Trans-bisglycoconjugation is an efficient and robust architecture for PDT photosensitizers based on 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin derivatives

Shiho Hirohara, Kohei Sharyo, Yuji Kawasaki, Masayasu Totani, Ayumi Tomotsuka, Ryota Funasako, Nobutaka Yasui, Yasuchika Hasegawa, Junpei Yuasa, Takuya Nakashima, Tsuyoshi Kawai, Chio Oka, Masashi Kawaichi, Makoto Obata, Masao Tanihara

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

To examine the versatility of the trans-bisglycoconjugation architecture for 5,10,15,20-tetrakis(pentafluorophenyl) porphyrin (TFPP) derivative-based photodynamic therapy (PDT), 25 porphyrin derivatives bearing D-glucopyranose moieties were prepared, and their in vitro photocytotoxicities were examined. trans-Bisglycoconjugated TFPP derivatives exerted the best photocytotoxicity among TFPP derivatives in the same category, regardless of the central metal ion and the type of glycoconjugation. trans-Bisglycoconjugated free-base TFPP bearing β-D-glucopyranosylthio groups (trans- H22 SGlc) was found to be the most potent photosensitizer, not only in HeLa cells (EC50 < 5 nM), but also in highly metastatic cancer cell lines such as B16-BL6 melanoma cells (EC50 < 10 nM). UVvis and dynamic light-scattering measurements suggested that trans- bisglycoconjugated TFPP derivatives formed relatively large J-aggregates in an aqueous solution. trans-Bisglycoconjugated TFPP derivatives exhibited greater uptake by HeLa cells than those with different glycoconjugation patterns, with the exception of Zn(II) complexes. trans-Bisglycoconjugated TFPP derivatives efficiently generated hydrogen peroxide and hydroxyl radical by a type I photoreaction, while no significant differences were found in the efficiency of singlet oxygen generation by a type II photoreaction. These unique characteristics of transbisglycoconjugated TFPP derivatives support the conclusion that trans-bisglycoconjugation is a highly efficient and robust architecture for TFPP-based PDT development.

Original languageEnglish
Pages (from-to)1295-1308
Number of pages14
JournalBulletin of the Chemical Society of Japan
Volume86
Issue number11
DOIs
Publication statusPublished - 2013
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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