PDT Research Institute, School of Nano System Engineering, Inje University, Gimhae 621-749, Republic of Korea.
Bioorg Med Chem Lett. 2012 Mar 1;22(5):1846-9. doi: 10.1016/j.bmcl.2012.01.088. Epub 2012 Jan 31.
Using stereoselective aldol-like condensation as a key methodology, a series of chlorophyll a-based long wavelength cationic chlorins were synthesized using methyl pyropheophorbide a (MPPa) and purpurin-18-N-methoxylimide methyl ester as starting materials. Such long wavelength cationic chlorins possess covalently linked cationic moieties (pyridinium or quinolinium) on the peripheral of their tetrapyrrole macrocycles. It was found that all long wavelength cationic chlorins showed their longest absorption maxima in the range of 712-763nm, making them potential photosensitizers in photodynamic therapy. The results of preliminary experiments probing in vitro photodynamic effects showed that the purpurinimide derivatives exhibit relatively high phototoxicity in HeLa cells as compared to MPPa derivatives.
采用立体选择性的羟醛缩合反应作为关键方法学，以甲基吡咯并 pheophorbide a（MPPa）和卟吩-18-N-甲氧基酰胺甲酯作为起始原料，合成了一系列基于叶绿素 a 的长波长阳离子叶绿醇。这些长波长阳离子叶绿醇在其四吡咯大环的外围具有共价连接的阳离子部分（吡啶鎓或喹啉鎓）。研究发现，所有长波长阳离子叶绿醇均在 712-763nm 的范围内显示出其最长的吸收最大值，这使得它们成为光动力疗法中潜在的光敏剂。初步实验探测体外光动力效应的结果表明，与 MPPa 衍生物相比，purpurinimide 衍生物在 HeLa 细胞中表现出相对较高的光毒性。
