Issue 6, 2019

Fluorogenic hydrogen sulfide (H2S) donors based on sulfenyl thiocarbonates enable H2S tracking and quantification

Abstract

Hydrogen sulfide (H2S) is an important cellular signaling molecule that exhibits promising protective effects. Although a number of triggerable H2S donors have been developed, spatiotemporal feedback from H2S release in biological systems remains a key challenge in H2S donor development. Herein we report the synthesis, evaluation, and application of caged sulfenyl thiocarbonates as new fluorescent H2S donors. These molecules rely on thiol cleavage of sulfenyl thiocarbonates to release carbonyl sulfide (COS), which is quickly converted to H2S by carbonic anhydrase (CA). This approach is a new strategy in H2S release and does not release electrophilic byproducts common from COS-based H2S releasing motifs. Importantly, the release of COS/H2S is accompanied by the release of a fluorescent reporter, which enables the real-time tracking of H2S by fluorescence spectroscopy or microscopy. Dependent on the choice of fluorophore, either one or two equivalents of H2S can be released, thus allowing for the dynamic range of the fluorescent donors to be tuned. We demonstrate that the fluorescence response correlates directly with quantified H2S release and also demonstrate the live-cell compatibility of these donors. Furthermore, these fluorescent donors exhibit anti-inflammatory effects in RAW 264.7 cells, indicating their potential application as new H2S-releasing therapeutics. Taken together, sulfenyl thiocarbonates provide a new platform for H2S donation and readily enable fluorescent tracking of H2S delivery in complex environments.

Graphical abstract: Fluorogenic hydrogen sulfide (H2S) donors based on sulfenyl thiocarbonates enable H2S tracking and quantification

Supplementary files

Article information

Article type
Edge Article
Submitted
21 nov 2018
Accepted
10 dec 2018
First published
10 dec 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 1873-1878

Fluorogenic hydrogen sulfide (H2S) donors based on sulfenyl thiocarbonates enable H2S tracking and quantification

Y. Zhao, Matthew M. Cerda and M. D. Pluth, Chem. Sci., 2019, 10, 1873 DOI: 10.1039/C8SC05200J

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