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Hydrogen sulfide (H2S) is a biologically important signaling molecule that exerts diverse roles in various physiological processes. However, recent reports indicate that much of the biological activities associated with H2S may be attributed to hydropersulfides (RSSH) and polysulfides (RSSnR). Although the presumed biological utility of RSSH is predicted to be based on their unique chemistry, the fundamental chemistry and biological role of RSSH are still poorly understood. This is mainly due to the instability of RSSH under physiological conditions. Few methods have been developed to produce RSSH however they are associated with several limitations. For example, reaction of an alkyl disulfide with H2S is a common method for RSSH generation, but this approach requires high concentrations of reactants and the reaction initiates a complex equilibrium that makes it difficult to analyze RSSH exclusively. In another approach, a compound containing an activated disulfide bond has been developed to spontaneously rearrange under physiological conditions producing RSSH. Recently, 9-fluorenilmethyl disulfide derivatives of cysteine thiols have also been developed for RSSH generation. To advance our understanding of the role of RSSH in biology, it is critical to develop new precursors that can cleanly and reliably produce RSSH under biological conditions. Here, we will present novel precursors that produce RSSH under physiological conditions, and other methods that may offer more spatio-temporal control of RSSH release. |
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