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

研究成果: Contribution to journalArticle査読

7 被引用数 (Scopus)

抄録

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.

本文言語英語
ページ(範囲)1295-1308
ページ数14
ジャーナルBulletin of the Chemical Society of Japan
86
11
DOI
出版ステータス出版済み - 2013
外部発表はい

All Science Journal Classification (ASJC) codes

  • 化学 (全般)

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