferably an integer of 1 to 3, more preferably 2. p is preferably 1. q is preferably an integer of 1 to 4, more preferably 3. r is preferably an integer of 0 to 5, more preferably an integer of 0 to 3, and even more preferably 0.

[0127] In formula (2), the optionally substituted amino group is preferably a di-C1-C6 alkylamino group (the di-C1-C6 alkyl of the di-C1-C6 alkylamino group are each independently optionally substituted with a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkylsulfonyl group, a sulfonyl group, or an amino-C1-C3 alkyl group), or a 3- to 8-membered nitrogen-containing saturated heterocyclic group (the 3- to 8-membered nitrogen-containing saturated heterocyclic group is optionally substituted with a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkylsulfonyl group, a sulfonyl group, or an amino-C1-C3 alkyl group).

[0128] In formula (2), specific examples of the optionally substituted amino group include the structures shown below.

[0129] In formula (2), specific examples of —X—R include the structures shown below.

[0130] <2.2 Linker in antibody-photosensitizer conjugate> The linker structure that binds the photosensitizer to the antibody in the antibody-photosensitizer conjugate of the present invention is described below. The linker used in the antibody-photosensitizer conjugate of the present invention is not particularly limited, as long as it is understood by those skilled in the art as a linker that connects the antibody and the photosensitizer. Examples of linker structures include linkers described in publicly known literature (Pharmacol Rev 68:3-19, January 2016, Protein Cell DOI 10.1007 / s13238-016-0323-0, etc.), and more specific examples include VC (valine-citrulline), MC (maleimidocaproyl), SMCC (succinimidyl 4-(N-maleimidomethyl) cyclohexane-1-carboxylate), and SPP (N-succinimidyl Examples of suitable linkers include 4-(2-pyridyldithio)pentanoic acid (N-succinimidyl 4-(2-pyridyldithio)pentanoate), SS (disulfide), SPDB (N-succinimidyl 4-(2-pyridyldithio)butyrate), SS / hydrazone, hydrazone, and carbonate. The linker may be either a linker that is cleaved in vivo or a linker that is not cleaved in vivo, but is preferably a linker that is cleaved in vivo.

[0131] Examples of linkers used in the antibody-photosensitizer conjugates of the present invention include, but are not limited to, linkers that bind a photosensitizer to a sugar chain or remodeled sugar chain of the Fc portion of an antibody (sometimes referred to herein as a "sugar chain conjugation linker") (e.g., as described in WO2018 / 003983), or linkers that bind a photosensitizer to any amino acid residue of an antibody (e.g., a cysteine ​​residue or a lysine residue) (e.g., as described in WO2014 / 057687). A linker that binds a photosensitizer to any amino acid residue of an antibody is preferably a linker that forms a thioether bond with a sulfhydryl group (-SH) of cysteine ​​in an Ab (sometimes referred to herein as a "cysteine ​​conjugation linker") or a linker that forms a thioether bond with an amino group (-NH) of lysine in an Ab. ２ ) and more preferably a cysteine ​​conjugation linker.

[0132] In one embodiment of the present invention, L is represented by the following: -Lb-La-Lp-NH-(CH ２ ) n ａ -Lc-Ld-* or -Lb-La-Lp-NH-(aromatic hydrocarbon group)-(CH ２ ) n ａ -Lc-Ld-* (wherein * indicates binding to P; Lb indicates a spacer that connects the sugar chains of La and Ab or a spacer that connects the cysteine ​​residues of La and Ab; La indicates a linker in which 0 to 20 groups selected from the following group are linked in any order, -(CH ２ CH ２ O)-, -(CH ２ )-, -C(=O)-NH-, -C(=O)- and -O-C(=O)-; ２ CH ２ O)- and -(CH ２any hydrogen atom of - may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a cyano group, a nitro group, an amino group, an azide group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; the —NH— of —C(═O)—NH— of La may be substituted by one or more substituents selected from the group consisting of a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; Lp represents a linker consisting of 1 to 10 amino acid residues or is absent; n ａ represents an integer of 0 to 6; Lc represents *-C(=O)-NH-, *-NR ７ - (CH ２ ) n ｂ represents -, -O- or a single bond, where * represents -(CH ２ ) n ａ - indicates bonding to n ｂ represents an integer of 1 to 6, and R ７ represents a hydrogen atom, a C1-C6 alkyl group, -(CH ２ ) n ｃ -COOH or -(CH ２ ) n ｄ represents —OH, and n ｃ represents an integer of 1 to 4, and n ｄ represents an integer of 1 to 6; Ld represents *-CHR ８ - (CH ２ )-C(=O)-, *-CH ２ - (CHR ８)-C(=O)-, *-CHR ８ -C(=O)-, *-CR ８ R ９ - (CH ２ )-C(=O)-, *-CR ８ R ９ -C(=O)-, *-(cyclic hydrocarbon group)-C(=O)-, *-O-C(=O)-, *-NR １０ -C(=O)- or *-C(=O)-, where * indicates bonding to Lc, R ８ and R ９ are each independently a C1-C6 alkyl group, a C3-C7 cyclic hydrocarbon group, or —(CH ２ ) n ｅ -NH ２ , -(CH ２ ) n ｆ -COOH or -(CH ２ ) n ｇ represents —OH, and R １０ represents a hydrogen atom or a C1-C6 alkyl group, n ｅ represents an integer of 0 to 6, and n ｆ represents an integer of 1 to 4, and n ｇ represents an integer of 1 to 4.)

[0133] In another aspect of the invention, L is: -Lb-La-Lp-NH-(CH ２ ) n ａ -Lc-Ld-* (wherein * indicates binding to P; Lb indicates a spacer that connects the sugar chains of La and Ab or a spacer that connects the cysteine ​​residues of La and Ab; La indicates a linker in which 0 to 20 groups selected from the following group are linked in any order, -(CH ２ CH ２ O)-, -(CH ２ )-, -C(=O)-NH-, -C(=O)- and -O-C(=O)-; ２ CH ２ O)- and -(CH ２any hydrogen atom of - may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group and an azido group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic aromatic hydrocarbon group, and a heterocyclic group; the —NH— of —C(═O)—NH— of La may be substituted by one or more substituents selected from the group consisting of a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; Lp represents a linker consisting of 1 to 10 amino acid residues or is absent; n ａ represents 1; Lc represents —O—; Ld represents the following formula (* represents bonding to P, and the wavy line represents bonding to Lc): It represents any one selected from the group consisting of

[0134] In yet another embodiment of the present invention, L is represented by the following formula: -Lb-La-Lp-* (wherein * indicates binding to P; Lb indicates a spacer that connects the sugar chains of La and Ab or a spacer that connects the cysteine ​​residues of La and Ab; La indicates a linker in which 0 to 20 groups selected from the following group are linked in any order, and -(CH ２ CH ２ O)-, -(CH ２)-, -C(=O)-NH-, -C(=O)- and -O-C(=O)-; ２ CH ２ O)- and -(CH ２ any hydrogen atom of - may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a cyano group, a nitro group, an amino group, an azide group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; The —NH— of —C(═O)—NH— of La is optionally substituted by one or more substituents selected from the group consisting of a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; Lp represents a linker consisting of 1 to 10 amino acid residues or is absent.

[0135] Hereinafter, La, Lp and Lb in all of the above Ls will be explained.

[0136] (Regarding La) La preferably represents any one selected from the following group: *-(CH ２ CH ２ O)n １ - (CH ２ ) n ２ -C(=O)-, *-(CH ２ ) n ３ -C(=O)-NH-(CH ２ CH ２ O)n １ - (CH ２ ) n ２-C(=O)-, *-(CH ２ ) n ４ -O-C(=O)- and *-(CH ２ ) n ５ -C(=O)- (where * indicates bonding to Lb, n １ represents an integer of 1 to 20, and n ２ represents an integer from 1 to 12, and n ３ represents an integer of 1 to 6, and n ４ represents an integer from 1 to 10, and n ５ represents an integer from 1 to 10).

[0137] La is more preferably *-(CH ２ CH ２ O)n １ - (CH ２ ) n ２ -C(=O)- or *-(CH ２ ) n ３ -C(=O)-NH-(CH ２ CH ２ O)n １ - (CH ２ ) n ２ -C(=O)- (where * indicates bonding to Lb, n １ represents an integer from 1 to 16, and n ２ represents an integer of 1 to 8, and n ３ represents an integer of 1 to 4), and more preferably *-(CH ２ CH ２ O)n １ - (CH ２ ) n ２ -C(=O)- or *-(CH ２ ) n ３ -C(=O)-NH-(CH ２ CH ２ O)n １ - (CH ２ ) n ２ -C(=O)- (where * indicates bonding to Lb, n １ represents an integer from 1 to 12, and n ２ represents an integer of 1 to 4, and n ３ represents an integer of 1 to 3), and even more preferably *-(CH ２ CH ２ O)n１ - (CH ２ ) n ２ -C(=O)- or *-(CH ２ ) n ３ -C(=O)-NH-(CH ２ CH ２ O)n １ - (CH ２ ) n ２ -C(=O)- (where * indicates bonding to Lb, n １ represents an integer of 1 to 8, and n ２ represents an integer of 1 to 2, and n ３ represents an integer of 1 or 2).

[0138] La is particularly preferably *—CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-(CH ２ ) n ２ -C(=O)- or *-(CH ２ ) n ３ -C(=O)-NH-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-(CH ２ ) n ２ -C(=O)- (where * indicates bonding to Lb, n ２represents an integer from 1 to 12, and n ３ represents an integer of 1 to 6), and particularly preferably *—CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ -C(=O)- or *-CH ２ CH ２ -C(=O)-NH-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ -C(=O)- (where * indicates a bond to Lb), and most preferably *-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH２ -C(=O)- (where * indicates a bond to Lb).

[0139] (Regarding Lp) Lp preferably consists of 1 to 8 amino acid residues, more preferably 1 to 6 amino acid residues, and even more preferably 2 to 4 amino acid residues.

[0140] Furthermore, Lp preferably represents an amino acid sequence consisting of at least one amino acid selected from phenine (F), glycine (G), valine (V), lysine (K), citrulline (Cit), serine (S), glutamic acid (E), aspartic acid (D), alanine (A), proline (P), isoleucine (I), methionine (M), leucine (L), glutamine (Q), and asparagine (N); More preferably, it represents any one selected from the group consisting of *-GGVA (SEQ ID NO: 37)-, *-AA-, *-AAN-, *-VA-, *-GGFG (SEQ ID NO: 38)-, *-FG-, *-GGPI (SEQ ID NO: 39)-, *-PI-, *-GGVCit (SEQ ID NO: 40)-, *-VCit-, *-ACit-, *-GGVK (SEQ ID NO: 41)-, *-VK-, *-GGFCit (SEQ ID NO: 42)-, *-FCit-, *-GGFM (SEQ ID NO: 43)-, *-FM-, *-GGLM (SEQ ID NO: 44)-, *-LM-, *-GGICit (SEQ ID NO: 45)- and *-ICit- (where * indicates binding to La), More preferably, it represents any one selected from the group consisting of *-AA-, *-AAN-, *-VA-, *-GGFG (SEQ ID NO: 38)-, *-VCit-, and *-ACit- (where * indicates binding to La), and particularly preferably *-AA- (where * indicates binding to La).

[0141] Preferably, Lp is cleavable in the target cell.

[0142] (Regarding Lb) Lb represents a spacer that links the sugar chains or remodeled sugar chains of La and Ab (also referred to herein as "spacer of the linker for sugar chain conjugation"), or a spacer that links the cysteine ​​residues of La and Ab (also referred to herein as "spacer of the linker for cysteine ​​conjugation").

[0143] <When Lb is a "spacer of a linker for sugar chain conjugation"> In one aspect of the present invention, when Lb is a "spacer of a linker for sugar chain conjugation", Lb is not particularly limited, and examples thereof include spacers represented by the following formula:

[0144]

[0145] Or,

[0146]

[0147] In each of the structural formulas shown above, the asterisk (*) represents -(C=O)- or -CH at the left end of La. ２ The dashed line indicates binding to the sugar chain of Ab or the remodeled sugar chain.

[0148] <When Lb is a "spacer of a linker for cysteine ​​conjugation"> When Lb is a "spacer of a linker for cysteine ​​conjugation", Lb is not particularly limited, and examples thereof include -(succinimide-3-yl-N)-. In the present invention, "-(succinimide-3-yl-N)-" refers to a group represented by the following formula:

[0149] In the structural formula shown above, * indicates binding to La, and the wavy line indicates binding to the side chain of a cysteine ​​residue of the antibody via a thioether.

[0150] A more preferred linker L of the present invention is shown below: -Lb-La-Lp-* (wherein * indicates a bond to P, Lp is -AA-, and La is *-(CH ２ CH ２ O) ８-CH ２ CH ２ represents —C(═O)— (wherein * indicates a bond to Lb), Lb is —(succinimide-3-yl-N)—, where —(succinimide-3-yl-N)— is a compound having the following structural formula: where * indicates binding to La, and the wavy line indicates binding via a thioether with the side chain of a cysteine ​​residue in the antibody.

[0151] Specific examples of "-LP" in formula (2) include the structure shown below: In the structure below, the wavy line forms a thioether bond with the side chain of a cysteine ​​residue in the antibody.

[0152] <2.3 Synthetic Intermediate of Antibody-Photosensitizer Conjugate> The antibody-photosensitizer conjugate of the present invention is produced using a photosensitizer linker, which is a synthetic intermediate. In the present invention, the "photosensitizer linker" refers to a compound represented by the formula: J-La-Lp-NH-(CH ２ ) n ａ -Lc-Ld-P, J-La-Lp-NH- (aromatic hydrocarbon group) -(CH ２ ) n ａ -Lc-Ld-P or J-La-Lp-P, or a pharmaceutically acceptable salt thereof. La, Lc, Ld, and Lp in the photosensitizer linker are as described in <2.2 Linkers in antibody-photosensitizer conjugates>. P in the photosensitizer linker represents a monovalent group derived from a photosensitizer that is linked to Ld or Lp, and the photosensitizer is as described in <2.1 Photosensitizer in antibody-photosensitizer conjugates>.

[0153] In the present invention, the photosensitizer linker of the present invention or a pharmaceutically acceptable salt thereof includes a hydrate thereof.

[0154] The scope of the present invention includes complexes formed by the photosensitizer linker of the present invention coordinating to a specific metal through a chelate effect, complexes formed by coordinating to phosphorus (P), or pharmaceutically acceptable salts thereof. The metals forming the complexes are not particularly limited, and examples include magnesium (Mg), aluminum (Al), silicon (Si), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), zinc (Zn), molybdenum (Mo), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), and tin (Sn). A preferred embodiment of the present invention is a complex formed by the chlorin skeleton contained in the photosensitizer linker of the present invention, its metal complex, or a pharmaceutically acceptable salt thereof coordinating to a specific metal through a chelate effect, or a complex formed by coordinating to phosphorus (P).

[0155] The maximum absorption wavelength in the Q band of the photosensitizer linker of the present invention, or the metal complex thereof, or a pharmaceutically acceptable salt thereof, when measured as a methanol solution, is preferably 600 nm to 800 nm, more preferably 640 nm to 780 nm, even more preferably 670 nm to 750 nm, and particularly preferably 690 nm to 710 nm or 715 nm to 735 nm.

[0156] The maximum absorption wavelength (nm) in the Q band of the photosensitizer linker of the present invention, its metal complex, or a pharmaceutically acceptable salt thereof can be measured by methods well known to those skilled in the art. For example, it can be determined from the ultraviolet-visible absorption spectrum in the wavelength range of 220 to 800 nm measured with a spectrophotometer using a solution obtained by dissolving the photosensitizer linker of the present invention in a good solvent. In general, porphyrin compounds including chlorin derivatives are known to have characteristic absorption bands called the Soret band (a region corresponding to wavelengths around 400 nm) and the Q band (a region corresponding to wavelengths of 600 to 800 nm).

[0157] J is not particularly limited as long as it is a cyclic structure containing an alkyne structure that reacts with an azide group to form a 1,2,3-triazole ring. Examples thereof include compounds represented by the following formula: In each structural formula of J shown above, * indicates that it is bonded to La.

[0158] J may be a compound or a halogen atom that bonds to the side chain of an amino acid residue (e.g., cysteine, lysine, etc.) of the antibody Ab, and examples thereof include a maleimidyl group represented by the following formula: In the maleimidyl group shown above, * indicates that it is bonded to La.

[0159] The photosensitizer linker of the present invention is preferably a compound selected from the following group or a pharmaceutically acceptable salt thereof:

[0160] 2.4 Antibody in Antibody-Photosensitizer Conjugate (Antibody) In the present invention, the term "gene" refers to a nucleotide or nucleotide sequence containing a nucleotide sequence encoding the amino acids of a protein, or a complementary strand thereof. For example, the term "gene" includes a polynucleotide, oligonucleotide, DNA, mRNA, cDNA, RNA, etc. that is a nucleotide sequence containing a nucleotide sequence encoding the amino acids of a protein, or a complementary strand thereof.

[0161] In the present invention, "nucleotide," "polynucleotide," or "nucleotide sequence" has the same meaning as "nucleic acid," and for example, DNA, RNA, probes, oligonucleotides, polynucleotides, primers, etc. are also included in the meaning of "nucleotide" or "nucleotide sequence."

[0162] In the present invention, the terms "polypeptide", "peptide" and "protein" may be used interchangeably.

[0163] Epithelial cell adhesion molecule (hereinafter sometimes referred to as "EpCAM") is a transmembrane glycoprotein associated with cell adhesion, differentiation, and proliferation, and is expressed in normal epithelial tissues and epithelial-derived tumors (Sergy V., et al. Ep-CAM: A Human Epithelial Antigen Is a Homophilic Cell-Cell Adhesion Molecule. J. Cell Biol. 1994; 125(2): 437-446). EpCAM has been reported to be highly expressed in many cancer cells of epithelial origin, and is expected to be a target molecule for molecular-targeted cancer drugs, a diagnostic marker, and a target for cancer vaccines (van der Gun BT et. al., Br J Cancer. 2011 Jul 12; 105(2):312-9. and Chaudry MA et. al., Br J Cancer. 2007 Apr 10; 96(7):1013-9.).

[0164] In the present invention, "EpCAM" can be used synonymously with EpCAM protein. In the present invention, EpCAM is used synonymously with CD326, GA733-2, HEA125, KS1 / 4, MK-1, MH99, MOC31, 323 / A3, 17-1A, CO-17A, ESA, EGP-2, EGP34, EGP40, KSA, KS1 / 4, TROP-1, and TACSTD-1.

[0165] Examples of EpCAM include human EpCAM containing the amino acid sequence shown in Genbank Accession No. NP_002345; monkey EpCAM containing the amino acid sequence shown in Genbank Accession No. NP_001035118; and mouse EpCAM containing the amino acid sequence shown in Genbank Accession No. NP_032558. Also included are, for example, EpCAMs listed in Genbank Accession No. NP_002345, Genbank Accession No. NP_001035118, or Genbank Accession No. NP_032558. Examples of such polypeptides include those consisting of an amino acid sequence in which one or more amino acids are deleted, substituted or added in the amino acid sequence shown in NP_032558, and which have the function of EpCAM.

