A highly selective turn-on fluorescent probe for hypochlorous acid based on hypochlorous acid-induced oxidative intramolecular cyclization of boron dipyrromethene-hydrazone

Anal Chim Acta. 2015 Jul 2:882:68-75. doi: 10.1016/j.aca.2015.04.012. Epub 2015 Apr 9.

Abstract

A BODIPY-based fluorescent probe, HBP, was developed for the detection of hypochlorous acid based on the specific hypochlorous acid-promoted oxidative intramolecular cyclization of heterocyclic hydrazone in response to the amount of HOCl. The reaction is accompanied by a 41-fold increase in the fluorescent quantum yield (from 0.004 to 0.164). The fluorescence intensity of the reaction between HOCl and HBP is linear in the HOCl concentration range of 1-8 μM with a detection limit of 2.4 nM (S/N=3). Confocal fluorescence microscopy imaging using RAW264.7 cells showed that the new probe HBP could be used as an effective fluorescent probe for detecting HOCl in living cells.

Keywords: Bioimaging; Boron dipyrromethene; Fluorescent probe; Hypochlorous acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Boron Compounds / chemistry*
  • Cell Line
  • Cyclization
  • Fluorescent Dyes / chemistry*
  • Hydrazones / chemistry*
  • Hypochlorous Acid / analysis*
  • Hypochlorous Acid / chemistry
  • Limit of Detection
  • Mice
  • Oxidation-Reduction
  • Spectrometry, Fluorescence

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Fluorescent Dyes
  • Hydrazones
  • Hypochlorous Acid