作为 HS 供体的合成有机四硫化物的应用。
Applications of Synthetic Organic Tetrasulfides as HS Donors.
机构信息
Department of Chemistry and Biochemistry, Materials Science Institute, Institute of Molecular Biology, University of Oregon , Eugene, Oregon 97403, United States.
出版信息
Org Lett. 2017 May 5;19(9):2314-2317. doi: 10.1021/acs.orglett.7b00858. Epub 2017 Apr 25.
Abstract
In an effort to expand the availability of simple polysulfides for HS donation, we report here the synthesis and HS release profiles of bis(aryl) and bis(alkyl) tetrasulfides. The tetrasulfide donors release HS in a first-order dependence on reduced glutathione (GSH) and release more HS than the commonly used trisulfide DATS.
摘要
为了扩大简单多硫化物作为 HS 供体的可用性，我们在此报告了双（芳基）和双（烷基）四硫化物的合成和 HS 释放曲线。四硫化物供体以依赖于还原型谷胱甘肽 (GSH) 的一级反应释放 HS，并且比常用的三硫化物 DATS 释放更多的 HS。
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本文引用的文献
1
Slow generation of hydrogen sulfide from sulfane sulfurs and NADH models.
Bioorg Med Chem Lett. 2017 Feb 1;27(3):542-545. doi: 10.1016/j.bmcl.2016.12.023. Epub 2016 Dec 9.
2
A Synthetic Supramolecular Receptor for the Hydrosulfide Anion.
Angew Chem Int Ed Engl. 2016 Sep 12;55(38):11480-4. doi: 10.1002/anie.201605757. Epub 2016 Aug 11.
3
Self-Immolative Thiocarbamates Provide Access to Triggered H2S Donors and Analyte Replacement Fluorescent Probes.
J Am Chem Soc. 2016 Jun 15;138(23):7256-9. doi: 10.1021/jacs.6b03780. Epub 2016 Jun 3.
4
A practical guide to working with HS at the interface of chemistry and biology.
Chem Soc Rev. 2016 Nov 7;45(22):6108-6117. doi: 10.1039/c6cs00212a.
5
Esterase-Sensitive Prodrugs with Tunable Release Rates and Direct Generation of Hydrogen Sulfide.
Angew Chem Int Ed Engl. 2016 Mar 24;55(14):4514-8. doi: 10.1002/anie.201511244. Epub 2016 Jan 28.
6
Diallyl Trisulfide Is a Fast H2S Donor, but Diallyl Disulfide Is a Slow One: The Reaction Pathways and Intermediates of Glutathione with Polysulfides.
Org Lett. 2015 Sep 4;17(17):4196-9. doi: 10.1021/acs.orglett.5b01962. Epub 2015 Aug 24.
7
Hydrogen sulfide in pharmacology and medicine--An update.
Pharmacol Rep. 2015 Jun;67(3):647-58. doi: 10.1016/j.pharep.2015.01.005. Epub 2015 Jan 22.
8
Hydrogen sulfide-based therapeutics: exploiting a unique but ubiquitous gasotransmitter.
Nat Rev Drug Discov. 2015 May;14(5):329-45. doi: 10.1038/nrd4433. Epub 2015 Apr 7.
9
Hydrogen sulfide (H2S) releasing agents: chemistry and biological applications.
Chem Commun (Camb). 2014 Oct 14;50(80):11788-805. doi: 10.1039/c4cc00968a.
10
Arylthioamides as H2S Donors: l-Cysteine-Activated Releasing Properties and Vascular Effects in Vitro and in Vivo.
ACS Med Chem Lett. 2013 Aug 8;4(10):904-8. doi: 10.1021/ml400239a. eCollection 2013 Oct 10.
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