Synthesis, photophysical properties and photocytotoxicity of mono-, di-, tri- and tetra-glucosylated fluorophenylporphyrins.
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.
Hirohara
Shiho
S
Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma, Nara 630-0192, Japan. hirohara@ms.naist.jp
Nishida
Masataka
M
Sharyo
Kohei
K
Obata
Makoto
M
Ando
Tsuyoshi
T
Tanihara
Masao
M
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
D011166:Porphyrins