Selective Detection and Visualization of Exogenous/endogenous Hypochlorous Acid in Living Cells using a BODIPY-based Red-emitting Fluorescent Probe

Chem Asian J. 2020 Mar 16;15(6):770-774. doi: 10.1002/asia.201901709. Epub 2020 Feb 24.

Abstract

Herein, a red-emitting fluorescent probe DM-BDP-OCl containing a para-DMTC benzyl pyridinium moiety at the meso position of BODIPY as self-immolative portion for the detection of HOCl was designed and synthesized. DM-BDP-OCl exhibited excellent specificity and a fast response for HOCl beyond other ROS/RNS. It was used for the accurately measurable detection of HOCl with a linear range from 0 μM to 50 μM, and the detection limit for HOCl reached 60 nM. Moreover, the probe could directly monitor fluctuations of exogenous and endogenous HOCl in living HeLa and RAW 264.7 cells. This work provided a powerful and convenient imaging tool for probing pathological and physiological actions of HOCl.

Keywords: BODIPY; cell imaging; fluorescent probe; hypochlorous acid; red-emitting.

MeSH terms

  • Animals
  • Boron Compounds / chemistry*
  • Density Functional Theory
  • Fluorescent Dyes / chemistry*
  • HeLa Cells
  • Humans
  • Hydrogen-Ion Concentration
  • Hypochlorous Acid / analysis*
  • Kinetics
  • Limit of Detection
  • Mice
  • Microscopy, Fluorescence
  • RAW 264.7 Cells

Substances

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