Pyridinium substituted BODIPY as NIR fluorescent probe for simultaneous sensing of hydrogen sulphide/glutathione and cysteine/homocysteine

摘要

Graphical abstractDisplay OmittedHighlights•A novel NIR fluorescent probe for simultaneous sensing of Hydrogen Sulfide/Glutathione and Cysteine/Homocysteine in dual channel was developed.•The probe carrys apara-nitrobenzofurazan (NBD) benzyl pyridinium moiety at themesoposition of a BODIPY dye as self-immolative linker.•The probe was successfully used to image GSH in living Hela cells.•The probe also could image biothiols in living mouse.AbstractA BODIPY based NIR turn-on fluorescent probe (1) carrying a 7-nitro-2,1,3-benzoxadiazole (NBD) moiety linked atmesoposition of the BODIPY through benzyl pyridinium moiety as self-immolative linker was designed and successfully constructed. Such a probe selectively respond to H2S and biothiol species. It was able to differentiate H2S/GSH and Cys/Hcy under dual channels imaging with good spectroscopic separation and fluorescence enhancement. The studies on sensing mechanism supported thiols-induced SNAr substitution–rearrangement cascade reaction which allowed differentiation of H2S/GSH and Cys/Hcy via amino- and thiol-NBD derivatives with exhibited distinct photo-physical properties. Such a probe was successfully used to image GSH in living Hela cells and to detect endogenous biothiols in living mouse.