A ratiometric small-molecule fluorescent probe for the selective detection of hypochlorite by an oxidative cyclization reaction: application to commercial disinfectants and live cells.
Shilpita BanerjeeDipanjan BanikSatyajit HalderAnirban KarakPintu GhoshKuladip JanaAjit Kumar MahapatraPublished in: Organic & biomolecular chemistry (2024)
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 1 H 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.
Keyphrases
- living cells
- fluorescent probe
- small molecule
- high resolution
- single molecule
- quantum dots
- loop mediated isothermal amplification
- ms ms
- endothelial cells
- label free
- breast cancer cells
- real time pcr
- density functional theory
- induced apoptosis
- magnetic resonance
- mass spectrometry
- multiple sclerosis
- stem cells
- molecular dynamics
- cell proliferation
- photodynamic therapy
- cell cycle arrest
- mesenchymal stem cells
- energy transfer
- bone marrow
- oxidative stress
- pi k akt
- signaling pathway