RRC ID 72651
Author Fadlan A, Tanimoto H, Ito T, Aritomi Y, Ueno M, Tokuda M, Hirohara S, Obata M, Morimoto T, Kakiuchi K.
Title Synthesis, photophysical properties, and photodynamic activity of positional isomers of TFPP-glucose conjugates.
Journal Bioorg Med Chem
Abstract The synthesis and characterization of a 'complete set' of positional isomers of tetrakis(perfluorophenyl)porphyrins (TFPP)-glucose conjugates (1OH, 2OH, 3OH, 4OH, and 6OH) are reported herein. The cellular uptake and photocytotoxicity of these conjugates were examined in order to investigate the influence of location of the TFPP moiety on the d-glucose molecule on the biological activity of the conjugates. An In vitro biological evaluation revealed that the certain of these isomers have a greater effect on cellular uptake and cytotoxicity than others. The TFPP-glucose conjugates 1OH, 3OH, and 4OH were found to exert exceptional photocytotoxicity in several types of cancer cells compared to 2OH and 6OH substituted isomers.
Volume 26(8)
Pages 1848-1858
Published 2018-5-1
DOI 10.1016/j.bmc.2018.02.031
PII S0968-0896(17)32442-2
PMID 29496414
MeSH Cell Line, Tumor Cell Survival / drug effects Glucose / chemistry* Humans Isomerism Light Photochemotherapy Photosensitizing Agents / chemical synthesis* Photosensitizing Agents / pharmacology Photosensitizing Agents / therapeutic use Porphyrins / chemistry* Stomach Neoplasms / drug therapy
IF 3.073
Resource
Human and Animal Cells HeLa