Construction of novel coumarin-carbazole-based fluorescent probe for tracking of endogenous and exogenous H2S in vivo with yellow-emission and large Stokes shift.

[Display omitted] • A novel fluorescent probe, COZ-DNB , for sensitive detection of H 2 S was developed. • Probe COZ-DNB performed sufficient selectivity, rapid detection, high sensitivity and a large Stokes to H 2 S. • COZ-DNB was applied for imaging of exogenous and endogenous H 2 S in living HeLa cells and zebrafish with satisfactory performances. Recent medical studies have confirmed that endogenous H 2 S serves as the third gas-messenger besides nitric oxide (NO) and carbon monoxide (CO), which is produced by enzyme-catalyzed metabolism of cysteine and takes part in multiple physiological processes. The abnormal levels induced by H 2 S overproduction in mammals can destroy tissues and organ systems, which lead to certain serious diseases, such as neurodegenerative diseases, cardiovascular diseases, and various cancers. In this work, we developed a novel coumarin-carbazole fluorescent probe COZ-DNB with yellow emission and a large Stokes shift for H 2 S detection. In probe COZ-DNB , the newly dye COZ-OH as a luminophore and the 2,4-dinitrophenyl ether moiety was chosen as a trigger group for H 2 S. Probe COZ-DNB itself displayed nearly non-fluorescent. However, COZ-DNB gave the remarkable fluorescence with an 83-fold enhancement in the yellow region after interaction with H 2 S. The sensing mechanism of COZ-DNB toward H 2 S was checked by means of UHPLC, HRMS and DFT/TD-DFT calculations. What's more, probe COZ-DNB also exhibited fast response (2.0 min), high sensitivity (65.0 nM), a large Stokes shift (161.0 nm), high stability and excellent selectivity. Furthermore, COZ-DNB was applied for imaging of exogenous and endogenous H 2 S in living HeLa cells and zebrafish with satisfactory performances. We anticipate COZ-DNB would be served as a potential tool for investigating the biological functions of H 2 S in pathological processes. [ABSTRACT FROM AUTHOR]