Dual-Responsive Near-Infrared BODIPY-Based Fluorescent Probe for the Detection of F- and HClO in Organisms

Anal Chem. 2024 Mar 5;96(9):3802-3809. doi: 10.1021/acs.analchem.3c04856. Epub 2024 Feb 21.

Abstract

Fluoride anions (F-) play a crucial role in human physiological processes. However, excessive intake of F- would affect oxygen metabolism and promote the generation of oxygen-free radicals. Hence, it is essential to develop a precise and efficient fluorescent probe for visualizing F--induced oxidative stress. In this work, we developed the first bifunctional BODIPY-based fluorescent probe dfBDP with p-tert-butyldimethylsilanolate benzyl thioether as the sensing site for the detection of F- and HClO via two distinct reactions, the self-immolative removal and the thioether oxidation, which generate the sensing products with two nonoverlap fluorescence bands: 800-1200 and 500-750 nm, respectively. The probe dfBDP displays rapid response, high specificity, and sensitivity for the detection of F- (LOD, 316.2 nM) and HClO (LOD, 33.9 nM) in vitro. Cellular imaging reveals a correlation between F--induced oxidative stress and the upregulation of HClO. Finally, probe dfBDP was employed to detect F- and HClO in mice under the stimulation of F-. The experimental results display that the level of HClO elevates in the liver of mice.

MeSH terms

  • Animals
  • Boron Compounds*
  • Fluorescent Dyes*
  • Humans
  • Hypochlorous Acid* / metabolism
  • Mice
  • Oxygen
  • Sulfides

Substances

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