Near-Infrared Fluorescence Probe with a New Recognition Moiety for the Specific Detection of Cysteine to Study the Corresponding Physiological Processes in Cells, Zebrafish, and Arabidopsis thaliana

Cysteine (Cys), as one of the biological thiols, is related to many physiological and pathological processes in humans and plants. Therefore, it is necessary to develop a sensitive and selective method for the detection and imaging of Cys in biological organisms. In this work, a novel near-infrared (NIR) fluorescent probe, Probe-Cys, was designed by connecting furancarbonyl, as a new recognition moiety, with Fluorophore–OH via the decomposition of IR-806. The use of the furan moiety is anticipated to produce more effective fluorescence quenching because of the electron-donating ability of the O atom. Probe-Cys has outstanding properties, such as a new recognition group, an emission wavelength in the infrared region at 710 nm, a linear range (0–100 μM), a low detection limit of 0.035 μM, good water solubility, excellent sensitivity, and selectivity without the interference of Hcy, GSH, and HS–. More importantly, Probe-Cys could achieve the detection of endogenous Cys by reacting with the stimulant 1,4-dimercaptothreitol (DTT) and the inhibitor N-ethylmaleimide (NEM) in HepG2 cells and zebrafish. Ultimately, it was successfully applied to obtain images of Arabidopsis thaliana, revealing that the content of Cys in the meristematic zone was higher than that in the elongation zone, which was the first time that the NIR fluorescence probe was used to obtain images of Cys in A. thaliana. The superior properties of the probe exhibit its great potential for use in biosystems to explore the physiological and pathological processes associated with Cys.