The development of reaction-based fluorescent probes for H2S detection has been of high interest in recent years. While numerous designs have been introduced, many of these scaffolds have displayed suboptimal selectivity and reactivity towards H2S and with inadequate physicochemical properties which render their use impractical within biological systems. Herein, we report on a new approach for H2S probe development that utilizes a highly versatile selenosulfide functional group. With the heightened electrophilic character of selenium relative to that of sulfur, we demonstrate that the selenium half, when tethered to a second electrophilic partner, can selectively scavenge and detect H2S while the sulfur half provides a suitable handle for tuning the probe’s physicochemical properties such that it may be used effectively within a biological setting. With continued structural modifications to the sulfur half of these probes that further improve cellular delivery and/or tissue specificity, we foresee this framework serving as the foundation for a valuable set of chemical probes that may be used to further investigate the physiological importance of H2S.

Selenosulfides as versatile, electrophilic triggers for H2S detection and imaging

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.