巯基激活的 1,2,4-噻二唑烷-3,5-二酮通过依赖于碳酰硫的途径释放硫化氢。
Thiol-Activated 1,2,4-Thiadiazolidin-3,5-diones Release Hydrogen Sulfide through a Carbonyl-Sulfide-Dependent Pathway.
机构信息
Department of Chemistry and Biochemistry, Materials Science Institute, Knight Campus for Accelerating Scientific Impact, Institute of Molecular Biology, University of Oregon, Eugene, Oregon 97403, United States.
出版信息
J Org Chem. 2022 Sep 16;87(18):12441-12446. doi: 10.1021/acs.joc.2c01220. Epub 2022 Sep 7.
Abstract
Recent efforts have expanded the development of small molecule donors that release the important biological signaling molecule hydrogen sulfide (HS). Previous work on 1,2,4-thiadiazolidin-3,5-diones (TDZNs) reported that these compounds release HS directly, albeit inefficiently. However, TDZNs showed promising efficacy in HS-mediated relaxation in ex vivo aortic ring relaxation models. Here, we show that TDZNs release carbonyl sulfide (COS) efficiently, which can be converted to HS by the enzyme carbonic anhydrase (CA) rather than releasing HS directly as previously reported.
摘要
最近的研究工作扩大了小分子供体的开发，这些供体能够释放重要的生物信号分子硫化氢（HS）。先前关于 1,2,4-噻二唑烷-3,5-二酮（TDZNs）的研究报告称，这些化合物直接释放 HS，尽管效率不高。然而，TDZNs 在 HS 介导的离体主动脉环松弛模型中的松弛作用中显示出了有前景的疗效。在这里，我们表明 TDZNs 能够有效地释放碳酰硫化物（COS），该物质可以通过酶碳酸酐酶（CA）转化为 HS，而不是像以前报道的那样直接释放 HS。
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