[0166] Trophoblast cell surface antigen 2 (TROP2) is a 323 amino acid transmembrane glycoprotein encoded by the Tacstd2 gene. It is an intracellular calcium signal transducer (Ripani E et al., Int. J. Cancer, 76(5), 671-676 (1998) and El Sewedy T et al., Int. J. Cancer, 75(2), 324-330 (1998)) that is differentially expressed in many cancers. It signals cells for self-renewal, proliferation, invasion, and survival. TROP2 has further been implicated in immune resistance common to human trophoblasts and cancer cells (Faulk WP et al., Proc. Natl. Acad. Sci. 75(4), 1947-1951 (1978) and Lipinski M et al., Proc. Natl. Acad. Sci. 78(8), 5147-5150 (1981)). The DNA and amino acid sequences of human TROP2 are available in public databases, e.g., under accession numbers NM_002353 and NP_002344 (NCBI).

[0167] TROP2 has been found to be overexpressed in various epithelial cell carcinomas compared to low levels of expression in normal epithelial cells. It has also been reported that TROP2 expression correlates with poor prognosis in, among others, colorectal cancer (Ohmachi T et al., Clin. Cancer Res., 12(10), 3057-3063 (2006)), gastric cancer (Muhlmann G et al., J. Clin. Pathol., 62(2), 152-158 (2009)), pancreatic cancer (Fong D et al., Br. J. Cancer, 99(8), 1290-1295 (2008)), oral cancer (Fong D et al., Mod. Pathol., 21(2), 186-191 (2008)), and glioma (Ning S et al., Neurol. Sci., 34(10), 1745-1750 (2013)). Using colorectal cancer cells as a model, it was further reported that TROP2 expression is involved in anchorage-independent cell growth and tumorigenesis of tumor cells in immunodeficient mice (Wang J et al., Mol. Cancer Ther., 7(2), 280-285 (2008)).

[0168] As used herein, the term "antigen-binding fragment of an antibody" refers to a partial fragment of an antibody that has antigen-binding activity, and includes Fab, F(ab'), and the like. ２ , Fv, scFv, VHH (variable domain of heavy chain of heavy-chain antibody) antibodies, diabodies, linear antibodies, and fusion proteins in which antigen-binding ability is imparted by linking scFv to the functional domain of another protein. Antigen-binding fragments of antibodies include multispecific antibodies formed from antibody fragments. In addition, F(ab') ２ Antigen-binding fragments of antibodies also include Fab', which is a monovalent fragment of the variable region of an antibody obtained by treating the antibody under reducing conditions. However, the antigen-binding fragment is not limited to these molecules as long as it has the ability to bind to an antigen. Furthermore, these antigen-binding fragments include not only those obtained by treating the full-length antibody protein molecule with an appropriate enzyme, but also proteins produced in appropriate host cells using genetically engineered antibody genes.

[0169] The antibody used in the antibody-photosensitizer conjugate of the present invention refers to an immunoglobulin, a molecule containing an antigen-binding site that immunospecifically binds to an antigen. The antibody of the present invention may be of any class, including IgG, IgE, IgM, IgD, IgA, and IgY, with IgG being preferred. The subclass may also be any of IgG1, IgG2, IgG3, IgG4, IgA1, and IgA2, with IgG1, IgG2, or IgG4 being preferred, and IgG1 being more preferred (including antibodies with mutations in the Fc region of the IgG heavy chain that affect ADCC and ADCP activity). When using IgG1 or IgG4, effector function can be adjusted by substituting some of the amino acid residues in the constant region (see WO88 / 07089, WO94 / 28027, and WO94 / 29351).

[0170] When the antibody of the present invention is of IgG1 isotype, effector function can be adjusted by substituting some of the amino acid residues in the constant region (see WO88 / 07089, WO94 / 28027, and WO94 / 29351). Examples of IgG1 mutants include IgG1 LALA mutant (IgG1-L234A, L235A) and IgG1 LALA-PA mutant (IgG1-L234A, L235A, P329A). The L234A, L235A, and P329A represent substitutions of leucine with alanine at positions 234 and 235, and substitution of proline with alanine at position 329, respectively, as specified by the EU index (Proceedings of the National Academy of Sciences of the United States of America, Vol. 63, No. 1 (May 15, 1969), pp. 78-85).

[0171] The antibody may be derived from any species, but examples include antibodies derived from humans, rats, mice, rabbits, camels, alpacas, or llamas. When derived from a species other than humans, it is preferable to chimerize or humanize the antibody using well-known techniques. Therefore, in one aspect of the present invention, the antibody is a human antibody, a chimerized antibody, or a humanized antibody, preferably a human antibody or a humanized antibody. The antibody of the present invention may be a polyclonal antibody or a monoclonal antibody, but monoclonal antibodies are preferred. Monoclonal antibodies include monoclonal antibodies derived from non-human animals such as rat antibodies, mouse antibodies, and rabbit antibodies, as well as chimeric antibodies, humanized antibodies, human antibodies, antigen-binding fragments thereof, and modified versions thereof.

[0172] The antibody in the antibody-photosensitizer conjugate of the present invention is not particularly limited, but is preferably an antibody that targets tumor cells, stromal cells, or immune cells, and more preferably an antibody that targets tumor cells.

[0173] When an antibody that targets tumor cells is used, it is preferable that the antibody has one or more of the following properties: the ability to recognize tumor cells, the ability to bind to tumor cells, the ability to be taken up and internalized by tumor cells, and the ability to damage tumor cells.

[0174] The binding of an antibody to tumor cells can be confirmed using flow cytometry. The uptake of an antibody into tumor cells can be confirmed by (1) an assay in which a secondary antibody (fluorescently labeled) that binds to the therapeutic antibody is used to visualize the antibody taken up into the cells under a fluorescent microscope (Cell Death and Differentiation (2008) 15, 751-761), or (2) an assay in which the amount of fluorescence taken up into the cells is measured using a secondary antibody (fluorescently labeled) that binds to the therapeutic antibody (Molecular Biology of the Cell Vol. 15, 5268-5282, December 2008). 2004) or (3) an Ab-ZAP assay using an immunotoxin that binds to a therapeutic antibody, which, upon internalization within cells, releases the toxin and inhibits cell proliferation (Funakoshi, "Saporin-Labeled Secondary Antibodies That Induce Selective Cell Death in Target Cells," March 19, 2021, [Retrieved November 10, 2023], URL: <https: / / www.funakoshi.co.jp / contents / 5113>). A recombinant conjugated protein consisting of the catalytic domain of diphtheria toxin and protein G can also be used as an immunotoxin.

[0175] In the present invention, "high internalization ability" means that the viability (expressed as a relative rate, with the cell viability when no antibody is added being 100%) of target antigen-expressing cells (e.g., EpCAM-expressing cells when an anti-EpCAM antibody is used) to which the antibody and immunotoxin have been added is preferably 70% or less, more preferably 60% or less.

[0176] When an antibody targeting tumor cells is used in the antibody-photosensitizer conjugate of the present invention, it is preferable, but not essential, that the antibody itself have an antitumor effect. The antibody used in the antibody-photosensitizer conjugate of the present invention preferably has the property of being internalized into tumor cells.

[0177] The antitumor activity of a photosensitizer or an antibody-photosensitizer conjugate refers to cytotoxic activity against tumor cells and inhibition of or reduction in tumor volume. Antitumor activity can be confirmed using known in vitro or in vivo evaluation systems.

[0178] In one aspect of the present invention, examples of the antibody or antigen-binding fragment of the antibody in the antibody-photosensitizer conjugate of the present invention include an anti-EpCAM antibody, an anti-TROP2 antibody, an anti-HER3 antibody, an anti-DLL3 antibody, an anti-FAP antibody, an anti-CDH11 antibody, an anti-A33 antibody, an anti-CanAg antibody, an anti-CD19 antibody, an anti-CD20 antibody, an anti-CD22 antibody, an anti-CD25 antibody, an anti-CD30 antibody, an anti-CD33 antibody, an anti-CD56 antibody, an anti-CD70 antibody, an anti- Examples of the antibody of the present invention include, but are not limited to, CD98 antibody, anti-CEA antibody, anti-Cripto antibody, anti-EphA2 antibody, anti-G250 antibody, anti-MUC1 antibody, anti-GPNMB antibody, anti-integrin antibody, anti-PSMA antibody, anti-tenascin-C antibody, anti-SLC44A4 antibody, anti-mesothelin antibody, anti-ENPP3 antibody, anti-CD47 antibody, anti-EGFR antibody, anti-GPR20 antibody, or anti-DR5 antibody, or an antigen-binding fragment of said antibody. The antibody of the present invention is preferably an anti-EpCAM antibody, anti-TROP2 antibody, anti-CD25 antibody, or anti-EGFR antibody, or an antigen-binding fragment of said antibody.

[0179] The anti-EpCAM antibody, anti-TROP2 antibody, anti-CD25 antibody, or anti-EGFR antibody, or antigen-binding fragment of said antibody, used in the present invention, is described below. Note that the embodiment described below is one representative embodiment of the present invention, and the scope of the present invention should not be construed as being narrow.

[0180] In one embodiment of the present invention, the antibody or antigen-binding fragment of the antibody in the antibody-photosensitizer conjugate of the present invention comprises a CDRH1, CDRH2, and CDRH3, and a CDRL1, CDRL2, and CDRL3 selected from the group consisting of the following (a) to (c): (a) a CDRH1 consisting of the amino acid sequence set forth in SEQ ID NO: 26, a CDRH2 consisting of the amino acid sequence set forth in SEQ ID NO: 27, and a CDRH3 consisting of the amino acid sequence set forth in SEQ ID NO: 28, and a CDRL1 consisting of the amino acid sequence set forth in SEQ ID NO: 30, a CDRL2 consisting of the amino acid sequence of QMS, and a CDRL3 consisting of the amino acid sequence set forth in SEQ ID NO: 31; (b) a CDRH1 consisting of the amino acid sequence set forth in SEQ ID NO: 26, a CDRH2 consisting of the amino acid sequence set forth in SEQ ID NO: 27, and a CDRH3 consisting of the amino acid sequence set forth in SEQ ID NO: 29, and a CDRL1 consisting of the amino acid sequence set forth in SEQ ID NO: 30, a CDRL2 consisting of the amino acid sequence of QMS, and a CDRL3 consisting of the amino acid sequence set forth in SEQ ID NO: 31; (c) a CDRH1 consisting of the amino acid sequence set forth in SEQ ID NO: 32, a CDRH2 consisting of the amino acid sequence set forth in SEQ ID NO: 33, a CDRH3 consisting of the amino acid sequence set forth in SEQ ID NO: 34, and a CDRL1 consisting of the amino acid sequence set forth in SEQ ID NO: 35, a CDRL2 consisting of the amino acid sequence of FVS, and a CDRL3 consisting of the amino acid sequence set forth in SEQ ID NO: 36, preferably comprising the CDRH1, CDRH2, and CDRH3, and CDRL1, CDRL2, and CDRL3 of (a) or (b) above, more preferably comprising the CDRH1, CDRH2, and CDRH3, and CDRL1, CDRL2, and CDRL3 of (b) above. Compared to an antibody or antigen-binding fragment of the antibody comprising the CDR of (a) above, an antibody or antigen-binding fragment of the antibody comprising the CDR of (b) above not only has improved stability due to suppression of deamidation, but also has enhanced binding activity compared to the antibody before modification.

[0181] As used herein, "CDR" refers to a complementarity-determining region (CDR). It is known that the heavy and light chains of an antibody molecule each contain three CDRs. CDRs, also known as hypervariable regions, are located within the variable regions of the heavy and light chains of an antibody and are particularly highly variable in their primary structure. They are separated into three regions in the primary structure of the heavy and light chain polypeptide chains. As used herein, the CDRs of an antibody are represented as CDRH1, CDRH2, and CDRH3 from the amino-terminus of the heavy chain amino acid sequence, and CDRL1, CDRL2, and CDRL3 from the amino-terminus of the light chain amino acid sequence. These regions are adjacent to each other in the three-dimensional structure and determine the specificity for the antigen to which they bind. Therefore, an antibody comprising the set of CDRs specified in (a) to (c) above is highly likely to specifically recognize the desired epitope in its antigen, EpCAM or CD25, and is expected to be useful. CDR sequences are defined according to definitions well known in the art, for example, schemes such as IMGT (Lefranc et al., 2003, Dev Comparat Immunol 27:55-77), Kabat (Kabat et al., 1991, Sequences of Proteins of Immunological Interest, 5th Ed. Public Health Service, National Institutes of Health, Bethesda, Md.), and Chothia (Al-Lazikani et al., 1997, J. Mol. Biol 273:927-948). In the present invention, the CDR sequences are determined according to the IMGT definition.

[0182] FR refers to the variable region other than the CDR residues. A variable region generally has four FRs: FR1, FR2, FR3, and FR4.

[0183] The CDRs and FRs in the heavy chain are arranged in the following order from the amino terminus to the carboxyl terminus: FRH1-CDRH1-FRH2-CDRH2-FRH3-CDRH3-FRH4, and the CDRs and FRs in the light chain are arranged in the following order: FRL1-CDRL1-FRL2-CDRL2-FRL3-CDRL3-FRL4.

[0184] In one embodiment of the present invention, the antibody or antigen-binding fragment of the antibody in the antibody-photosensitizer conjugate of the present invention comprises a heavy chain variable region and a light chain variable region selected from the group consisting of the following (a) to (f): (a) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 9 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 4, (b) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 10 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 5, (c) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 10 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 6, (d) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 12 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 5, (e) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 15 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 4; (f) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 133 of SEQ ID NO: 23 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 21; and (g) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 140 of SEQ ID NO: 16 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 129 of SEQ ID NO: 17. Preferably, the heavy chain variable region and light chain variable region are selected from the group consisting of (a) to (e) above, and more preferably, they comprise the heavy chain variable region and light chain variable region of (d) above.

[0185] In another embodiment of the present invention, the antibody or antigen-binding fragment of the antibody in the antibody-photosensitizer conjugate of the present invention comprises a heavy chain variable region and a light chain variable region selected from the group consisting of the following (a) to (f): (a) a heavy chain variable region consisting of an amino acid sequence that has 100% sequence identity with the CDR sequence in the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 9 and has at least 80% or more, preferably 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, or 94% or more, more preferably 95%, 96%, 97%, or 98% or more, and most preferably 99% or more or 100% sequence identity with the CDR sequence in the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 9 and an amino acid sequence having 100% sequence identity with the CDR sequence in a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 4, and having at least 80% or more, preferably 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, or 94% or more, more preferably 95%, 96%, 97%, or 98% or more, and most preferably 99% or more or 100% sequence identity with the sequence of the framework region of the same. (b) a heavy chain variable region consisting of an amino acid sequence that has 100% sequence identity with the CDR sequence in the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 10 and has at least 80% or more, preferably 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, or 94% or more, more preferably 95%, 96%, 97%, or 98% or more, and most preferably 99% or more or 100% sequence identity with the sequence of the framework region of the same; and an amino acid sequence having 100% sequence identity with the CDR sequence in a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 in SEQ ID NO: 5, and having at least 80% or more, preferably 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, or 94% or more, more preferably 95%, 96%, 97%, or 98% or more, and most preferably 99% or more or 100% sequence identity with the sequence of the framework region of the same;(c) a heavy chain variable region consisting of an amino acid sequence that has 100% sequence identity with the CDR sequence in the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 10 and has at least 80% or more, preferably 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, or 94% or more, more preferably 95%, 96%, 97%, or 98% or more, and most preferably 99% or more or 100% sequence identity with the sequence of the framework region of the same; and an amino acid sequence having 100% sequence identity with the CDR sequence in a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 in SEQ ID NO: 6, and having at least 80% or more, preferably 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, or 94% or more, more preferably 95%, 96%, 97%, or 98% or more, and most preferably 99% or more or 100% sequence identity with the sequence of the framework region of the same; (d) a heavy chain variable region consisting of an amino acid sequence that has 100% sequence identity with the CDR sequence in the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 12 and has at least 80% or more, preferably 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, or 94% or more, more preferably 95%, 96%, 97%, or 98% or more, and most preferably 99% or more or 100% sequence identity with the sequence of the framework region of the same; and a light chain variable region consisting of an amino acid sequence having 100% sequence identity with the CDR sequence in the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO:5 and having at least 80% or more, preferably 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, or 94% or more, more preferably 95%, 96%, 97%, or 98% or more, and most preferably 99% or more or 100% sequence identity with the sequence of the framework region of the same.(e) a heavy chain variable region consisting of an amino acid sequence that has 100% sequence identity with the CDR sequence in the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 15 and has at least 80% or more, preferably 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, or 94% or more, more preferably 95%, 96%, 97%, or 98% or more, and most preferably 99% or more or 100% sequence identity with the sequence of the framework region of the same; and a light chain variable region consisting of an amino acid sequence having 100% sequence identity with the CDR sequence in the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 4 and having at least 80% or more, preferably 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, or 94% or more, more preferably 95%, 96%, 97%, or 98% or more, and most preferably 99% or more or 100% sequence identity with the sequence of the framework region of the same. (f) a heavy chain variable region consisting of an amino acid sequence that has 100% sequence identity with the CDR sequence in the amino acid sequence set forth in amino acid numbers 20 to 133 of SEQ ID NO: 23 and has at least 80% or more, preferably 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, or 94% or more, more preferably 95%, 96%, 97%, or 98% or more, and most preferably 99% or more or 100% sequence identity with the sequence of the framework region of the same; and a light chain variable region consisting of an amino acid sequence having 100% sequence identity with the CDR sequence in the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 21, and having at least 80% or more, preferably 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, or 94% or more, more preferably 95%, 96%, 97%, or 98% or more, and most preferably 99% or more or 100% sequence identity with the sequence of the framework region;(g) a heavy chain variable region consisting of an amino acid sequence that has 100% sequence identity with the CDR sequence in the amino acid sequence set forth in amino acid numbers 20 to 140 of SEQ ID NO: 16 and has at least 80% or more, preferably 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, or 94% or more, more preferably 95%, 96%, 97%, or 98% or more, and most preferably 99% or more or 100% sequence identity with the sequence of the framework region of the same; and a light chain variable region consisting of an amino acid sequence having 100% sequence identity to the CDR sequence in the amino acid sequence set forth in amino acid numbers 21 to 129 of SEQ ID NO: 17, and having at least 80% or more, preferably 85%, 86%, 87%, 88%, 89%, 90%, 91%, 92%, 93%, or 94% or more, more preferably 95%, 96%, 97%, or 98% or more, and most preferably 99% or more or 100% sequence identity to the sequence of the framework regions thereof. Preferably, the heavy chain variable region and light chain variable region are selected from the group consisting of (a) to (e) above, and more preferably, the heavy chain variable region and light chain variable region are selected from the group consisting of (d) above.

[0186] In the present invention, identity between amino acid sequences can be evaluated based on any known method. In one embodiment of the present invention, identity between two types of amino acid sequences can be evaluated using, for example, ClustalW version 2 (Larkin MA, Blackshields G, Brown NP, Chenna R, McGettigan PA, McWilliam H, Valentin F, Wallace IM, Wilm A, Lopez R, Thompson JD, Gibson TJ and Higgins DG (2007), "Clustal W and Clustal X version 2.0"). The sequence identity can be determined by aligning the sequences using the default parameters of the method described in Bioinformatics. 23(21):2947-2948.

