Compound, composition including the same, composition for diagnosis or therapy of tumors including the composition, and photodynamic or sonodynamic therapy using the composition for mitochondria-targeted diagnosis or therapy of tumors

Abstract

A compound represented by the following chemical formula 1, a composition comprising said compound, a composition for diagnosing or treating tumors comprising said composition, and a photodynamic or sonication therapy method using said composition for diagnosing or treating tumors are provided: Refer to the description of the above chemical formula 1 as described in this specification.

Description

Technology Field

[0001] The invention relates to a compound, a composition containing the same, a composition for diagnosing or treating tumors containing the said composition, and a photodynamic or ultrasonodynamic treatment method using the said composition for diagnosing or treating tumors. Background Technology

[0002] Photodynamic therapy (PDT) and ultrasonic therapy (SDT) are medical technologies for the treatment of various types of cancer and other diseases.

[0003] Photodynamic therapy (PDT) requires a photosensitizer (PS), light, and oxygen. Specifically, the photosensitizer (PS) is activated under light irradiation; the excited photosensitizer interacts with oxygen molecules to generate cytotoxic reactive oxygen species (ROS), which can kill cancer cells by oxidizing molecules within the body. Ultrasonic therapy (SDT) is carried out through a process similar to photodynamic therapy, except that sound waves are irradiated instead of light.

[0004] Since both photodynamic therapy (PDT) and sonicational therapy (SDT) utilize cell death through ROS generation as a treatment method, it is important to enhance the selectivity of photosensitizers (PS) for cancer cells or tumors. The problem to be solved

[0005] The present invention provides a compound having high tumor selectivity and therapeutic efficiency, a composition containing the same, a composition for diagnosing or treating tumors containing the said composition, and a photodynamic or sonication therapy method using the said composition for diagnosing or treating tumors. means of solving the problem

[0006] According to one aspect, a compound represented by the following chemical formula 1 is provided:

[0007] <Chemical Formula 1>

[0008]

[0009] Among the above chemical formula 1,

[0010] A is a photosensitizer, and

[0011] L1 and L-2 are independently *-C(R6)(R7)-*', *-C(R6)=*', *=C(R7)-*', *-C(R6)=C(R7)-*', *-C(=O)-*', *-C(=S)-*', *-N(R6)-*', *-O-*', *-S-*', at least one R 10a C6-C substituted or unsubstituted 30 Arylgi, at least one R 10a C1-C substituted or unsubstituted 30 It is a heteroaryl group or any combination thereof, and

[0012] n1 and n2 are independent integers from 1 to 20, and

[0013] R1 to R7 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, at least one R 10a C1-C substituted or unsubstituted 30 alkyl group, at least one R 10a C2-C substituted or unsubstituted 30 alkenyl group, at least one R 10a C2-C substituted or unsubstituted 30 alkynyl group, at least one R 10a C1-C substituted or unsubstituted 30 Alkoxy group, at least one R 10a C1-C substituted or unsubstituted 30 alkylthio group, at least one R 10a C6-C substituted or unsubstituted 30 Arylgi, at least one R 10a C6-C substituted or unsubstituted 30 aryloxy group, at least one R10a C6-C substituted or unsubstituted 30 arylthio, -C(Q1)(Q2)(Q3), -N(Q1)(Q2), -C(=O)(Q1), or any combination thereof, and

[0014] The above R 10a Is,

[0015] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group;

[0016] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 30 Carbocyclic group, C1-C 30 Heterocyclic group, C6-C 30 aryloxy group, C6-C 30 Arylthiogi, -N(Q 11 )(Q 12 ), -C(=O)(Q 11 ), or substituted or unsubstituted with any combination thereof, C1-C 20 Alkyl group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, or C1-C 20 Alkoxygenation;

[0017] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, C1-C 20 Alkoxy group, C3-C 30 Carbocyclic group, C1-C 30 Heterocyclic group, C6-C 30 aryloxy group, C6-C 30 Arylthiogi, -N(Q 21 )(Q 22 ), -C(=O)(Q 21 ), or substituted or unsubstituted with any combination thereof, C3-C 30 Carbocyclic group, C1-C 30 Heterocyclic group, C6-C 30aryloxy group, or C6-C 30 Arylthiogi; or

[0018] -N(Q 31 )(Q 32 ) or -C(=O)(Q 31 );

[0019] And,

[0020] The above Q1 to Q3, Q 11 , Q 12 , Q 21 , Q 22 , Q 31 and Q 32 They are independently hydrogen; deuterium; hydroxyl group; cyano group; nitro group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 alkynyl group; C1-C 20 Alkoxy group; or deuterium, -F, cyano group, C1-C 10 Alkyl group, C1-C 10 C3-C substituted or unsubstituted with an alkoxy group, a phenyl group, a biphenyl group, or any combination thereof 30 Carbocyclic group or C1-C 30 It is a heterocyclic group.

[0021] According to another aspect, a composition comprising the aforementioned compound or a pharmaceutically acceptable salt thereof; and water, a buffer solution, or an organic solvent is provided.

[0022] The compound included in the above composition can form a self-assembled nanostructure.

[0023] The above composition may further include antimony-doped tin oxide (ATO).

[0024] The above composition can generate reactive oxygen species (ROS) by light or sound wave irradiation in the wavelength range of 350 nm to 750 nm.

[0025] According to another aspect, a composition for diagnosing or treating tumors, comprising the aforementioned composition, is provided.

[0026] The above tumors may include breast cancer, kidney cancer, testicular cancer, prostate cancer, ovarian cancer, uterine cancer, cervical cancer, vaginal cancer, fallopian tube cancer, rectal cancer, lung cancer, stomach cancer, liver cancer, esophageal cancer, small intestine cancer, pancreatic cancer, oral cancer, melanoma, or sarcoma.

