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Water-soluble sugar phthalocyanine and a method for preparing same

A water-soluble sugar and sugar phthalocyanine technology, applied in the field of organic compound synthesis, can solve the problem of little improvement in the biocompatibility of phthalocyanine, and achieve good biocompatibility, good water solubility, and broad application prospects

Inactive Publication Date: 2009-09-16
INST OF BIOMEDICAL ENG CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, neither the introduction of carboxyl group nor the introduction of sulfonic acid group improved the biocompatibility of phthalocyanine much.

Method used

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  • Water-soluble sugar phthalocyanine and a method for preparing same
  • Water-soluble sugar phthalocyanine and a method for preparing same
  • Water-soluble sugar phthalocyanine and a method for preparing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The preparation method of water-soluble sugar phthalocyanine comprises the steps:

[0028] (1) Dissolve 1.638g of 4-chlorophthalonitrile, 1.2g of propynyl alcohol, and 8.3g of anhydrous potassium carbonate in 40ml of N,N-dimethylformamide (DMF), and react at 60°C for 1 sky;

[0029] Post-processing: Put ice cubes into a 1000ML large beaker, add about 500ML of distilled water, pour the reaction solution into the beaker, then add dichloromethane for extraction, combine the extracts, wash with water, combine the organic phases, concentrate by rotary evaporation, concentrate A small amount of anhydrous methanol was added to the solution for recrystallization to obtain alkynylphthalonitrile;

[0030] (2) 100 mg of alkynylphthalonitrile, 205 mg of azide-substituted glucose, 9 mg of anhydrous copper sulfate, and 22 mg of sodium ascorbate were dissolved in 15 methylene chloride and petroleum ether at a volume ratio of 4:1. In a mixed solvent, react with electromagnetic stirri...

Embodiment 2

[0036] The preparation method of water-soluble sugar phthalocyanine comprises the steps:

[0037] (1) Dissolve 1.6g of 4-nitrophthalonitrile, 1.2g of methyl butynol, and 8.3g of anhydrous potassium carbonate in 30ml of N,N-dimethylformamide, and react at 50°C for 3 day, pour it into a container filled with cold water, extract with chloroform, combine the extracts, wash with water, combine the organic phases, concentrate, add a small amount of anhydrous methanol to the concentrated solution for recrystallization, and obtain alkynylphthalonitrile;

[0038] (2) Dissolve 0.1g of alkynylphthalonitrile and 0.2g of azide-substituted fructose in 15ml of a mixed solvent of dichloromethane and petroleum ether at a volume ratio of 4:1, and stir at room temperature under the catalysis of 10mgCuBr React for 12 hours, wash the reaction solution with water, extract with chloroform, combine the organic phases, spin dry; obtain acetylated sugar phthalonitrile;

[0039] (3) Dissolve 0.6g of ac...

Embodiment 3

[0042] The preparation method of water-soluble sugar phthalocyanine comprises the steps:

[0043] (1) Dissolve 3.2g of 4-iodophthalonitrile, 2.4g of propargylamine, and 32.6g of anhydrous sodium carbonate in 50ml of N,N-dimethylformamide, react at 80°C for 1 day, pour In a container filled with cold water, extract with dichloromethane, combine the extracts, wash with water, combine the organic phases, concentrate, add a small amount of anhydrous methanol to the concentrated solution for recrystallization, and obtain alkynylphthalonitrile;

[0044](2) Dissolve 0.2g of alkynylphthalonitrile and 0.4g of azide-substituted galactose in 30ml of a mixed solvent of dichloromethane and petroleum ether at a volume ratio of 4:3, under the catalysis of 20mgCuCl, at room temperature Stir the reaction for 72 hours, wash the reaction solution with water, extract with dichloromethane, combine the organic phases, and spin dry; obtain acetylated sugar phthalonitrile;

[0045] (3) Dissolve 0.8g...

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Abstract

The invention relates to water-soluble sugar phthalocyanine and a method for preparing same. The water-soluble sugar phthalocyanine has the structure (I). The water-soluble sugar phthalocyanine of the invention has high water solubility, and is absorbent in the near-infrared region of 600nm to 900nm, therefore, the water-soluble sugar phthalocyanine can overcome various biological barriers; and the water-soluble sugar phthalocyanine has good biocompatibility, so that the invention is applicable to the fields, such as non-linear photoelectric materials, near-infrared molecular probes, photodynamical cancer treatment and the like. The method of the invention is simple and easy to operate.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and in particular relates to water-soluble sugar phthalocyanine and a preparation method thereof. Background technique [0002] Phthalocyanine has good light, oxygen and thermal stability, and has extensive and important applications in many fields. In particular, water-soluble phthalocyanine is widely used in biochemical analysis due to its unique absorption and fluorescence characteristics. Its non-specific strong adsorption to protein makes it be used as a new type of protein labeling reagent, and its high fluorescence quantum yield makes it used to label antibodies or DNA probes in fluorescent immunoassays. In addition, as an optoelectronic material, phthalocyanine has been widely used in the fields of photodynamic medicine, laser dye and ink. How to increase its water solubility and biocompatibility is the key to promote the application of phthalocyanine in the field of biomedicin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/02C07H1/00C08B37/08C08B37/16
Inventor 刘天军何绪军吕丰
Owner INST OF BIOMEDICAL ENG CHINESE ACAD OF MEDICAL SCI
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