[0187] In one embodiment of the present invention, the antibody or antigen-binding fragment of the antibody in the antibody-photosensitizer conjugate of the present invention comprises a heavy chain and a light chain selected from the group consisting of the following (a) to (h): (a) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 in SEQ ID NO: 9 and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO: 4, (b) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 in SEQ ID NO: 10 and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO: 5, (c) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 in SEQ ID NO: 10 and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO: 6, (d) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 in SEQ ID NO: 12 and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO: 5, (e) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 in SEQ ID NO: 15 and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO: 4; (f) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 470 in SEQ ID NO: 16 and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 234 in SEQ ID NO: 17; (g) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 463 in SEQ ID NO: 23 and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO: 21; and (h) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 468 in SEQ ID NO: 24 and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 234 in SEQ ID NO: 25. Preferably, the heavy chain and light chain are selected from the group consisting of (a) to (e) and (g) above, more preferably selected from the group consisting of (a) to (e) above, and even more preferably the heavy chain and light chain of (d) above.

[0188] In the light chain amino acid sequence shown in SEQ ID NO: 4, 5, or 6 in the Sequence Listing, the amino acid sequence consisting of amino acid residues 1 to 20 is a signal sequence, the amino acid sequence consisting of amino acid residues 21 to 133 is a variable region, and the amino acid sequence consisting of amino acid residues 134 to 239 is a constant region. The amino acid sequences of SEQ ID NO: 4, 5, or 6 are set forth in Figures 10, 11, and 12, respectively. In the heavy chain amino acid sequence shown in SEQ ID NO: 9, 10, 12, or 15, the amino acid sequence consisting of amino acid residues 1 to 19 is a signal sequence, the amino acid sequence consisting of amino acid residues 20 to 135 is a variable region, and the amino acid sequence consisting of amino acid residues 136 to 465 is a constant region. The amino acid sequences of SEQ ID NO: 9, 10, 12, or 15 are set forth in Figures 13, 14, 15, and 16, respectively.

[0189] The antibodies of the present invention can be obtained by immunizing an animal with an antigenic polypeptide and collecting and purifying the antibodies produced in the body using methods commonly used in this field. The origin of the antigen is not limited to humans; animals can also be immunized with antigens derived from animals other than humans, such as mice or rats. In this case, antibodies that can be applied to human diseases can be selected by testing the cross-reactivity of the obtained antibodies that bind to heterologous antigens with human antigens.

[0190] Alternatively, a monoclonal antibody can be obtained by fusing antibody-producing cells that produce an antibody against an antigen with myeloma cells to establish a hybridoma according to known methods (e.g., Kohler and Milstein, Nature (1975) 256, pp. 495-497; Kennett, R. ed., Monoclonal Antibodies, pp. 365-367, Plenum Press, N.Y. (1980)).

[0191] The antigen can be obtained by known methods, for example, by causing a host cell to produce a gene encoding the antigen protein through genetic manipulation.

[0192] The humanized antibody of the present invention can be obtained according to known methods (for example, Proc. Natl. Acad. Sci. USA, 81, 6851-6855, (1984), Nature (1986) 321, pp. 522-525, WO90 / 07861).

[0193] For example, anti-EpCAM antibodies (see Example 48 below), anti-TROP2 antibodies (see Reference Example 1 below), anti-CD25 antibodies (see Example 88 below), anti-EGFR antibodies (WO1998 / 050433, WO2002 / 092771, WO2021 / 177438, etc.), anti-HER2 antibodies (US5821337, WO2004 / 008099, etc.), anti-CD33 antibodies (WO2014 / 057687, etc.), anti-CD70 antibodies (WO2004 / 073656, etc.), anti-EphA2 antibodies (WO2009 / 028639, etc.), and anti-CDH6 antibodies (WO2018 / 212136, etc.) can be obtained by known means.

[0194] (Method for producing antibodies) When an antibody gene is isolated and then introduced into a suitable host to produce an antibody, a combination of a suitable host and an expression vector can be used. Specific examples of antibody genes include a combination of a gene encoding the heavy chain sequence and a gene encoding the light chain sequence of an antibody described herein. When transforming a host cell, the heavy chain sequence gene and the light chain sequence gene can be inserted into the same expression vector, or they can be inserted into separate expression vectors.

[0195] When eukaryotic cells are used as hosts, animal cells, plant cells, and eukaryotic microorganisms can be used. Particularly, examples of animal cells include mammalian cells, such as monkey COS cells (Gluzman, Y. Cell (1981) 23, pp. 175-182, ATCC CRL-1650), mouse fibroblast NIH3T3 (ATCC No. CRL-1658), dihydrofolate reductase-deficient strains of Chinese hamster ovary cells (CHO cells, ATCC CCL-61) (Urlaub, G. and Chasin, L.A. Proc. Natl. Acad. Sci. U.S.A. (1980) 77, pp. 4126-4220), and FreeStyle 293F cells (Invitrogen). When prokaryotic cells are used, examples include Escherichia coli and Bacillus subtilis.

[0196] Antibodies can be obtained by introducing the desired antibody gene into these cells by transformation and culturing the transformed cells in vitro. The yield of the antibody during this culture may vary depending on the antibody sequence, and antibodies with equivalent binding activity can be selected based on the yield as an indicator to determine which antibodies are easy to produce as pharmaceuticals. Therefore, the antibodies of the present invention also include antibodies obtained by a method for producing the antibody, which method comprises the steps of culturing the transformed host cells and recovering the desired antibody or an antigen-binding fragment of the antibody from the culture obtained in this step.

[0197] It is known that the lysine residue at the carboxyl terminus of the heavy chain of an antibody produced in cultured mammalian cells is deleted (Journal of Chromatography A, 705:129-134 (1995)), and that two amino acid residues, glycine and lysine, are deleted at the carboxyl terminus of the heavy chain, and a proline residue newly positioned at the carboxyl terminus is amidated (Analytical Biochemistry, 360:75-83 (2007)). However, these deletions and modifications of the heavy chain sequence do not affect the antigen-binding ability or effector functions (complement activation, antibody-dependent cellular cytotoxicity, etc.) of the antibody. Therefore, the antibodies of the present invention also include antibodies and antigen-binding fragments of such antibodies that have been modified in this manner, as well as deletions in which one or two amino acids have been deleted from the carboxyl terminus of the heavy chain, and amidated deletions (e.g., heavy chains in which the proline residue at the carboxyl terminus has been amidated). However, as long as the antigen-binding ability and effector function are maintained, the deletions at the carboxyl termini of the heavy chains of the antibodies of the present invention are not limited to the above types. The two heavy chains constituting the antibodies of the present invention may be any one type of heavy chain selected from the group consisting of full-length heavy chains and the above-mentioned deletions, or a combination of two types of heavy chains. The quantitative ratio of each deletion may be affected by the type and culture conditions of the cultured mammalian cells that produce the antibodies of the present invention, but an example of a major component of the antibodies of the present invention is one in which one amino acid residue has been deleted from the carboxyl terminus of each heavy chain.

[0198] The isotype of the antibody of the present invention can be, for example, IgG (IgG1, IgG2, IgG3, IgG4), etc., preferably IgG1, IgG2 or IgG4, more preferably IgG1.

[0199] The biological activities of an antibody generally include antigen-binding activity, the activity of internalizing into cells expressing the antigen by binding to the antigen, the activity of neutralizing antigen activity, the activity of enhancing antigen activity, antibody-dependent cellular cytotoxicity (ADCC), complement-dependent cytotoxicity (CDC), and antibody-dependent cell-mediated phagocytosis (ADCP). The function of the antibody of the present invention is binding activity to EpCAM, preferably the activity of internalizing into EpCAM-expressing cells by binding to EpCAM. Furthermore, the antibody of the present invention may have ADCC activity, CDC activity, and / or ADCP activity in addition to the cell-internalizing activity.

[0200] The resulting antibodies can be purified to homogeneity. Antibody isolation and purification can be performed using isolation and purification methods commonly used for proteins. For example, antibodies can be separated and purified by appropriately selecting and combining methods such as column chromatography, filtration, ultrafiltration, salting out, dialysis, preparative polyacrylamide gel electrophoresis, and isoelectric focusing (Strategies for Protein Purification and Characterization: A Laboratory Course Manual, Daniel R. Marshak et al. eds., Cold Spring Harbor Laboratory Press (1996); Antibodies: A Laboratory Manual, Ed Harlow and David Lane, Cold Spring Harbor Laboratory Press (1996)). Laboratory (1988)), but is not limited thereto.

[0201] Examples of chromatography include affinity chromatography, ion exchange chromatography, hydrophobic chromatography, gel filtration chromatography, reverse phase chromatography, adsorption chromatography, etc. These chromatographies can be performed using liquid chromatography such as HPLC or FPLC.

[0202] Examples of columns used in affinity chromatography include protein A columns and protein G columns. For example, columns using protein A columns include Hyper D, POROS, and Sepharose FF (Pharmacia).

[0203] It is also possible to purify antibodies by using a carrier on which an antigen is immobilized, and taking advantage of their binding to the antigen.

[0204] The following describes in detail how to obtain antibodies against EpCAM. (Obtaining antibodies) (1) Preparation of antigens Antigens can be obtained by genetically engineering a gene encoding an antigen protein in a host cell to produce it. Specifically, a vector capable of expressing the antigen gene is prepared, introduced into a host cell to express the gene, and the expressed antigen is purified. Antibodies can also be obtained by immunizing an animal with the above-mentioned genetically engineered antigen-expressing cells or a cell line expressing the antigen.

[0205] Alternatively, an antibody can be obtained without using an antigen protein by incorporating the cDNA of the antigen protein into an expression vector and administering it to an animal to be immunized, thereby expressing the antigen protein in the body of the animal to produce an antibody against the antigen protein.

[0206] (2) Production of anti-EpCAM monoclonal antibodies The anti-EpCAM antibody used in the present invention is not particularly limited, but for example, an antibody specified by the amino acid sequence shown in the sequence listing of the present application can be preferably used. The anti-EpCAM antibody used in the present invention preferably has the following properties: (I) An antibody characterized by the following properties: (a) specifically binds to EpCAM. (b) has the activity of being internalized into EpCAM-expressing cells by binding to EpCAM. (II) The antibody according to (I) above, wherein the EpCAM is human EpCAM. (III) The antibody according to (I) or (II) above, which recognizes the higher-order structure of EpCAM.

[0207] The method for obtaining an antibody against EpCAM of the present invention is not particularly limited as long as an anti-EpCAM antibody can be obtained, but since EpCAM is a transmembrane protein, it is preferable to use EpCAM that retains its higher-order structure as an antigen.

[0208] An example of a preferred method for obtaining antibodies is DNA immunization. DNA immunization is a method in which an antigen expression plasmid is introduced into an individual animal such as a mouse or rat, and the antigen is expressed within the individual, thereby inducing immunity against the antigen. Gene introduction techniques include direct injection of a plasmid into the muscle, intravenous injection of an introduction reagent such as liposomes or polyethyleneimine, a method using a viral vector, injection of gold particles with a plasmid attached using a gene gun, and the hydrodynamic method in which a large amount of plasmid solution is rapidly injected intravenously. Regarding gene transfer by intramuscular injection of an expression plasmid, a technique called in vivo electroporation, in which the plasmid is injected intramuscularly and then electroporated at the same site, is known as a method for improving the expression level (Aihara H, Miyazaki J. Nat Biotechnol. 1998 Sep;16(9):867-70 or Mir LM, Bureau MF, Gehl J, Rangara R, Rouy D, Caillaud JM, Delaere P, Branellec D, Schwartz B, Scherman D. Proc Natl Acad Sci U S A. 1999 Apr). 13;96(8):4262-7. In this method, the expression level can be further improved by treating the muscle with hyaluronidase before intramuscular injection of the plasmid (McMahon JM1, Signori E, Wells KE, Fazio VM, Wells DJ. Gene Ther. 2001 Aug;8(16):1264-70). Hybridomas can also be produced by known methods, for example, using the Hybrimune Hybridoma Production System (Cyto Pulse Sciences).

[0209] Specific examples of obtaining monoclonal antibodies include the following: (a) EpCAM cDNA can be incorporated into an expression vector and then directly administered to an immunized animal by electroporation, a gene gun, or other methods to express EpCAM in the animal, thereby eliciting an immune response. The vector can be administered by electroporation or other methods once or multiple times, preferably multiple times, as needed to increase antibody titers. (b) Collection of tissue (e.g., lymph nodes) containing antibody-producing cells from the animal in which an immune response has been elicited. (c) Preparation of myeloma cells (hereinafter referred to as "myeloma"). (d) Cell fusion between antibody-producing cells and myelomas. (e) Selection of hybridomas producing the desired antibody. (f) Division into single-cell clones (cloning). (g) Culturing hybridomas to mass-produce monoclonal antibodies, or raising animals transplanted with hybridomas.

[0210] The obtained monoclonal antibody has high antigen specificity to EpCAM. The monoclonal antibody is not particularly limited, but an example thereof is the anti-EpCAM mouse monoclonal antibody 323 / A3 (British Journal of Cancer (1998) 78(11), 1407-1416).

[0211] (h) Examination of the physiological activity (internalization activity) and binding specificity of the monoclonal antibody thus produced, or assay of its properties as a labeling reagent. Methods for measuring antibody titers used here include, but are not limited to, flow cytometry or Cell-ELISA.

[0212] Furthermore, even if a monoclonal antibody is obtained separately and independently by repeating steps (a) to (h) of the specific monoclonal antibody obtaining example described in "(2) Production of Anti-EpCAM Monoclonal Antibody," or if a monoclonal antibody is obtained separately by another method, it is possible to obtain an antibody having cytotoxic activity equivalent to that of the anti-EpCAM antibody obtained in step (g). An example of such an antibody is an antibody that binds to the same epitope as the anti-EpCAM antibody obtained in step (g). If the newly produced monoclonal antibody binds to the partial peptide or partial three-dimensional structure to which the anti-EpCAM antibody binds, it can be determined that the monoclonal antibody binds to the same epitope. Furthermore, by confirming that the monoclonal antibody competes with the binding of the anti-EpCAM antibody to EpCAM (i.e., that the monoclonal antibody inhibits the binding of the anti-EpCAM antibody to EpCAM), it can be determined that the monoclonal antibody binds to the same epitope as the anti-EpCAM, even if the specific sequence or structure of the epitope has not been determined. If it is confirmed that the epitope is the same, it is highly expected that the monoclonal antibody has antigen-binding ability or biological activity equivalent to that of the anti-EpCAM antibody.

[0213] (3) Other Antibodies In addition to the above-mentioned monoclonal antibodies against EpCAM, the antibodies of the present invention also include genetically engineered antibodies that have been artificially modified for the purposes of reducing xenoantigenicity to humans, improving the physical properties of antibody-photosensitizer conjugates, etc., such as chimeric antibodies, humanized antibodies, and human antibodies. These antibodies can be produced using known methods.

[0214] Chimeric antibodies include antibodies in which the variable and constant regions are heterologous, for example, chimeric antibodies in which the variable regions of a mouse- or rat-derived antibody are joined to the constant regions of human origin (see Proc. Natl. Acad. Sci. U.S.A., 81, 6851-6855, (1984)).

[0215] Examples of humanized antibodies include antibodies in which only the CDRs have been incorporated into a human-derived antibody (see Nature (1986) 321, pp. 522-525), antibodies in which not only the CDR sequences but also some framework amino acid residues have been grafted onto a human antibody by CDR grafting (WO 90 / 07861), and antibodies in which the amino acid sequences of some CDRs have been modified while maintaining the antigen-binding ability.

[0216] Conservative amino acid substitutions are preferred herein. Conservative amino acid substitutions are those that occur within amino acid groups that are related by their amino acid side chains. Preferred amino acid groups are as follows: acidic group = aspartic acid (D), glutamic acid (E); basic group = lysine (K), arginine (R), histidine (H); nonpolar group = alanine (A), valine (V), leucine (L), isoleucine (I), proline (P), phenylalanine (F), methionine (M), tryptophan (W); and uncharged polar group = glycine (G), asparagine (N), glutamine (Q), cysteine ​​(C), serine (S), threonine (T), tyrosine (Y). Other preferred amino acid groups are as follows: aliphatic hydroxy group = serine and threonine; amide-containing group = asparagine and glutamine; aliphatic group = alanine, valine, leucine, and isoleucine; and aromatic group = phenylalanine, tryptophan, and tyrosine. Such amino acid substitutions are preferably made within a range that does not impair the properties of the substance having the original amino acid sequence.

[0217] The antibody of the present invention further includes a human antibody that binds to EpCAM. An anti-EpCAM human antibody refers to a human antibody that has only the gene sequence of an antibody derived from a human chromosome. The anti-EpCAM human antibody was produced by a method using a human antibody-producing mouse carrying a human chromosome fragment containing the heavy and light chain genes of a human antibody (Tomizuka, K. et al., Nature Genetics (1997) 16, pp. 133-143; Kuroiwa, Y. et al., Nucl. Acids Res. (1998) 26, pp. 3447-3448; Yoshida, H. et al., Animal Cell Technology: Basic and Applied Aspects vol. 10, pp. 69-73 (Kitagawa, Y., Matsuda, T. and Iijima, S. eds.), Kluwer Academic Publishers, 1999; Tomizuka, K. et al., Proc. Natl. Acad. Sci. USA (2000) 97, pp. 722-727, etc.

[0218] Specifically, such human antibody-producing mice can be produced by producing knockout animals and transgenic animals as genetically modified animals in which the endogenous immunoglobulin heavy and light chain loci have been disrupted and instead the human immunoglobulin heavy and light chain loci have been introduced via yeast artificial chromosome (YAC) vectors, etc., and then crossbreeding these animals. Alternatively, eukaryotic cells can be transformed using genetic recombination technology with cDNA encoding each of the heavy and light chains of such human antibodies, preferably with a vector containing said cDNA, and the transformed cells that produce recombinant human monoclonal antibodies can be cultured to obtain the antibodies from the culture supernatant.

[0219] Here, as the host, for example, eukaryotic cells, preferably mammalian cells such as CHO cells, lymphocytes, and myeloma cells can be used.

[0220] Also known are methods for obtaining phage-display-derived human antibodies selected from a human antibody library (see, for example, Wormstone, I.M. et al., Investigative Ophthalmology & Visual Science. (2002) 43(7), pp. 2301-2308; Carmen, S. et al., Briefings in Functional Genomics and Proteomics (2002), 1(2), pp. 189-203; Siriwardena, D. et al., Ophthalmology (2002) 109(3), pp. 427-431).

[0221] For example, a phage display method (Nature Biotechnology (2005), 23, (9), pp. 1105-1116) can be used, in which the variable regions of human antibodies are expressed on the surface of phages as single-chain fragments (scFv), and phages that bind to the antigen are selected. By analyzing the genes of phages selected by binding to the antigen, the DNA sequence encoding the variable regions of human antibodies that bind to the antigen can be determined.

[0222] Once the DNA sequence of an scFv that binds to an antigen is clarified, an expression vector containing that sequence can be prepared and introduced into an appropriate host for expression to obtain a human antibody (WO 92 / 01047, WO 92 / 20791, WO 93 / 06213, WO 93 / 11236, WO 93 / 19172, WO 95 / 01438, WO 95 / 15388, Annu. Rev. Immunol (1994) 12, pp. 433-455, Nature Biotechnology (2005) 23(9), pp. 1105-1116).

[0223] If a newly created human antibody binds to a partial peptide or partial three-dimensional structure to which the EpCAM antibody described herein binds, it can be determined that the human antibody binds to the same epitope. Furthermore, by confirming that the human antibody competes with the EpCAM antibody described herein for binding to EpCAM (i.e., that the human antibody interferes with the binding of the EpCAM antibody described herein to EpCAM), it can be determined that the human antibody binds to the same epitope as the EpCAM antibody described herein, even if the specific sequence or structure of the epitope has not been determined. If it is confirmed that the epitope is the same, it is highly expected that the human antibody has antigen-binding ability or biological activity equivalent to that of the EpCAM antibody described herein.