[0027] According to another aspect, the step of bringing the aforementioned tumor diagnostic or therapeutic composition into contact with a mammalian subject excluding humans;

[0028] A step of allowing time for the above-mentioned tumor diagnostic or therapeutic composition to be distributed within target cells; and

[0029] A photodynamic or sonication therapy method is provided, comprising the step of irradiating light onto a target cell site of the subject or the step of irradiating sound waves onto a target cell site of the subject. Effects of the invention

[0030] By using the compound represented by the above chemical formula 1, it is possible to provide a tumor diagnosis or treatment composition and a photodynamic therapy or sonication therapy method having high selectivity for tumors and high therapeutic efficiency. Brief explanation of the drawing

[0031] FIG. 1a is a figure showing the UV-vis absorption spectra of the compositions according to Examples 1-1, 1-2 and Comparative Examples 1-1 and 1-2. FIG. 1b is a figure showing the fluorescence spectra of the compositions according to Examples 1-1 and 1-2. FIG. 2a is a figure showing the size of nanoparticles in the composition according to Examples 2-1, 2-2, and 2-3. FIG. 2b is a figure showing the size of nanoparticles in the composition according to Examples 2-1, 2-2 and 2-3, measured 5 days after the composition was prepared. FIG. 2c is a TEM image of nanoparticles in the composition according to Examples 2-1, 2-2 and 2-3. Figure 3a is a diagram showing the size of nanoparticles in the composition according to Example 3-2 over time. Figure 3b is a TEM image of nanoparticles in the composition according to Example 3-2. Figure 4 is a figure showing the results of measuring the amount of superoxide radicals generated after irradiating compositions according to Examples 1-1, 3-1, Comparative Examples 1-1 and 2 with a 655 nm laser using DHE as a label, according to irradiation time. FIG. 5 is a figure showing the results of measuring the amount of singlet oxygen generated after irradiating the compositions according to Examples 1-1, 3-1, Comparative Examples 1-1 and 2 with a 655 nm laser using ABDA as a label, according to the irradiation time. FIG. 6 is a figure showing the amount of reactive oxygen species (ROS) generated after irradiating compositions according to Examples 1-1, 3-1, Comparative Examples 1-1, 2, and 5 with a 655 nm laser as a function of irradiation time. FIG. 7 is a figure showing the amount of superoxide radicals generated after irradiating the compositions according to Examples 1-1, 3-1, Comparative Examples 1-1 and 2 with sound waves as a function of irradiation time. FIG. 8 is a figure showing the amount of reactive oxygen species (ROS) generated after irradiating the compositions according to Examples 1-1, 3-1, Comparative Examples 2 and 5 with sound waves as a function of irradiation time. Figure 9 is an image of a cell taken after treating the cell with the composition according to Example 3-1. Figure 10 is an image of each cell after treating the cell with the composition according to Example 3-1 and irradiating it with a 635 nm laser. Specific details for implementing the invention

[0032] Hereinafter, with reference to the attached drawings, a compound according to one embodiment of the present invention, a composition containing the same, a composition for diagnosing or treating tumors containing said composition, and a photodynamic or sonication therapy method using said composition for diagnosing or treating tumors will be described in detail. The following is presented as an example and is not intended to limit the present invention, and the present invention is defined only by the scope of the claims set forth below.

[0033] In this specification, the term “includes” is used to indicate that other components may be added or / and interposed, rather than excluding other components, unless specifically stated otherwise.

[0034] In this specification, the term “combination of these” means a mixture or combination with one or more of the described components.

[0035] In this specification, "pharmaceuticalally acceptable salt" refers to any organic or inorganic addition salt of a compound represented by Formula 1, etc., at a concentration that has a relatively non-toxic and harmless active effect on the patient, such that side effects caused by this salt do not reduce the beneficial efficacy. As free acids, inorganic and organic acids may be used for these salts; as inorganic acids, hydrochloric acid, bromic acid, nitric acid, sulfuric acid, perchloric acid, phosphoric acid, etc. may be used, and as organic acids, citric acid, acetic acid, lactic acid, maleic acid, fumaric acid, gluconic acid, methanesulfonic acid, glyconic acid, succinic acid, tartaric acid, galacturonic acid, emvonic acid, glutamic acid, aspartic acid, oxalic acid, (D) or (L) malic acid, maleic acid, methanesulfonic acid, ethanesulfonic acid, 4-toluenesulfonic acid, salicylic acid, citric acid, benzoic acid, or malonic acid, etc. In addition, these salts include alkali metal salts (sodium salts, potassium salts, etc.) and alkaline earth metal salts (calcium salts, magnesium salts, etc.). For example, acid addition salts include acetate, aspartate, benzate, besylate, bicarbonate / carbonate, bisulfate / sulfate, borate, camsylate, citrate, edicilate, esylate, formate, fumarate, gluteptate, gluconate, glucuronate, hexafluorophosphate, bibenzate, hydrochloride / chloride, hydrobromide / bromide, hydroiodide / iodide, isethionate, lactate, malate, maliate, malonate, mesylate, methyl sulfate, naphthylate, 2-naphthylate, nicotinate, nitrate, orotate, oxalate, palmitate, pamoate, phosphate / hydrogen phosphate / dihydrogen phosphate, saccharate, stearate, succinate, tartrate, It may include tosylate, trifluoroacetate, aluminum, arginine, benzathine, calcium, choline, diethylamine, diolamine, glycine, lysine, magnesium, meglumine, olamine, potassium, sodium, tromethamine, zinc salt, etc., and among these may be hydrochloride or trifluoroacetate.

[0036] In this specification, the term "self-assembly" refers to a phenomenon in which materials existing in a disordered manner form a controlled structure according to certain rules or materials are arranged in a certain pattern.

[0037] In this specification, the term "nanostructure" refers to a structural material having a size of 1 to 100 nanometers (nm) in which phenomena rarely seen in micro-sized structures are observed.

[0038] According to one aspect, a compound represented by the following chemical formula 1 is provided:

[0039] <Chemical Formula 1>

[0040]

[0041] In the above chemical formula 1, A is a photosensitizer.

[0042] According to one embodiment, A may be a photosensitive agent that generates active oxygen by light irradiation in the wavelength range of 620 nm to 800 nm.

[0043] According to one embodiment, the above A may be Pheophorbide-a.

[0044] In the above Chemical Formula 1, L1 and L-2 are independently *-C(R6)(R7)-*', *-C(R6)=*', *=C(R7)-*', *-C(R6)=C(R7)-*', *-C(=O)-*', *-C(=S)-*', *-N(R6)-*', *-O-*', *-S-*', at least one R 10a C6-C substituted or unsubstituted 30 Arylgi, at least one R 10a C1-C substituted or unsubstituted 30 It is a heteroaryl group or any combination thereof, and

[0045] n1 and n2 are independent integers from 1 to 20.

