Alkylsulfenyl thiocarbonates: precursors to hydropersulfides potently attenuate oxidative stress.
Alkylsulfenyl thiocarbonates: precursors to hydropersulfides potently attenuate oxidative stress.
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DOI：
10.1039/d1sc01550h
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发表时间：
2021-05-14
期刊：
影响因子：
8.4
通讯作者：
Toscano JP
中科院分区：
文献类型：
--
作者：
Khodade VS;Aggarwal SC;Pharoah BM;Paolocci N;Toscano JP
最近发现的流行氢过硫化物（RSSH）的物种在生物系统中表明，它们在细胞调控过程中的潜在作用。然而，RSSH的反应性和瞬时性使得它们的研究困难，并且依赖于供体分子的使用。在此，我们报告烷基硫基硫代碳酸酯作为一类新的RSSH前体，有效地释放RSSH在生理相关的条件下。从这些前体的RSSH释放动力学可通过硫代碳酸酯羰基的亲电性的电子改性来调节。此外，这些前体还与硫醇反应以释放具有少量羰基硫（COS）的RSSH。重要的是，这些前体产生的RSSH保护H9c2心肌成肌细胞免受氧化应激。此外，我们证明了这些前体增加细胞内RSSH水平的能力。已经开发了一系列新颖的烷基硫基硫代碳酸酯，其在一定范围的半衰期内有效地释放过硫化物（RSSH）。这些前体产生的RSSH有效地改善了H9c2心肌成肌细胞的氧化应激。
The recent discovery of the prevalence of hydropersulfides (RSSH) species in biological systems suggests their potential roles in cell regulatory processes. However, the reactive and transient nature of RSSH makes their study difficult, and dependent on the use of donor molecules. Herein, we report alkylsulfenyl thiocarbonates as a new class of RSSH precursors that efficiently release RSSH under physiologically relevant conditions. RSSH release kinetics from these precursors are tunable through electronic modification of the thiocarbonate carbonyl group's electrophilicity. In addition, these precursors also react with thiols to release RSSH with a minor amount of carbonyl sulfide (COS). Importantly, RSSH generation by these precursors protects against oxidative stress in H9c2 cardiac myoblasts. Furthermore, we demonstrate the ability of these precursors to increase intracellular RSSH levels. A series of novel alkylsulfenyl thiocarbonates have been developed that efficiently release hydropersulfides (RSSH) over a range of half-lives. RSSH generation by these precursors potently ameliorates oxidative stress in H9c2 cardiac myoblasts.
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