Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 18, Issue 4, Pages 1526-1535Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2010.01.006
Keywords
Photodynamic therapy (PDT); S-Glucosylated porphyrin; Photocytotoxicity; Cellular uptake; Reactive oxygen species (ROS)
Funding
- NAIST Presidential Special Fund
- Ministry of Education, Culture, Sport, Science and Technology (MEXT) of the Japanese Government
- The Japan Science Society
- Nara Women's University Intramural
- The Kao Foundation for Arts and Sciences
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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. (C) 2010 Elsevier Ltd. All rights reserved.
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