[0046] According to one embodiment, the above L -1It may include a group represented by the following chemical formula L-1:

[0047] <Chemical Formula L-1>

[0048]

[0049] Among the above chemical formula L-1,

[0050] R 11 to R 14 are independently hydrogen, deuterium, a hydroxyl group, a carboxylic acid group, or a salt thereof, at least one R 10a C1-C substituted or unsubstituted 10 alkyl group, at least one R 10a C1-C substituted or unsubstituted 10 an alkoxy group, -N(Q1)(Q2), -C(=O)(Q1), or any combination thereof, and

[0051] p is an integer of 0 or 1, and

[0052] q is an integer from 1 to 10, and

[0053] R 10a The descriptions of , Q1 and Q2 are each the same as those described in this specification, and

[0054] * and *' are bonding sites with neighboring atoms.

[0055] For example, the above R 11 to R 14 are independently hydrogen, deuterium, carboxylic acid groups or salts thereof, C1-C 10 alkyl group or C1-C 10 It could be an alkoxygenase.

[0056] For example, * in the above chemical formula L-1 may be a binding site with A in chemical formula 1, and *' may be a binding site with L2 in chemical formula 1.

[0057] According to one embodiment, the L2 may include a group represented by the following chemical formula L-2:

[0058] Chemical Formula L-2

[0059]

[0060] Among the above chemical formula L-2,

[0061] R 20 to R 26 are independently hydrogen, deuterium, a hydroxyl group, a carboxylic acid group, or a salt thereof, at least one R 10a C1-C substituted or unsubstituted 10 alkyl group, at least one R 10a C1-C substituted or unsubstituted 10 an alkoxy group, -N(Q1)(Q2), -C(=O)(Q1), or any combination thereof, and

[0062] r is an integer from 1 to 5, and

[0063] R 10a The descriptions of , Q1 and Q2 are each the same as those described in this specification, and

[0064] * and *' are bonding sites with neighboring atoms, respectively.

[0065] For example, the above R 20 to R 26 are independently hydrogen, deuterium, carboxylic acid groups or salts thereof, C1-C 10 alkyl group or C1-C 10 It could be an alkoxygenase.

[0066] For example, * in the above chemical formula L-2 may be a binding site with L1 in chemical formula 1, and *' may be a binding site with C(R1)(R2) in chemical formula 1.

[0067] In the above Chemical Formula 1, R1 to R7 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphate group or salt thereof, at least one R 10a C1-C substituted or unsubstituted 30 alkyl group, at least one R 10a C2-C substituted or unsubstituted 30alkenyl group, at least one R 10a C2-C substituted or unsubstituted 30 alkynyl group, at least one R 10a C1-C substituted or unsubstituted 30 Alkoxy group, at least one R 10a C1-C substituted or unsubstituted 30 alkylthio group, at least one R 10a C6-C substituted or unsubstituted 30 Arylgi, at least one R 10a C6-C substituted or unsubstituted 30 aryloxy group, at least one R 10a C6-C substituted or unsubstituted 30 It is an arylthio group, -C(Q1)(Q2)(Q3), -N(Q1)(Q2), -C(=O)(Q1), or any combination thereof.

[0068] According to one embodiment, R1 to R5 are independently hydrogen, deuterium, a hydroxyl group, a carboxylic acid group or a salt thereof, C1-C 10 Alkyl group, C1-C 10 Alkoxy group, phenyl group, -N(Q 31 )(Q 32 ), -C(=O)(Q 31 ) or any combination thereof, and

[0069] Q 31 and Q 32 are independently hydrogen, deuterium, hydroxyl groups, C1-C 10 Alkyl group, C1-C 10 It can be an alkoxy group or a phenyl group.

[0070] According to one embodiment, the compound can be represented by the following chemical formula 1-1:

[0071] <Chemical Formula 1-1>

[0072]

[0073] Among the above chemical formula 1-1,

[0074] A is a photosensitizer, and

[0075] L1 and L-2 are independently of each other *-C(R 61 )(R 71 )-*', *-C(R 61 )=*', *=C(R 71 )-*', *-C(R 61 )=C(R 71 )-*', *-C(=O)-*', *-N(R 61 )-*', *-O-*' or any combination thereof, and

[0076] n1 and n2 are independent integers from 1 to 20, and

[0077] R 61 and R 71 are independently hydrogen, deuterium, a hydroxyl group, a carboxylic acid group, or a salt thereof, at least one R 10b C1-C substituted or unsubstituted 10 alkyl group

[0078] R 31 to R 33 are independently hydrogen, deuterium, or at least one R 10b C1-C substituted or unsubstituted 10 It is an alkyl group, and

[0079] The above R 10b is deuterium, hydroxyl group, carboxylic acid or its salt, C1-C 10 alkyl group or C1-C 10 It is the alkoxy period.

[0080] According to one embodiment, the compound may be represented by the following compound 1:

[0081] [Compound 1]

[0082]

[0083] According to one embodiment, the compound can bind to a membrane protein on the cell surface. For example, the group containing the urea group (-NHCONH-) in Formula 1 can bind to a membrane protein on the cell surface. Here, the membrane protein on the cell surface may be a prostate-specific membrane antigen (PSMA).

[0084] The compound represented by the above chemical formula 1 comprises a photosensitive agent A, a group represented by the following chemical formula 1A, and L1 and L2 which are linkers between A and the group represented by the chemical formula 1A.

[0085] <Chemical Formula 1A>

[0086]

[0087] The compound represented by Chemical Formula 1 above contains photosensitive agent A, and can generate active oxygen (e.g., singlet oxygen or superoxide radical) when irradiated with light or sound waves in a specific wavelength range, thereby killing tumor or cancer cells. In addition, the group represented by Chemical Formula 1A in Chemical Formula 1 can bind to membrane proteins on the cell surface, for example, prostate-specific membrane antigen (PSMA) on the surface of a tumor. Therefore, it can exhibit high selectivity for tumors and therapeutic efficiency.

[0088] According to another aspect, a composition is provided comprising the aforementioned compound or a pharmaceutically acceptable salt thereof; and water, a buffer solution or an organic solvent.

[0089] The compound included in the above composition can form a self-assembled nanostructure.

[0090] The average diameter of the self-assembled nanostructure may be 100 nm to 1,000 nm.

[0091] The above composition may further include antimony-doped tin oxide (ATO).

