A turn-on fluorescence probe for cysteine/homocysteine based on the nucleophilic-induced rearrangement of benzothiazole thioether

A fluorescent probe, 4-(benzothiazole-2-ylthio)-7-nitro-2,1,3-benzoxadiazole (TBT-NBD) was developed for cysteine (Cys) and homocysteine (Hcy). The reaction mechanism was based on the Cys/Hcy-induced nucleophilic substitution of benzothiazole thioether then Smiles rearrangement reaction to form corresponding amino-nitrobenzoxadiazole, which emitted yellow-green fluorescence and guaranteed the high selectivity for Cys/Hcy over glutathione (GSH). TBT-NBD could detect Cys/Hcy within 5 min in the presence of high concentration of GSH and other amino acids. Moreover, TBT-NBD had been exploited to identify intracellular Cys/Hcy in living cells in light of its low toxicity. [Display omitted] •A fluorescent probe (TBT-NBD) was designed based on nucleophilic-rearrangement mechanism of benzothiazole thioether.•TBT-NBD had fast response, low detection limits, high selectivity and sensitivity for Cys/Hcy.•TBT-NBD monitored endogenous and exogenous Cys/Hcy by imaging.