An aggregation induced emission chalcone fluorescent probe with large Stokes shift for biothiols detection

Abstract

The homeostasis of biothiols is closely related to the health of organisms. In view of the important role of biothiols, a fluorescent probe (7HIN-D) for the detection of intracellular biothiols was developed based on a simple chalcone fluorophore 7HIN with “ESIPT + AIE” characteristics. The probe 7HIN-D was obtained by introducing a biothiols specific DNBS (2,4-dinitrobenzenesulfonyl) unit as a fluorescence quencher to the fluorophore 7HIN. The nucleophilic substitution reaction between biothiols and probe 7HIN-D will release the DNBS unit and the fluorophore 7HIN, which exhibits a “turn on” AIE fluorescence with a large Stokes shift of 113 nm. The probe 7HIN-D displays high sensitivity and good selectivity to biothiols, and the detection limits value of probe 7HIN-D for GSH, Cys and Hcy were 0.384 μmol/L, 0.471 μmol/L and 0.638 μmol/L, respectively. In addition, the probe has been successfully used for fluorescence detection of endogenous biothiols in living cells due to its excellent performance, good biocompatibility and low cytotoxicity.