Development of a NIR fluorescent probe for highly selective and sensitive detection of cysteine in living cells and in vivo.

Abstract Cysteine (Cys) plays important physiological roles in the human body, and abnormal Cys concentrations can cause a variety of diseases. Thus, detecting Cys with high selectivity and sensitivity in vivo is important. Near-infrared (NIR) fluorescent probes are widely employed in biological detection because of their excellent optical properties such as minimal damage to biological samples, low background interference and high signal-to-noise ratio. However, few NIR fluorescent probes that can detect Cys over homocysteine (Hcy) and glutathione (GSH) have been reported because of their similar reactivity and structure. In this work, a highly water-soluble NIR probe (CYNA) for detecting Cys whose structure is similar to that of indocyanine green and is based on cyanine skeleton was synthesized and via aromatic nucleophilic substitution–rearrangement (SNAr-rearrangement) to specific recognize the cysteine. The probe showed high selectivity toward Cys and superior biosecurity, excellent biocompatibility and prolonged dynamic imaging. It also has long fluorescence emission wavelength (820 nm), low detection limit (14 nM) and was successfully applied for visualizing Cys in living cells and mice, which has great promise for applications in noninvasive vivo biological imaging and detection.