[0224] The chimeric, humanized, or human antibodies obtained by the above methods can be evaluated for their antigen-binding ability by known methods, and suitable antibodies can be selected.

[0225] Another example of an index used to compare antibody properties is antibody stability. Differential scanning calorimetry (DSC) is an instrument that can quickly and accurately measure the thermal denaturation midpoint (Tm), which is a good indicator of the relative structural stability of a protein. Differences in thermal stability can be compared by measuring Tm values ​​using DSC and comparing the values. It is known that the storage stability of an antibody correlates to a certain extent with its thermal stability (Lori Burton, et al., Pharmaceutical Development and Technology (2007) 12, pp. 265-273), and suitable antibodies can be selected using thermal stability as an index. Other indices for antibody selection include high yield in appropriate host cells and low aggregation tendency in aqueous solution. For example, the antibody with the highest yield does not necessarily exhibit the highest thermal stability, so it is necessary to make a comprehensive judgment based on the above-mentioned indicators and select the antibody that is most suitable for administration to humans.

[0226] (Modified Antibodies) The antibodies of the present invention also include modified antibodies. The term "modified antibodies" refers to antibodies of the present invention that have been chemically or biologically modified. Chemical modifications include those in which a chemical moiety is attached to the amino acid backbone, or N- or O-linked carbohydrate chains are chemically modified, etc. Biological modifications include those that have undergone post-translational modifications (e.g., N- or O-linked glycosylation, N- or C-terminal processing, deamidation, aspartic acid isomerization, or methionine oxidation), or those in which a methionine residue has been added to the N-terminus by expression in a prokaryotic host cell, etc. Also included within the meaning of modified antibodies are those labeled to enable detection or isolation of the antibodies or antigens of the present invention, such as enzyme-labeled, fluorescent-labeled, or affinity-labeled antibodies. Such modified antibodies of the present invention are useful for improving antibody stability and blood retention, reducing antigenicity, and detecting or isolating antibodies or antigens, etc.

[0227] Thus, in one aspect of the present invention, the antibody or antigen-binding fragment of the antibody in the antibody-photosensitizer conjugate of the present invention comprises a deletion or absence of one or two amino acids at the carboxyl terminus of the heavy chain, and in another aspect of the present invention, the antibody or antigen-binding fragment of the antibody in the antibody-photosensitizer conjugate of the present invention lacks a lysine residue at the carboxyl terminus of the heavy chain.

[0228] Furthermore, antibody-dependent cellular cytotoxicity can be enhanced by modulating the sugar chain modification (glycosylation, defucosylation, etc.) attached to the antibody of the present invention. Techniques for modulating antibody sugar chain modification are known, including, but not limited to, those described in WO1999 / 54342, WO2000 / 61739, and WO2002 / 31140. The antibodies of the present invention also include antibodies in which the sugar chain modification has been modulated. Such modifications may be made at any position or desired positions in the antibody or antigen-binding fragment thereof, and the same or two or more different modifications may be made at one or more positions.

[0229] Recently, a method has been reported in which heterogeneous antibody sugar chains are remodeled by enzymatic reaction to uniformly introduce sugar chains having functional groups (ACS Chem. Biol. 2012, 7, 110-122, ACS Med. Chem. Lett. 2016, 7, 1005-1008). Attempts have also been made to use this sugar chain remodeling technique to site-specifically introduce drugs and synthesize homogeneous ADCs (Bioconjugate Chem. 2015, 26, 2233-2242, Angew. Chem. Int. Ed. 2016, 55, 2361-2367, US2016361436).

[0230] Glycosylation remodeling involves first using a hydrolase to remove heterogeneous glycans attached to an antibody, leaving only the terminal GlcNAc, to prepare a homogeneous antibody moiety with GlcNAc attached (hereinafter referred to as "acceptor"). Next, a separately prepared glycan of your choice (hereinafter referred to as "donor") is prepared, and this acceptor and donor are linked using a glycosyltransferase. This allows the synthesis of a homogeneous antibody with a desired glycan structure. The glycan of the antibody in the antibody-photosensitizer conjugate of the present invention may be a remodeled glycan.

[0231] The antibody-photosensitizer conjugate of the present invention has the following formula:

[0232] and the antibody or antigen-binding fragment thereof, designated as Ab, is directly bound to L via its amino acid residues or indirectly bound to L via its sugar chains.

[0233] The antibody or antigen-binding fragment of the antibody is preferably bound to L directly through the side chain of an amino acid residue thereof (eg, cysteine, lysine, etc.).

[0234] For example, a sulfhydryl group (—SH) of a cysteine ​​of an antibody or an antigen-binding fragment of the antibody may be bound to L. The sulfhydryl group can bind to L by forming a thioether.

[0235] In addition, the amino group (—NH ２) may be bonded to L. The amino group can be bonded to L by forming an amide bond.

[0236] The sugar chain of the Ab in the present invention is an N-linked sugar chain or an O-linked sugar chain, preferably an N-linked sugar chain.

[0237] N-linked glycans are bound to amino acid side chains of antibodies via N-glycosidic bonds, and O-linked glycans are bound to amino acid side chains of antibodies via O-glycosidic bonds.

[0238] The Ab of the present invention is preferably IgG, more preferably IgG1, IgG2 or IgG4, and even more preferably IgG1.

[0239] IgG has a well-conserved N-linked glycan at the 297th asparagine residue (hereinafter referred to as "Asn297 or N297") in the Fc region of its heavy chain, which is known to contribute to the activity, kinetics, etc. of antibody molecules (Eon-Duval, A. et al., Biotechnol. Prog. 2012, 28, 608-622; Sanglier-Cianferani, S., Anal. Chem. 2013, 85, 715-736).

[0240] The amino acid sequence in the constant region of IgG is well conserved, and in a report by Edelman et al. (Proc. Natl. Acad. Sci. U.S.A., 63, 78-85, (1969)), each amino acid is identified by an EU number (EU INDEX). For example, Asn297, to which an N-linked sugar chain is added in the Fc region, corresponds to position 297 in the EU numbering. Even if the actual amino acid position changes due to molecular fragmentation or region deletion, the amino acid can be uniquely identified by displaying it by EU numbering.

[0241] In the antibody-photosensitizer conjugate of the present invention, a sugar chain bound to Asn297 of the antibody or antigen-binding fragment thereof (N297 sugar chain) may be indirectly bound to L. The N297 sugar chain may be a remodeled sugar chain.

[0242] In one aspect of the present invention, an antibody or an antigen-binding fragment of the antibody is provided that specifically binds to EpCAM and comprises a combination of CDRH1, CDRH2, and CDRH3, and CDRL1, CDRL2, and CDRL3, each consisting of a specific amino acid sequence; a combination of a heavy chain variable region and a light chain variable region consisting of a specific amino acid sequence; or a combination of a heavy chain and a light chain consisting of a specific amino acid sequence. All of the descriptions regarding the antibody or antigen-binding fragment of the antibody presented in this chapter also apply to the antibody or antigen-binding fragment of the antibody in one aspect of the present invention.

[0243] 2.5 Preferred Embodiments of Antibody-Photosensitizer Conjugates Preferred embodiments of the antibody-photosensitizer conjugates of the present invention are antibody-photosensitizer conjugates shown below. (wherein Ab represents a humanized anti-EpCAM antibody represented by the following heavy and light chains or an antibody in which the lysine residue at the carboxyl terminal of the heavy chain of the anti-EpCAM antibody has been deleted, wherein the heavy chain consists of the amino acid sequence represented by amino acid numbers 20 to 465 in SEQ ID NO: 12 and the light chain consists of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO: 5; -L-P represents a group represented by the following formula: and x is 7.5 to 8 or 4 to 5.

[0244] A preferred embodiment of the antibody-photosensitizer conjugate of the present invention is an antibody-photosensitizer conjugate shown below. (wherein Ab represents a humanized anti-EpCAM antibody represented by the following heavy and light chains or an antibody in which the lysine residue at the carboxyl terminal of the heavy chain of the anti-EpCAM antibody has been deleted, wherein the heavy chain consists of the amino acid sequence represented by amino acid numbers 20 to 465 in SEQ ID NO: 12 and the light chain consists of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO: 5; -L-P represents a group represented by the following formula: and x is 7.5 to 8 or 4 to 5.

[0245] A preferred embodiment of the antibody-photosensitizer conjugate of the present invention is an antibody-photosensitizer conjugate shown below. (wherein Ab represents a humanized anti-EpCAM antibody represented by the following heavy and light chains or an antibody in which the lysine residue at the carboxyl terminal of the heavy chain of the anti-EpCAM antibody has been deleted, wherein the heavy chain consists of the amino acid sequence represented by amino acid numbers 20 to 465 in SEQ ID NO: 12 and the light chain consists of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO: 5; -L-P represents a group represented by the following formula: and x is 7.5 to 8 or 4 to 5.

[0246] A preferred embodiment of the antibody-photosensitizer conjugate of the present invention is an antibody-photosensitizer conjugate shown below. (wherein Ab represents a humanized anti-EpCAM antibody represented by the following heavy and light chains or an antibody in which the lysine residue at the carboxyl terminal of the heavy chain of the anti-EpCAM antibody has been deleted, wherein the heavy chain consists of the amino acid sequence represented by amino acid numbers 20 to 465 in SEQ ID NO: 12 and the light chain consists of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO: 5; -L-P represents a group represented by the following formula: and x is 7.5 to 8 or 4 to 5.

[0247] 2.6 Effects of Antibody-Photosensitizer Conjugate, Metal Complex Thereof, or Pharmaceutically Acceptable Salt Thereof The antibody-photosensitizer conjugate, metal complex thereof, or pharmaceutically acceptable salt thereof of the present invention can be used for photodynamic therapy. The antibody-photosensitizer conjugate, metal complex thereof, or pharmaceutically acceptable salt thereof of the present invention is thought to act, for example, as follows. That is, after administration into the body, the antibody-photosensitizer conjugate, metal complex thereof, or pharmaceutically acceptable salt thereof is delivered to the tumor site and taken up into tumor cells, where the linker moiety is partially or completely cleaved by peptidase or the like, liberating the photosensitizer. By irradiating the tumor site with light in a specific wavelength band depending on the antibody-photosensitizer conjugate or photosensitizer, the antibody-photosensitizer conjugate and the liberated photosensitizer undergo a photochemical reaction to generate reactive oxygen species (singlet oxygen, etc.). This reactive oxygen species exhibits cytotoxic activity against tumor cells in which the photosensitizer has accumulated. The antibody-photosensitizer conjugate of the present invention, or a metal complex thereof, or a pharmaceutically acceptable salt thereof is thought to exert its antitumor effect via this cytotoxic activity.

[0248] The antibody-photosensitizer conjugate of the present invention, or a metal complex thereof, or a pharmaceutically acceptable salt thereof, exhibits a stronger antitumor effect than previously reported compounds for photodynamic therapy, and is therefore useful for tumor photodynamic therapy.

[0249] The antibody-photosensitizer conjugate of the present invention, or a metal complex thereof, or a pharmaceutically acceptable salt thereof, exhibits high selectivity against cancer, and therefore can suppress side effects.

[0250] The maximum absorption wavelength in the Q band of the antibody-photosensitizer conjugate of the present invention, or a metal complex thereof, or a pharmaceutically acceptable salt thereof, when measured in an alkylbenzenesulfonic acid (hereinafter sometimes referred to as "ABS") solution, is preferably 600 nm to 800 nm, more preferably 640 nm to 780 nm, even more preferably 670 nm to 750 nm, and particularly preferably 705 nm to 720 nm or 730 nm to 745 nm. The antibody-photosensitizer conjugate of the present invention, or a metal complex thereof, or a pharmaceutically acceptable salt thereof, exhibits light absorption in the long wavelength region and can therefore be applied not only to superficial cancers but also to cancers that are located in deep areas or that have infiltrated deep into the body.

[0251] The maximum absorption wavelength (nm) in the Q band of the antibody-photosensitizer conjugate of the present invention, or a metal complex thereof, or a pharmaceutically acceptable salt thereof, can be measured by methods well known to those skilled in the art. For example, it can be determined from the ultraviolet-visible absorption spectrum in the wavelength range of 220 to 800 nm measured with a spectrophotometer using a solution obtained by dissolving the antibody-photosensitizer conjugate of the present invention, or a metal complex thereof, or a pharmaceutically acceptable salt thereof in a good solvent. Porphyrin compounds, including chlorin derivatives, are generally known to have characteristic absorption bands called the Soret band (a region corresponding to wavelengths around 400 nm) and the Q band (a region corresponding to wavelengths of 600 to 800 nm).

[0252] <3. Production Method> Next, a representative method for producing the antibody-photosensitizer conjugate of the present invention or a production intermediate thereof will be described. Note that, hereinafter, the compound numbers shown in each reaction scheme will be used to indicate the compounds. That is, they will be referred to as "compound of formula (1)," "compound (1)," etc. Compounds with other numbers will also be referred to in the same manner.

[0253] 1. Production Method 1 Compound (2) of the present invention can be produced according to Methods A to T described below.

[0254] Methods A to E and Methods H to S are methods for producing the chlorin derivatives and synthetic intermediates of the present invention. Methods F, G, and T are methods for producing the photosensitizer linkers of the present invention.

[0255] In each step of the following Methods A to T, the desired reaction can be carried out using known organic chemistry techniques.

[0256] The solvent used in the reactions in each step of the following Methods A to T is not particularly limited as long as it does not inhibit or adversely affect the reaction and can dissolve the starting materials to some extent.

[0257] In the reactions in each step of the following Methods A to T, the reaction temperature varies depending on the solvent, starting materials, reagents, etc., and the reaction time varies depending on the solvent, starting materials, reagents, reaction temperature, etc.

[0258] In the reactions of each step of the following Methods A to T, after completion of the reaction, each target compound is collected from the reaction mixture in a conventional manner. For example, the reaction mixture is suitably neutralized, and if any insoluble matter is present, it is removed by filtration. Then, an immiscible organic solvent such as water and ethyl acetate or water and chloroform is added, and the organic layer containing the target compound is separated, washed with water or the like, dried over anhydrous magnesium sulfate, anhydrous sodium sulfate or the like, filtered, and the solvent is distilled off to obtain the target compound. If necessary, the obtained target compound can be separated and purified by a suitable combination of conventional methods commonly used for separating and purifying organic compounds, such as recrystallization, reprecipitation, chromatography (e.g., adsorption column chromatography using a carrier such as silica gel, alumina, magnesium-silica gel-based Florisil, or amino-silica (manufactured by Fuji Silysia Chemical Co.); methods using synthetic adsorbents such as partition column chromatography using a carrier such as Sephadex LH-20 (manufactured by Cytiva Corporation), Amberlite XAD-11 (manufactured by Dow Chemical Co.), or Diaion HP-20 (manufactured by Mitsubishi Chemical Corporation); methods using ion exchange chromatography; and a suitable combination of normal-phase and reverse-phase column chromatography (preferably high performance liquid chromatography) using silica gel or alkylated silica gel, eluted with a suitable eluent). Target compounds that are insoluble in solvents can be purified by washing the obtained solid crude product with a solvent. Alternatively, the target compounds of each step can be used directly in the next reaction without purification. In the reactions of each step of the following Methods A to T, Ab, L, P, R, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , X, m, n, p, q, r, and x have the same meanings as those described above. １ represents an amino-protecting group. Preferred is a tert-butoxycarbonyl group, a benzyloxycarbonyl group, a 9-fluorenylmethyloxycarbonyl group, or the like. ２represents a protective group for a hydroxy group used in the field of organic synthetic chemistry, and is preferably an acetyl group, a benzyl group, a tert-butyldimethylsilyl group, a triisopropylsilyl group, a tert-butyl group, or the like.

[0259] W represents a leaving group used in the field of organic synthetic chemistry, and is preferably a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, or a p-toluenesulfonyloxy group.

[0260] M refers to alkali metals such as potassium, calcium, and sodium, and M ＋ represents the respective monovalent metal cations. -XH represents -SH, -OH, -CH ３ or -NH ２ indicates an anion, -X － is M ＋ It can form a stable ionic bond with

[0261] R ａ represents a substituent bonded to a carboxyl group, and is preferably a methyl group, an ethyl group, a benzyl group, a tert-butyl group, or the like.

[0262] Furthermore, amino groups and hydroxy groups not specifically protected in Methods A to T may be protected using a protecting group as needed. Furthermore, they may be deprotected as needed, or after protection, they may be deprotected and replaced with another protecting group.

[0263] Method A This production method is a method for preparing the compound (2) R ２ to an alkylalkoxy structure (e.g., -(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -), among compounds having R ２ The method for producing compounds (7a), (8a), (10a), and (11a) in which a functional group contained in

[0264] A-1 Step (1a) → (2a): Introduction of an Alkoxy Group Compound (1a) is dissolved in hydrobromic acid (5-40 wt. % acetic acid solution) and stirred at -30°C to 100°C, preferably 0°C to 35°C, for 30 minutes to 24 hours, preferably 1 hour to 12 hours. Hydrobromic acid (5-40 wt. % acetic acid solution) is used in an amount of 1 mole to an excess mole per mole of compound (1a). The reaction mixture is distilled under reduced pressure, and the resulting crude product is dissolved in a solvent (dichloromethane, diethyl ether, acetonitrile, 1,4-dioxane, THF, DMF, or a mixed solvent thereof) and the alcohol (PRO) to be introduced is added. １ -NH-(CH ２ ) ｎ -(OCH ２ CH ２ ) ｍ If necessary, a base (triethylamine, diisopropylethylamine, pyridine, sodium carbonate, potassium carbonate, sodium hydroxide, etc.) is added. １ -NH-(CH ２ ) ｎ -(OCH ２ CH ２ ) ｍ The amount of the base used is 1 mole to an excess amount, preferably 1 to 10 moles. The reaction time is 10 minutes to 72 hours, preferably 30 minutes to 48 hours.

[0265] Step A-2 (2a) → (3a): Alkaline Hydrolysis and Oxidative Cyclization Compound (2a) is dissolved in a solvent (dichloromethane, diethyl ether, toluene, 1,4-dioxane, DMF, tetrahydrofuran, acetonitrile, water, or a mixture thereof), and then a solution of an alkaline reagent (lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, etc.) and a base (pyridine, triethylamine, diisopropylethylamine, N-methylmorpholine, 4-dimethylaminopyridine, etc.) in an alcohol (methanol, ethanol, isopropyl alcohol, etc.) is added. The reaction is carried out while passing an oxygen-containing gas, such as air, through the reaction mixture. The alkaline reagent and the base are used in amounts of 1 to excess moles per mole of compound (2a), and the reaction time is 5 minutes to 12 hours, preferably 30 minutes to 4 hours.

[0266] Step A-3 (3a)→(4a): Methyl Esterification Reaction Compound (3a) is reacted with (trimethylsilyl)diazomethane (0.6 mol / L hexane solution) in a mixed solvent of a solvent (dichloromethane, benzene, toluene, diethyl ether, acetonitrile, 1,4-dioxane, THF, or a mixed solvent thereof) and methanol (5:1 to 1:1 (vol / vol)) at a temperature from −30° C. to the boiling point of the solvent used in the reaction, preferably −10° C. to 50° C. 1 to 15 moles, preferably 1 to 6 moles, of (trimethylsilyl)diazomethane are used per mole of compound (3a), and the reaction time is 3 minutes to 24 hours, preferably 10 minutes to 4 hours.