[0092] If the above composition further includes antimony tin oxide (ATO), the antimony tin oxide may be located inside the self-assembled nanostructure formed by the compound included in the composition. Since antimony tin oxide can improve the hypoxic environment in vivo by interfering with electron transfer, it can increase the efficiency of photodynamic therapy (PDT).

[0093] If the above composition further includes antimony tin oxide (ATO), the ratio of the compound to the antimony tin oxide (ATO) in the composition may be 1:1 to 1:3 based on the number of moles.

[0094] The peak of the fluorescence spectrum of the above composition may appear at 620 nm to 800 nm. For example, the peak of the fluorescence spectrum of the above composition may appear at 600 nm to 750 nm or at 650 nm to 750 nm.

[0095] The above composition may be a fluorescent probe for cell imaging.

[0096] The above composition can generate reactive oxygen species (ROS) by light or sound wave irradiation in the wavelength range of 350 nm to 750 nm.

[0097] The above composition can generate singlet oxygen or superoxide radicals by light irradiation in the wavelength range of 350 nm to 750 nm.

[0098] The above composition can generate superoxide radicals by sound wave irradiation in the wavelength range of 350 nm to 750 nm.

[0099] According to another aspect, a composition for diagnosing or treating tumors, comprising the aforementioned composition, is provided.

[0100] Among the above-mentioned compositions for diagnosing or treating tumors, the tumor may include breast cancer, kidney cancer, testicular cancer, prostate cancer, ovarian cancer, uterine cancer, cervical cancer, vaginal cancer, fallopian tube cancer, rectal cancer, lung cancer, stomach cancer, liver cancer, esophageal cancer, small intestine cancer, pancreatic cancer, oral cancer, melanoma, or sarcoma.

[0101] According to another aspect, a photodynamic therapy method is provided, comprising the steps of: bringing the aforementioned tumor diagnostic or therapeutic composition into contact with a mammalian subject excluding humans; allowing time for the tumor diagnostic or therapeutic composition to be distributed within a target cell; and irradiating light onto a target cell site of the subject.

[0102] The above photodynamic therapy method can exhibit advantages such as spatiotemporal selectivity, non-invasiveness, and reduced side effects.

[0103] According to another aspect, a sonication therapy method is provided, comprising the steps of: bringing the aforementioned tumor diagnostic or therapeutic composition into contact with a mammalian subject excluding humans; allowing time for the tumor diagnostic or therapeutic composition to be distributed within a target cell; and irradiating a target cell site of the subject with sound waves.

[0104] In this specification, a substituent is derived by exchanging one or more hydrogens from an unsubstituted mother group with another atom or functional group. Unless otherwise stated, when a functional group is considered to be "substituted," it means that the functional group is substituted with one or more substituents selected from an alkyl group having 1 to 40 carbon atoms, an alkenyl group having 2 to 40 carbon atoms, an alkynyl group having 2 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, a cycloalkenyl group having 3 to 40 carbon atoms, or an aryl group having 7 to 40 carbon atoms. When a functional group is described as "optionally substituted," it means that the functional group may be substituted with the substituents described above.

[0105] In this specification, a and b of “carbon number a to b” refer to the number of carbon atoms of a specific functional group. That is, the functional group may include carbon atoms from a to b. For example, “alkylene group having 1 to 4 carbon atoms” refers to an alkylene group having 1 to 4 carbons, namely -CH2-, -CH2CH2-, -CH2CH2CH2-, -(CH3)2C-, -CH2CH2CH2CH2-, -CH2CH2CH(CH3)- and -(CH3)2C-.

[0106] In this specification, the term "alkyl" means a branched or unbranched aliphatic hydrocarbon. In one embodiment, the alkyl group may or may not be substituted. The alkyl group includes, but is not necessarily limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, etc., and each of these may optionally be substituted or not substituted. In one embodiment, the alkyl group may have 1 to 6 carbon atoms. For example, the alkyl group having 1 to 6 carbon atoms may be methyl, ethyl, propyl, isopropyl, butyl, iso-butyl, sec-butyl, pentyl, 3-pentyl, hexyl, etc., but is not necessarily limited to these.

[0107] In this specification, the term "alkenyl" means a branched or unbranched hydrocarbon having at least one carbon-carbon double bond. Non-limiting examples of alkenyl groups include vinyl, allyl, butenyl, isopropenyl, or isobutenyl.

[0108] In this specification, the term "alkynyl" refers to a branched or unbranched hydrocarbon having at least one carbon-carbon triple bond. Non-limiting examples of alkynyl groups include ethinyl, butynyl, isobutynyl, isopropynyl, etc.

[0109] C3-C in this specification 30 A carbocyclic group refers to a cyclic group having 3 to 60 carbon atoms, consisting solely of carbon as ring-forming atoms, and C1-C 30 A heterocyclic group refers to a cyclic group having 1 to 60 carbon atoms that includes, in addition to carbon, a heteroatom as a ring-forming atom. The above C3-C 30 Carbocyclic group and C1-C 30Each heterocyclic group may be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed together. For example, the above C1-C 30 The number of ring-forming atoms in a heterocyclic group can be 3 to 61.

[0110] In this specification, the term “aryl” refers to an aromatic ring, a ring system (i.e., two or more fused rings sharing two adjacent carbon atoms), or a plurality of aromatic rings having a ring backbone consisting of only carbons, single bonds, -O-, -S-, -C(=O)-, -S(=O)2-, -Si(R a )(R b )-(R a and R b represents a ring connected to each other by -C(=O)-NH-, which is independently an alkyl group having 1 to 10 carbon atoms, an alkylene group having 1 to 10 carbon atoms substituted or unsubstituted with a halogen, or -C(=O)-NH-. If the aryl group is a ring system, each ring in the system is aromatic. For example, the aryl group includes, but is not limited to, phenyl groups, biphenyl groups, naphthyl groups, phenanthrenyl groups, naphthacenyl groups, etc. The aryl group may or may not be substituted.

[0111] In this specification, the term "heteroaryl" means a monocyclic or bicyclic organic compound comprising one or more heteroatoms selected from N, O, P, or S, and the remaining ring atom being carbon. The heteroaryl group may comprise, for example, 1 to 5 heteroatoms and may comprise 5 to 10 ring members. The S or N may be oxidized to have various oxidation states.

