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Disubstituted zinc phthalocyanine composite, and preparation method and application thereof

A technology of zinc phthalocyanine and its composition, which is applied in the field of double-substituted zinc phthalocyanine composition and its preparation and application, can solve the difference in the effect of photodynamic therapy and has not been studied by anyone, the composition of isomers is complex, and no one has proposed industrialization Production technology and other issues, to achieve the effect of photodynamic killing effect

Active Publication Date: 2011-05-18
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although the zinc phthalocyanine composition obtained by this synthetic method has amphiphilicity, due to the complex composition and target component isomers, the composition is potassium disulfonate diphthalimide methylphthalein Zinc cyanine just contains 10 kinds of cis-isomers and 5 kinds of trans-isomers (in the description of the present invention, zinc disulfodiphthalimide methyl phthalocyanine and its sulfonate are referred to as ZnPcS 2 P 2 At the same time, in the description of the present invention, the zinc phthalocyanine compounds involved in the similar but different numbers of substituents are abbreviated as follows. If there are three -S substituents and one -P substituent on the zinc phthalocyanine ring, the abbreviation ZnPcS 3 P, if there are 2 -S substituents and 2 -P substituents on the zinc phthalocyanine ring, it is referred to as ZnPcS 2 P 2 , and so on ZnPcS 4 , ZnPcP 4 , ZnPcSP 3 etc., the -S substituent is a sulfonic acid group or its salt, and the -P substituent is a phthalimide methyl group), but the difference in the photodynamic therapy effect between the isomers has not yet been studied, and it is also No one has proposed an industrial production process to separate the isomer with better photodynamic therapy effect from the mixture

Method used

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  • Disubstituted zinc phthalocyanine composite, and preparation method and application thereof
  • Disubstituted zinc phthalocyanine composite, and preparation method and application thereof
  • Disubstituted zinc phthalocyanine composite, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0064] raw material:

[0065] The zinc phthalocyanine mixture synthesized by the "semi-phthalocyanine zinc ring method" can be referred to the Chinese patent with the application number "200410013492.4", which contains ZnPcS 2 P 2 A total of 15 cis and trans isomers and ZnPcS 4 , ZnPcS 3 P, ZnPcSP 3 with ZnPcP 4 , a mixture of other raw material fragments and intermediate products, the HPLC spectrum of the synthetic product is shown in figure 1 .

[0066] 1) Coarse separation:

[0067] a. Equilibrium coarse separation column: the packing length of the coarse separation column is 300mm, the diameter is 50mm, and the filler is Japanese YMC * Expere C1850μ,

[0068] b. Sampling: get a certain amount of raw material, make a pH value of 7.0 to 8.0, contain 65% DMF in the aqueous solution, pump it into the rough separation column, the zinc phthalocyanine content in the solution is 0.5% of the weight of the filler, The zinc phthalocyanine concentration is 8g / L, the injection...

Embodiment 2

[0081] Step is the same as embodiment 1, and parameter is adjusted to some extent, specifically as follows:

[0082] Raw material: with embodiment 1;

[0083] 1) Coarse separation:

[0084] a. Equilibrium coarse separation column: the packing length of the coarse separation column is 600mm, the diameter is 100mm, and the filler is Japanese Daisogel C1850μ,

[0085] b. Sampling: take the raw material, make a pH value of 7.0 to 8.0, and pump it into an aqueous solution containing 70% DMF, and pump it into the rough separation column. The concentration is 12g / L, the injection column temperature is 28°C, and the injection flow rate is 400ml / min;

[0086] c. Elution: The temperature of the elution column is 28° C., and the rest are the same as in Example 1.

[0087] d. Column enrichment: the same as in Example 1, but when eluted with a concentration of 20% DMF aqueous solution and a concentration of 75% DMF aqueous solution, the fraction with high zinc phthalocyanine content was...

Embodiment 3

[0094] Raw material: with embodiment 1

[0095] 1) Coarse separation:

[0096] a. Equilibrium coarse separation column: the packing length of the coarse separation column is 1000mm, the diameter is 200mm, and the filler is Capcell PaR C18 UG-8050μ;

[0097] b. Sampling: take the raw material, make a pH value of 7.0 to 8.0, and pump it into an aqueous solution containing 65% DMF. The content of zinc phthalocyanine in the solution is 0.35% of the weight of the filler. The concentration is 15g / L, the injection column temperature is 35°C, and the injection flow rate is 800ml / min;

[0098] c. Elution: The temperature of the elution column is 28° C., and the rest are the same as in Example 1.

[0099] d. Column enrichment: the same as in Example 1, but when eluted with a concentration of 30% DMF aqueous solution and a concentration of 80% DMF aqueous solution, the fraction with high zinc phthalocyanine content was collected.

[0100] 3) fine separation:

[0101] a. Equilibrium fin...

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Abstract

The invention discloses a new medicine for treating cancers or precancerous lesions by utilizing a photodynamic therapy, and the medicine provided by the invention contains 4 zinc phthalocyanine isomer composites. The invention simultaneously provides the industrial chromatograph preparation process of the medicine. The preparation method provided by the invention comprises the following steps: separating 10 cis-isomers from the synthetic bisulfo biphthalyl dicarboximide zinc phthalocyanine; and further separating 4 isomers with better amphipathy from the synthetic bisulfo biphthalyl dicarboximide zinc phthalocyanine. The experiment indicates that the properties of the composite provided by the invention are superior to the mixture containing the 10 cis-isomers.

Description

technical field [0001] The invention relates to a double-substituted zinc phthalocyanine composition and its preparation method and application, in particular to a zinc phthalocyanine composition used as a photosensitizer for photodynamic therapy. Background technique [0002] Phthalocyanine compounds have been widely concerned and researched in recent years as photosensitizer drugs for photodynamic therapy of diseases such as cancer. For example, Chinese patent application No. 200410013492.4 discloses a preparation method of a phthalocyanine metal complex, which is based on 4-Potassium sulfonate phthalonitrile and 4-phthalimidomethyl phthalonitrile are used as raw materials, first react in lithium alkoxide solution to generate corresponding potassium sulfonate substituted hemiphthalonitrile Zinc cyanine and half phthalocyanine zinc substituted with phthalimidomethyl were used as precursors, and then, a cyclization reaction was carried out in 2-ethoxyethanol to generate bis(...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/555A61K41/00A61P35/00C07D487/22
CPCA61K31/555C07D487/22A61P35/00
Inventor 陈耐生黄金陵薛金萍刘宏王建王俊生江舟
Owner FUZHOU UNIV