[0267] Step A-4 (4a) → (5a): Imide Cyclization Reaction Compound (4a) is reacted with R ５ -NH ２ The reaction is carried out by reacting with an amine represented by the above R ５ -NH ２The amines represented by the formula (I) are used in an amount of 1 to an excess mole, preferably 1 to 10 moles. The reaction time is 10 minutes to 72 hours, preferably 30 minutes to 48 hours.

[0268] Step A-5 (5a)→(6a): Alkaline Hydrolysis Compound (5a) is reacted with an alkaline reagent such as lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, etc. in a mixed solvent of a solvent (acetonitrile, THF, 1,4-dioxane, DMF, methanol, or a mixed solvent thereof) and water (9:1 to 1:1 (vol / vol)) at a temperature from −30° C. to the boiling point of the solvent used in the reaction, preferably 0° C. to 50° C. The alkaline reagent is used in an amount of 1 mole to an excess mole per mole of compound (5a), and the reaction time is 30 minutes to 72 hours, preferably 1 hour to 24 hours.

[0269] A-6 step (5a) → (7a): Deprotection group reaction PRO １ can be deprotected by known methods depending on the protecting group used (tert-butoxycarbonyl group, benzyloxycarbonyl group, 9-fluorenylmethyloxycarbonyl group, etc.). １ When is a tert-butoxycarbonyl group, the reaction is carried out using compound (5a) in a solvent (dichloromethane, chloroform, DMF, THF, 1,4-dioxane, water, etc., or a mixture thereof) at a temperature ranging from -20°C to the boiling point of the solvent used in the reaction, preferably 0°C to 30°C, using an acid (trifluoroacetic acid, hydrochloric acid, sulfuric acid, etc.). The acid is used in an amount of 0.5 to an excess mole per mole of compound (5a). The reaction time is 10 minutes to 72 hours, preferably 30 minutes to 24 hours.

[0270] Step A-7 (7a)→(8a): Acylation Reaction Compound (7a) is dissolved in a solvent (dichloromethane, chloroform, DMF, THF, 1,4-dioxane, water, etc., or a mixture thereof), and HO—(CH ２ ) ｑ -CO ２The reaction is carried out by reacting with an acylating agent such as an acid chloride or N-hydroxysuccinimidyl ester derived from H. The acylating agent is used in an amount of 1 to 10 moles, preferably 1 to 5 moles, per mole of compound (5a), and the reaction time is 10 minutes to 24 hours, preferably 30 minutes to 12 hours.

[0271] Step A-8 (6a) → (9a): Condensation reaction R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ In the case of an optionally substituted amino group, compound (6a) is reacted with an alcohol (R 1 ) in a solvent (dichloromethane, acetonitrile, THF, 1,4-dioxane, DMF, water, or a mixed solvent thereof) at a temperature from −30° C. to the boiling point of the solvent used in the reaction, preferably from 0° C. to 50° C., in the presence of a condensing agent such as N,N′-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline, or 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride and 4-dimethylaminopyridine. ６ｂ The reaction is carried out by reacting the alcohol (R —H) with 1 mole of the compound (6a). ６ｂ—H) is used in an amount of 1 to 10 moles, preferably 1 to 5 moles, 4-dimethylaminopyridine in an amount of 1 to 5 moles, preferably 1 to 3 moles, and the condensing agent in an amount of 1 to 10 moles, preferably 1 to 5 moles. The reaction time is 10 minutes to 72 hours, preferably 30 minutes to 24 hours.

[0272] R ６ｂ -N (R ６ｃ )-R ６ｄ In the case of (I), compound (6a) is reacted with an amine (R) in a solvent (benzene, toluene, diethyl ether, dichloromethane, THF, 1,4-dioxane, DMF, water, or a mixture thereof) at a temperature from −30° C. to the boiling point of the solvent used in the reaction, preferably from 0° C. to 50° C., in the presence of a condensing agent such as N,N′-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline, or 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride. ６ｄ -N(R ６ｃ )-H) relative to 1 mole of compound (6a). ６ｄ -N(R ６ｃ )-H) is used in an amount of 1 to 10 moles, preferably 1 to 5 moles, and the condensing agent is used in an amount of 1 to 10 moles, preferably 1 to 5 moles. Furthermore, a base (triethylamine, diisopropylethylamine, N-methylmorpholine, 4-dimethylaminopyridine, etc.) and an additive (1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, etc.) are added as needed. The base is used in an amount of 1 to 10 moles, preferably 1 to 5 moles, per mole of compound (6a). The additive is used in an amount of catalytically effective to 5 moles, preferably 0.05 to 3 moles, per mole of compound (6a). The reaction time is 10 minutes to 72 hours, preferably 30 minutes to 24 hours.

[0273] Step A-9 (9a)→(10a): Deprotection Reaction Prepared according to Method A, Step A-6.

[0274] Step A-10 (10a)→(11a): Acylation reaction Prepared according to Method A, Step A-7.

[0275] Method B This production method is a method for preparing the R ２ Among the compounds having an alkylalkoxy structure in R ２ The functional group contained in R is bonded to L. ６ｅ The compound (7b) having a sugar at the amino acid residue is prepared by the method of the present invention.

[0276] Step B-1 (1b) and (2b) → (3b): Substitution Reaction Compound (2b) having a leaving group W is reacted with compound (1b) in a solvent (acetonitrile, chloroform, dichloromethane, THF, 1,4-dioxane, DMF, water, etc., or a mixture thereof) at a temperature ranging from −30°C to the boiling point of the solvent used in the reaction, preferably from 0°C to 50°C. Compound (2b) is used in an amount of 1 to 10 moles, preferably 1 to 5 moles, per mole of compound (1b). A base (triethylamine, diisopropylethylamine, N-methylmorpholine, 4-dimethylaminopyridine, etc.) is added as needed. The base is used in an amount of 1 to 10 moles, preferably 1 to 5 moles, per mole of compound (1b). The reaction time is 10 minutes to 72 hours, preferably 30 minutes to 48 hours.

[0277] Step B-2 (3b)→(4b): Deprotection reaction Prepared according to Step A-6 of Method A.

[0278] Step B-3 (6a) → (5b): Condensation Reaction Compound (6a) is reacted with compound (4b) in a solvent (benzene, toluene, diethyl ether, dichloromethane, THF, 1,4-dioxane, DMF, water, etc., or a mixed solvent thereof) at a temperature from −30° C. to the boiling point of the solvent used in the reaction, preferably 0° C. to 50° C., in the presence of a condensing agent such as N,N′-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride, or the like. Relative to 1 mole of compound (6a), 1 to 5 moles, preferably 1 to 3 moles, of compound (4b) are used, and 1 to 5 moles, preferably 1 to 3 moles, of the condensing agent are used. If necessary, a base (e.g., triethylamine, diisopropylethylamine, N-methylmorpholine, 4-dimethylaminopyridine) and an additive (e.g., 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole) are added. The base is used in an amount of 1 to 10 moles, preferably 1 to 5 moles, relative to 1 mole of compound (6a). The additive is used in a catalytic amount to an excess amount, preferably 0.05 to 3 moles, relative to 1 mole of compound (6a). The reaction time is 10 minutes to 72 hours, preferably 30 minutes to 24 hours.

[0279] B-4 Step (5b) → (6b): Deprotection reaction PRO ２ can be deprotected by known methods depending on the protecting group used (acetyl group, benzyl group, tert-butyldimethylsilyl group, triisopropylsilyl group, tert-butyl group, etc.). ２When is an acetyl group, the reaction is carried out by reacting compound (5b) with an appropriate base (potassium carbonate, sodium methoxide, sodium hydroxide, etc.) in a solvent (methanol, ethanol, toluene, dichloromethane, THF, 1,4-dioxane, DMF, water, etc., or a mixture thereof) at a temperature ranging from −20° C. to the boiling point of the solvent used in the reaction, preferably 0° C. to 50° C. The amount of the base used ranges from a catalytic amount to a molar excess, preferably 0.1 to 10 moles. The reaction time is 10 minutes to 72 hours, preferably 30 minutes to 24 hours.

[0280] Step B-5 (6b)→(7b): Deprotection Reaction Prepared according to Step A-6 of Method A.

[0281] Method C This method involves the synthesis of the intermediates necessary for producing compound (2) and R ６ The functional group contained in R is bonded to L. ２ The method for producing compounds (7c), (8c) and (10c) each having acrylic acid at the base is also described.

[0282] Step C-1 (1c) → (2c): Condensation Reaction Compound (1c) is reacted in a solvent (benzene, toluene, diethyl ether, dichloromethane, THF, 1,4-dioxane, DMF, water, or a mixture thereof) at a temperature ranging from −30° C. to the boiling point of the solvent used in the reaction, preferably from 0° C. to 50° C., in the presence of a condensing agent such as N,N′-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline, or 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride, with an amine (PRO １ -NH-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -N(R ６ｈ The condensation agent is an amine (PRO)-H) with respect to 1 mole of compound (1c). １-NH-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -N(R ６ｈ )-H) is used in an amount of 1 to 10 moles, preferably 1 to 5 moles, and the condensing agent is used in an amount of 1 to an excess mole, preferably 1 to 5 moles. If necessary, a base (triethylamine, diisopropylethylamine, N-methylmorpholine, 4-dimethylaminopyridine, etc.) and an additive (1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, etc.) are added. The base is used in a catalytic amount to an excess mole, preferably 1 to 3 moles, per mole of compound (1c). The additive is used in a catalytic amount to an excess mole, preferably 0.05 to 3 moles, per mole of compound (1c). The reaction time is 10 minutes to 72 hours, preferably 30 minutes to 24 hours.

[0283] Step C-2 (2c)→(3c): Metathesis Reaction Compound (2c) is subjected to a metathesis reaction in a solvent (dichloromethane, toluene, 1,4-dioxane, DMF, tetrahydrofuran, water, or a mixed solvent thereof) at a temperature from 0° C. to the boiling point of the solvent used in the reaction, preferably from 0° C. to 140° C., using an acrylate ester (tert-butyl acrylate, or the like) in the presence of an olefin metathesis catalyst such as ...

Claims

1. The following formula (1): (In the formula, Ab represents an antibody or an antigen-binding fragment of the antibody, L represents a linker linking Ab and P, Ab is directly bound to L through its amino acid residue or indirectly bound to L through its sugar chain, P represents a monovalent group derived from a photosensitizer linked to L, x represents a number in the range of 1 to 10, and the photosensitizer is represented by the following formula (2): (where R １ , R ３ and R ４ each independently represents a hydrogen atom, a formyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group or an aromatic heterocyclic group, The C1-C6 alkoxycarbonyl group, the C1-C6 alkanoyl group, the mono-C1-C6 aminocarbonyl group, the di-C1-C6 alkylaminocarbonyl group, the mono-C1-C6 alkylamino group, the di-C1-C6 alkylamino group, the C1-C6 alkyl alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the cyclic hydrocarbon group, the aromatic hydrocarbon group or the aromatic heterocyclic group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group and an azide group; R ２ The functional group contained in R ５ The functional groups contained in R ６ (i) a group selected from the group consisting of functional groups included in R ２ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ａ (R ２ａ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｂ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｂ is a hydrogen atom or a C1-C6 alkyl group, or an optionally substituted amino group; ２ｃ (R ２ｃ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ -R ２ｄ -R ２ｅ (R ２ｄ is a C1-C6 alkylene group, R ２ｅ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ Or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH-C(=O)-(CH ２ ) ｐ -OH) or -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｇ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｇ is a hydrogen atom or a C1-C6 alkyl group) or a 5-6 membered aromatic heterocyclic group (the 5-6 membered aromatic heterocyclic group is -(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ R ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, -X-R (wherein X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, R ５ｄ is a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or ５ｆ (R ５ｆ is a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C6 alkylene group, R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide ６ｅ (-R ６ｅ is a C1-C6 alkyl group substituted with one or more hydroxy groups; (ii) R ６ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, -X-R (wherein X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, R ５ｄ is a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or ５ｆ (R ５ｆ is a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C6 alkylene group, R ６ｇ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ Or -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH(R ６ｉ ) (R ６ｈ is a hydrogen atom or a C1-C6 alkyl group, R ６ｉ is a hydrogen atom, -C(=O)-(CH ２ ) ｐ -NH ２ Or -C(=O)-(CH ２ ) ｐ (iii) R ５ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group; or ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ Or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ｇ -R ５ｈ (R ５ｇ is a C1-C6 alkylene group, R ５ｈ represents an optionally substituted amino group; R ６ is -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C6 alkylene group, R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide ６ｅ (-R ６ｅ and n is an integer from 1 to 6, p is an integer from 1 to 3, q ​​is an integer from 1 to 6, and r is an integer from 0 to 6.

2. R １ The antibody-photosensitizer conjugate or metal complex thereof according to claim 1, or a pharma- ceutical acceptable salt thereof, wherein represents a methyl group.

3. R ３ The antibody-photosensitizer conjugate or metal complex thereof according to claim 1 or 2, or a pharma- ceutical acceptable salt thereof, wherein represents a methyl group.

4. R ４ The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 3, or a pharma- ceutical acceptable salt thereof, wherein represents an ethyl group.

5. R １ and R ３ represents a methyl group, R ４ The antibody-photosensitizer conjugate or metal complex thereof, or a pharma- ceutical acceptable salt thereof according to any one of claims 1 to 4, wherein represents an ethyl group.

6. R ２ The functional group contained in R is bonded to L. ２ The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 5, or a pharma- ceutically acceptable salt thereof, wherein an amino group, a hydroxyl group or a thiol group contained in 7. R ２ The functional group contained in R is bonded to L. ２ The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 6, or a pharma- ceutical acceptable salt thereof, wherein an amino group or a hydroxy group contained in 8. R ２ The amino group or hydroxy group at the end of R is bonded to L, ２ -CH=CH-C(=O)-R ２ａ (R ２ａ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｂ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｂ is a hydrogen atom or a C1-C3 alkyl group, or an optionally substituted amino group substituted with an amino C1-C3 alkyl group, ２ｃ (R ２ｃ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ -R ２ｄ -R ２ｅ (R ２ｄ is a C1-C3 alkylene group, R ２ｅ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ Or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH-C(=O)-(CH ２ ) ｐ -OH) or -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｇ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｇ is a hydrogen atom or a C1-C3 alkyl group) or a 5-membered aromatic heterocyclic group (the 5-membered aromatic heterocyclic group is -(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, R ５ｂ represents an optionally substituted amino group, a 6-membered aromatic heterocyclic group, -X-R (wherein X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C3 alkanoyl group, R ５ｄ is a C1-C3 alkyl group, which is substituted with one or more optionally substituted amino groups; or ５ｆ (R ５ｆ is a C1-C3 alkoxy group, and the C1-C3 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ But, -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C3 alkylene group, R ６ｂ is a C1-C3 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C3 alkyl group, R ６ｄ represents a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide ６ｅ (-R ６ｅ is a C1-C3 alkyl group substituted by 1 to 3 hydroxy groups), and in all of the above formulas, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, and q is an integer of 1 to 6. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 7, or a pharma- ceutical acceptable salt thereof.

9. R ２ The amino group or hydroxy group at the end of R is bonded to L, ２ is expressed by the following formula: and the amino or hydroxy group indicated by the arrow is bonded to L; R ５ is expressed by the following formula: R is a group selected from the group consisting of ６ is expressed by the following formula: The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 8, or a pharma- ceutically acceptable salt thereof, wherein the conjugate is a group selected from the group consisting of:

10. R ２ The amino group at the end of R is bonded to L. ２ is -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ ) and R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, R ５ｂ is a 6-membered nitrogen-containing saturated heterocyclic group; R ６ But, -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C3 alkylene group, R ６ｂ is -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C3 alkyl group, R ６ｄ is a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups), and in all of the above formulas, m is an integer of 0 to 10, and n is an integer of 1 to 6. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 8, or a pharma- ceutical acceptable salt thereof.

11. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 10, wherein the photosensitizer is represented by the following formula, and the amino group indicated by the arrow is bonded to L, or a pharma- ceutical acceptable salt thereof.

12. The antibody-photosensitizer conjugate or metal complex thereof, or a pharma- ceutical acceptable salt thereof, according to any one of claims 1 to 10, wherein the photosensitizer is selected from the following, and the amino group indicated by the arrow is bound to L:

13. R ６ The functional group contained in R is bonded to L. ６ The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 5, or a pharma- ceutically acceptable salt thereof, wherein an amino group, a hydroxyl group or a thiol group contained in 14. R ６ The functional group contained in R is bonded to L. ６ The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 5 and 13, or a pharma- ceutically acceptable salt thereof, wherein an amino group or a hydroxy group contained in 15. R ６ The amino group or hydroxy group at the end of R is bonded to L, ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C3 alkyl group) or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C3 alkyl group) or ２ｊ -R ２ｋ (R ２ｊ is a C1-C3 alkylene group, R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ Or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, R ５ｂ represents an optionally substituted amino group, a 6-membered aromatic heterocyclic group, -X-R (wherein X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C3 alkanoyl group, R ５ｄ is a C1-C3 alkyl group, which is substituted with one or more optionally substituted amino groups; or ５ｆ (R ５ｆ is a C1-C3 alkoxy group, and the C1-C3 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ But, -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C3 alkylene group, R ６ｇ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ Or -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH(R ６ｉ ) (R ６ｈ is a hydrogen atom or a C1-C3 alkyl group, R ６ｉ is a hydrogen atom, -C(=O)-(CH ２ ) ｐ -NH ２ Or -C(=O)-(CH ２ ) ｐ In all of the above formulas, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, q ​​is an integer of 1 to 6, and r is an integer of 0 to 6. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 5, 13 and 14, or a pharma- ceutical acceptable salt thereof.

16. R ６ The amino group or hydroxy group at the end of R is bonded to L, ２ is expressed by the following formula: R is a group selected from the group consisting of ５ is expressed by the following formula: R is a group selected from the group consisting of ６ is expressed by the following formula: and the amino group or hydroxy group indicated by the arrow is bonded to L. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 5 and 13 to 15, or a pharma- ceutical acceptable salt thereof, 17. R ６ The amino group or hydroxy group at the end of R is bonded to L, ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C3 alkyl group; R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, R ５ｂ is a 6-membered nitrogen-containing saturated heterocyclic group; R ６ But, -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C3 alkylene group, R ６ｇ is -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH ２ (R ６ｈ wherein m is an integer of 0 to 10, n is an integer of 1 to 6, and r is an integer of 0 to 6. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 5 and 13 to 15, or a pharma- ceutical acceptable salt thereof, wherein m is an integer of 0 to 10, n is an integer of 1 to 6, and r is an integer of 0 to 6.

18. The antibody-photosensitizer conjugate or metal complex thereof, or a pharma- ceutical acceptable salt thereof, according to any one of claims 1 to 5 and 13 to 17, wherein the photosensitizer is selected from the following, and the amino group indicated by the arrow is bound to L:

19. R ５ The functional group contained in R is bonded to L. ５ The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 5, or a pharma- ceutically acceptable salt thereof, wherein an amino group, a hydroxyl group or a thiol group contained in 20. R ５ The functional group contained in R is bonded to L. ５ The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 5 and 19, wherein an amino group contained in is bonded to L, or a pharma- ceutical acceptable salt thereof.

