A small-molecule fluorogenic probe for the detection of hypochlorite and its application in the bio-imaging of human breast cancer cells.

Abstract

A certain amount of hypochlorite can help to regulate the body's defense system while excessive hypochlorite has some complex influence on health. Herein, a thiophene-derived biocompatible turn-on fluorescent probe (TPHZ) was synthesized and characterized for the detection of hypochlorite (ClO-). The fluorescence and colorimetric sensing of the probe followed an ICT OFF strategy. The experimental results showed a remarkable turn on fluorescence enhancement from colorless to bright blue after the addition of ClO- within 130 s in a solvent system having 80% water with high selectivity and a low detection limit of 53.8 nM. The sensing mechanism was attributed to ClO- mediated electrophilic addition to the imine bond which was justified by DFT calculations, and ESI-MS and 1H-NMR titration experiments. The probe was used in an application to visualize ClO- in human breast cancer cells which can be helpful for investigating the functions of hypochlorite in living cells. Finally, by virtue of fine photophysical properties, good sensing performance, good water solubility and low limit of detection, the probe TPHZ was successfully applied to TLC test strips, and commercial bleach and water samples.