Development of a highly sensitive fluorescence probe for hydrogen peroxide

J Am Chem Soc. 2011 Jul 13;133(27):10629-37. doi: 10.1021/ja203521e. Epub 2011 Jun 21.

Abstract

Hydrogen peroxide is believed to play a role in cellular signal transduction by reversible oxidation of proteins. Here, we report the design and synthesis of a novel fluorescence probe for hydrogen peroxide, utilizing a photoinduced electron transfer strategy based on benzil chemistry to control the fluorescence. The practical value of this highly sensitive and selective fluorescence probe, NBzF, was confirmed by its application to imaging of hydrogen peroxide generation in live RAW 264.7 macrophages. NBzF was also employed for live cell imaging of hydrogen peroxide generated as a signaling molecule in A431 human epidermoid carcinoma cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Electron Transport
  • Fluoresceins / analysis*
  • Fluoresceins / chemistry*
  • Fluorescence
  • Fluorescent Dyes / chemistry*
  • Humans
  • Hydrogen Peroxide / analysis*
  • Macrophages / chemistry
  • Mice

Substances

  • 5-benzoylcarbonylfluorescein
  • Fluoresceins
  • Fluorescent Dyes
  • Hydrogen Peroxide