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Purpurin-18 ether derivative, and preparation method and use thereof

A violetin and derivative technology, applied in the field of medicine, can solve the problems of short tumor killing depth, small molar absorption coefficient, and high retention phototoxicity, and achieve the effect of excellent PDT killing effect.

Inactive Publication Date: 2016-11-09
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first generation of porphyrin photosensitizers such as porfimer sodium (porfimer sodium) have been successfully used in the clinical treatment of tumors, and have achieved remarkable curative effects, but there are also obvious defects: (1) the maximum absorption wavelength in the red light region is short ( 630nm) makes the laser with a matching wavelength penetrate and kill the tumor not deep enough; and the molar absorption coefficient (ε) is small, resulting in low photosensitivity; (2) is a multi-component porphyrin mixture; (3) slow clearance in the body leads to retention Phototoxic
[0006] At present, there is no literature report on purpurin-18 as the leading structure, only the etherification structure design of its 3-vinyl group

Method used

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  • Purpurin-18 ether derivative, and preparation method and use thereof
  • Purpurin-18 ether derivative, and preparation method and use thereof
  • Purpurin-18 ether derivative, and preparation method and use thereof

Examples

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Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1: Preparation of pheophorbide a (IV)

[0050] The crude extract of chlorophyll a (Ⅴ) from silkworm excrement (paste chlorophyll) was purchased from Fengming Chlorophyll Co., Ltd., Haining City, Zhejiang Province.

[0051] Dissolve 100g of silkworm excrement chlorophyll a (Ⅴ) crude extract in 500mL ether, add an equal volume of concentrated hydrochloric acid at 0-5°C and stir for 1 hour, then separate the acid solution from the lower layer, add 2 times the amount of water to dilute, and use it under cooling 10mol / L NaOH neutralized to pH 5-6, suction filtered, P 2 o 5 After drying, 15 g of crude black powder IV was obtained, which was directly used in the next reaction without further purification.

Embodiment 2

[0052] Embodiment 2: the preparation of purpurin-18 (Ⅲ)

[0053] Ⅳ Dissolve 15g of crude product in 50mL of tetrahydrofuran, add 300mL of diethyl ether to dilute, then add 25% (w / v) potassium hydroxide n-propanol solution 20mL, and pass O at 0-5°C 2 Reacted for 2h, extracted with water (300mL×2), 10%H 2 SO 4 Neutralize, filter, P 2 o 5 It was dried and separated by silica gel H column chromatography to obtain 2.7 g of black powder III.

Embodiment 3

[0054] Example 3: Preparation of 3-(1-bromoethyl)-3-desvinylpurpurin-18(Ⅲ)

[0055] Compound III (1.0 g) was added with 100 mL of 33% HBr glacial acetic acid solution, sealed at room temperature for 24 hours, and the glacial acetic acid was evaporated under reduced pressure to obtain dark green solid compound II, which was directly used in the next reaction.

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Abstract

The invention relates to the technical field of medicines, and concretely relates to a novel dihydroporphine photosensitizer - purpurin-18 ether derivative, a preparation method thereof, and a use of the purpurin-18 ether derivative in the preparation of antitumor medicines. The chemical structure of the purpurin-18 ether derivative is represented by general formula (I) shown in the description. The purpurin-18 ether derivative has the advantages of high efficiency and low toxicity, and can be used for preparing new photodynamic therapy medicines of cancers, photodynamic therapy medicines of benign diseases, such as senile macula lutea denaturation and nevus flammeus, and photodynamic therapy medicines of condyloma acuminatum.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a novel chlorin-type photosensitizer—purpurin-18 ether derivatives, a preparation method thereof, and an application in the preparation of antitumor drugs. Background technique [0002] Photodynamic therapy (PDT) is a new technology for tumor targeting therapy gradually developed in the 1980s, that is, the wavelength after administration (photosensitizer) matches the maximum absorption wavelength in the red light region of the photosensitizer. Laser irradiates the focus (tumor) tissue in a targeted manner, and the photosensitizer induces matrix oxygen (O 2 ) excited to produce singlet oxygen ( 1 o 2 ) and other reactive oxygen species (ROS), lead to apoptosis or necrosis of tumor cells and play a role in tumor targeting therapy. Because PDT only implements targeted light on tumor tissue, it can selectively destroy tumor cells while causing little or no damage to normal tissue...

Claims

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Application Information

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IPC IPC(8): C07D491/22A61K41/00A61P35/00A61P27/02A61P17/00A61P17/12A61P31/20
CPCA61K41/0076C07D491/22
Inventor 姚建忠孟志张万年盛春泉缪震元董国强贾宁阳韩贵焱刘明辉刘娜
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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