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

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

Research output: Contribution to journalArticle

4 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. This journal is

Original languageEnglish
Pages (from-to)8832-8835
Number of pages4
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number44
DOIs
Publication statusPublished - 2014 Nov 28

Fingerprint

Coumarins
antibiotics
cysteine
sugars
Ketones
Fluorescent Dyes
cultured cells
Sulfhydryl Compounds
thiols
ketones
Sugars
Cysteine
cancer
Cells
Anti-Bacterial Agents
Cell Line
evaluation
probes
cells
Neoplasms

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Chemical and biological evaluation of unusual sugars, α-aculosides, as novel Michael acceptors. / Ikeda, Hiromasa; Kaneko, Erika; Okuzawa, Shunsuke; Takahashi, Daisuke; Toshima, Kazunobu.

In: Organic and Biomolecular Chemistry, Vol. 12, No. 44, 28.11.2014, p. 8832-8835.

Research output: Contribution to journalArticle

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