title: Chemical and biological evaluation of unusual sugars, α-aculosides, as novel Michael acceptors.
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.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan. toshima@applc.keio.ac.jp.
authors.forename: Hiromasa
authors.initials: H
authors.lastname: Ikeda
authors.forename: Erika
authors.initials: E
authors.lastname: Kaneko
authors.forename: Shunsuke
authors.initials: S
authors.lastname: Okuzawa
authors.forename: Daisuke
authors.initials: D
authors.lastname: Takahashi
authors.forename: Kazunobu
authors.initials: K
authors.lastname: Toshima
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D061986:MCF-7 Cells; D051379:Mice; D008856:Microscopy, Fluorescence; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D005456:Fluorescent Dyes; D006027:Glycosides; D011753:Pyrones