Dual-mode chemosensor for the fluorescence detection of zinc and hypochlorite on a fluorescein backbone and its cell-imaging applications

Fluorescein coupled with 3-(aminomethyl)-4,6-dimethylpyridin-2(1H)-one (FAD) was synthesized for the selective recognition of Zn2+ over other interfering metal ions in acetonitrile/aqueous buffer (1: 1). Interestingly, there was a significant fluorescence enhancement of FAD in association with Zn2+ at 426 nm by strong chelation-induced fluorescence enhancement (CHEF) without interrupting the cyclic spirolactam ring. A binding stoichiometric ratio of 1: 2 for the ligand FAD with metal Zn(2+ )was proven by a Jobs plot. However, the cyclic spirolactam ring was opened by hypochlorite (OCl-) as well as oxidative cleavage of the imine bond, which resulted in the emission enhancement of the wavelength at 520 nm. The binding constant and detection limit of FAD towards Zn2+ were determined to be 1 x 10(4) M-1 and 1.79 mu M, respectively, and the detection limit for OCl- was determined as 2.24 mu M. We introduced here a dual-mode chemosensor FAD having both the reactive functionalities for the simultaneous detection of Zn2+ and OCl- by employing a metal coordination (Zn2+) and analytes (OCl-) induced chemodosimetric approach, respectively. Furthermore, for the practical application, we studied the fluorescence imaging inside HeLa cells by using FAD, which demonstrated it can be very useful as a selective and sensitive fluorescent probe for zinc.

Automated summary

A fluorescent chemosensor, FAD, was developed for the selective detection of Zn2+ and OCl- simultaneously by employing a metal coordination and analyte-induced chemodosimetric approach. The binding constant and detection limits for Zn2+ were determined, and the potential application of FAD in fluorescence imaging inside HeLa cells was demonstrated.