A selective phosphine-based fluorescent probe for nitroxyl in living cells

Bioorg Med Chem Lett. 2015 Jan 1;25(1):16-9. doi: 10.1016/j.bmcl.2014.11.041. Epub 2014 Nov 21.

Abstract

A novel fluorescein-based fluorescent probe for nitroxyl (HNO) based on the reductive Staudinger ligation of HNO with an aromatic phosphine was prepared. This probe reacts with HNO derived from Angeli's salt and 4-bromo Piloty's acid under physiological conditions without interference by other biological redox species. Confocal microscopy demonstrates this probe detects HNO by fluorescence in HeLa cells and mass spectrometric analysis of cell lysates confirms this probe detects HNO following the proposed mechanism.

Publication types

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

MeSH terms

  • Dose-Response Relationship, Drug
  • Fluorescent Dyes / analysis*
  • Fluorescent Dyes / metabolism*
  • HeLa Cells
  • Humans
  • Nitrogen Oxides / analysis*
  • Nitrogen Oxides / metabolism*
  • Phosphines / chemistry*
  • Phosphines / metabolism*

Substances

  • Fluorescent Dyes
  • Nitrogen Oxides
  • Phosphines
  • phosphine
  • nitroxyl