Synthesis, photophysical properties and photocytotoxicity of mono-, di-, tri- and tetra-glucosylated fluorophenylporphyrins Original Research Article

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 β-d-glucopyranosylthio groups on the phenyl ring. Among five possible derivatives, trans-substituted S-glucosylated porphyrin trans-2OH exerted outstanding photocytotoxicity (EC50 value was <5 nM) in HeLa cells. The excellent photocytotoxicity of trans-2OH was found to be attributable to several factors, namely high optical transition probability in aqueous media, efficient type I photoreactions and enhanced cellular uptake.