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

doi:10.1016/j.bmc.2018.02.031

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

Bioorg Med Chem. 2018 May 1;26(8):1848-1858. doi: 10.1016/j.bmc.2018.02.031. Epub 2018 Feb 19.

Authors

Affiliations

¹ Graduate School of Materials Science, Nara Institute of Science and Technology, Takayama 8916-5, Ikoma, Nara 630-0192, Japan.
² Department of Chemical and Biological Engineering, National Institute of Technology, Ube College, 2-14-1 Tokiwadai, Ube, Yamaguchi 755-8555, Japan.
³ Department of Chemical and Biological Engineering, National Institute of Technology, Ube College, 2-14-1 Tokiwadai, Ube, Yamaguchi 755-8555, Japan. Electronic address: hirohara@ube-k.ac.jp.
⁴ Interdisciplinary Graduate School of Medicine and Engineering, University of Yamanashi, Kofu 400-8510, Japan.
⁵ Graduate School of Materials Science, Nara Institute of Science and Technology, Takayama 8916-5, Ikoma, Nara 630-0192, Japan. Electronic address: kakiuchi@ms.naist.jp.

PMID: 29496414
DOI: 10.1016/j.bmc.2018.02.031

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.

Keywords: Cellular uptake; Glucosylated TFPP; Photocytotoxicity; Photodynamic therapy (PDT); Positional isomers.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

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

Substances

Photosensitizing Agents
Porphyrins
Glucose