[0112] Non-limiting examples of "heteroaryl" include thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl group, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isooxazol-3-yl, isooxazol-4-yl, isooxazol-5-yl, 1,2,4-triazol-3-yl, Examples include 1,2,4-triazole-5-yl, 1,2,3-triazole-4-yl, 1,2,3-triazole-5-yl, tetrazolyl, pyrid-2-yl, pyrid-3-yl, 2-pyrazine-2-yl, pyrazine-4-yl, pyrazine-5-yl, 2-pyrimidine-2-yl, 4-pyrimidine-2-yl, or 5-pyrimidine-2-yl.

[0113] In this specification, R 10a Is,

[0114] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group;

[0115] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 30 Carbocyclic group, C1-C 30 Heterocyclic group, C6-C 30 aryloxy group, C6-C 30 Arylthiogi, -N(Q 11 )(Q 12 ), -C(=O)(Q 11 ), or substituted or unsubstituted with any combination thereof, C1-C 20 Alkyl group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, or C1-C 20 Alkoxygenation;

[0116] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20Alkyl group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, C1-C 20 Alkoxy group, C3-C 30 Carbocyclic group, C1-C 30 Heterocyclic group, C6-C 30 aryloxy group, C6-C 30 Arylthiogi, -N(Q 21 )(Q 22 ), -C(=O)(Q 21 ), or substituted or unsubstituted with any combination thereof, C3-C 30 Carbocyclic group, C1-C 30 Heterocyclic group, C6-C 30 aryloxy group, or C6-C 30 Arylthiogi; or

[0117] -N(Q 31 )(Q 32 ) or -C(=O)(Q 31 );

[0118] It could be.

[0119] Q1 to Q3, Q in this specification 11 , Q 12 , Q 21 , Q 22 , Q 31 and Q 32 They are independently hydrogen; deuterium; hydroxyl group; cyano group; nitro group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 alkynyl group; C1-C 20 Alkoxy group; or deuterium, -F, cyano group, C1-C 10 Alkyl group, C1-C 10 C3-C substituted or unsubstituted with an alkoxy group, a phenyl group, a biphenyl group, or any combination thereof 30 Carbocyclic group or C1-C 30 It can be a heterocyclic group.

[0120] Examples and comparative examples of the present invention are described below. However, the following examples are merely one example of the present invention, and the present invention is not limited to the following examples.

[0121] [Example]

[0122] Synthesis Example 1: Synthesis of Compound 1

[0123]

[0124] 1) Compound 1A-NO 2 Synthesis of

[0125] Compound 1A (100 mg, 0.14 mmol, 1.0 eq) and 4-nitrophenyl carbonochloridate (42 mg, 0.21 mmol, 1.5 eq) were dissolved in 5 mL of anhydrous dichloromethyl (DCM), and then triethylamine (21 mg, 0.21 mmol, 1.5 eq) was added to form a mixture. After stirring the mixture at room temperature for 12 hours, the solvent was evaporated, and the resulting product was purified by column chromatography to obtain 96 mg of Compound 1A-NO2 (yield: 78%). This 1 H NMR, 13 It was confirmed through 3C NMR and ESI-HRMS.

[0126] 1H NMR (300 MHz, CDCl3) δ 9.31 (d, J = 13.5 Hz, 1H), 9.13 (d, J = 11.2 Hz, 1H), 8.53 (d, J = 16.5 Hz, 1H), 8.09 - 7.95 (m, 2H), 7.83 (dd, J = 17.8, 11.5 Hz, 1H), 7.16 - 7.05 (m, 2H), 6.32 (s, 1H), 6.25 - 6.04 (m, 2H), 4.60 - 4.45 (m, 3H), 4.29 (d, J = 8.4 Hz, 1H), 4.14 - 4.05 (m, 2H), 3.81 - 3.73 (m, 2H), 3.69 - 3.58 (m, 6H), 3.58 - 3.44 (m, 5H), 3.43 - 3.38 (m, 2H), 3.37 - 3.31 (m, 5H), 3.05 (s, 3H), 2.74 - 2.55 (m, 1H), 2.45 - 2.26 (m, 2H), 1.89 (d, J = 7.2 Hz, 3H), 1.71 - 1.54 (m, 3H), 1.29 (s, 1H), -1.78 (s, 1H).

[0127] 13 C NMR (75 MHz, CDCl3) δ 189.57, 173.45, 172.26, 169.17, 161.24, 155.24, 152.24, 150.81, 149.66, 145.06, 142.02, 137.81, 136.41, 136.15, 136.06, 131.83, 128.89, 128.88, 128.86, 124.97, 122.73, 121.49, 121.46, 105.15, 104.24, 97.39, 93.10, 70.50, 70.45, 69.03, 68.30, 68.05, 64.95, 64.81, 51.73, 51.10, 50.18, 31.05, 29.85, 23.18, 19.27, 17.37, 12.09, 12.06, 11.06.

[0128] ESI-HRMS: m / z calcd for C48H52N5O12+ [M+H]+ 890.3607, found 890.3615.

[0129] 2) Synthesis of Compound 1B

[0130] Compound 1A-NO2 (96 mg, 0.011 mmol, 1 eq) was dissolved in 3 mL of anhydrous DCM, after which compound 1B(1) (63 mg, 0.013 mmol, 1.2 eq) and trimethylamine (65 mg i.e., 0.09 mL, 0.065 mmol, 6.0 eq) were added. After stirring the mixture at room temperature for 12 hours, the solvent was evaporated to obtain a compound, which was then purified by flash chromatography to obtain 110 mg of compound 1B (yield: 82%). 1 H NMR, 13 It was confirmed through 3C NMR and ESI-HRMS.

