A red-emitting naphthofluorescein-based fluorescent probe for selective detection of hydrogen peroxide in living cells

Bioorg Med Chem Lett. 2008 Nov 15;18(22):5948-50. doi: 10.1016/j.bmcl.2008.08.035. Epub 2008 Aug 14.

Abstract

We report the synthesis, properties, and cellular application of Naphtho-Peroxyfluor-1 (NPF1), a new fluorescent indicator for hydrogen peroxide based on a red-emitting naphthofluorescein platform. Owing to its boronate cages, NPF1 features high selectivity for hydrogen peroxide over a panel of biologically relevant reactive oxygen species (ROS), including superoxide and nitric oxide, as well as excitation and emission profiles in the far-red region of the visible spectrum (>600nm). Flow cytometry experiments in RAW264.7 macrophages establish that NPF1 can report changes in peroxide levels in living cells.

Publication types

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

MeSH terms

  • Animals
  • Boronic Acids / chemical synthesis*
  • Boronic Acids / chemistry
  • Fluorescein / chemistry
  • Fluorescence Resonance Energy Transfer / methods*
  • Fluorescent Dyes / chemistry*
  • Hydrogen Peroxide / chemistry*
  • Macrophages / drug effects*
  • Mice
  • Molecular Structure

Substances

  • Boronic Acids
  • Fluorescent Dyes
  • Hydrogen Peroxide
  • Fluorescein