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Preparation method of methyl pheophorbide-a

A technology of pheophorbide and methyl ester, which is applied in the direction of organic chemistry, can solve the problems of ecological and environmental protection hazards, low purity, low yield of target products, etc., and achieve the effect of increasing processing output and reducing emissions

Active Publication Date: 2020-02-07
康俄(上海)医疗科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The main disadvantage of the preparation of pheophorbide a methyl ester from land plant raw materials is: low yield of the target product
However, the disadvantage of the above preparation method is that it is difficult to introduce complex equipment for ultrasonic treatment.
[0015] 2. Many invalid and waste substances in the remaining reactants include: plant raw materials that do not contain chlorophyll, and plant raw materials that have not fully extracted chlorophyll. As the solvent volume continues to increase, it hinders the purification and filtration of the target product.
[0016] 3.10g of Spirulina platensis prepared 0.06g of pheophorbide a methyl ester, but the purity is low
[0017] 4. The solvents (methanol, hexane, chloroform) used to prepare a-methyl pheophorbide exist in the mixed solution and cannot be separated and recycled
In this case, it is economically uneconomical to discharge the flushing solution into the sewer, and it is also dangerous from an ecological point of view

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Inject 3kg of chlorella into 18L of methanol, slowly add 0.9L of concentrated H 2 SO 4 , and then mixed and stirred at 22°C for 48 hours.

[0044] The excess waste material was filtered off, the filtrate was concentrated by evaporation, the residue was added to water, and neutralized with 10% NaOH to form a precipitate. Put the precipitate in the cooling box for 12 hours, separate layers, take out and remove the clear liquid, filter the remaining part through diatomaceous earth, rinse with water for 5 times, and then rinse the product with 1800ml of hexane to remove impurities. Then, the target product was washed with acetone (2100ml) and acetone: chloroform (1:1) (5000ml) mixture successively, the washing liquid was combined, evaporated and separated to obtain the target product—a methyl pheophorbide. The solid was then washed sequentially with methanol and petroleum ether and dried.

[0045] After the solid was dissolved in dichloromethane, it was purified by silic...

Embodiment 2

[0048] Inject 10kg of Spirulina platensis into 60L of methanol, slowly add 3L of concentrated H 2 SO 4 , and then mixed and stirred at room temperature for 40 hours.

[0049] The excess waste material was filtered off, the filtrate was concentrated by evaporation, the residue was added to water, and neutralized with 10% KOH to form a precipitate. Put the precipitate in the cooling box for 18 hours, separate layers, take out and remove the clear liquid, filter the remaining part through diatomaceous earth, rinse with water 10 times, and then rinse the product with 8L of hexane to remove impurities. Then, the target product was washed with acetone (9 L) and a mixture of acetone:chloroform (1:1) (20 L) successively, the washing liquid was combined, evaporated and separated to obtain the target product—a methyl pheophorbide. It was then washed sequentially with methanol and hexane, and dried.

[0050] After the solid was dissolved in chloroform, it was purified by silica gel co...

Embodiment 3

[0053] Inject 0.1kg of Spirulina platensis into 0.6L of methanol, slowly add 0.03L of concentrated H 2 SO 4 , and then mixed and stirred at 22°C for 50 hours.

[0054] The excess waste material was filtered off, the filtrate was concentrated by evaporation, the residue was added to water, and neutralized with 10% NaOH to form a precipitate. Put the precipitate in the cooling box for 24 hours, separate layers, take out and remove the clear liquid, filter the remaining part through diatomaceous earth, rinse with water for 3 times, and then rinse the product with 60ml of hexane to remove impurities. Then, the target product was washed with acetone (70ml) and acetone:chloroform (1:1) (200ml) solution successively, the washing liquid was combined, evaporated and separated to obtain the target product--a methyl pheophorbide. It was then washed sequentially with methanol and hexane, and dried.

[0055] After the solid was dissolved in dichloromethane, it was purified by silica gel...

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PUM

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Abstract

The invention belongs to the field of chemical pharmacy synthesis. More particularly, the invention relates to a preparation method of methyl pheophorbide-a, and an application of the methyl pheophorbide-a obtained by the method to preparation of a photosensitizer. The method disclosed by the invention is economical, environment-friendly and high in primary processing amount, and the purity and the yield of the target product is high.

Description

technical field [0001] The invention belongs to the field of chemical pharmaceutical synthesis. More specifically, the present invention relates to the preparation method of a-methyl pheophorbide, on the basis of which porphyrin and chlorin can be synthesized, and finally used in photodynamic therapy. Background technique [0002] Photodynamic therapy is a new treatment method for malignant tumors. It is precisely because of the biochemical characteristics of malignant cells that photosensitizers can be selectively gathered in tumor tissues, and the tissues will react when irradiated with light of specific wavelengths, producing Singlet oxygen and other active groups can have toxic effects on tumor cells (photodynamic therapy of tumors, second and third generation photosensitizers. Ed.J.G.Moser, Harwood Academic Publishers, 1998, Amsterdam; AllmanR., Cowburn P., Mason M. "Therapeutic effect of photodynamic therapy combined with ionizing radiation on squamous cell carcinoma ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22
CPCC07D487/22
Inventor 宋治国
Owner 康俄(上海)医疗科技有限公司
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