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. 2017 May 5;19(9):2314-2317.
doi: 10.1021/acs.orglett.7b00858. Epub 2017 Apr 25.

Applications of Synthetic Organic Tetrasulfides as H2S Donors

Matthew M Cerda  1 , Matthew D Hammers  1 , Mary S Earp  1 , Lev N Zakharov  1 , Michael D Pluth  1
Affiliations

Applications of Synthetic Organic Tetrasulfides as H2S Donors

Matthew M Cerda et al. Org Lett. .

Abstract

In an effort to expand the availability of simple polysulfides for H2S donation, we report here the synthesis and H2S release profiles of bis(aryl) and bis(alkyl) tetrasulfides. The tetrasulfide donors release H2S in a first-order dependence on reduced glutathione (GSH) and release more H2S than the commonly used trisulfide DATS.

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Conflict of interest statement

Notes

The authors declare no competing financial interests

Figures

Figure 1
Figure 1
(a) Mechanism of H2S release from DATS in the presence of GSH. (b) Representative examples of natural products containing polysulfides.
Figure 2
Figure 2
(a) Mass spectrum (EI-MS) of 3. (b) ORTEP representation (50% ellipsoids) of the molecular structure of 4.
Figure 3
Figure 3
Proposed mechanisms of H2S release from tetrasulfides, including initial nucleophilic attack by GSH at the (a) β-sulfur or (b) α-sulfur.
Figure 4
Figure 4
(a) GSH-dependent H2S release from 3. (b) log(k) vs. log[GSH] plot demonstrating a 1st-order dependence in [GSH] on H2S release from 3.
Figure 5
Figure 5
GSH-triggered (250 equiv) H2S release from 5 μM tetrasulfides 1–8 and 5 μM DATS (pH 7.4, room temperature).
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