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3-sulfopropane mercapto-modified phthalocyanine and its preparation method and application in pharmaceutical field

A sulfonic acid propane and sulfhydryl modification technology, which is applied in chemical instruments and methods, drug combinations, antitumor drugs, etc., can solve problems such as poor water solubility, and achieve the effects of stable properties, high antitumor activity, and easy storage.

Active Publication Date: 2021-11-02
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With the modification of the structure of phthalocyanine, various functions of phthalocyanine have been gradually developed, but it is also faced with challenges including how to overcome the poor water solubility caused by its macrocyclic skeleton structure, improve targeting and improve its therapeutic effect. efficiency, making it an ideal photosensitizer and the challenge of photothermal agents

Method used

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  • 3-sulfopropane mercapto-modified phthalocyanine and its preparation method and application in pharmaceutical field
  • 3-sulfopropane mercapto-modified phthalocyanine and its preparation method and application in pharmaceutical field
  • 3-sulfopropane mercapto-modified phthalocyanine and its preparation method and application in pharmaceutical field

Examples

Experimental program
Comparison scheme
Effect test

Embodiment example 1

[0034] The synthesis of zinc phthalocyanine complexes substituted by β-position monosulfonic acid groups with the structure shown in the following formula:

[0035]

[0036] (1) prepare the phthalonitrile derivative of following formula of structure:

[0037] With 4-nitrophthalonitrile (10mmol) and sodium 3-mercaptopropanesulfonate (10-40mmol, preferably 20mmol) as reactants, dimethyl sulfoxide (DMSO) (20-100mL, preferably 30mL) as reactant Solvent, in the presence of potassium carbonate (30-90mmol, preferably 50mmol) and under the protection of nitrogen, stir the reaction at 20-45°C (preferably 45°C) for 17-24 hours, and monitor by thin layer chromatography. After the reaction, the reaction solution was suction filtered to remove unreacted potassium carbonate, the filtrate was poured into chloroform, part of the milky white precipitate was precipitated, filtered, washed with chloroform, acetone, and absolute ethanol respectively, the filter residue was collected, and vac...

Embodiment example 2

[0044] Synthesis of a disulfonic acid group substituted zinc phthalocyanine complex with the structure shown in the following formula

[0045]

[0046] (3) prepare the phthalonitrile derivative of following formula of structure:

[0047] With 4,5-dichlorophthalonitrile (10mmol) and sodium 3-mercaptopropanesulfonate (20-70mmol, preferably 30mmol) as reactants, DMSO (20-60mL) as solvent, potassium carbonate (30 In the presence of -90mmol, preferably 80mmol) and nitrogen protection, the reaction was stirred at 40-80°C (preferably 50°C) for 24-72 hours, and monitored by thin-layer chromatography. After the reaction, the reaction solution was suction filtered to remove unreacted potassium carbonate, the filtrate was poured into chloroform, part of the milky white precipitate was precipitated, filtered, washed with chloroform, acetone, and absolute ethanol respectively, the filter residue was collected, and vacuum-dried to obtain a white solid. The yield was 60%.

[0048] NM...

Embodiment example 3

[0054] Synthesis of α-position monosubstituted sulfonic acid zinc phthalocyanine complexes with the following structure:

[0055]

[0056] (5) Preparation of phthalonitrile derivatives with the following formula

[0057] With 3-nitrophthalonitrile (10mmol) and sodium 3-mercaptopropanesulfonate (10-40mmol, preferably 20mmol) as reactants, DMSO (20-100mL, preferably 30mL) as solvent, in potassium carbonate ( In the presence of 30-90mmol, preferably 50mmol) and nitrogen protection, the reaction was stirred at 20-45°C (preferably 45°C) for 17-24 hours, and monitored by thin-layer chromatography. After the reaction, the reaction solution was suction filtered to remove unreacted potassium carbonate, the filtrate was poured into chloroform, part of the milky white precipitate was precipitated, filtered, washed with chloroform, acetone, and absolute ethanol respectively, the filter residue was collected, and vacuum-dried to obtain a white solid. The yield was 75%.

[0058] NMR...

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Abstract

The invention discloses a 3-sulfopropane mercapto-modified phthalocyanine, a preparation method and an application thereof. The absorption spectra of metallophthalocyanines and cavity phthalocyanines substituted by sulfur bridges according to the present invention have obvious red shift relative to phthalocyanines substituted by oxygen bridges; under the irradiation of near-infrared laser and the participation of oxygen , will efficiently generate singlet oxygen; in vivo fluorescence imaging shows that the sulfur bridge substituted phthalocyanine of the present invention has high tumor targeting, and can selectively enrich the tumor in the absence of other auxiliary agents. Set; Both in vitro and in vivo experiments prove that the 3-sulfopropane mercapto-modified phthalocyanine of the present invention has high antitumor activity, and can realize efficient photodynamic therapy as a photosensitizer.

Description

technical field [0001] The invention belongs to the field of photosensitizers and photodynamic therapy drugs, and in particular relates to functionalized modified metal-cavity phthalocyanine complexes and applications thereof. Background technique [0002] At present, malignant tumors have become one of the main diseases that affect human health and threaten human life. However, traditional tumor treatment methods, including surgery and chemotherapy, have major shortcomings and deficiencies, making tumor prevention and treatment an urgent problem to be solved. With the development of science and technology, some methods of treating malignant tumors are emerging, including photodynamic therapy (PDT). As a non-invasive treatment, it has attracted people's attention and expectation because of its advantages of non-invasiveness, less toxic and side effects, quick effect, and no drug resistance under repeated application. [0003] PDT is a treatment method based on photochemistr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22C09B47/06C09K11/06A61K41/00A61P35/00
CPCA61K41/0076A61P35/00C07D487/22C09B47/045C09B47/063C09K11/06C09K2211/188
Inventor 黄剑东赵园园李兴淑柯美荣郑碧远
Owner FUZHOU UNIV
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