Biothiol-Triggered Hydrogen Sulfide (H2S) Release from Near-Infrared Fluorescence H2S Donor for Promoting Cutaneous Wound Healing

Cell Biology
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Xinyue Zhao# 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

Mengbin Ding# Shanghai Engineering Research Center of Nano-Biomaterials and Regenerative Medicine, College of Biological Science and Medical Engineering, Donghua University, Shanghai 201620, China

Lulu Ning 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

Fang Yuan 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

Jingchao Li Shanghai Engineering Research Center of Nano-Biomaterials and Regenerative Medicine, College of Biological Science and Medical Engineering, Donghua University, Shanghai 201620, China

Yuan Guo 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

Yuguang Mu School of Biological Sciences, Nanyang Technological University, 60 Nanyang Drive, Singapore 637551, Singapore

Jianjian Zhang* 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++Qinghai Provincial Key Laboratory of Salt Lake Resources Chemistry, Xining, 810008, P. R. China

# contributed equally to this work


Abstract

Hydrogen sulfide (H2S) plays crucial roles in antioxidation, anti-inflammation, and cytoprotection. Despite the great progress in the design and synthesis of activatable H2S donors, high-precision detection and imaging of released H2S in living systems is still an outstanding issue. In this study, a biothiol-activated near-infrared (NIR) fluorescent H2S donor PRO-ST for real-time visualization of H2S release is developed. PRO-ST, consisting of a dicyanoisophorone-based NIR fluorescence moiety (TCOO), a biothiol-trigger moiety (4-isothiocyanate benzyl alcohol), and a sulfur-source group (thiophosgene), is characterized by large NIR fluorescence enhancement (45-fold), outstanding H2S release efficiency (73%), prominent controllable H2S release (60 min) and excellent cell compatibility. The distinctive features render PRO-ST capable of visualizing H2S release in cells, zebrafish, and mice. Moreover, PRO-ST has exhibited excellent performance of real-time anti-inflammation and wound healing enhancement in biological systems, which has been confirmed by in-situ visualization of H2S release.  The versatile PRO-ST provides possible and effective solution to the detection and visualization of H2S release, which will benefit the comprehension of underlying mechanisms of wound healing and the optimization of interventional therapy.

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