[0131] 1 H NMR (300 MHz, CDCl3) δ 9.35 (d, J = 10.1 Hz, 1H), 9.16 (d, J = 10.4 Hz, 1H), 8.52 (d, J = 18.3 Hz, 1H), 7.85 (dd, J = 17.8, 11.5 Hz, 1H), 6.30 (s, 1H), 6.25 - 6.02 (m, 2H), 5.38 (dd, J = 7.9, 3.8 Hz, 2H), 5.23 (t, J = 5.6 Hz, 1H), 4.56 - 4.44 (m, 3H), 4.42 - 4.25 (m, 3H), 4.10 - 4.03 (m, 2H), 3.79 - 3.72 (m, 2H), 3.67 - 3.56 (m, 6H), 3.50 (dd, J= 8.3, 3.4 Hz, 5H), 3.44 - 3.32 (m, 7H), 3.14 - 3.03 (m, 5H), 2.75 - 2.50 (m, 2H), 2.42 - 2.21 (m, 4H), 2.16 - 2.03 (m, 2H), 1.93 - 1.81 (m, 4H), 1.66 (ddd, J = 15.1, 8.5, 5.0 Hz, 5H), 1.48 - 1.40 (m, 27H), 1.35 - 1.24 (m, 2H), 0.46 (s, 1H), -1.72 (s, 1H)

[0132] 13 C NMR (75 MHz, CDCl3) δ 189.64, 173.49, 172.51, 172.47, 172.34, 172.28, 169.25, 161.24, 157.06, 156.60, 155.54, 150.85, 149.70, 145.09, 142.03, 137.84, 136.43, 136.15, 136.05, 131.83, 128.94, 128.89, 122.72, 105.17, 104.29, 97.39, 93.12, 81.93, 81.55, 80.47, 70.42, 69.45, 68.96, 64.97, 64.76, 63.71, 53.36, 52.94, 51.71, 51.07, 50.17, 40.52, 32.46, 31.62, 31.02, 29.83, 29.40, 28.50, 23.16, 22.24, 19.30, 17.38, 12.09, 12.07, 11.09.

[0133] ESI-HRMS: m / z calcd for C66H92N7O16+ [M+H]+ 1238.6595, found 1238.6597.

[0134] 3) Synthesis of Compound 1

[0135] Compound 1B (100 mg, 0.008 mmol, 1 eq) was dissolved in 3.0 mL of anhydrous DCM, and then 1.5 mL of TFA was added at 0°C. The mixture was stirred at 0°C for 30 minutes, and then stirred at room temperature for 1.5 hours. After the reaction was complete, the solvent was evaporated under vacuum to obtain 85 mg of Compound 1 (yield: 94%).

[0136] 1 H NMR (300 MHz, MeOD) δ 9.26 (s, 1H), 9.09 - 8.80 (m, 2H), 7.79 (dd, J = 17.4, 11.8 Hz, 1H), 6.27 (d, J = 15.1 Hz, 1H), 6.21 - 6.05 (m, 2H), 4.50 (dd, J = 33.2, 10.1 Hz, 4H), 4.26 - 4.09 (m, 3H), 3.85 - 3.64 (m, 10H), 3.55 - 3.38 (m, 7H), 3.02 - 2.83 (m, 3H), 2.69 (dt, J = 18.8, 9.6 Hz, 6H), 2.40 (dd, J = 36.6, 12.4 Hz, 4H), 2.22 - 2.00 (m, 3H), 1.85 (d, J = 7.2 Hz, 4H), 1.71 (dd, J = 12.9, 7.0 Hz, 2H), 1.61 - 1.47 (m, 2H), 1.47 - 1.24 (m, 9H).

[0137] FAB-HRMS: m / z calcd for C54H68N7O16+ [M+H]+ 1070.4717, found 1070.4726.

[0139] A composition having the composition as described in Table 1 below was prepared.

[0140] compound menstruum ATO Example 1-1 10 μM compound 1 DMSO - Examples 1-2 10 μM compound 1 H2O - Example 2-1 100 μM Compound 1 DMSO 100 μM Example 2-2 100 μM Compound 1 DMSO 200 μM Examples 2-3 100 μM Compound 1 DMSO 300 μM Example 3-1 10 μM compound 1 DMSO 30 μM Example 3-2 10 μM Compound 1 + FBS DMSO 30 μM Comparative Example 1-1 10 μM Ppa DMSO - Comparative Example 1-2 10 μM Ppa H2O - Comparative Example 2 - DMSO 30 μM

[0142] Experimental Example 1. Measurement of UV-vis absorption and fluorescence spectra

[0143] The UV-vis absorption spectra of the compositions according to Examples 1-1, 1-2 and Comparative Examples 1-1 and 1-2 were measured and are shown in Fig. 1a, and the fluorescence spectra of Examples 1-1 and 1-2 were measured and are shown in Fig. 1b.

[0144] Experimental Example 2. Observation of Nanoparticles

[0145] (1) Compound 1 + ATO

[0146] Solutions of PPa and ATO were prepared by dissolving them in DMSO, respectively. Then, PBS was added to the compositions according to Examples 2-1, 2-2, and 2-3 to make the total volume 1000 μL, and sonication stirring was performed to prepare samples. The size of the nanoparticles was measured, and the results are shown in Fig. 2a. The size of the nanoparticles after 5 days of each composition was measured, and the results are shown in Fig. 2b. The size of the nanoparticles was measured using a Nano-ZS from Mervern.

[0147] In addition, nanoparticles produced in the compositions according to Examples 2-1, 2-2, and 2-3 were photographed by TEM, and the results are shown in Fig. 2c.

[0148] Referring to Figures 2a, 2b, and 2c, it can be seen that the nanoparticles in the composition according to Examples 2-1, 2-2, and 2-3 are uniformly formed.

[0149] (2) Compound 1 + ATO + FBS

[0150] The size of the nanoparticles in the composition according to Example 3-2 was measured over time, and the results are shown in FIG. 3a. The nanoparticles in the composition according to Example 3-2 were photographed using TEM, and the results are shown in FIG. 3b.

[0151] Referring to Figures 3a and 3b, it can be seen that the nanoparticles in the composition according to Example 3-2 are uniformly formed. That is, it can be seen that the compound according to the present invention forms nanoparticles well even when Fetal Bovine Serum (FBS) is added.

[0152] Experimental Example 3. Measurement of superoxide radical, singlet oxygen, and total reactive oxygen (ROS) generation amounts according to light irradiation

[0153] (1) Measurement of superoxide radical generation

[0154] A 655 nm laser (0.2 W / cm²) to the compositions according to Examples 1-1, 3-1, and Comparative Examples 1-1 and 2 2 The amount of superoxide radicals generated after investigating was measured and is shown in Figure 4.

