Dithioesters release H2S upon treatment with cysteine, and the rate can be tuned by structural and electronic modifications.

Hydrolysis-based H2Se donors provide new chemical tools for investigating biological H2Se.

Hydrogen selenide (H 2 Se) is a central metabolite in the biological processing of selenium for incorporation into selenoproteins, which play crucial antioxidant roles in biological systems. Despite being integral to proper physiological function, this reactive selenium species (RSeS) has received limited attention. We recently reported an early example of a H 2 Se donor (TDN1042) that exhibited slow, sustained release through hydrolysis. Here we expand that technology based on the PSe motif to develop cyclic-PSe compounds with increased rates of hydrolysis and function through well-defined mechanisms as monitored by 31 P and 77 Se NMR spectroscopy. In addition, we report a colorimetric method based on the reaction of H 2 Se with NBD-Cl to generate NBD-SeH (λ max = 551 nm), which can be used to detect free H 2 Se. Furthermore, we use TOF-SIMS (time of flight secondary ion mass spectroscopy) to demonstrate that these H 2 Se donors are cell permeable and use this technique for spatial mapping of the intracellular Se content after H 2 Se delivery. Moreover, these H 2 Se donors reduce endogenous intracellular reactive oxygen species (ROS) levels. Taken together, this work expands the toolbox of H 2 Se donor technology and sets the stage for future work focused on the biological activity and beneficial applications of H 2 Se and related bioinorganic RSeS.

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Hydrogen selenide (H2Se) is a possible bioregulator, potential gasotransmitter, and important precursor in biological organoselenium compound synthesis. Early tools for H2Se research have benefitted from available mechanistic understanding of analogous...

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