6493-73-8Relevant articles and documents
Selectivity of diallyl trisulfides (DATS) in reducing HAuCl4 to produce gold nanoparticles: a detailed investigation
Chatterjee, Arunavo,Mandal, Niladri Sekhar,Purkayastha, Pradipta
, (2021/09/08)
The bulbous root garlic (Allium sativum) with a strong taste and pungent odor is used widely in culinary preparations and folk medicine. Silver and gold nanoparticles (NPs) synthesized using this ingredient have also shown medicinal and therapeutic potency. Garlic contains organosulfur compounds, such as diallyl sulfide (DAS), diallyl disulfide (DADS) and diallyl trisulfide (DATS). These compounds are of crucial significance as anticancer drugs. Reported here is a synthesis of a series of DATS with varying substituents and plausible application as capping as well as reducing agent to synthesize gold nanoparticles (TS-GNPs). In the process, it was discovered that among the selected DATs, only 1,3-di(but-1-ene)trisulfane could serve the purpose because of structural reasons. The reason for this intriguing selectivity has been investigated in detail using the experimental findings and theoretical calculations of the frontier molecular orbitals (FMO). Graphic abstract: Synthesis of a series of medicinally important symmetrical organic trisulfides as a structural analogue of diallyl trisulfides (DATS) in an attempt to construct organosulfur compound induced gold nanoparticles (GNPs), has been reported. Only 1,3-Di(but-1-ene)trisulfane in the lot is capable of reducing the chloroauric acid to synthesize the protected GNPs.[Figure not available: see fulltext.].
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 (2019/01/04)
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.
An Esterase-Sensitive Prodrug Approach for Controllable Delivery of Persulfide Species
Zheng, Yueqin,Yu, Bingchen,Li, Zhen,Yuan, Zhengnan,Organ, Chelsea L.,Trivedi, Rishi K.,Wang, Siming,Lefer, David J.,Wang, Binghe
supporting information, p. 11749 - 11753 (2017/09/20)
A strategy to deliver a well-defined persulfide species in a biological medium is described. Under near physiological conditions, the persulfide prodrug can be activated by an esterase to generate a “hydroxymethyl persulfide” intermediate, which rapidly collapses to form a defined persulfide. Such persulfide prodrugs can be used either as chemical tools to study persulfide chemistry and biology or for future development as H2S-based therapeutic reagents. Using the persulfide prodrugs developed in this study, the reactivity between S-methyl methanethiosulfonate (MMTS) with persulfide was unambiguously demonstrated. Furthermore, a representative prodrug exhibited potent cardioprotective effects in a murine model of myocardial ischemia-reperfusion (MI/R) injury with a bell shape therapeutic profile.