Target-Selective Fluorescence Imaging and Photocytotoxicity against H2O2 High-Expressing Cancer Cells Using a Photoactivatable Theranostic Agent

Ryoma Takagi; Ayano Takeda; Daisuke Takahashi; Kazunobu Toshima

doi:10.1002/asia.201701004

Target-Selective Fluorescence Imaging and Photocytotoxicity against H₂O₂ High-Expressing Cancer Cells Using a Photoactivatable Theranostic Agent

Ryoma Takagi, Ayano Takeda, Daisuke Takahashi, Kazunobu Toshima

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

A purpose-designed and synthesized H₂O₂-reactive and photoactivatable theranostic agent 1 consisting of 1) an arylboronic acid moiety, 2) pro-fluorophore moiety, and 3) photoactivatable moiety (photosensitizer), selectively and effectively reacted with H₂O₂ while simultaneously releasing resorufin for fluorescence detection under neutral aqueous conditions. In addition, 1 was cell-permeable, and exhibited effective photocytotoxicity against fluorescently visualized cells only upon photoirradiation. The results also showed that 1 produced a selective fluorescence response to H₂O₂, even in living cultured cells.

Original language	English
Pages (from-to)	2656-2659
Number of pages	4
Journal	Chemistry - An Asian Journal
Volume	12
Issue number	20
DOIs	https://doi.org/10.1002/asia.201701004
Publication status	Published - 2017 Oct 18

Keywords

cytotoxicity
fluorescent probes
peroxides
sensitizers
theranostics

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1002/asia.201701004

Cite this

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title = "Target-Selective Fluorescence Imaging and Photocytotoxicity against H2O2 High-Expressing Cancer Cells Using a Photoactivatable Theranostic Agent",

abstract = "A purpose-designed and synthesized H2O2-reactive and photoactivatable theranostic agent 1 consisting of 1) an arylboronic acid moiety, 2) pro-fluorophore moiety, and 3) photoactivatable moiety (photosensitizer), selectively and effectively reacted with H2O2 while simultaneously releasing resorufin for fluorescence detection under neutral aqueous conditions. In addition, 1 was cell-permeable, and exhibited effective photocytotoxicity against fluorescently visualized cells only upon photoirradiation. The results also showed that 1 produced a selective fluorescence response to H2O2, even in living cultured cells.",

keywords = "cytotoxicity, fluorescent probes, peroxides, sensitizers, theranostics",

author = "Ryoma Takagi and Ayano Takeda and Daisuke Takahashi and Kazunobu Toshima",

note = "Funding Information: Strategic Research Foundation at Private Universities, 2012– 2016 (No. S1201020), JSPS KAKENHI Grant Numbers JP16H01161 in Middle Molecular Strategy and Scientific Research (B) (No. 26282212), and Keio Gijuku Academic Development Funds. Funding Information: We wish to thank Prof. Dr. Siro Simizu of the Faculty of Science and Technology, Keio University, for helpful discussions regarding the fluorescence microscopy experiments. This research was supported in part by the MEXT-supported Program for the Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "10.1002/asia.201701004",

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AU - Takeda, Ayano

AU - Takahashi, Daisuke

AU - Toshima, Kazunobu

N1 - Funding Information: Strategic Research Foundation at Private Universities, 2012– 2016 (No. S1201020), JSPS KAKENHI Grant Numbers JP16H01161 in Middle Molecular Strategy and Scientific Research (B) (No. 26282212), and Keio Gijuku Academic Development Funds. Funding Information: We wish to thank Prof. Dr. Siro Simizu of the Faculty of Science and Technology, Keio University, for helpful discussions regarding the fluorescence microscopy experiments. This research was supported in part by the MEXT-supported Program for the Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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N2 - A purpose-designed and synthesized H2O2-reactive and photoactivatable theranostic agent 1 consisting of 1) an arylboronic acid moiety, 2) pro-fluorophore moiety, and 3) photoactivatable moiety (photosensitizer), selectively and effectively reacted with H2O2 while simultaneously releasing resorufin for fluorescence detection under neutral aqueous conditions. In addition, 1 was cell-permeable, and exhibited effective photocytotoxicity against fluorescently visualized cells only upon photoirradiation. The results also showed that 1 produced a selective fluorescence response to H2O2, even in living cultured cells.

AB - A purpose-designed and synthesized H2O2-reactive and photoactivatable theranostic agent 1 consisting of 1) an arylboronic acid moiety, 2) pro-fluorophore moiety, and 3) photoactivatable moiety (photosensitizer), selectively and effectively reacted with H2O2 while simultaneously releasing resorufin for fluorescence detection under neutral aqueous conditions. In addition, 1 was cell-permeable, and exhibited effective photocytotoxicity against fluorescently visualized cells only upon photoirradiation. The results also showed that 1 produced a selective fluorescence response to H2O2, even in living cultured cells.

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KW - peroxides

KW - sensitizers

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