title: Mitochondria-targeting properties and photodynamic activities of porphyrin derivatives bearing cationic pendant.
abstract: Four meso-tetraphenylporphyrin derivatives bearing either triphenylphosphonium ion-(P1 and P2) or triethylammonium ion-(P3 and P4) terminated alkoxy group at either para-(P1 and P3) or meta-(P2 and P4) position of one meso-phenyl group were designed and synthesized. P1-P4 show similar absorption and fluorescence emission spectra and (1)O(2) quantum yields. The more lipophilic nature of triphenylphosphonium ion over triethylammonium ion renders P1 and P2 higher octanol/water partition coefficients than P3 and P4. Confocal fluorescence microscopy proved that P1-P4 are all mitochondria-targeting. MTT assay showed that P1-P4 presented significant phototoxicity at the concentrations that dark toxicity is negligible towards human breast cancer cell line MCF-7 cells, displaying their application potential in PDT.
authors.affiliation: Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, PR China.
authors.forename: Wanhua
authors.initials: W
authors.lastname: Lei
authors.forename: Jingfan
authors.initials: J
authors.lastname: Xie
authors.forename: Yuanjun
authors.initials: Y
authors.lastname: Hou
authors.forename: Guoyu
authors.initials: G
authors.lastname: Jiang
authors.forename: Hongyan
authors.initials: H
authors.lastname: Zhang
authors.forename: Pengfei
authors.initials: P
authors.lastname: Wang
authors.forename: Xuesong
authors.initials: X
authors.lastname: Wang
authors.forename: Baowen
authors.initials: B
authors.lastname: Zhang
mesh_terms: D045744:Cell Line, Tumor; D006801:Humans; D008928:Mitochondria / Q000187:drug effects* / Q000528:radiation effects; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D026082:Singlet Oxygen / Q000378:metabolism
chemical_list: D017319:Photosensitizing Agents; D011166:Porphyrins; C409084:tetraphenylporphyrin; D026082:Singlet Oxygen