Fluorescent probes based on nucleophilic substitution-cyclization for hydrogen sulfide detection and bioimaging

Chemistry. 2014 Jan 20;20(4):1010-6. doi: 10.1002/chem.201303757. Epub 2013 Dec 11.

Abstract

The design, synthesis, properties, and cell imaging applications of a series of 2-pyridyl disulfide based fluorescent probes (WSP1, WSP2, WSP3, WSP4 and WSP5) for hydrogen sulfide detection are reported. The strategy is based on the dual-nucleophilicity of hydrogen sulfide. A hydrogen sulfide mediated tandem nucleophilic substitution-cyclization reaction is used to release the fluorophores and turn on the fluorescence. The probes showed high sensitivity and selectivity for hydrogen sulfide over other reactive sulfur species, including cysteine and glutathione.

Keywords: cell imaging; cyclization; fluorescence; fluorescent probes; hydrogen sulfide.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Cysteine / analysis
  • Disulfides / chemical synthesis
  • Disulfides / chemistry
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Glutathione / analysis
  • HeLa Cells
  • Humans
  • Hydrogen Sulfide / analysis*
  • Microscopy, Fluorescence

Substances

  • Disulfides
  • Fluorescent Dyes
  • Glutathione
  • Cysteine
  • Hydrogen Sulfide