Chemical and biological evaluation of unusual sugars, α-aculosides, as novel Michael acceptors

Hiromasa Ikeda; Erika Kaneko; Shunsuke Okuzawa; Daisuke Takahashi; Kazunobu Toshima

doi:10.1039/c4ob01877j

Chemical and biological evaluation of unusual sugars, α-aculosides, as novel Michael acceptors

Hiromasa Ikeda, Erika Kaneko, Shunsuke Okuzawa, Daisuke Takahashi, Kazunobu Toshima

Department of Applied Chemistry

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

5 Citations (Scopus)

Abstract

The unusual sugars, α-aculosides, which appear in certain antibiotics and have an α,β-unsaturated ketone structure, were found to be novel and selective Michael acceptors for the thiol function of cysteine residues. A coumarin derivative possessing α-aculoside as a Michael acceptor effectively and irreversibly operated as a fluorescent probe in cells. Furthermore, α-aculosides exhibited cytotoxic activity against several cancer cell lines.

Original language	English
Pages (from-to)	8832-8835
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	12
Issue number	44
DOIs	https://doi.org/10.1039/c4ob01877j
Publication status	Published - 2014 Nov 28

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

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10.1039/c4ob01877j

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abstract = "The unusual sugars, α-aculosides, which appear in certain antibiotics and have an α,β-unsaturated ketone structure, were found to be novel and selective Michael acceptors for the thiol function of cysteine residues. A coumarin derivative possessing α-aculoside as a Michael acceptor effectively and irreversibly operated as a fluorescent probe in cells. Furthermore, α-aculosides exhibited cytotoxic activity against several cancer cell lines.",

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AU - Kaneko, Erika

AU - Okuzawa, Shunsuke

AU - Takahashi, Daisuke

AU - Toshima, Kazunobu

PY - 2014/11/28

Y1 - 2014/11/28

N2 - The unusual sugars, α-aculosides, which appear in certain antibiotics and have an α,β-unsaturated ketone structure, were found to be novel and selective Michael acceptors for the thiol function of cysteine residues. A coumarin derivative possessing α-aculoside as a Michael acceptor effectively and irreversibly operated as a fluorescent probe in cells. Furthermore, α-aculosides exhibited cytotoxic activity against several cancer cell lines.

AB - The unusual sugars, α-aculosides, which appear in certain antibiotics and have an α,β-unsaturated ketone structure, were found to be novel and selective Michael acceptors for the thiol function of cysteine residues. A coumarin derivative possessing α-aculoside as a Michael acceptor effectively and irreversibly operated as a fluorescent probe in cells. Furthermore, α-aculosides exhibited cytotoxic activity against several cancer cell lines.

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Chemical and biological evaluation of unusual sugars, α-aculosides, as novel Michael acceptors

Abstract

ASJC Scopus subject areas

UN SDGs

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