Coumarin-based thiol chemosensor: synthesis, turn-on mechanism, and its biological application

Org Lett. 2011 Mar 18;13(6):1498-501. doi: 10.1021/ol2001864. Epub 2011 Feb 16.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Coumarins / chemical synthesis*
  • Coumarins / chemistry
  • Cysteine / analysis*
  • Cysteine / chemistry
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Hep G2 Cells
  • Humans
  • Microscopy, Confocal
  • Molecular Structure
  • Spectrometry, Fluorescence
  • Sulfhydryl Compounds / analysis*

Substances

  • Coumarins
  • Fluorescent Dyes
  • Sulfhydryl Compounds
  • coumarin
  • Cysteine