A novel visual and far-red fluorescent dual-channel probe for the rapid and sensitive detection of hypochlorite in aqueous solution and living cells

Abstract

The development of selective fluorescent probes for rapid and sensitive detection of hypochlorite anion (OCl−) is of great importance for biomedical researchers to investigate the detailed functions and mechanisms of OCl− in living systems. Herein, based on the internal charge transfer (ICT) mechanism, employing 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (TCF) fluorophore, we developed a novel visual and far-red fluorescent dual-channel probe TCF-OCl for the rapid and sensitive detection of OCl− in aqueous solution and living cells. TCF-OCl exhibits high OCl−-selectivity even in the presence of other reactive oxygen species (ROS), which may be ascribed to the excellent reactivity of the arylboronate recognition moiety toward OCl−. ICT-based fluorescent probe TCF-OCl displays a considerable absorption spectrum (at 570nm) enhancement and the color changes from faint yellow to red upon addition of OCl−. In addition, the results showed that TCF-OCl could quantitatively detect OCl− in the range of 0 to 50μM with the detection limit of 0.4μM by visual and fluorescent spectrometry methods. Importantly, TCF-OCl was successfully applied to the fluorescence imaging of OCl− levels in living cells, and it is expected to be a useful chemical tool for investigating the detailed functions and mechanisms of OCl− in living systems.