title: Synthesis of novel long wavelength cationic chlorins via stereoselective aldol-like condensation.
abstract: 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.
authors.affiliation: PDT Research Institute, School of Nano System Engineering, Inje University, Gimhae 621-749, Republic of Korea.
authors.forename: Jia Zhu
authors.initials: JZ
authors.lastname: Li
authors.forename: Jin Jun
authors.initials: JJ
authors.lastname: Wang
authors.forename: Il
authors.initials: I
authors.lastname: Yoon
authors.forename: Bing Cun
authors.initials: BC
authors.lastname: Cui
authors.forename: Young Key
authors.initials: YK
authors.lastname: Shim
mesh_terms: D002470:Cell Survival / Q000187:drug effects; D002734:Chlorophyll / Q000138:chemical synthesis / Q000737:chemistry; D000077194:Chlorophyll A; D006367:HeLa Cells; D006801:Humans; D009369:Neoplasms / Q000188:drug therapy; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D017319:Photosensitizing Agents; D011166:Porphyrins; C452939:pyropheophorbide-a methylester; D002734:Chlorophyll; C059051:purpurin 18; C006969:chlorin; D000077194:Chlorophyll A