21. R ５ The amino group at the end of R is bonded to L. ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is hydrogen or a C1-C3 alkyl group) or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C3 alkyl group) or ２ｊ -R ２ｋ (R ２ｊ is a C1-C3 alkylene group, R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ Or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ But, -R ５ｇ -R ５ｈ (R ５ｇ is a C1-C3 alkylene group, R ５ｈ represents a 6-membered nitrogen-containing saturated heterocyclic group substituted with an amino group or an amino C1-C3 alkyl group; ６ But, -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C3 alkylene group, R ６ｂ is a C1-C3 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is hydrogen or a C1-C3 alkyl group; R ６ｄ represents a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide ６ｅ (-R ６ｅ is a C1-C3 alkyl group substituted by 1 to 3 hydroxy groups), and in all of the above formulas, m is an integer of 0 to 10, n is an integer of 1 to 6, and q is an integer of 1 to 6. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 5 and 19 to 20, or a pharma- ceutical acceptable salt thereof.

22. The antibody-photosensitizer conjugate or metal complex thereof or a pharma- ceutical acceptable salt thereof according to claims 1 to 5 and 19 to 21, wherein the photosensitizer is selected from the following, and the amino group indicated by the arrow is bound to L:

23. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 22, wherein m is an integer of 0 to 5, or a pharma- ceutically acceptable salt thereof.

24. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 23, wherein m is an integer of 0 to 3, or a pharma- ceutically acceptable salt thereof.

25. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 24, or a pharma- ceutically acceptable salt thereof, wherein m is 1 or 2.

26. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 25, wherein m is 2, or a pharma- ceutically acceptable salt thereof.

27. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 26, wherein n is an integer of 1 to 3, or a pharma- ceutically acceptable salt thereof.

28. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 27, wherein n is 2, or a pharma- ceutically acceptable salt thereof.

29. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 28, wherein p is 1, or a pharma- ceutically acceptable salt thereof.

30. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 29, wherein q is an integer of 1 to 4, or a pharma- ceutically acceptable salt thereof.

31. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 30, wherein q is 3, or a pharma- ceutically acceptable salt thereof.

32. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 31, wherein r is an integer of 0 to 5, or a pharma- ceutically acceptable salt thereof.

33. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 32, wherein r is an integer of 0 to 3, or a pharma- ceutically acceptable salt thereof.

34. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 33, wherein r is 0, or a pharma- ceutically acceptable salt thereof.

35. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 34, or a pharma- ceutical acceptable salt thereof, wherein in formula (2), the optionally substituted amino group is a di-C1-C6 alkylamino group (the di-C1-C6 alkyl of the di-C1-C6 alkylamino group are each independently optionally substituted with a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkylsulfonyl group, a sulfonyl group, or an amino C1-C3 alkyl group) or a 3-8 membered nitrogen-containing saturated heterocyclic group (the 3-8 membered nitrogen-containing saturated heterocyclic group is optionally substituted with a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkylsulfonyl group, a sulfonyl group, or an amino C1-C3 alkyl group).

36. In the formula (2), the optionally substituted amino group is represented by the following formula: The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 35, or a pharma- ceutically acceptable salt thereof, wherein the conjugate is a group selected from the group consisting of:

37. In the above formula (2), -X-R is the following formula: The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 36, or a pharma- ceutical acceptable salt thereof, wherein the conjugate is a group selected from the group consisting of:

38. L is -Lb-La-Lp-NH-(CH ２ ) n ａ -Lc-Ld-* or -Lb-La-Lp-NH-(aromatic hydrocarbon group)-(CH ２ ) n ａ The antibody-photosensitizer conjugate according to any one of claims 1 to 37, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, represented by -Lc-Ld-*: In the formula, * indicates binding to P; Lb indicates a spacer that bonds the sugar chains of La and Ab, or a spacer that bonds the cysteine ​​residues of La and Ab; La indicates a linker in which 0 to 20 groups selected from the following group are linked in any order, and -(CH ２ CH ２ O) -, -(CH ２ )-, -C(=O)-NH-, -C(=O)- and -O-C(=O)-; ２ CH ２ O)- and -(CH ２ )- may be substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a cyano group, a nitro group, an amino group, an azido group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; The -NH- of -C(=O)-NH- of La may be substituted with one or more substituents selected from the group consisting of a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; Lp represents a linker consisting of 1 to 10 amino acid residues or is absent; n ａ represents an integer of 0 to 6; Lc represents *-C(=O)-NH-, *-NR ７ - (CH ２ ) n ｂ represents -, -O-, or a single bond, where * represents -(CH ２ ) n ａ - indicates that it is bonded to n ｂ represents an integer of 1 to 6; R ７ represents a hydrogen atom, a C1-C6 alkyl group, -(CH ２ ) n ｃ -COOH or -(CH ２ ) n ｄ represents —OH, ｃ represents an integer of 1 to 4, n ｄ represents an integer of 1 to 6; Ld represents *-CHR ８ - (CH ２ )-C(=O)-, *-CH ２ - (CHR ８ )-C(=O)-, *-CHR ８ -C(=O)-, *-CR ８ R ９ - (CH ２ )-C(=O)-, *-CR ８ R ９ -C(=O)-, *-(cyclic hydrocarbon group)-C(=O)-, *-O-C(=O)-, *-NR １０ -C(=O)- or *-C(=O)-, where * indicates a bond to Lc, R ８ and R ９ each independently represents a C1-C6 alkyl group, a C3-C7 cyclic hydrocarbon group, -(CH ２ ) n ｅ -NH ２ , -(CH ２ ) n ｆ -COOH or -(CH ２ ) n ｇ represents —OH, and R １０ represents a hydrogen atom or a C1-C6 alkyl group, n ｅ represents an integer of 0 to 6, n ｆ represents an integer of 1 to 4, n ｇ represents an integer of 1 to 4.

39. L is -Lb-La-Lp-NH-(CH ２ ) n ａ The antibody-photosensitizer conjugate according to any one of claims 1 to 38, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, represented by -Lc-Ld-*: In the formula, * indicates binding to P; Lb indicates a spacer binding the sugar chains of La and Ab, or a spacer binding the cysteine ​​residues of La and Ab; La indicates a linker in which 0 to 20 groups selected from the following group are linked in any order, and -(CH ２ CH ２ O) -, -(CH ２ )-, -C(=O)-NH-, -C(=O)- and -O-C(=O)-; ２ CH ２ O)- and -(CH ２ )- may be substituted with one or more substituents selected from the group consisting of halogen atoms, hydroxy groups, C1-C6 alkoxy groups, oxo groups, C1-C6 alkoxycarbonyl groups, C1-C6 alkanoyl groups, cyano groups, nitro groups, amino groups, and azido groups, C1-C6 alkoxycarbonyl groups, C1-C6 alkanoyl groups, aminocarbonyl groups, mono-C1-C6 alkylaminocarbonyl groups, di-C1-C6 alkylaminocarbonyl groups, mono-C1-C6 alkylamino groups, di-C1-C6 alkylamino groups, C1-C6 alkyl groups, C2-C6 alkenyl groups, C2-C6 alkynyl groups, cyclic hydrocarbon groups, aromatic aromatic hydrocarbon groups, and heterocyclic groups; The -NH- of -C(=O)-NH- of La may be substituted with one or more substituents selected from the group consisting of a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; Lp represents a linker consisting of 1 to 10 amino acid residues or is absent; n ａ represents 1; Lc represents -O-; Ld represents the following formula (* represents bonding to P, and the wavy line represents bonding to Lc): It indicates any one selected from the group consisting of:

40. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 37, or a pharma- ceutically acceptable salt thereof, wherein L is represented by -Lb-La-Lp-*: in the formula, * represents a bond to P; Lb represents a spacer that bonds the sugar chains of La and Ab, or a spacer that bonds the cysteine ​​residues of La and Ab; La represents a linker in which 0 to 20 groups selected from the following group are linked in any order, -(CH ２ CH ２ O) -, -(CH ２ )-, -C(=O)-NH-, -C(=O)- and -O-C(=O)-; ２ CH ２ O)- and -(CH ２ )- may be substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a cyano group, a nitro group, an amino group, an azido group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; The -NH- of -C(=O)-NH- of La may be substituted by one or more substituents selected from the group consisting of a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; Lp represents a linker consisting of 1 to 10 amino acid residues or is absent.

41. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 38 to 40, or a pharma- ceutical acceptable salt thereof, wherein La represents any one selected from the following group: *-(CH ２ CH ２ O) n １ - (CH ２ ) n ２ -C(=O)-, *-(CH ２ ) n ３ -C(=O)-NH-(CH ２ CH ２ O) n １ - (CH ２ ) n ２ -C(=O)-, *-(CH ２ ) n ４ -O-C(=O)- and *-(CH ２ ) n ５ -C(=O)- (wherein * indicates a bond to Lb, n １ represents an integer from 1 to 20, n ２ represents an integer from 1 to 12, and n ３ represents an integer from 1 to 6; n ４ represents an integer from 1 to 10, n ５ represents an integer from 1 to 10).

42. La is the following: *-(CH ２ CH ２ O) n １ - (CH ２ ) n ２ -C(=O)- or *-(CH ２ ) n ３ -C(=O)-NH-(CH ２ CH ２ O) n １ - (CH ２ ) n ２ -C(=O)- (wherein * indicates a bond to Lb, n １ represents an integer from 1 to 16, and n ２ represents an integer from 1 to 8; ３ The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 38 to 41, or a pharma- ceutically acceptable salt thereof, wherein R represents an integer of 1 to 4.

43. La is the following: *-(CH ２ CH ２ O) n １ - (CH ２ ) n ２ -C(=O)- or *-(CH ２ ) n ３ -C(=O)-NH-(CH ２ CH ２ O) n １ - (CH ２ ) n ２ -C(=O)- (wherein * indicates a bond to Lb, n １ represents an integer from 1 to 12, and n ２ represents an integer of 1 to 4, n ３ The antibody-photosensitizer conjugate according to any one of claims 38 to 42, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein R represents an integer of 1 to 3.

44. La is the following: *-(CH ２ CH ２ O) n １ - (CH ２ ) n ２ -C(=O)- or *-(CH ２ ) n ３ -C(=O)-NH-(CH ２ CH ２ O) n １ - (CH ２ ) n ２ -C(=O)- (wherein * indicates a bond to Lb, n １ represents an integer from 1 to 8; ２ represents an integer of 1 to 2, n ３ The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 38 to 43, or a pharma- ceutically acceptable salt thereof, wherein R represents an integer of 1 or 2.

45. La is the following: *-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-(CH ２ ) n ２ -C(=O)- or *-(CH ２ ) n ３ -C(=O)-NH-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-(CH ２ ) n ２ -C(=O)- (wherein * indicates a bond to Lb, n ２ represents an integer from 1 to 12, and n ３ The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 38 to 44, or a pharma- ceutical acceptable salt thereof, wherein R represents an integer of 1 to 6.

46. ​​La is the following: *-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ -C(=O)- or *-CH ２ CH ２ -C(=O)-NH-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ The antibody-photosensitizer conjugate according to any one of claims 38 to 45, which represents -C(=O)- (wherein * indicates that it is bound to Lb), or a metal complex thereof, or a pharma- ceutical acceptable salt thereof.

47. La is *-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ O-CH ２ CH ２ The antibody-photosensitizer conjugate according to any one of claims 38 to 46, which represents -C(=O)- (wherein * indicates that it is bound to Lb), or a metal complex thereof, or a pharma- ceutical acceptable salt thereof.

48. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 38 to 47, or a pharma- ceutically acceptable salt thereof, wherein Lp consists of 1 to 8 amino acid residues.

49. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 38 to 48, or a pharma- ceutically acceptable salt thereof, wherein Lp consists of 1 to 6 amino acid residues.

50. The antibody-photosensitizer conjugate or metal complex thereof, or a pharma- ceutical acceptable salt thereof, according to any one of claims 38 to 49, wherein Lp consists of 2 to 4 amino acid residues.

51. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 38 to 50, or a pharma- ceutically acceptable salt thereof, wherein Lp represents an amino acid sequence consisting of at least one amino acid selected from phenylalanine, glycine, valine, lysine, citrulline, serine, glutamic acid, aspartic acid, glutamine, alanine, proline, isoleucine, methionine, leucine, and asparagine.

52. Lp is any of the following: *-GGVA (SEQ ID NO: 37)-, *-AA-, *-AAN-, *-VA-, *-GGFG (SEQ ID NO: 38)-, *-FG-, *-GGPI (SEQ ID NO: 39)-, *-PI-, *-GGVCit (SEQ ID NO: 40)-, *-VCit-, *-ACit-, *-GGVK (SEQ ID NO: 41)-, *-VK-, *-GGFCit (SEQ ID NO: 42)-, *-FCit-, *-GGFM (SEQ ID NO: 43)-, *-FM-, *-GGLM (SEQ ID NO: 44)-, *-LM-, *-GGICit (SEQ ID NO: 45)- and *-ICit- (wherein * indicates binding to La). The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 38 to 51, or a pharma- ceutically acceptable salt thereof, which is any one selected from the group consisting of:

53. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 38 to 52, or a pharma- ceutically acceptable salt thereof, wherein Lp is any one selected from the group consisting of: *-AA-, *-AAN-, *-VA-, *-GGFG (sequence number 38)-, *-VCit- and *-ACit-, (wherein * indicates binding to La).

54. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 38 to 53, or a pharma- ceutical acceptable salt thereof, wherein Lp is *-AA- (where * indicates binding to La).

55. The antibody-photosensitizer conjugate or metal complex thereof, or a pharma- ceutical acceptable salt thereof, according to any one of claims 38 to 54, wherein Lp is cleavable in a target cell.

56. Lb is -(succinimide-3-yl-N)-, where -(succinimide-3-yl-N)- has the following structural formula: wherein * indicates binding to La, and the wavy line indicates binding via thioether formation with a side chain of a cysteine ​​residue in the antibody.

57. L is represented by -Lb-La-Lp-*, in which * indicates bonding with P, Lp is *-AA- (where * indicates bonding with La), and La is *-(CH ２ CH ２ O) ８ -CH ２ CH ２ -C(=O)- (wherein * indicates a bond to Lb), Lb is -(succinimid-3-yl-N)-, where -(succinimid-3-yl-N)- is represented by the following structural formula: wherein * indicates binding to La, and the wavy line indicates binding via thioether formation with a side chain of a cysteine ​​residue in the antibody.

58. -L-P has the formula: and the wavy line is bonded to a side chain of a cysteine ​​residue of the antibody by forming a thioether, or the antibody-photosensitizer conjugate or a metal complex thereof, or a pharma- ceutical acceptable salt thereof according to claim 1.

59. -L-P is a compound of the formula: and the wavy line is bonded to a side chain of a cysteine ​​residue of the antibody by forming a thioether, or the antibody-photosensitizer conjugate or a metal complex thereof, or a pharma- ceutical acceptable salt thereof according to claim 1.

60. -L-P has the formula: and the wavy line is bonded to a side chain of a cysteine ​​residue of the antibody by forming a thioether, or the antibody-photosensitizer conjugate or a metal complex thereof, or a pharma- ceutical acceptable salt thereof according to claim 1.

61. -L-P is a compound of the formula: and the wavy line is bonded to a side chain of a cysteine ​​residue of the antibody by forming a thioether, or the antibody-photosensitizer conjugate or a metal complex thereof, or a pharma- ceutical acceptable salt thereof according to claim 1.

62. -L-P is a compound of the formula: and the wavy line is bonded to a side chain of a cysteine ​​residue of the antibody by forming a thioether, or the antibody-photosensitizer conjugate or a metal complex thereof, or a pharma- ceutical acceptable salt thereof according to claim 1.

63. -L-P is a compound of the formula: and the wavy line is bonded to a side chain of a cysteine ​​residue of the antibody by forming a thioether, or the antibody-photosensitizer conjugate or a metal complex thereof, or a pharma- ceutical acceptable salt thereof according to claim 1.

64. -L-P is a compound of the formula: and the wavy line is bonded to a side chain of a cysteine ​​residue of the antibody by forming a thioether, or the antibody-photosensitizer conjugate or a metal complex thereof, or a pharma- ceutical acceptable salt thereof according to claim 1.

65. The antibody-photosensitizer conjugate according to any one of claims 1 to 64, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein x is in the range of 1 to 8.

66. The antibody-photosensitizer conjugate according to any one of claims 1 to 65, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein x is in the range of 3 to 8.

67. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 66, or a pharma- ceutically acceptable salt thereof, wherein x is in the range of 3.5 to 5.

5.

68. The antibody-photosensitizer conjugate according to any one of claims 1 to 67, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein x is in the range of 4 to 5.

69. The antibody-photosensitizer conjugate according to any one of claims 1 to 66, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein x is in the range of 7 to 8.

70. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 66 and 69, or a pharma- ceutically acceptable salt thereof, wherein x is in the range of 7.5 to 8.

71. The antibody or antigen-binding fragment of the antibody is anti-EpCAM antibody, anti-TROP2 antibody, anti-HER3 antibody, anti-DLL3 antibody, anti-FAP antibody, anti-CDH11 antibody, anti-A33 antibody, anti-CanAg antibody, anti-CD19 antibody, anti-CD20 antibody. Antibodies, anti-CD22 antibodies, anti-CD25 antibodies, anti-CD30 antibodies, anti-CD33 antibodies, anti-CD56 antibodies, anti-CD70 antibodies, anti-CD98 antibodies, anti-CEA antibodies, anti-Cripto antibodies, anti-EphA2 antibodies, anti-G250 antibodies, anti-MU The antibody-photosensitizer conjugate according to any one of claims 1 to 70, which is an anti-C1 antibody, an anti-GPNMB antibody, an anti-integrin antibody, an anti-PSMA antibody, an anti-tenascin-C antibody, an anti-SLC44A4 antibody, an anti-mesothelin antibody, an anti-ENPP3 antibody, an anti-CD47 antibody, an anti-EGFR antibody, an anti-GPR20 antibody or an anti-DR5 antibody, or an antigen-binding fragment of said antibody, or a metal complex thereof, or a pharma- ceutical acceptable salt thereof.

72. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 70, wherein the antibody or antigen-binding fragment of the antibody is an anti-EpCAM antibody, an anti-TROP2 antibody, an anti-CD25 antibody or an anti-EGFR antibody, or an antigen-binding fragment of the antibody, or a pharma-ceutical acceptable salt thereof.

73. The antibody-photosensitizer conjugate or metal complex thereof according to claim 72, or a pharma- ceutically acceptable salt thereof, wherein the anti-EpCAM antibody or antigen-binding fragment of said antibody comprises a CDRH1, a CDRH2 and a CDRH3, and a CDRL1, a CDRL2 and a CDRL3 of the following (a) or (b): (a) a CDRH1 consisting of the amino acid sequence set forth in SEQ ID NO:26, a CDRH2 consisting of the amino acid sequence set forth in SEQ ID NO:27 and a CDRH3 consisting of the amino acid sequence set forth in SEQ ID NO:28, a CDRL1 consisting of the amino acid sequence set forth in SEQ ID NO:30, a CDRL2 consisting of the amino acid sequence of QMS and a CDRL3 consisting of the amino acid sequence set forth in SEQ ID NO:31, and (b) a CDRH1 consisting of the amino acid sequence set forth in SEQ ID NO:26, a CDRH2 consisting of the amino acid sequence set forth in SEQ ID NO:27 and a CDRH3 consisting of the amino acid sequence set forth in SEQ ID NO:29, a CDRL1 consisting of the amino acid sequence set forth in SEQ ID NO:30, a CDRL2 consisting of the amino acid sequence of QMS and a CDRL3 consisting of the amino acid sequence set forth in SEQ ID NO:

31.