[0155] Dihydroethidium (DHE) was used as a fixed label at a concentration of 50 μM. Since the intensity of the fluorescence spectrum is higher when the amount of superoxide radicals generated is greater, a larger value obtained by subtracting the intensity of the fluorescence spectrum corresponding to the initial (0s) from the intensity of the fluorescence spectrum corresponding to the irradiation time (s) indicates that the amount of superoxide radicals generated is greater. The fluorescence spectrum was measured using an FS-2 spectrometer (Scinco), and all subsequent fluorescence spectra were measured using the same equipment.

[0156] Referring to FIG. 4, it can be seen that the amount of superoxide radical generated by the compositions according to Examples 1-1 and 3-1 is greater than that of the compositions according to Comparative Examples 1-1 and 2.

[0157] (2) Measurement of singlet oxygen production

[0158] A 655 nm laser (0.2 W / cm²) to the compositions according to Examples 1-1, 3-1, and Comparative Examples 1-1 and 2 2The amount of singlet oxygen generated after irradiation was measured and is shown in Figure 5. 9,10-anthracenediyl-bis(methylene)dimalonic acid (ABDA) was used as a label at a fixed concentration of 20 μM. Since the intensity of the absorption spectrum appears lower as the amount of singlet oxygen generated increases, a smaller value (larger absolute value) obtained by subtracting the intensity of the fluorescence spectrum corresponding to the initial (0s) from the intensity of the fluorescence spectrum corresponding to the irradiation time (IrradiationTime, s) indicates that the amount of singlet oxygen generated is greater.

[0159] Referring to FIG. 5, it can be seen that the amount of singlet oxygen produced by the compositions according to Examples 1-1 and 3-1 is greater than that of the compositions according to Comparative Examples 1-1 and 2.

[0160] (3) Measurement of total reactive oxygen species (ROS) production

[0161] A 655 nm laser (0.2 W / cm²) to the compositions according to Examples 1-1, 3-1, and Comparative Examples 1-1 and 2 2 The total amount of reactive oxygen species (ROS) generated after irradiation was measured and is shown in Figure 6. 2,7-dichlorofluorescin diacetate (DCFHDA) was used as a fixed marker at a concentration of 20 μM. Since the intensity of the fluorescence spectrum is higher when the amount of reactive oxygen species generated is greater, the larger the value obtained by subtracting the intensity of the fluorescence spectrum corresponding to the initial (0s) from the intensity of the fluorescence spectrum corresponding to the irradiation time (s), the greater the amount of reactive oxygen species generated.

[0162] Referring to FIG. 6, it can be seen that the amount of active oxygen (ROS) generated by the compositions according to Examples 1-1 and 3-1 is greater than that of the compositions according to Comparative Examples 1-1 and 2.

[0163] Experimental Example 4. Measurement of superoxide radical and total reactive oxygen species (ROS) generated by sound wave irradiation

[0164] (1) Measurement of superoxide radical generation

[0165] Sound waves (0.5 W / cm²) to the compositions according to Examples 1-1, 3-1, and Comparative Examples 1-1 and 2 2 The amount of superoxide radicals generated after irradiation was measured and is shown in Figure 7. DHE was used as a fixed label at a concentration of 50 μM. Since the intensity of the fluorescence spectrum is higher when the amount of superoxide radicals generated is greater, a larger value obtained by subtracting the intensity of the fluorescence spectrum corresponding to the initial time (0 min) from the intensity of the fluorescence spectrum corresponding to the irradiation time (min) indicates that the amount of superoxide radicals generated is greater.

[0166] Referring to FIG. 7, it can be seen that the amount of superoxide radical generated by the compositions according to Examples 1-1 and 3-1 is greater than that of the compositions according to Comparative Examples 1-1 and 2.

[0167] (2) Measurement of total reactive oxygen species (ROS) production

[0168] Sound waves (0.5 W / cm²) to the compositions according to Examples 1-1, 3-1, and Comparative Examples 1-1 and 2 2 The total amount of reactive oxygen species (ROS) generated after irradiation was measured and is shown in Figure 8. DCFHDA was used as a fixed marker at a concentration of 20 μM. Since the intensity of the fluorescence spectrum is higher when the amount of reactive oxygen species generated is greater, a larger value obtained by subtracting the intensity of the fluorescence spectrum corresponding to the initial time (0 min) from the intensity of the fluorescence spectrum corresponding to the irradiation time (min) indicates that the amount of reactive oxygen species generated is greater.

[0169] Referring to FIG. 8, it can be seen that the amount of active oxygen (ROS) generated by the compositions according to Examples 1-1 and 3-1 is greater than that of the compositions according to Comparative Examples 1-1 and 2.

[0170] Experimental Example 5. Confirmation of cell surface membrane protein binding and intracellular reactive oxygen species generation

[0171] (1) Check whether membrane proteins on the cell surface are bound

[0172] After treating LNCaP-NL3 cells with the composition according to Example 3-1, the cells were photographed using an Olympus FV300 confocal microscope, and the results are shown in Fig. 9. DiO (20 μM) was used as a marker.

[0173] Referring to FIG. 9, it can be seen that the compound according to the present invention appears only on the surface of the cell.

[0174] (2) Confirmation of intracellular reactive oxygen species generation

[0175] The composition according to Example 3-1 was applied to cells, and after irradiating them with a 635 nm laser, the cells were photographed, and the results are shown in Fig. 10. DCFHDA (20 μM) was used as a marker, and cells treated only with the marker DCFHDA were used as a control group.

[0176] Referring to FIG. 10, it can be seen that when the composition according to Example 3-1 is applied, the amount of active oxygen produced in the cell increases compared to when it is not.

