A new long-wavelength emission fluorescent probe for imaging biothiols with remarkable Stokes shift.

By using BPMOH as the fluorophore and 2, 4-dinitrobenzenesulfonate moiety as the recognition site for thiols, a new long-wavelength emission (645 nm) fluorescent probe BPMSH with large Stokes shift (133 nm) was designed and synthesized. Probe BPMSH exhibited almost no fluorescence emission because of the PET process. When adding thiols, BPMSH could be quickly converted into BPMOH emitting a significant red fluorescence at 645 nm. In addition, BPMSH displayed high selectivity toward thiols among various biologically related analytes. Probe BPMSH has been applied to exogenous and endogenous thiols detection and imaging in living MCF-7 cells and MGC-803 cells. Most importantly, this probe BPMSH was successfully utilized for imaging thiols in zebrafish.