A Selective Imidazoline-2-thione-Bearing Two-Photon Fluorescent Probe for Hypochlorous Acid in Mitochondria

Anal Chem. 2016 Jun 21;88(12):6615-20. doi: 10.1021/acs.analchem.6b01738. Epub 2016 Jun 2.

Abstract

Hypochlorite (OCl(-)) plays a key role in the immune system and is involved in various diseases. Accordingly, direct detection of endogenous OCl(-) at the subcellular level is important for understanding inflammation and cellular apoptosis. In the current study, a two-photon fluorescent off/on probe (PNIS) bearing imidazoline-2-thione as an OCl(-) recognition unit and triphenylphosphine (TPP) as a mitochondrial-targeting group was synthesized and examined for its ability to image mitochondrial OCl(-) in situ. This probe, based on the specific reaction between imidazoline-2-thione and OCl(-), displayed a selective fluorescent off/on response to OCl(-) with the various reactive oxygen species in a physiological medium. PNIS was successfully applied to image of endogenously produced mitochondrial OCl(-) in live RAW 264.7 cells via two-photon microscopy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Ethylenethiourea / chemistry*
  • Fluorescent Dyes / chemistry*
  • HeLa Cells
  • Humans
  • Hypochlorous Acid / analysis*
  • Mice
  • Microscopy, Fluorescence, Multiphoton / methods
  • Mitochondria / chemistry*
  • Mitochondria / ultrastructure
  • RAW 264.7 Cells

Substances

  • Fluorescent Dyes
  • Ethylenethiourea
  • Hypochlorous Acid