BODIPY-based Fluorescent Probe for Fast Detection of Hydrogen Sulfide and Lysosome-targeting Applications in Living Cells

Chem Asian J. 2021 Apr 1;16(7):850-855. doi: 10.1002/asia.202100041. Epub 2021 Mar 10.

Abstract

Hydrogen sulfide (H2 S) is recognized as an endogenous gaseous signaling agent in many biological activities. Lysosomes are the main metabolic site and play a pivotal role in cells. Herein, we designed and synthesized two new fluorescent probes BDP-DNBS and BDP-DNP with a BODIPY core to distinguish H2 S. The sensing mechanism is based on the inhibition-recovery of the photo-induced electron transfer (PET) process. Through comparing the responsive behaviors of the two probes toward H2 S, BDP-DNBS showed a fast response time (60 s), low limit of detection (LOD, 51 nM), high sensitivity and selectivity. Moreover, the reaction mechanism was demonstrated by mass spectrometry and fluorescence off-on mechanism was proved by density functional theory (DFT). Significantly, confocal fluorescence imaging indicated that BDP-DNBS was successfully used to visualize H2 S in lysosomes in living HeLa cells.

Keywords: BODIPY; fluorescent probes; hydrogen sulfide; lysosomal localization.

MeSH terms

  • Boron Compounds / chemical synthesis
  • Boron Compounds / chemistry*
  • Density Functional Theory
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • HeLa Cells
  • Humans
  • Hydrogen Sulfide / analysis*
  • Hydrogen Sulfide / chemistry
  • Limit of Detection
  • Lysosomes / metabolism*
  • Microscopy, Confocal
  • Microscopy, Fluorescence
  • Models, Chemical

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Fluorescent Dyes
  • Hydrogen Sulfide