Rational design of a new near-infrared fluorophore and apply to the detection and imaging study of cysteine and thiophenol.

The development of a near-infrared fluorophore with excellent fluorescence performance, a large Stokes shift, and good biocompatibility has become a focus in the field of fluorescence imaging in recent years. Based on quantum chemistry calculations and reasonable molecular design strategies, a new NIR fluorophore was developed and characterized by simple synthesis, easy structural modification, and a large Stokes shift (105 nm). Furthermore, two new "activatable" fluorescent probes QN-Cys and QN-DNP were synthesized using a simple structural modification. The probe QN-Cys can recognize Cys with high sensitivity (LOD = 128 nM) and high selectivity, and its fluorescence intensity has a good linear relationship with the Cys concentration in the range of 5–35 μM. Furthermore, probe QN-Cys can effectively distinguish Cys from Hcy and GSH, and was successfully applied to the detection and imaging of Cys in human serum, cells, and zebrafish. The probe QN-DNP showed a good specific and sensitive (LOD = 78 nM) fluorescence response to thiophenol, and its fluorescence intensity has a good linear relationship with the thiophenol concentration in the range of 5–30 μM. Furthermore, it was successfully applied to detect thiophenol in real water samples with good recoveries (97–102%), and image thiophenol in living cells, zebrafish and mice. Notebly, the QN-DNP probe could be applied to visualize the distribution of thiophenol in the mice. [Display omitted] • Reasonably designed a fluorophore QN-OH with NIR fluorescence properties (λem = 685 nm) and large Stokes shift (105 nm). • Probe QN-Cys can be used to discriminate detection of Cys from Hcy and GSH, imaging Cys in cells and zebrafish. • Probe QN-DNP was used for detection of PhSH in water samples, and imaging PhSH in living cells, zebrafishs and mice. [ABSTRACT FROM AUTHOR]