Claims

Claim 1 Compound represented by the following chemical formula 1: <Chemical Formula 1> In the above Chemical Formula 1, A is Pheophorbide-a, and L1 and L2 are independently *-C(R6)(R7)-*', *-C(R6)=*', *=C(R7)-*', *-C(R6)=C(R7)-*', *-C(=O)-*', *-C(=S)-*', *-N(R6)-*', *-O-*', *-S-*', at least one R 10a C6-C substituted or unsubstituted 30 It is an aryl group or any combination thereof, n1 and n2 are independently integers from 1 to 20, and R1 to R7 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a nitro group, a carboxylic acid group or a salt thereof, at least one R 10a C1-C substituted or unsubstituted 30 alkyl group, at least one R 10a C1-C substituted or unsubstituted 30 Alkoxy group, at least one R 10a C1-C substituted or unsubstituted 30 alkylthio group, at least one R 10a C6-C substituted or unsubstituted 30 An aryl group, -N(Q1)(Q2), -C(=O)(Q1), or any combination thereof, and the above R 10a is, deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group; deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 30 Carbocyclic group, C1-C 30 Heterocyclic group, C6-C 30 aryloxy group, C6-C 30 Arylthiogi, -N(Q 11 )(Q 12 ), -C(=O)(Q 11 ), or substituted or unsubstituted with any combination thereof, C1-C 20 Alkyl group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, or C1-C 20 Alkoxy group; deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, C1-C 20 Alkoxy group, C3-C 30 Carbocyclic group, C1-C 30 Heterocyclic group, C6-C 30 aryloxy group, C6-C 30 Arylthiogi, -N(Q 21 )(Q 22 ), -C(=O)(Q 21 ), or substituted or unsubstituted with any combination thereof, C3-C 30 Carbocyclic group, C1-C 30 Heterocyclic group, C6-C 30 aryloxy group, or C6-C 30 Arylthiogi; or-N(Q 31 )(Q 32 ) or -C(=O)(Q 31 ); and, above Q1 to Q3, Q 11 , Q 12 , Q 21 , Q 22 , Q 31 and Q 32 They are independently hydrogen; deuterium; hydroxyl group; cyano group; nitro group; C1-C 20 Alkyl group; C2-C 20 Alkenyl group; C2-C 20 alkynyl group; C1-C 20 Alkoxy group; or deuterium, -F, cyano group, C1-C 10 Alkyl group, C1-C 10 C3-C substituted or unsubstituted with an alkoxy group, a phenyl group, a biphenyl group, or any combination thereof 30 Carbocyclic group or C1-C 30 It is a heterocyclic group. Claim 2 delete Claim 3 delete Claim 4 In claim 1, L1 is a compound comprising a group represented by the following chemical formula L-1.<Chemical Formula L-1> In the above chemical formula L-1, R 11 to R 14 are independently hydrogen, deuterium, a hydroxyl group, a carboxylic acid group, or a salt thereof, at least one R 10a C1-C substituted or unsubstituted 10 alkyl group, at least one R 10a C1-C substituted or unsubstituted 10 an alkoxy group, -N(Q1)(Q2), -C(=O)(Q1), or any combination thereof, p is an integer of 0 or 1, q is an integer from 1 to 10, and R 10a The descriptions for , Q1 and Q2 are the same as those described in paragraph 1, and * and *' are bonding sites with neighboring atoms. Claim 5 In claim 1, L2 is a compound comprising a group represented by the following chemical formula L-2: <Chemical Formula L-2> In the above chemical formula L-2, R 20 to R 26 are independently hydrogen, deuterium, a hydroxyl group, a carboxylic acid group, or a salt thereof, at least one R 10a C1-C substituted or unsubstituted 10 alkyl group, at least one R 10a C1-C substituted or unsubstituted 10 an alkoxy group, -N(Q1)(Q2), -C(=O)(Q1), or any combination thereof, r is an integer from 1 to 5, and R 10a The descriptions for , Q1 and Q2 are the same as those described in paragraph 1, and * and *' are bonding sites with neighboring atoms, respectively. Claim 6 In paragraph 1, R1 to R5 are independently hydrogen, deuterium, hydroxyl groups, carboxylic acid groups or salts thereof, C1-C 10 Alkyl group, C1-C 10 Alkoxy group, phenyl group, -N(Q 31 )(Q 32 ), -C(=O)(Q 31 ) or any combination thereof, and Q 31 and Q 32 are independently hydrogen, deuterium, hydroxyl groups, C1-C 10 Alkyl group, C1-C 10 Alkoxy group or phenyl group, compound. Claim 7 In claim 1, a compound represented by the following chemical formula 1-1: <Chemical Formula 1-1> In the above chemical formula 1-1, A is Pheophorbide-a, and L1 and L2 are independently *-C(R 61 )(R 71 )-*', *-C(R 61 )=*', *=C(R 71 )-*', *-C(R 61 )=C(R 71 )-*', *-C(=O)-*', *-N(R 61 )-*', *-O-*' or any combination thereof, n1 and n2 are integers from 1 to 20 independently of each other, and R 61 and R 71 are independently hydrogen, deuterium, a hydroxyl group, a carboxylic acid group, or a salt thereof, at least one R 10b C1-C substituted or unsubstituted 10 Alkyl group R 31 to R 33 are independently hydrogen, deuterium, or at least one R 10b C1-C substituted or unsubstituted 10 It is an alkyl group, and the above R 10b is deuterium, hydroxyl group, carboxylic acid or its salt, C1-C 10 alkyl group or C1-C 10 It is the alkoxy period. Claim 8 In paragraph 1, the compound represented by the following compound 1: [Compound 1] Claim 9 In claim 1, the compound is a compound that binds to membrane proteins on the cell surface. Claim 10 A composition for the diagnosis or treatment of tumors comprising: a compound according to any one of claims 1 and 4 through 9, or a pharmaceutically acceptable salt thereof; and water, a buffer solution, or an organic solvent. Claim 11 In claim 10, the above compound is a composition that forms a self-assembled nanostructure. Claim 12 A composition according to claim 10, further comprising antimony-doped tin oxide (ATO). Claim 13 A composition according to claim 10, wherein the peak of the fluorescence spectrum appears at 620 nm to 800 nm. Claim 14 A composition according to claim 10 that generates reactive oxygen species (ROS) by light or sound wave irradiation in the wavelength range of 350 nm to 750 nm. Claim 15 delete Claim 16 A composition for diagnosing or treating tumors according to claim 10, wherein the tumor comprises breast cancer, kidney cancer, testicular cancer, prostate cancer, ovarian cancer, uterine cancer, cervical cancer, vaginal cancer, fallopian tube cancer, rectal cancer, lung cancer, stomach cancer, liver cancer, esophageal cancer, small intestine cancer, pancreatic cancer, oral cancer, melanoma, or sarcoma. Claim 17 A photodynamic or ultrasonic kinetic therapy method comprising: a step of bringing a tumor diagnostic or therapeutic composition according to claim 10 into contact with a mammalian subject excluding humans; a step of allowing time for the tumor diagnostic or therapeutic composition to be distributed within a target cell; and a step of irradiating light to a target cell site of the subject or irradiating sound waves to a target cell site of the subject.

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