A ratiometric small-molecule fluorescent probe for the selective detection of hypochlorite by an oxidative cyclization reaction: application to commercial disinfectants and live cells

Org Biomol Chem. 2024 Feb 21;22(8):1662-1670. doi: 10.1039/d3ob01831h.

Abstract

A highly selective thiophene-thioimidazole hydrazine-based ratiometric chemodosimeter (TPBN) was designed and synthesized to detect hypochlorite (ClO-). The probe showed yellow fluorescence and exhibited ultra sensitivity towards hypochlorite (detection limit 8.74 nM) through the oxidative intramolecular cyclization process to give a blue fluorescent triazole product (TPBN-P). Additionally, the as-designed sensor displayed a fast response (80 s) to hypochlorite with excellent selectivity over other competing analytes. DFT calculations, ESI-MS, and 1H NMR titration experiments supported the detection mechanism. The probe was a valuable and practical ratiometric sensor for test strips, commercial disinfectants, and water samples. The probe was successfully used in the bio-imaging of hypochlorite in human breast cancer cells due to its noteworthy photophysical characteristics and good cell permeability.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Fluorescent Dyes* / chemistry
  • Humans
  • Hypochlorous Acid*
  • Oxidative Stress
  • Spectrometry, Fluorescence

Substances

  • Fluorescent Dyes
  • Hypochlorous Acid