BODIPY-based ratiometric fluorescent sensor for highly selective detection of glutathione over cysteine and homocysteine

J Am Chem Soc. 2012 Nov 21;134(46):18928-31. doi: 10.1021/ja309079f. Epub 2012 Nov 8.

Abstract

We report a ratiometric fluorescent sensor based on monochlorinated BODIPY for highly selective detection of glutathione (GSH) over cysteine (Cys)/homocysteine (Hcy). The chlorine of the monochlorinated BODIPY can be rapidly replaced by thiolates of biothiols through thiol-halogen nucleophilic substitution. The amino groups of Cys/Hcy but not GSH further replace the thiolate to form amino-substituted BODIPY. The significantly different photophysical properties of sulfur- and amino-substituted BODIPY enable the discrimination of GSH over Cys and Hcy. The sensor was applied for detection of GSH in living cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron Compounds / chemistry*
  • Cysteine / analysis*
  • Fluorescent Dyes / chemistry*
  • Glutathione / analysis*
  • HeLa Cells
  • Humans
  • Limit of Detection

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Fluorescent Dyes
  • Glutathione
  • Cysteine