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Bi-zinc-phthalocyanine coordination compound and preparation method and application thereof

A technology of diphthalocyanine zinc and complexes, which is applied in the field of diphthalocyanine zinc complexes and their preparation, and can solve the problem of low tumor targeting

Active Publication Date: 2014-12-24
SHENZHEN CHINA RESOURCES GOSUN PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The purpose of the present invention is to overcome the above-mentioned deficiencies of the prior art, to provide a diphthalocyanine zinc complex and its preparation method and application, so as to overcome the technical problem of the low photoactivity of the existing phthalocyanine complexes on tumor targeting

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  • Bi-zinc-phthalocyanine coordination compound and preparation method and application thereof
  • Bi-zinc-phthalocyanine coordination compound and preparation method and application thereof

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preparation example Construction

[0029] Correspondingly, the embodiment of the present invention also provides a preparation method of the above-mentioned ZnPc-S-S-ZnPc. The method comprises the steps of:

[0030] S01: Preparation of reaction solution: dissolve β-monocarboxyl substituted zinc phthalocyanine and 2,2'-dithiodiethanol in an organic reaction solvent, cool down to below 5°C, and then add condensing agent, condensation activator and catalyst to obtain Reactant mixed solution;

[0031] S02: make the reaction solution react: the step reactant mixed solution is warmed up to 30~60 ℃ to carry out condensation reaction until the end of the reaction; ) shown in the zinc diphthalocyanine complex,

[0032]

[0033]Specifically, in the above step S01, the molecular structural formula of β-monocarboxyl substituted zinc phthalocyanine is as compound a in the following reaction formula (2), which can be combined with 2,2'-disulfide in the reaction system of the above step S02 Ethanol undergoes a condensat...

Embodiment 1

[0049] Diphthalocyanine zinc complex (ZnPc-S-S-ZnPc) and its synthesis method. The molecular structural formula of the zinc diphthalocyanine complex (ZnPc-S-S-ZnPc) is shown in formula (I) above.

[0050] Its synthesis method is as follows:

[0051] Dissolve β-monosubstituted phthalocyanine zinc complex (620mg, 1mmol) and 2,2'-dithiodiethanol (154mg, 1mmol) in N,N'-dimethylformamide (50mL), and the temperature of the solution was reduced to Stir at 0°C for 0.5 hours, slowly add dicyclohexylcarbodiimide (824mg, 4mmol), N-hydroxysuccinimide (460mg, 4mmol), 4-N,N-lutidine (244mg, 2mmol) , the temperature of the reaction solution was raised to 60° C. for 12 hours. The reaction solution was cooled to room temperature, filtered, the yield filtrate was dried under reduced pressure to remove the solvent, and the remaining solid was separated and purified by silica gel chromatography, and the analytical agent was chloroform / methanol (10:1v / v) to collect the main components and dried ...

Embodiment 2

[0054] Diphthalocyanine zinc complex (ZnPc-S-S-ZnPc) and its synthesis method. The molecular structural formula of the zinc diphthalocyanine complex (ZnPc-S-S-ZnPc) is shown in formula (I) above.

[0055] Its synthesis method is as follows:

[0056] Dissolve β-monosubstituted zinc phthalocyanine complex (620mg, 1mmol) and 2,2'-dithiodiethanol (77mg, 0.5mmol) in acetonitrile (50mL), lower the temperature of the solution to 5°C and stir for 0.5 hours, slowly Add 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (382mg, 2mmol), 1-hydroxybenzotriazole (270mg, 2mmol), triethylamine (404mg, 4mmol ), the temperature of the reaction solution was raised to 50°C for 20 hours. The reaction solution was cooled to room temperature, filtered, the yield filtrate was dried under reduced pressure to remove the solvent, and the remaining solid was separated and purified by silica gel chromatography. The analytical agent was dichloromethane / ethanol (10:1), and the main components were ...

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Abstract

The invention discloses a bi-zinc-phthalocyanine coordination compound and a preparation method and an application thereof. A molecular structural formula of the bi-zinc-phthalocyanine coordination compound is as described in a specification (I). The preparation method of the bi-zinc-phthalocyanine coordination compound comprises steps of preparing a reaction solution and enabling the reaction solution to be reacted. The above bi-zinc-phthalocyanine coordination compound has no photosensitive activity when being stimulated by red light. A disulfide chemical bond of the bi-zinc-phthalocyanine coordination compound is restored by GSH (Glutathione) in a certain concentration and accordingly a zinc phthalocyanine coordination compound monomer is obtained, the photosensitive capability of the zinc phthalocyanine coordination is restored, a tumor tissue is high in GSH level, and the optical activity of the bi-zinc-phthalocyanine coordination compound is high in targeting of tumor. According to the preparation method of the bi-zinc-phthalocyanine coordination compound, only the reactant beta- single carboxyl replaced zinc phthalocyanine and 2, 2'-disulfanediyldiethanol are reacted, the reaction technology is simple and the target product yield and purity are high. The bi-zinc-phthalocyanine coordination compound can be widely applied to photodynamic drugs or photosensitive drugs.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a diphthalocyanine zinc complex and its preparation method and application. Background technique [0002] Photodynamic therapy (PDT for short), also known as photoradiation therapy (PRT for short) or photochemotherapy (Photochemotherapy), is a treatment method based on the photochemical reaction principle of specific chemical substances. The chemical substances used are called tumor chemotherapeutic drugs (also known as photosensitizer, Photosensitizer, PS for short). The process of PDT therapy is to inject the photosensitizer into the body through intravenous injection (for the skin, it can also be applied to the affected area), and after a certain period of time, the tumor tissue is irradiated with light of a specific wavelength, and the photosensitizer enriched in the tumor tissue is stimulated by light. , produce a series of photophysical and c...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K41/00A61P35/00
CPCA61K41/0071C07D487/22
Inventor 蒋雄杰黄权华杨战鏖
Owner SHENZHEN CHINA RESOURCES GOSUN PHARMA CO LTD
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