title: Synthesis, photophysical properties and photocytotoxicity of mono-, di-, tri- and tetra-glucosylated fluorophenylporphyrins.
abstract: In order to explore the effect of substitution patterns on the photocytotoxicity of glycoconjugated porphyrins, we synthesized and characterized a 'complete set' of tetrakis(perfluorophenyl)porphyrins having beta-d-glucopyranosylthio groups on the phenyl ring. Among five possible derivatives, trans-substituted S-glucosylated porphyrin trans-2(OH) exerted outstanding photocytotoxicity (EC(50) value was < 5 nM) in HeLa cells. The excellent photocytotoxicity of trans-2(OH) was found to be attributable to several factors, namely high optical transition probability in aqueous media, efficient type I photoreactions and enhanced cellular uptake.
authors.affiliation: Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma, Nara 630-0192, Japan. hirohara@ms.naist.jp
authors.forename: Shiho
authors.initials: S
authors.lastname: Hirohara
authors.forename: Masataka
authors.initials: M
authors.lastname: Nishida
authors.forename: Kohei
authors.initials: K
authors.lastname: Sharyo
authors.forename: Makoto
authors.initials: M
authors.lastname: Obata
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Ando
authors.forename: Masao
authors.initials: M
authors.lastname: Tanihara
mesh_terms: D002470:Cell Survival / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D006367:HeLa Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D010777:Photochemistry; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013056:Spectrophotometry, Ultraviolet
chemical_list: D011166:Porphyrins