74. The antibody-photosensitizer conjugate or metal complex thereof or a pharma- ceutically acceptable salt thereof according to claim 72 or 73, wherein the anti-EpCAM antibody or antigen-binding fragment of said antibody comprises a heavy chain variable region and a light chain variable region selected from the group consisting of the following (a) to (e): (a) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 in SEQ ID NO:9 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 in SEQ ID NO:4, (b) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 in SEQ ID NO:10 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 in SEQ ID NO:5, (c) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 in SEQ ID NO:10 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 in SEQ ID NO:6, (d) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 12 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO: 5; and (e) a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 15 and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO:

4.

75. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 72 to 74, or a pharma- ceutically acceptable salt thereof, wherein the anti-EpCAM antibody or antigen-binding fragment of the antibody comprises a heavy chain and a light chain selected from the group consisting of the following (a) to (e): (a) a heavy chain consisting of the amino acid sequence represented by amino acid numbers 20 to 465 in SEQ ID NO:9 and a light chain consisting of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO:4, (b) a heavy chain consisting of the amino acid sequence represented by amino acid numbers 20 to 465 in SEQ ID NO:10 and a light chain consisting of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO:5, (c) a heavy chain consisting of the amino acid sequence represented by amino acid numbers 20 to 465 in SEQ ID NO:10 and a light chain consisting of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO:6, (d) a heavy chain consisting of the amino acid sequence represented by amino acid numbers 20 to 465 in SEQ ID NO:12 and a light chain consisting of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO:5, and (e) a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 of SEQ ID NO: 15, and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 of SEQ ID NO:

4.

76. The antibody-photosensitizer conjugate or metal complex thereof, or a pharma- ceutical acceptable salt thereof, according to any one of claims 72 to 74, wherein the anti-EpCAM antibody or antigen-binding fragment of said antibody comprises the following heavy chain variable region and light chain variable region: a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 135 of SEQ ID NO: 12, and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 of SEQ ID NO:

5.

77. The antibody-photosensitizer conjugate or metal complex thereof or a pharma- ceutical acceptable salt thereof according to any one of claims 72 to 76, wherein the anti-EpCAM antibody or antigen-binding fragment of said antibody comprises the following heavy and light chains: a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 465 of SEQ ID NO: 12, and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 of SEQ ID NO:

5.

78. The antibody-photosensitizer conjugate or metal complex thereof or a pharma- ceutical acceptable salt thereof according to claim 72, wherein the anti-TROP2 antibody or antigen-binding fragment of said antibody comprises the following heavy chain variable region and light chain variable region: a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 140 of SEQ ID NO: 16, and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 129 of SEQ ID NO:

17.

79. The antibody-photosensitizer conjugate or metal complex thereof or a pharma- ceutical acceptable salt thereof according to claim 72 or 78, wherein the anti-TROP2 antibody or antigen-binding fragment of said antibody comprises the following heavy and light chains: a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 470 of SEQ ID NO: 16, and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 234 of SEQ ID NO:

17.

80. The antibody-photosensitizer conjugate according to claim 72, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein the anti-CD25 antibody or antigen-binding fragment of said antibody comprises the following CDRH1, CDRH2 and CDRH3, and CDRL1, CDRL2 and CDRL3: CDRH1 consisting of the amino acid sequence set forth in SEQ ID NO: 32, CDRH2 consisting of the amino acid sequence set forth in SEQ ID NO: 33 and CDRH3 consisting of the amino acid sequence set forth in SEQ ID NO: 34, CDRL1 consisting of the amino acid sequence set forth in SEQ ID NO: 35, CDRL2 consisting of the amino acid sequence of FVS and CDRL3 consisting of the amino acid sequence set forth in SEQ ID NO:

36.

81. The antibody-photosensitizer conjugate or metal complex thereof or a pharma- ceutical acceptable salt thereof according to claim 72 or 80, wherein the anti-CD25 antibody or antigen-binding fragment of said antibody comprises the following heavy chain variable region and light chain variable region: a heavy chain variable region consisting of the amino acid sequence set forth in amino acid numbers 20 to 133 in SEQ ID NO:23, and a light chain variable region consisting of the amino acid sequence set forth in amino acid numbers 21 to 133 in SEQ ID NO:

21.

82. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 72, 80 and 81, or a pharma- ceutically acceptable salt thereof, wherein the anti-CD25 antibody or antigen-binding fragment of said antibody comprises the following heavy and light chains: a heavy chain consisting of the amino acid sequence set forth in amino acid numbers 20 to 463 in SEQ ID NO:23, and a light chain consisting of the amino acid sequence set forth in amino acid numbers 21 to 239 in SEQ ID NO:

21.

83. The antibody-photosensitizer conjugate according to claim 72, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein the anti-EGFR antibody or antigen-binding fragment of said antibody comprises the following heavy and light chains: a heavy chain consisting of the amino acid sequence represented by amino acid numbers 20 to 468 in SEQ ID NO:24, and a light chain consisting of the amino acid sequence represented by amino acid numbers 21 to 234 in SEQ ID NO:

25.

84. An antibody-photosensitizer conjugate or a metal complex thereof according to any one of claims 1 to 83, or a pharma- ceutical acceptable salt thereof, wherein the antibody or antigen-binding fragment of said antibody comprises a deletion or absence of one or two amino acids at the carboxyl terminus of the heavy chain.

85. An antibody-photosensitizer conjugate or a metal complex thereof according to any one of claims 1 to 84, wherein the antibody or antigen-binding fragment of said antibody lacks a lysine residue at the carboxyl terminus of the heavy chain, or a pharma- ceutical acceptable salt thereof.

86. An antibody-photosensitizer conjugate or a metal complex thereof, or a pharma- ceutical acceptable salt thereof, according to any one of claims 1 to 85, wherein the sugar chain of the antibody or the antigen-binding fragment of said antibody is a remodeled sugar chain.

87. The antibody-photosensitizer conjugate or metal complex thereof according to any one of claims 1 to 86, or a pharma- ceutical acceptable salt thereof, having a maximum absorption wavelength in the Q band of 600 nm to 800 nm.

88. An antibody-photosensitizer conjugate or a metal complex thereof according to any one of claims 1 to 87, or a pharma- ceutical acceptable salt thereof, having a maximum absorption wavelength in the Q band of 670 nm to 750 nm.

89. The antibody-photosensitizer conjugate or metal complex thereof, or a pharma- ceutical acceptable salt thereof, according to any one of claims 1 to 88, having a maximum absorption wavelength in the Q band of 705 nm to 720 nm or 730 nm to 745 nm.

90. The following formula (1): (wherein Ab represents a humanized anti-EpCAM antibody represented by the following heavy and light chains, or an antibody in which the lysine residue at the carboxyl terminus of the heavy chain of the anti-EpCAM antibody has been deleted, a heavy chain consisting of the amino acid sequence represented by amino acid numbers 20 to 465 in SEQ ID NO: 12, and a light chain consisting of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO: 5; -L-P represents the following formula: and x is 7.5 to 8, or 4 to 5, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

91. The following formula (1): (wherein Ab represents a humanized anti-EpCAM antibody represented by the following heavy and light chains, or an antibody in which the lysine residue at the carboxyl terminus of the heavy chain of the anti-EpCAM antibody has been deleted, a heavy chain consisting of the amino acid sequence represented by amino acid numbers 20 to 465 in SEQ ID NO: 12, and a light chain consisting of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO: 5; -L-P represents the following formula: and x is 7.5 to 8, or 4 to 5, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

92. The following formula (1): (wherein Ab represents a humanized anti-EpCAM antibody represented by the following heavy and light chains, or an antibody in which the lysine residue at the carboxyl terminus of the heavy chain of the anti-EpCAM antibody has been deleted, a heavy chain consisting of the amino acid sequence represented by amino acid numbers 20 to 465 in SEQ ID NO: 12, and a light chain consisting of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO: 5; -L-P represents the following formula: and x is 7.5 to 8, or 4 to 5, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

93. The following formula (1): (wherein Ab represents a humanized anti-EpCAM antibody represented by the following heavy and light chains, or an antibody in which the lysine residue at the carboxyl terminus of the heavy chain of the anti-EpCAM antibody has been deleted, a heavy chain consisting of the amino acid sequence represented by amino acid numbers 20 to 465 in SEQ ID NO: 12, and a light chain consisting of the amino acid sequence represented by amino acid numbers 21 to 239 in SEQ ID NO: 5; -L-P represents the following formula: and x is 7.5 to 8, or 4 to 5, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

94. J-La-Lp-NH-(CH ２ ) n ａ -Lc-Ld-P or J-La-Lp-NH-(aromatic hydrocarbon group)-(CH ２ ) n ａ a compound represented by the formula (I)-Lc-Ld-P, a metal complex thereof, or a pharma- ceutically acceptable salt thereof: J represents a cyclic structure containing an alkyne structure which reacts with an azide group to form a 1,2,3-triazole ring, or a compound which bonds to a side chain of an amino acid residue of an antibody or an antigen-binding fragment of the antibody, or a halogen atom; La represents a linker in which 0 to 20 groups selected from the following group are linked in any order, and ２ CH ２ O) -, -(CH ２ )-, -C(=O)-NH-, -C(=O)- and -O-C(=O)-; ２ CH ２ O)- and -(CH ２ )- may be substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a cyano group, a nitro group, an amino group, an azido group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; The -NH- of -C(=O)-NH- of La may be substituted with one or more substituents selected from the group consisting of a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; Lp represents a linker consisting of 1 to 10 amino acid residues or is absent; n ａ represents an integer of 0 to 6; Lc represents *-C(=O)-NH-, *-NR ７ - (CH ２ ) n ｂ represents -, -O-, or a single bond, where * represents -(CH ２ ) n ａ - indicates that it is bonded to n ｂ represents an integer of 1 to 6; R ７ represents a hydrogen atom, a C1-C6 alkyl group, -(CH ２ ) n ｃ -COOH or -(CH ２ ) n ｄ represents —OH, ｃ represents an integer of 1 to 4, n ｄ represents an integer of 1 to 6; Ld represents *-CHR ８ - (CH ２ )-C(=O)-, *-CH ２ - (CHR ８ )-C(=O)-, *-CHR ８ -C(=O)-, *-CR ８ R ９ - (CH ２ )-C(=O)-, *-CR ８ R ９ -C(=O)-, *-(cyclic hydrocarbon group)-C(=O)-, *-O-C(=O)-, *-NR １０ -C(=O)- or *-C(=O)-, where * indicates a bond to Lc, R ８ and R ９ each independently represents a C1-C6 alkyl group, a C3-C7 cyclic hydrocarbon group, -(CH ２ ) n ｅ -NH ２ , -(CH ２ ) n ｆ -COOH or -(CH ２ ) n ｇ represents —OH, and R １０ represents a hydrogen atom or a C1-C6 alkyl group, n ｅ represents an integer of 0 to 6, n ｆ represents an integer of 1 to 4, n ｇ represents an integer of 1 to 4; P represents a monovalent group derived from a photosensitizer linked to Ld, and the photosensitizer is represented by the following formula (2): (where R １ , R ３ and R ４ each independently represents a hydrogen atom, a formyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group or an aromatic heterocyclic group, The C1-C6 alkoxycarbonyl group, the C1-C6 alkanoyl group, the mono-C1-C6 aminocarbonyl group, the di-C1-C6 alkylaminocarbonyl group, the mono-C1-C6 alkylamino group, the di-C1-C6 alkylamino group, the C1-C6 alkyl alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the cyclic hydrocarbon group, the aromatic hydrocarbon group or the aromatic heterocyclic group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group and an azide group; R ２ The functional group contained in R ５ The functional groups contained in R ６ (i) a group selected from the group consisting of functional groups included in R ２ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ａ (R ２ａ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｂ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｂ is a hydrogen atom or a C1-C6 alkyl group, or an optionally substituted amino group; ２ｃ (R ２ｃ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ ), -R ２ｄ -R ２ｅ (R ２ｄ is a C1-C6 alkylene group, R ２ｅ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH-C(=O)-(CH ２ ) ｐ -OH) or -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｇ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｇ is a hydrogen atom or a C1-C6 alkyl group) or a 5-6 membered aromatic heterocyclic group (the 5-6 membered aromatic heterocyclic group is -(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ R ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, -X-R (wherein X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, R ５ｄ is a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or ５ｆ (R ５ｆ is a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C6 alkylene group, R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide ６ｅ (-R ６ｅ is a C1-C6 alkyl group substituted with one or more hydroxy groups; (ii) R ６ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, -X-R (wherein X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, R ５ｄ is a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or ５ｆ (R ５ｆ is a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C6 alkylene group, R ６ｇ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ Or -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH(R ６ｉ ) (R ６ｈ is a hydrogen atom or a C1-C6 alkyl group, R ６ｉ is a hydrogen atom, -C(=O)-(CH ２ ) ｐ -NH ２ Or -C(=O)-(CH ２ ) ｐ (iii) R ５ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group; or ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ｇ -R ５ｈ (R ５ｇ is a C1-C6 alkylene group, R ５ｈ represents an optionally substituted amino group; R ６ is -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C6 alkylene group, R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide ６ｅ (-R ６ｅ is a C1-C6 alkyl group substituted with one or more hydroxy groups; in all of the above formulas, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, q ​​is an integer of 1 to 6, and r is an integer of 0 to 6.

95. A compound represented by the formula J-La-Lp-P, a metal complex thereof, or a pharma- ceutically acceptable salt thereof: J represents a cyclic structure containing an alkyne structure that reacts with an azide group to form a 1,2,3-triazole ring, or a compound that bonds to a side chain of an amino acid residue of an antibody or an antigen-binding fragment of the antibody, or a halogen atom; La represents a linker in which 0 to 20 groups selected from the following group are linked in any order, and is -(CH ２ CH ２ O) -, -(CH ２ )-, -C(=O)-NH-, -C(=O)- and -O-C(=O)-; ２ CH ２ O)- and -(CH ２ )-, any hydrogen atom may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a cyano group, a nitro group, an amino group, an azido group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; The -NH- of -C(=O)-NH- of La may be substituted with one or more substituents selected from the group consisting of a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group, and an aromatic heterocyclic group; Lp represents a linker consisting of 1 to 10 amino acid residues or is absent; P represents a monovalent group derived from a photosensitizer linked to Ld, and the photosensitizer is represented by the following formula (2): (where R １ , R ３ and R ４ each independently represents a hydrogen atom, a formyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group or an aromatic heterocyclic group, The C1-C6 alkoxycarbonyl group, the C1-C6 alkanoyl group, the mono-C1-C6 aminocarbonyl group, the di-C1-C6 alkylaminocarbonyl group, the mono-C1-C6 alkylamino group, the di-C1-C6 alkylamino group, the C1-C6 alkyl alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the cyclic hydrocarbon group, the aromatic hydrocarbon group or the aromatic heterocyclic group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group and an azide group; R ２ The functional group contained in R ５ The functional groups contained in R ６ (i) a group selected from the group consisting of functional groups included in R ２ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ａ (R ２ａ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｂ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｂ is a hydrogen atom or a C1-C6 alkyl group, or an optionally substituted amino group; ２ｃ (R ２ｃ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ ), -R ２ｄ -R ２ｅ (R ２ｄ is a C1-C6 alkylene group, R ２ｅ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH-C(=O)-(CH ２ ) ｐ -OH) or -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｇ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｇ is a hydrogen atom or a C1-C6 alkyl group) or a 5-6 membered aromatic heterocyclic group (the 5-6 membered aromatic heterocyclic group is -(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ R ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, -X-R (wherein X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, R ５ｄ is a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or ５ｆ (R ５ｆ is a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C6 alkylene group, R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide ６ｅ (-R ６ｅ is a C1-C6 alkyl group substituted with one or more hydroxy groups; (ii) R ６ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ Or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, -X-R (wherein X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, R ５ｄ is a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or ５ｆ (R ５ｆ is a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C6 alkylene group, R ６ｇ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ Or -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH(R ６ｉ ) (R ６ｈ is a hydrogen atom or a C1-C6 alkyl group, R ６ｉ is a hydrogen atom, -C(=O)-(CH ２ ) ｐ -NH ２ Or -C(=O)-(CH ２ ) ｐ (iii) R ５ When the functional group contained in R is bonded to L, ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group; or ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ｇ -R ５ｈ (R ５ｇ is a C1-C6 alkylene group, R ５ｈ represents an optionally substituted amino group; R ６ is -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C6 alkylene group, R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide ６ｅ (-R ６ｅ is a C1-C6 alkyl group substituted with one or more hydroxy groups; in all of the above formulas, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, q ​​is an integer of 1 to 6, and r is an integer of 0 to 6.

96. J is a compound represented by the following formula (in each structural formula, * indicates that it is bonded to La): Or a maleimidyl group represented by the following formula (* indicates that it is bonded to La):

96. The compound according to claim 94 or 95, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

97. The following formula: The compound according to any one of claims 94 to 96, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein:

98. The following formula: The compound according to any one of claims 94 to 96, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein:

99. The following formula: The compound according to any one of claims 94 to 96, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein:

100. The following formula: The compound according to any one of claims 94 to 96, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein:

101. The following formula: The compound according to any one of claims 94 to 96, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein:

102. The following formula: The compound according to any one of claims 94 to 96, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein:

103. The following formula: The compound according to any one of claims 94 to 96, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein:

104. The following formula (Ia): (where R １ , R ３ and R ４ each independently represents a hydrogen atom, a formyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, a mono-C1-C6 alkylamino group, a di-C1-C6 alkylamino group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyclic hydrocarbon group, an aromatic hydrocarbon group or an aromatic heterocyclic group, The C1-C6 alkoxycarbonyl group, the C1-C6 alkanoyl group, the mono-C1-C6 aminocarbonyl group, the di-C1-C6 alkylaminocarbonyl group, the mono-C1-C6 alkylamino group, the di-C1-C6 alkylamino group, the C1-C6 alkyl alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the cyclic hydrocarbon group, the aromatic hydrocarbon group or the aromatic heterocyclic group may be substituted by one or more substituents selected from the group consisting of a halogen atom, a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkanoyl group, an aminocarbonyl group, a mono-C1-C6 alkylaminocarbonyl group, a di-C1-C6 alkylaminocarbonyl group, a cyano group, a nitro group, an amino group and an azide group; R ２ , R ５ and R ６ The combination is selected from the following groups (i) to (iii): Group (i): R ２ is -CH=CH-C(=O)-R ２ａ (R ２ａ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｂ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｂ is a hydrogen atom or a C1-C6 alkyl group, or an optionally substituted amino group; ２ｃ (R ２ｃ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ -R ２ｄ -R ２ｅ (R ２ｄ is a C1-C6 alkylene group, R ２ｅ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ Or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH-C(=O)-(CH ２ ) ｐ -OH) or -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｇ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｇ is a hydrogen atom or a C1-C6 alkyl group) or a 5-6 membered aromatic heterocyclic group (the 5-6 membered aromatic heterocyclic group is -(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ R ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, -X-R (wherein X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, R ５ｄ is a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or ５ｆ (R ５ｆ is a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C6 alkylene group, R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide ６ｅ (-R ６ｅ represents a C1-C6 alkyl group substituted with one or more hydroxy groups; Group (ii): R ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ Or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ａ -R ５ｂ (R ５ａ is a C1-C6 alkylene group, R ５ｂ represents an optionally substituted amino group, a 5- or 6-membered aromatic heterocyclic group, -X-R (wherein X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C6 alkanoyl group, R ５ｄ is a C1-C6 alkyl group, and the C1-C6 alkyl group is substituted with one or more optionally substituted amino groups; or ５ｆ (R ５ｆ is a C1-C6 alkoxy group, and the C1-C6 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ is -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C6 alkylene group, R ６ｇ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ Or -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH(R ６ｉ ) (R ６ｈ is a hydrogen atom or a C1-C6 alkyl group, R ６ｉ is a hydrogen atom, -C(=O)-(CH ２ ) ｐ -NH ２ Or -C(=O)-(CH ２ ) ｐ Group (iii): R ２ is -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C6 alkyl group) or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C6 alkyl group; or ２ｊ -R ２ｋ (R ２ｊ is a C1-C6 alkylene group, R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ Or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ is -R ５ｇ -R ５ｈ (R ５ｇ is a C1-C6 alkylene group, R ５ｈ represents an optionally substituted amino group; R ６ is -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C6 alkylene group, R ６ｂ is a C1-C6 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C6 alkyl group, R ６ｄ represents a C1-C6 alkyl group optionally substituted with one or more hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide ６ｅ (-R ６ｅ is a C1-C6 alkyl group substituted with one or more hydroxy groups; in all of the above formulas, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, q ​​is an integer of 1 to 6, and r is an integer of 0 to 6), or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

105. R １ The compound according to claim 104, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein represents a methyl group.

