title: Synthesis and in vitro photodynamic activities of water-soluble fluorinated tetrapyridylporphyrins as tumor photosensitizers.
abstract: A series of water-soluble fluorinated cationic porphyrins were designed, synthesized, and characterized. In vitro photocytotoxicity of these compounds was evaluated by MTT assay on HeLa cells. Their photocytotoxicity was dependent on the positions of the cations and the fluorines in the pyridine ring, and 5,10,15,20-tetrakis-(N-methyl-2-fluoro-pyridin-3-yl)-porphyrin (8) showed the most potent photo-induced cytotoxicity without photobleaching. PDT-induced ROS inside HeLa cells was measured with flow cytometry using ROS-sensitive fluorometric probe, 2,7-dichlorofluororescin (DCF), which revealed high correlations of ROS with cellular cytotoxicity. FACS analysis shows that PDT with porphyrin 8 induced apoptosis in HeLa cells. In summary, efficient generation of ROS, biological effectiveness, and good photostability of porphyrin 8 indicate its potential application in photodynamic therapy (PDT) in the near future.
authors: Department of Chemistry, Seoul National University, Seoul 151-747, South Korea.
authors: Yoon-Joo
authors: YJ
authors: Ko
authors: Kyung-Jin
authors: KJ
authors: Yun
authors: Min-Seok
authors: MS
authors: Kang
authors: Jongmin
authors: J
authors: Park
authors: Kyung-Tae
authors: KT
authors: Lee
authors: Seung Bum
authors: SB
authors: Park
authors: Jung-Hyu
authors: JH
authors: Shin
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000627:therapeutic use; D002470:Cell Survival / Q000187:drug effects*; D004354:Drug Screening Assays, Antitumor; D005461:Fluorine / Q000737:chemistry; D006367:HeLa Cells; D006801:Humans; D010777:Photochemistry; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D011166:Porphyrins / Q000138:chemical synthesis* / Q000627:therapeutic use; D012995:Solubility; D014867:Water / Q000737:chemistry
chemical_list: D000970:Antineoplastic Agents; D017319:Photosensitizing Agents; D011166:Porphyrins; D014867:Water; D005461:Fluorine