Design and synthesis of photosensitizer,13,15-cycloimides chlorin p6
10.3969/j.issn.1006-0111.2017.01.007
- VernacularTitle:二氢卟吩p6-13，15-环酰亚胺类光敏剂的设计合成
- Author:
Minghui LIU
1
;
Junhong LIU
;
Guiyan HAN
;
Xingjie ZHANG
;
Chunquan SHENG
;
Jianzhong YAO
Author Information
1. 福建中医药大学药学院
- Keywords:
photodynamic therapy;
photosensitizer;
chlorine p6;
cycloimide;
antitumor
- From:
Journal of Pharmaceutical Practice
2017;35(1):26-30,35
- CountryChina
- Language:Chinese
-
Abstract:
Objective To design and prepare 13 ,15-cycloimides chlorin p6 (1) ,a class of chlorin related antitumor photo-sensitizers ,which contain a more stable six-membered cyclic imide comparing to the exocyclic anhydride ring of purpurin-18 (2) .Compounds (1) exhibit strong absorption at long wavelengths near λmax 700 nm to take full advantage of greater tissue penetration .Methods Pheophorbide a (3) was obtained by acid hydrolysis of chlorophyll a ,which was from crude chlorophyll extracts of Chinese traditional herb named Silkworm excrement .Purpurin-18 (2) was prepared by air oxidation and alkali open loop simultaneously on five-membered beta-keto carboxylic ester ring of pheophorbide a (3) .Finally ,the target compounds 1a~1j were synthesized via condensation of its anhydride ring with various amines including carboxyl-protected amino acids . Results Target compounds 1a~1j were successfully synthesized in yields ranged from 32 .6% to 65 .2% .Their structures were confirmed by elemental analysis ,ESI-MS and 1 H NMR spectra .Conclusion Treatment of purpurin-18 (2) with amines can produce target compounds 1a~1j .The starting raw material was inexpensive and readily available .The reaction conditions were mild and workup was convinient .
