Synthesis, photophysical properties, and photodynamic activity of positional isomers of TFPP-glucose conjugates

Arif Fadlan, Hiroki Tanimoto, Tatsuya Ito, Yusuke Aritomi, Maho Ueno, Masaya Tokuda, Shiho Hirohara*, Makoto Obata, Tsumoru Morimoto, Kiyomi Kakiuchi

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1848-1858
Number of pages11
JournalBioorganic and Medicinal Chemistry
Volume26
Issue number8
DOIs
Publication statusPublished - 1 May 2018
Externally publishedYes

Keywords

  • Cellular uptake
  • Glucosylated TFPP
  • Photocytotoxicity
  • Photodynamic therapy (PDT)
  • Positional isomers

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