106. R ３ 106. The compound according to claim 104 or 105, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein represents a methyl group.

107. R ４ The compound according to any one of claims 104 to 106, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein represents an ethyl group.

108. R １ and R ３ represents a methyl group, R ４ The compound according to any one of claims 104 to 107, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein represents an ethyl group.

109. R ２ , R ５ and R ６ is selected from group (i), ２ -CH=CH-C(=O)-R ２ａ (R ２ａ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｂ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｂ is a hydrogen atom or a C1-C3 alkyl group, or an optionally substituted amino group substituted with an amino C1-C3 alkyl group, ２ｃ (R ２ｃ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ ), -R ２ｄ -R ２ｅ (R ２ｄ is a C1-C3 alkylene group, R ２ｅ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH-C(=O)-(CH ２ ) ｐ -OH) or -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ , -N(R ２ｇ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ (R ２ｇ is a hydrogen atom or a C1-C3 alkyl group) or a 5-membered aromatic heterocyclic group (the 5-membered aromatic heterocyclic group is -(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, R ５ｂ represents an optionally substituted amino group, a 6-membered aromatic heterocyclic group, -X-R (wherein X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C3 alkanoyl group, R ５ｄ is a C1-C3 alkyl group, which is substituted with one or more optionally substituted amino groups; or ５ｆ (R ５ｆ is a C1-C3 alkoxy group, and the C1-C3 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ But, -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C3 alkylene group, R ６ｂ is a C1-C3 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C3 alkyl group, R ６ｄ represents a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide ６ｅ (-R ６ｅ is a C1-C3 alkyl group substituted with 1 to 3 hydroxy groups, and in all of the above formulas, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, and q is an integer of 1 to 6. The compound or metal complex thereof according to any one of claims 104 to 108, or a pharma- ceutically acceptable salt thereof.

110. R ２ , R ５ and R ６ is selected from group (i), ２ is expressed by the following formula: R is a group selected from the group consisting of ５ is expressed by the following formula: R is a group selected from the group consisting of ６ is expressed by the following formula: The compound according to any one of claims 104 to 109, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein R is a substituted or unsubstituted aryl group.

111. R ２ , R ５ and R ６ is selected from group (i), ２ is -C(=O)-R ２ｆ (R ２ｆ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ ) and R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, R ５ｂ is a 6-membered nitrogen-containing saturated heterocyclic group; R ６ But, -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C3 alkylene group, R ６ｂ is -N(R ６ｃ )-R ６ｄ (R ６ｃ is a hydrogen atom or a C1-C3 alkyl group, R ６ｄ is a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups), and in all of the above formulas, m is an integer of 0 to 10, and n is an integer of 1 to 6. The compound or metal complex thereof according to any one of claims 104 to 109, or a pharma- ceutically acceptable salt thereof.

112. The compound represented by formula (Ia) according to any one of claims 104 to 111, wherein the compound is represented by the following formula:

113. The compound represented by formula (Ia) according to any one of claims 104 to 111, wherein the compound is represented by the following formula:

114. R ２ , R ５ and R ６ is selected from group (ii), R ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C3 alkyl group) or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C3 alkyl group) or ２ｊ -R ２ｋ (R ２ｊ is a C1-C3 alkylene group, R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, R ５ｂ represents an optionally substituted amino group, a 6-membered aromatic heterocyclic group, -X-R (wherein X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ -N(R ５ｃ )-R ５ｄ (R ５ｃ is a hydrogen atom or a C1-C3 alkanoyl group, R ５ｄ is a C1-C3 alkyl group, which is substituted with one or more optionally substituted amino groups; or ５ｆ (R ５ｆ is a C1-C3 alkoxy group, and the C1-C3 alkoxy group is substituted with one or more optionally substituted amino groups; R ６ But, -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C3 alkylene group, R ６ｇ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -NH ２ Or -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH(R ６ｉ ) (R ６ｈ is a hydrogen atom or a C1-C3 alkyl group, R ６ｉ is a hydrogen atom, -C(=O)-(CH ２ ) ｐ -NH ２ Or -C(=O)-(CH ２ ) ｐ In all of the above formulas, m is an integer of 0 to 10, n is an integer of 1 to 6, p is an integer of 1 to 3, q ​​is an integer of 1 to 6, and r is an integer of 0 to 6. The compound or metal complex thereof according to any one of claims 104 to 108, or a pharma- ceutically acceptable salt thereof.

115. R ２ , R ５ and R ６ is selected from group (ii), R ２ is expressed by the following formula: R is a group selected from the group consisting of ５ is expressed by the following formula: R is a group selected from the group consisting of ６ is expressed by the following formula: The compound according to any one of claims 104 to 108 and 114, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein R is a group selected from the group consisting of:

116. R ２ , R ５ and R ６ is selected from group (ii), R ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is a hydrogen atom or a C1-C3 alkyl group; R ５ But, -R ５ａ -R ５ｂ (R ５ａ is a C1-C3 alkylene group, R ５ｂ is a 6-membered nitrogen-containing saturated heterocyclic group; R ６ But, -R ６ｆ -C(=O)-R ６ｇ (R ６ｆ is a C1-C3 alkylene group, R ６ｇ is -N(R ６ｈ )-(CH ２ CH ２ O) ｒ - (CH ２ ) ｎ -NH ２ (R ６ｈ In all of the above formulas, m is an integer of 0 to 10, n is an integer of 1 to 6, and r is an integer of 0 to 6. The compound or metal complex thereof according to any one of claims 104 to 108 and 114, or a pharma- ceutically acceptable salt thereof.

117. The compound represented by formula (Ia) according to any one of claims 104 to 108 and 114 to 116, wherein the compound is represented by the following formula:

118. R ２ , R ５ and R ６ is selected from group (iii), R ２ -CH=CH-C(=O)-R ２ｈ (R ２ｈ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide), -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH(R ２ｉ is hydrogen or a C1-C3 alkyl group) or -N(R ２ｉ )-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ (R ２ｉ is a hydrogen atom or a C1-C3 alkyl group) or ２ｊ -R ２ｋ (R ２ｊ is a C1-C3 alkylene group, R ２ｋ is -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ or -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, and R is a residue of a monosaccharide; ５ But, -R ５ｇ -R ５ｈ (R ５ｇ is a C1-C3 alkylene group, R ５ｈ represents a 6-membered nitrogen-containing saturated heterocyclic group substituted with an amino group or an amino C1-C3 alkyl group; ６ But, -R ６ａ -C(=O)-R ６ｂ (R ６ａ is a C1-C3 alkylene group, R ６ｂ is a C1-C3 alkoxy group, —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OH, -O-(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -OCH ３ , —O—(CH ２ CH ２ O) ｍ - (CH ２ ) ｎ -Optionally substituted amino group, -O-(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide) or -N(R ６ｃ )-R ６ｄ (R ６ｃ is hydrogen or a C1-C3 alkyl group; R ６ｄ represents a C1-C3 alkyl group optionally substituted with 1 to 3 hydroxy groups or -(CH ２ ) ｑ -X-R (X is -S-, -O-, -CH ２ - or -NH-, where R is a residue of a monosaccharide ６ｅ (-R ６ｅ is a C1-C3 alkyl group substituted with 1 to 3 hydroxy groups, and in all of the above formulas, m is an integer of 0 to 10, n is an integer of 1 to 6, and q is an integer of 1 to 6. The compound or metal complex thereof according to any one of claims 104 to 108, or a pharma- ceutically acceptable salt thereof.

119. The compound represented by formula (Ia) according to any one of claims 104 to 108 and 118, wherein the compound is represented by the following formula:

120. The compound according to any one of claims 104 to 119, wherein m is an integer of 0 to 5, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

121. The compound according to any one of claims 104 to 120, wherein m is an integer of 0 to 3, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

122. The compound according to any one of claims 104 to 121, wherein m is 1 or 2, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

123. The compound according to any one of claims 104 to 122, wherein m is 2, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

124. The compound according to any one of claims 104 to 123, wherein n is an integer of 1 to 3, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

125. The compound according to any one of claims 104 to 124, wherein n is 2, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

126. The compound according to any one of claims 104 to 125, wherein p is 1, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

127. The compound according to any one of claims 104 to 126, wherein q is an integer of 1 to 4, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

128. The compound according to any one of claims 104 to 127, wherein q is 3, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

129. The compound according to any one of claims 104 to 128, wherein r is an integer of 0 to 5, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

130. The compound according to any one of claims 104 to 129, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof, wherein r is an integer of 0 to 3.

131. The compound according to any one of claims 104 to 130, wherein r is 0, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

132. The compound or metal complex thereof according to any one of claims 104 to 131, or a pharma- ceutically acceptable salt thereof, wherein in formula (Ia), the optionally substituted amino group is a di-C1-C6 alkylamino group (the di-C1-C6 alkyl of the di-C1-C6 alkylamino group may each independently be substituted with a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkylsulfonyl group, a sulfonyl group, or an amino C1-C3 alkyl group), or a 3-8 membered nitrogen-containing saturated heterocyclic group (the 3-8 membered nitrogen-containing saturated heterocyclic group may be substituted with a hydroxy group, a C1-C6 alkoxy group, an oxo group, a C1-C6 alkylsulfonyl group, a sulfonyl group, or an amino C1-C3 alkyl group).

133. The compound according to any one of claims 104 to 132, wherein in formula (Ia), the optionally substituted amino group is represented by the following formula: or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

134. In the formula (Ia), -X-R is the following: The compound according to any one of claims 104 to 133, or a metal complex thereof, or a pharma- ceutically acceptable salt thereof.

135. The compound according to any one of claims 104 to 134, or a metal complex thereof, or a pharma- ceutical acceptable salt thereof, having a maximum absorption wavelength in the Q band of 600 nm to 800 nm.

136. The compound according to any one of claims 104 to 135, or a metal complex thereof, or a pharma- ceutical acceptable salt thereof, having a maximum absorption wavelength in the Q band of 640 nm to 780 nm.

137. The compound according to any one of claims 104 to 136, or a metal complex thereof, or a pharma- ceutical acceptable salt thereof, having a maximum absorption wavelength in the Q band of 670 nm to 750 nm.

138. The compound according to any one of claims 104 to 137, or a metal complex thereof, or a pharma- ceutical acceptable salt thereof, having a maximum absorption wavelength in the Q band of 690 to 710 nm or 715 to 735 nm.

139. A pharmaceutical composition comprising any one selected from the antibody-photosensitizer conjugate according to claims 1 to 93, and the compounds according to claims 104 to 138 and pharma- ceutically acceptable salts or metal complexes thereof.

140. An antitumor agent comprising any one selected from the group consisting of an antibody-photosensitizer conjugate according to claims 1 to 93, a compound according to claims 104 to 138 and a pharma- ceutical acceptable salt or metal complex thereof, and a pharmaceutical composition according to claim 139.

141. The antitumor agent according to claim 140, for use in photodynamic therapy (PDT).

142. The antitumor agent according to claim 140 or 141, wherein the tumor to which the antitumor agent is applied is lung cancer, renal cancer, urothelial cancer, colon cancer, prostate cancer, glioblastoma multiforme, ovarian cancer, pancreatic cancer, breast cancer, melanoma, skin cancer, liver cancer, bladder cancer, gastric cancer, esophageal cancer, uterine cancer, testicular cancer, cervical cancer, placental choriocarcinoma, glioblastoma multiforme, brain tumor, head and neck cancer, thyroid cancer, mesothelioma, gastrointestinal stromal tumor (GIST), gallbladder cancer, bile duct cancer, adrenal cancer, squamous cell carcinoma, leukemia, malignant lymphoma, plasmacytoma, myeloma, or sarcoma.

143. The antitumor agent according to any one of claims 140 to 142, wherein the tumor to which the antitumor agent is applied is lung cancer, breast cancer, stomach cancer, bladder cancer, bile duct cancer, esophageal cancer, prostate cancer, or head and neck cancer.

144. An antitumor agent according to any one of claims 140 to 143, characterized in that the antitumor agent is administered to a subject and then the tumor site is irradiated with light.

145. The antitumor agent according to claim 144, which is applied to a tumor site of a subject with light having a wavelength of 600 nm to 800 nm.

146. The antitumor agent according to claim 144 or 145, which is applied to the tumor site of a subject with light having a wavelength of 640 nm to 780 nm.

147. The antitumor agent according to any one of claims 144 to 146, which is applied to a tumor site of a subject by irradiation with light having a wavelength of 670 nm to 750 nm.

148. The antitumor agent according to any one of claims 144 to 147, which is applied to a tumor site of a subject by irradiation with light having a wavelength of 680 to 700 nm or 720 to 745 nm.

149. The antitumor agent according to any one of claims 144 to 148, in which the antitumor agent is administered once to a subject, and then light irradiation is performed once a day for a total of 1 to 21 times.

150. The antitumor agent according to any one of claims 144 to 149, in which the antitumor agent is administered once to a subject, and then light irradiation is carried out once a day for a total of 4 to 21 times.

151. The antitumor agent according to any one of claims 144 to 150, wherein the antitumor agent is administered once to a subject, and then light irradiation is performed once a day for a total of 4 to 14 times.

152. The antitumor agent according to any one of claims 144 to 151, wherein the antitumor agent is administered once to a subject, and then light irradiation is performed once a day for a total of 4 to 7 times.

153. The antitumor agent according to any one of claims 144 to 152, wherein the antitumor agent is administered once to a subject, and then light irradiation is performed once a day for a total of seven times.

154. The antitumor agent according to any one of claims 144 to 152, wherein the antitumor agent is administered once to a subject, and then light irradiation is performed once a day for a total of four times.

155. The antitumor agent according to any one of claims 144 to 154, wherein the antitumor agent is administered once to a subject, and then the first light irradiation is carried out 1 to 72 hours later.

156. The antitumor agent according to any one of claims 144 to 155, wherein the antitumor agent is administered once to a subject, and then the first light irradiation is carried out 20 to 28 hours later.

157. The antitumor agent according to any one of claims 144 to 156, wherein the antitumor agent is administered once to a subject, and then the first light irradiation is carried out about 24 hours later.

158. The antitumor agent according to any one of claims 144 to 155, which is administered once to a subject, and then irradiated once with light approximately 48 hours later.

159. The antitumor agent according to any one of claims 144 to 158, wherein the light irradiation is carried out approximately every 24 hours.

160. After the antitumor agent is administered to the subject, the light irradiation dose per irradiation is 2 to 500 J / cm ２ , preferably 10 to 500 J / cm ２ The antitumor agent according to any one of claims 144 to 159, 161. After the antitumor agent is administered to the subject, the light irradiation dose per irradiation is 50-450 J / cm ２ The antitumor agent according to any one of claims 144 to 160, 162. After the antitumor agent is administered to the subject, the light irradiation dose per irradiation is 50-300 J / cm ２ The antitumor agent according to any one of claims 144 to 161, 163. The antitumor agent according to any one of claims 144 to 162, wherein light irradiation is performed by adjusting the light irradiation intensity so that the irradiation time is from 100 seconds to 10 days.

164. The antitumor agent according to any one of claims 144 to 163, wherein the irradiation time per irradiation is from 100 seconds to 1 day.

165. After the antitumor agent is administered to the subject, the irradiation intensity per irradiation is 1000 mW / cm ２ The antitumor agent according to any one of claims 144 to 164, wherein:

166. After the antitumor agent is administered to the subject, the irradiation intensity per irradiation is 10 μW / cm ２ ~1000mW / cm ２ The antitumor agent according to any one of claims 144 to 165, 167. After the antitumor agent is administered to the subject, the irradiation intensity per irradiation is 60 μW / cm ２ ~800mW / cm ２ The antitumor agent according to any one of claims 144 to 166, 168. After the antitumor agent is administered to the subject, the irradiation intensity per irradiation is 30 mW / cm ２ ~400mW / cm ２ The antitumor agent according to any one of claims 144 to 167, 169. After the antitumor agent is administered to the subject, the irradiation intensity per irradiation is 10 mW / cm ２ ~200mW / cm ２ The antitumor agent according to any one of claims 144 to 168, 170. After the antitumor agent is administered to the subject, the irradiation intensity per irradiation is about 780 mW / cm ２ The antitumor agent according to any one of claims 144 to 167, 171. After the antitumor agent is administered to the subject, the irradiation intensity per irradiation is about 156 mW / cm ２ The antitumor agent according to any one of claims 144 to 169, 172. After the antitumor agent is administered to the subject, the irradiation intensity per irradiation is about 78 mW / cm ２ The antitumor agent according to any one of claims 144 to 169, 173. The antitumor agent according to any one of claims 144 to 172, which is used to comprise one or more treatment cycles comprising the administration and irradiation.

174. The antitumor agent of claim 173, comprising at least three of said treatment cycles.

175. The antitumor agent of claim 173, comprising four or more cycles of said treatment.

176. The antitumor agent according to any one of claims 173 to 175, wherein the administration interval of the antitumor agent is from 1 day to 2 months.

177. The antitumor agent according to any one of claims 173 to 175, wherein the administration interval of the antitumor agent is from 3 days to 1 month.

178. The antitumor agent according to any one of claims 173 to 175, wherein the administration interval of the antitumor agent is 5 to 10 days.

179. An antitumor agent according to any one of claims 144 to 178, used in combination with an immune checkpoint inhibitor.

180. The antitumor agent according to claim 179, wherein the immune checkpoint inhibitor is any one or more selected from the group consisting of anti-PD-1 antibody, anti-PD-L1 antibody, anti-CTLA-4 antibody, anti-TIM-3 antibody, anti-LAG-3 antibody, anti-TIGIT antibody, anti-BTLA antibody, and anti-VISTA antibody.

181. The antitumor agent according to claim 179, wherein the immune checkpoint inhibitor is one or more selected from the group consisting of anti-PD-1 antibody, anti-PD-L1 antibody, and anti-CTLA-4 antibody.

182. The antitumor agent of claim 179, wherein the immune checkpoint inhibitor is an anti-PD-1 antibody.

183. The antitumor agent of claim 179, wherein the immune checkpoint inhibitor is one or more selected from the group consisting of nivolumab, pembrolizumab, pidilizumab, cemiplimab, toripalimab, dostallimab, atezolizumab, durvalumab, avelumab, ipilimumab, tremelimumab, tiragolumab, leratolimab, LAG525, MAB10, BTLA-8.2, and JNJ-61610588.

184. The antitumor agent of any one of claims 144 to 183, wherein the subject is a human.

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