Zinc phthalocyanine hydriodate photosensitizer, as well as preparation method and application thereof

A technology of zinc phthalocyanine hydroiodide and photosensitizer, which is applied in the field of photosensitizers, can solve problems such as complex organic reactions and separation and purification processes, and achieve good application prospects, low dark toxicity, and high singlet oxygen quantum yield Effect

Inactive Publication Date: 2016-02-10
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of quaternary ammonium phthalocyanine involves complex organic reactions and separation and purification processes

Method used

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  • Zinc phthalocyanine hydriodate photosensitizer, as well as preparation method and application thereof
  • Zinc phthalocyanine hydriodate photosensitizer, as well as preparation method and application thereof
  • Zinc phthalocyanine hydriodate photosensitizer, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 12

[0052] The synthesis of embodiment 12,9,16,23-four-((4-aminomethyl) phenoxy group) zinc phthalocyanine hydroiodide

[0053] (1) Synthesis of 4-((4-aminomethyl)phenoxy)phthalonitrile

[0054] The reaction formula is as follows:

[0055]

[0056] Under nitrogen protection, 4-nitrophthalonitrile, p-hydroxybenzylamine and K 2 CO 3 Added into DMF at a molar ratio of 1:1:2, then added 10mL of dichloromethane as a solvent, and reacted at 60°C for 6h to obtain intermediate 3;

[0057] (2) Synthesis of 4-(4-((tritylamino)methyl)phenoxy)phthalonitrile

[0058] The reaction formula is as follows:

[0059]

[0060] Under the protection of nitrogen, triphenylchloromethane was dissolved in dichloromethane, and slowly dropped into the dichloromethane solution of intermediate 3 and potassium carbonate with a constant pressure dropping funnel, intermediate 3 was mixed with triphenylchloromethane and potassium carbonate The molar ratio is 1:1.2:2.5, titrate for about 5 hours, and the...

Embodiment 2

[0074] The synthetic method of 2,9,16,23-tetra-((4-aminomethyl) phenoxy) zinc phthalocyanine hydroiodide, the steps are as follows:

[0075] (1) Synthesis of 4-((4-aminomethyl)phenoxy)phthalonitrile

[0076] Under nitrogen protection, 4-nitrophthalonitrile, p-hydroxybenzylamine and LiOH were added to DMF at a molar ratio of 1:1.5:2, and then 10 mL of dichloromethane was added as a solvent to react at 80°C for 6 hours to obtain intermediate 3 ;

[0077] (2) Synthesis of 4-(4-((tritylamino)methyl)phenoxy)phthalonitrile

[0078] Under the protection of nitrogen, triphenylchloromethane was dissolved in dichloromethane, and the constant pressure dropping funnel was slowly dropped into the dichloromethane solution of intermediate 3 and LiOH. The molar ratio of intermediate 3 to triphenylchloromethane and LiOH was 1:1.5:2, titrate for about 5 hours, and then react at room temperature for 4 hours to obtain intermediate 4;

[0079] (3) Synthesis of 2,9,16,23-tetra-((4-(((trityl)amin...

Embodiment 3

[0086] The synthesis of 2,9,16,23-tetrakis-((4-aminomethyl)phenoxy)zinc phthalocyanine hydrochloride (II) is as follows:

[0087]

[0088] (1) According to the steps (1) to (4) of Example 1, 2,9,16,23-tetrakis-((4-aminomethyl)phenoxy)zinc phthalocyanine was obtained;

[0089] (2) Synthesis of 2,9,16,23-tetrakis-((4-aminomethyl)phenoxy)zinc phthalocyanine hydrochloride

[0090] Suspend 2,9,16,23-tetrakis-((4-aminomethyl)phenoxy)zinc phthalocyanine 6 in distilled water, add 30 equivalents of 5% hydrochloric acid, and stir at room temperature until 2,9,16 , 23-Tetrakis-((4-aminomethyl)phenoxy)zinc phthalocyanine 6 was completely dissolved. The reaction solution was concentrated, poured into 50 mL of acetone, and blue-green flocculent solids were precipitated. After filtration, 2,9,16,23-tetrakis-((4-aminomethyl)phenoxy)zinc phthalocyanine hydrochloride II was obtained.

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Abstract

The invention discloses a 2,9,16,23-tetra-((4-aminomethyl) phenoxy) zinc phthalocyanine hydroiodide, as well as a preparation method and application thereof to a photodynamic therapy method, and relates to a 2,9,16,23-tetra-((4-aminomethyl) phenoxy) zinc phthalocyanine hydroiodide photosensitizer. The 2,9,16,23-tetra-((4-aminomethyl) phenoxy) zinc phthalocyanine hydroiodide photosensitizer not only is simple in synthetic method, excellent in solubility (based on the protonation principle) in water, high in anti-tumor activity (based on the heavy atom effect) and low in dark toxicity, but also has a good application prospect in the field of photodynamic therapy methods.

Description

technical field [0001] The invention belongs to the technical field of photosensitizers with photodynamic activity, and relates to a zinc phthalocyanine hydroiodate photosensitizer, its synthesis method and its application in photodynamic therapy. Background technique [0002] Molecules containing phthalocyanine macrocycles are known to generate reactive oxygen species, such as singlet oxygen, and are characterized as highly fluorescent by interaction with visible light. Due to these properties, phthalocyanine compounds have been used for some time both for therapeutic treatment and for diagnostic purposes in photodynamic therapy (hereinafter denoted by the abbreviation "PDT"). As described in European patents EP0906758, EP1164135, EP1381611 and EP1883641, phthalocyanines have proven to be effective photosensitizers in the PDT treatment of tumors and microbial infections. [0003] PDT includes three basic elements: light source, oxygen and photosensitizer. Among them, with...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K41/00
CPCY02P20/55C07D487/22A61K41/00
Inventor 魏少华靳维维周林周家宏林云
Owner NANJING NORMAL UNIVERSITY
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