Hydrogen Sulfide Mediated Tandem Reaction of Selenenyl Sulfides and Its Application in Fluorescent Probe Development

Org Lett. 2019 Sep 20;21(18):7573-7576. doi: 10.1021/acs.orglett.9b02844. Epub 2019 Sep 6.

Abstract

A unique reaction between H2S and a selenenyl sulfide containing benzoate ester template was discovered. This reaction could be specifically triggered by H2S and lead to ester bond cleavage. The reaction was not affected by the presence of thiols such as glutathione and cysteine. With this reaction, a series of fluorescent probes were synthesized and evaluated. The probes exhibited high sensitivity/selectivity for H2S in both buffers and cells.

Publication types

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

MeSH terms

  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • HeLa Cells
  • Humans
  • Hydrogen Sulfide / analysis*
  • Molecular Structure
  • Optical Imaging*
  • Selenium / chemistry*
  • Sulfides / chemistry*

Substances

  • Fluorescent Dyes
  • Sulfides
  • Selenium
  • Hydrogen Sulfide