Chlorophyllin salt compound and preparation method thereof

A chlorophyll compound, compound technology, applied in the directions of organic chemistry, pharmaceutical combination, pharmaceutical formulation, etc., can solve the problems of incomplete clarity of active ingredients, poor water solubility of porphyrin salts, and ineffectiveness, etc., and achieve beneficial effects on the human body. The effect of health, strong water solubility, and low dark toxicity

Active Publication Date: 2011-12-07
太阳升(亳州)生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since the active ingredients of xibofen are not completely clear, the popularization and application of xibofen as the first generation anticancer photosensitizer has not achieved the expected effect
[0007] At present, the patent application "Water-Soluble Porphyrin Derivatives for Photodynamic Therapy, Its Use and Preparation" (Patent No. 02811141.9) and the patent application "Water-Soluble Porphyrin Salts for Photodynamic Therapy" in China Preparation method" (patent application No. 200910130260.X) all involve a water-soluble porphyrin salt for photodynamic therapy, the R of the porphyrin salt 5 , R 6 The substituents are all alkyl substituents, resulting in poor water solubility of the porphyrin salt, which is more difficult in subsequent pharmaceutical preparations

Method used

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  • Chlorophyllin salt compound and preparation method thereof
  • Chlorophyllin salt compound and preparation method thereof
  • Chlorophyllin salt compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] A chlorophyllin compound, the general formula is as follows:

[0038]

[0039] Among them, R 1 independently selected from C 1-18 Alkyl, C 1-18 Alkenyl, C 1-8 Alkoxy and C 1-18 Acyl, which is optionally substituted by one or more substituents selected from halogen and hydroxy; R 2 for Na + , sodium carboxylate, or glucoside; R 3 Is H, carboxyl, or sodium carboxylate.

[0040] In a preferred embodiment, R 1 independently selected from CH 2 (CH 2 ) 4 CH 3 , R 2 for Na + , sodium carboxylate, or glucoside, R 3 is H or carboxyl.

[0041] [0023] Examples of water-soluble chlorophyllin compounds in this embodiment include but are not limited to:

[0042]

[0043] (I)

[0044]

[0045] (II)

[0046] The preparation method of the above-mentioned chlorophyllin salt compound comprises the following steps:

[0047] 1. Convert pheophorbide into acidic porphyrin;

[0048] II. Derivatizing the acidic porphyrin to obtain a complex derivative acidic porphy...

Embodiment 2

[0062] In this example, 2-desvinyl-2-(1-hexylhydroxyethyl)-pyropheophorbide-a sodium (1) was prepared from silkworm excrement chlorophyll.

[0063] Ⅰ. Convert pheophorbide into acidic porphyrin:

[0064] A, preparation of pheophorbide-a methyl ester:

[0065] Dissolve 200g silkworm excrement chlorophyll in 4000mL methanol solution containing 5% sulfuric acid; then stir under nitrogen protection at 15-25°C in the dark for 12 hours; then filter; add water and dichloromethane for extraction; The organic phase is washed with water; then dried and concentrated under reduced pressure; and then the obtained concentrate is subjected to silica gel column chromatography separation treatment. In the chromatography separation treatment, the eluent is petroleum ether and ethyl acetate ester, the volume ratio of the petroleum ether and ethyl acetate was 3:1, and the dark green solid A6.9g was obtained, which contained the pheophorbide-a methyl ester, and the yield was 85%. UV-vis (CHCl 3...

Embodiment 3

[0077] In this example, 2-desvinyl-2-(1-hexylhydroxyethyl)-pheophorbide-a disodium (2) was prepared from silkworm excrement chlorophyll.

[0078] Ⅰ. Convert pheophorbide into acidic porphyrin:

[0079] A. Preparation of pheophorbide-a methyl ester:

[0080] Dissolve 100g silkworm excrement chlorophyll in 2000mL methanol solution containing 5% sulfuric acid; then stir under nitrogen protection at 15-25°C and avoid light for 12 hours; then filter; add water and dichloromethane for extraction; The organic phase is washed with water; then dried and concentrated under reduced pressure; and then the obtained concentrate is subjected to silica gel column chromatography separation treatment. In the chromatography separation treatment, the eluent is petroleum ether and ethyl acetate , the volume ratio of petroleum ether and ethyl acetate was 3:1, and 3.50 g of dark green solid A was obtained, which contained the pheophorbide-a methyl ester, and the yield was 85%. UV-vis (CHCl 3 ) λm...

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PUM

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Abstract

The invention belongs to the field of heterocyclic compounds and particularly relates to a chlorophyllin salt compound and a preparation method thereof. The chlorophyllin salt compound is a novel photosensitizer which is stable in nature, high in photodynamic activity, low in skin toxicity and controllable in quality and is used for photodynamic treatment of cancers, infections and other diseasesrequired to be treated by optical radiation. In the invention, the substituent of R3 is inform of a carboxylate, so the water solubility is high and the preparation of subsequent medicinal preparations is promoted; the absorption wavelength is more than 650 nanometers; the quantum yield of triplet state and the quantum yield of low singlet oxygen are high; the toxicity in darkness is low, and health of human body can be improved; the selectivity is high; the structure is clear and the performance is stable; and the fat water compatibility is high.

Description

technical field [0001] The invention belongs to the field of heterocyclic compounds, and in particular relates to a chlorophyllin compound and a preparation method thereof. Background technique [0002] Photodynamic therapy (Photodynamic Therapy, PDT) is a new technology that uses photodynamic effect for disease diagnosis and treatment. Its basis is the photodynamic effect. This is a photosensitization reaction accompanied by biological effects involving oxygen molecules. The process is that the photosensitizer absorbed by the tissue is excited by the laser irradiation of a specific wavelength, and the photosensitizer in the excited state transfers energy to the surrounding oxygen to generate highly active singlet oxygen, and the singlet oxygen and adjacent biological Oxidation of macromolecules produces cytotoxicity, which in turn leads to cell damage and even death. [0003] As a new technology for tumor treatment, photodynamic therapy has many important advantages comp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K41/00A61P35/00
Inventor 郭鸿旭张卫东缪也夫
Owner 太阳升(亳州)生物医药科技有限公司
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