Novel chlorin e6 derivative and preparation method and application thereof

A technology for chlorin and derivatives, which is applied in the field of novel chlorin e6 derivatives and their preparation, can solve the problems of high cost, difficulty in popularization and application, difficulty in separation and preparation, and the like

Inactive Publication Date: 2018-11-23
陈志龙
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by the present invention is to overcome the defects of very difficult separation and preparation of the chlorin-type photosensitizer taraporfin, high cost, high price, and difficulty in popularization and application. carried out modification and transformation, and synthesized a new chlorin e6 derivative with a very simple method after paying a lot of creative work, and completed the present invention

Method used

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  • Novel chlorin e6 derivative and preparation method and application thereof
  • Novel chlorin e6 derivative and preparation method and application thereof
  • Novel chlorin e6 derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 1, 13 1 Preparation of -N-[2-(2-pyridine)ethyl]chlorphine e6 amide dimethyl ester

[0021]

[0022] In a 25mL three-necked flask, pheophorbide-a methyl ester (100mg, 0.18mmol), tetrahydrofuran (4mL) and 2-pyridylethylamine (2mL) were stirred at room temperature for 16h, and the reaction was monitored by thin-layer chromatography until the reaction was complete . 40 mL of dichloromethane was added to the reaction solution for extraction. The organic phase was washed with water (20 mL×3), washed with saturated brine (20 mL×3), dried over anhydrous sodium sulfate, and filtered. Concentrated under reduced pressure to remove the solvent, and separated by silica gel column chromatography (methanol / dichloromethane=1:10) to obtain 13 1 -N-[2-(2-Pyridine)ethyl]chlorin e6 amide dimethyl ester green solid powder (43.8 mg), yield about 38%. 1 H NMR (400MHz, CDCl 3 ): δppm 9.65 (1H, s, H10), 9.62 (1H, s, H5), 8.79 (1H, s, H20), 8.39 (1H, d, J=4.8Hz, H13 6 ), 8.07 (1H, dd, J...

Embodiment 2

[0024] 1. Photodynamic anti-proliferation experiment of photosensitizers on human esophageal cancer cell line Eca-109

[0025] Tested cells: human esophageal cancer cells (Eca-109)

[0026] Drugs tested: 13 1 -N-[2-(2-pyridine)ethyl]chlorin e6 amide dimethyl ester (hereinafter referred to as photosensitizer 1), temoporfin (comparative drug, provided by Shanghai Xianhui Pharmaceutical Technology Co., Ltd.).

[0027] Light source: XD-650AB laser; SD2490 laser power measuring instrument.

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PUM

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Abstract

The invention relates to a novel chlorin e6 derivative and a preparation method and application thereof. The compound is of a following structure shown in the description. The invention relates to thefield of photosensitive medicine (also called as a photosensitizer or photodynamic medicine) and photodynamic therapy and especially relates to a chlorin photosensitizer, a preparation method thereofand application thereof to the field of medicine. The photosensitive medicine disclosed by the invention has advantages of stable chemical property, very strong photodynamic activity and applicationto photodynamic therapy of diseases of tumor, macular degeneration of retina, actinic keratosis, nevus flammeus, condyloma acuminata and the like.

Description

technical field [0001] The invention belongs to the fields of chemical pharmacy and photodynamic therapy, and in particular relates to a novel chlorin e6 derivative and its preparation method and application. technical background [0002] Photodynamic therapy (PDT) is a new method for the treatment of tumors, macular degeneration, actinic keratosis, port wine stains, genital warts and other diseases. Since entering clinical research in the 1970s, PDT has made remarkable achievements in clinical treatment because of its good selectivity, low toxicity, good reproducibility, safety, minimal invasiveness, synergy and Advantages such as relatively low cost stand out, showing huge potential and strong vitality. [0003] The principle of photodynamic therapy is that after the photosensitizer enters the body, it selectively gathers in the target tissue along with the blood circulation, and then directly irradiates the tumor tissue with a laser of a certain wavelength. After absorbi...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K41/00A61P35/00A61P27/02A61P17/12A61P17/00
CPCC07D487/22A61K41/0071
Inventor 陈志龙达沃·马格提高迎华索尼娅·桑拉娜维克朱维陈聃烨
Owner 陈志龙
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