Mitochondria-targeting properties and photodynamic activities of porphyrin derivatives bearing cationic pendant.
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.
Lei
Wanhua
W
Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, PR China.
Xie
Jingfan
J
Hou
Yuanjun
Y
Jiang
Guoyu
G
Zhang
Hongyan
H
Wang
Pengfei
P
Wang
Xuesong
X
Zhang
Baowen
B
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
D017319:Photosensitizing Agents; D011166:Porphyrins; C409084:tetraphenylporphyrin; D026082:Singlet Oxygen