NBD-based colorimetric and fluorescent turn-on probes for hydrogen sulfide

Org Biomol Chem. 2014 Jan 21;12(3):479-85. doi: 10.1039/c3ob41870g. Epub 2013 Nov 25.

Abstract

Hydrogen sulfide (H2S) is an important endogenous signalling molecule and also an important environmental target for detection. New reaction-based colorimetric and fluorescent turn-on probes based on selective thiolyling of NBD (7-nitro-1,2,3-benzoxadiazole) ether were explored for sensing of H2S in aqueous buffer. The syntheses of both probes are simple and quite straightforward. The probes are highly sensitive and selective toward H2S over other biologically relevant species. Probe 1 can be used to directly visualize H2S by the naked eye and shows more than 1000-fold fluorescence increase upon reaction with H2S. Probe 2 is a near-infrared fluorescent sensor for H2S at physiological pH.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azoles / chemistry*
  • Colorimetry
  • Fluorescent Dyes / chemistry*
  • Hydrogen Sulfide / analysis*
  • Molecular Structure
  • Nitrobenzenes / chemistry*
  • Spectrometry, Fluorescence
  • Time Factors

Substances

  • 7-nitrobenz-2-oxa-1,3-diazol-4-yl
  • Azoles
  • Fluorescent Dyes
  • Nitrobenzenes
  • Hydrogen Sulfide