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Use of non-periphery substituted phthalocyaniu metal complex

A metal complex and non-peripheral technology, which is applied in the field of non-peripheral substituted phthalocyanine metal complexes, can solve problems such as difficult aggregation, and achieve the effects of difficult aggregation, improved photodynamic activity, and increased fluorescence quantum yield

Inactive Publication Date: 2007-08-29
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a fluorescent probe used in the field of medicine, it also needs to have the characteristics of hydrophilicity, low aggregation, high stability and easy synthesis. However, there are still few reports on phthalocyanine complexes with high fluorescence quantum yields with the above characteristics.

Method used

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  • Use of non-periphery substituted phthalocyaniu metal complex
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Examples

Experimental program
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preparation example Construction

[0041] The steps of the preparation method of the non-peripheral substituted phthalocyanine metal complex of structural formula (1) are:

[0042] (1): With 3-nitrophthalonitrile and the alcohol derivative of the substituting group described in claim 1 as the reactant, the molar ratio of the two is 1: 0.8-1.2; the alcohol derivative is butylparaben, 4-hydroxybenzoic acid, 3-(4-hydroxyphenyl)propionic acid, 3-hydroxybenzoic acid, methyl salicylate, ethyl N-acetyltyrosine, or N-acetyl One of the base tyrosine;

[0043] (2): With dimethyl sulfoxide or N, N-dimethylformamide as solvent, the amount of solvent needs 3-8ml for every mmol reactant 3-nitrophthalonitrile, in the presence of potassium carbonate and nitrogen Under the protection of , react for 8-24 hours under room temperature-60 waste, obtain intermediate substituted phthalonitrile, described substituted phthalonitrile is as shown in formula (7), R and claim 1 described substituting group R same;

[0044] (3): Using th...

Embodiment 1

[0077] Synthesis of 1,8(11), 15(18), 22(25)-tetrakis(4-butoxycarbonylphenoxy)phthalocyanine zinc(II)

[0078] This compound can also be called four-a-(4-butoxycarbonylphenoxy)zinc phthalocyanine (II), and its structure is shown in formula 1, wherein:

[0079]

[0080] (1) Preparation of intermediate 3-(4-butoxycarbonylphenoxy) phthalonitrile:

[0081] Under the protection of nitrogen, 5mmol butylparaben and 4-6mmol (preferably 5mmol) 3-nitrophthalonitrile were added to 15-40ml (preferably 20ml) dimethyl sulfoxide (DMSO) or N, N - In dimethylformamide (DMF), after stirring at room temperature for 10 minutes, add 1.5 g (10.9 mmol) of anhydrous potassium carbonate, and react for 12 to 24 hours (preferably 16 hours). The reaction mixture was added to 200ml of ice-water mixture, stirred to precipitate a large amount of white precipitate, left to stand, filtered by suction, washed with water until neutral, the filter cake was collected, dried under normal pressure at 70°C to obt...

Embodiment 2

[0088] Synthesis of 1,8(11), 15(18), 22(25)-tetrakis(4-carboxyphenoxy)phthalocyanine zinc(II)

[0089] This compound can also be called four-a-(4-carboxyphenoxy) zinc phthalocyanine (II), and its structure is shown in formula 1, wherein:

[0090]

[0091] (1) Preparation of intermediate 3-(4-carboxyphenoxy) phthalonitrile:

[0092] Under the protection of nitrogen, 0.69g (5mmol) 4-hydroxybenzoic acid, 0.87g (5mmol) 3-nitrophthalonitrile were dissolved in 20ml dimethyl sulfoxide (DMSO), after stirring at room temperature for 10 minutes, add 1.5 g (10.9 mmol) of anhydrous potassium carbonate, after 10 minutes, add 1.0 g of potassium carbonate, and continue the reaction for 12 to 24 hours (preferably 14 hours). Suction filter the reaction mixture, collect the filtrate, add 200ml ice-water mixture to the filtrate, adjust the pH value to 1~3 (preferably 2) with 2mol / L HCl solution, the product is precipitated out, filter, wash with water until neutral, collect The filter cake ...

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Abstract

The present invention provides several application of non-peripheral substituted phthalocyanine metal coordination compound. The invented phthalocyanine metal coordination compound has the application for preparing photosensitive medicine preparation which can be used in photodynamic therapy or photodynamic diagnosis, and has the application for preparing photosensitizer which can be used in photodynamic purification or disinfection. Besides, it can be used as fluorescence probe or can be used for determining protein content.

Description

technical field [0001] The invention belongs to the field of organic functional materials (including medical materials), and specifically relates to the use of non-peripheral substituted phthalocyanine metal complexes. Background technique [0002] Phthalocyanine complexes are an important class of functional materials, which have been widely used in textile, printing and many other high-tech fields. Phthalocyanine metal complexes are also used as photosensitizers in photodynamic therapy or diagnosis, or in photodynamic purification or disinfection. [0003] The process of photodynamic therapy is to irradiate the photosensitizer enriched in the target body with light of a specific wavelength. Under the light excitation, the photosensitizer inspires a series of photophysical and photochemical reactions to generate active oxygen, and then destroys the target body (such as cancer cells, cancerous tissues, bacteria and viruses, etc.). The biggest advantage of photodynamic ther...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/409A61K49/00A61P35/00A61P17/00A61P31/12A61P9/10A61P27/02
Inventor 黄剑东
Owner FUZHOU UNIV
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