An Activatable Near-Infrared Fluorescence Hydrogen Sulfide (H(2)S) Donor for Imaging H(2)S Release and Inhibiting Inflammation in Cells.

Affiliation

Zhao X(1), Ning L(2), Zhou X(3), Song Z(3), Zhang J(1), Guan F(3), Yang XF(1).
Author information:
(1)Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Key Lab of Modern Separation Science in Shaanxi Province, College of Chemistry and Materials Science, Northwest University, Xi'an, Shaanxi 710127, P. R. China.
(2)Shaanxi Provincial Key Laboratory of Papermaking Technology and Specialty Paper Development, College of Bioresources Chemical and Materials Engineering, Shaanxi University of Science & Technology, Xi'an 710021, P. R. China.
(3)Shaanxi Provincial Key Laboratory of Biotechnology, Joint International Research Laboratory of Glycobiology and Medicinal Chemistry, College of Life Science, Northwest University, Xi'an, Shaanxi 710127, P. R. China.

Abstract

Hydrogen sulfide (H2S) is a vital endogenous signal molecule that exerts critical physiological functions such as biological regulation and cytoprotection. Despite significant progress in developing H2S donors, site-specific delivery and controllable release of H2S in biological systems remain a key challenge. Herein, we develop new Cys-triggered fluorescent H2S donor Pro-S that is composed of a dicyanoisophorone-based near-infrared (NIR) fluorescent dye and a thiocarbamate moiety. The H2S donor releases H2S under the attack of Cys, accompanied by the release of a fluorescent reporter, which enables the real-time capturing of H2S by fluorescence spectroscopy or microscopy. Pro-S exhibits strong NIR fluorescence enhancement (70-fold), excellent controllable H2S release (30 min), high H2S release efficiency (62%), and well live-cell compatibility, allowing for visualization of H2S release in cells and zebrafish. Moreover, Pro-S presents a good effect of anti-inflammation in RAW 264.7 cells. This work provides a new idea for the design of H2S donors, which may be beneficial to the comprehension of the potential mechanism of inflammation and optimization of treatment strategies.