title: Coumarin-based thiol chemosensor: synthesis, turn-on mechanism, and its biological application.
abstract: A new chemodosimetric probe (1) is reported that selectively detects thiols over other relevant biological species by the turning on of its fluorescence through a Michael type reaction. The fluorogenic process upon its reaction was revealed to be mediated by intramolecular charge transfer, as confirmed by time-dependent density functional theory calculations. The application of probe 1 to cells is also examined by confocal microscopy, and its cysteine preference was observed by an ex vivo LC-MS analysis of the cellular metabolite.
authors.affiliation: Department of Chemistry, Korea University, Seoul, 136-704, Korea.
authors.forename: Hyo Sung
authors.initials: HS
authors.lastname: Jung
authors.forename: Kyoung Chul
authors.initials: KC
authors.lastname: Ko
authors.forename: Gun-Hee
authors.initials: GH
authors.lastname: Kim
authors.forename: Ah-Rah
authors.initials: AR
authors.lastname: Lee
authors.forename: Yun-Cheol
authors.initials: YC
authors.lastname: Na
authors.forename: Chulhun
authors.initials: C
authors.lastname: Kang
authors.forename: Jin Yong
authors.initials: JY
authors.lastname: Lee
authors.forename: Jong Seung
authors.initials: JS
authors.lastname: Kim
mesh_terms: D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D003545:Cysteine / Q000032:analysis* / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D056945:Hep G2 Cells; D006801:Humans; D018613:Microscopy, Confocal; D015394:Molecular Structure; D013050:Spectrometry, Fluorescence; D013438:Sulfhydryl Compounds / Q000032:analysis*
chemical_list: D003374:Coumarins; D005456:Fluorescent Dyes; D013438:Sulfhydryl Compounds; C030123:coumarin; D003545:Cysteine