4816-54-0Relevant articles and documents
Effects of sulfane sulfur content in benzyl polysulfides on thiol-triggered H2S release and cell proliferation
Bolton, Sarah G.,Cerda, Matthew M.,Gilbert, Annie K.,Pluth, Michael D.
, p. 393 - 398 (2019)
Investigations into hydrogen sulfide (H2S) signaling pathways have demonstrated both the generation and importance of persulfides, which are reactive sulfur species that contain both reduced and oxidized sulfur. These observations have led researchers to suggest that oxidized sulfur species, including sulfane sulfur (S0), are responsible for many of the physiological phenomena initially attributed to H2S. A common method of introducing S0 to biological systems is the administration of organic polysulfides, such as diallyl trisulfide (DATS). However, prior reports have demonstrated that commercially-available DATS often contains a mixture of polysulfides, and furthermore a lack of structure-activity relationships for organic polysulfides has limited our overall understanding of different polysulfides and their function in biological systems. Advancing our interests in the chemical biology of reactive sulfur species including H2S and S0, we report here our investigations into the rates and quantities of H2S release from a series of synthetic, pure benzyl polysulfides, ranging from monosulfide to tetrasulfide. We demonstrate that H2S is only released from the trisulfide and tetrasulfide, and that this release requires thiol-mediated reduction in the presence of cysteine or reduced glutathione. Additionally, we demonstrate the different effects of trisulfides and tetrasulfides on cell proliferation in murine epithelial bEnd.3 cells.
Silylating Disulfides and Thiols with Hydrosilicones Catalyzed by B(C6F5)3
Brook, Michael A.,Liao, Mengchen,Zheng, Sijia
supporting information, p. 2694 - 2700 (2021/06/25)
Hydrosilanes and silicones, catalyzed with B(C6F5)3, may be used to silylate thiols or cleave disulfides giving silyl thio ethers. Alcohols were found to react faster than thiols or disulfides, while alkoxysilanes (the Piers-Rubinsztajn reaction) were slower such that the overall order of reactivity was found to be HO>HS>SS>SiOEt. The resulting silane and silicone-protected thio ethers produced from the sulfur-based functional groups could be cleaved to thiols using alcohols or mild acid with rates that depend on the steric bulk of the siloxane.
Direct preparation of anhydrous sodium oligosulfides from metal sodium and elemental sulfur in aprotic organic media directed toward synthesis of silane coupling agent
Yamada, Nobuo,Furukawa, Mutsuhisa,Nishi, Masayuki,Takata, Toshikazu
, p. 454 - 455 (2007/10/03)
Anhydrous sodium oligosulfide was prepared by the heterogeneous reaction of metal sodium and elemental sulfur in aprotic solvents. The oligosulfide consisted of a mixture of several Na2Sn (n = 2 - 8). Organic oligosulfides (R2Sn, n ≥ 2) including moisture-sensitive one were synthesized by the reaction with organic halides in high yeilds under mild conditions.