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Highly efficient H2S scavengers via thiolysis of positively-charged NBD amines
Chemical Science ( IF 7.6 ) Pub Date : 2020-07-09 , DOI: 10.1039/d0sc01518k Ismail Ismail 1 , Zhuoyue Chen 2 , Lu Sun 3 , Xiuru Ji 3 , Haishun Ye 2 , Xueying Kang 2 , Haojie Huang 2 , Haibin Song 1 , Sarah G Bolton 4 , Zhen Xi 1 , Michael D Pluth 4 , Long Yi 2
Chemical Science ( IF 7.6 ) Pub Date : 2020-07-09 , DOI: 10.1039/d0sc01518k Ismail Ismail 1 , Zhuoyue Chen 2 , Lu Sun 3 , Xiuru Ji 3 , Haishun Ye 2 , Xueying Kang 2 , Haojie Huang 2 , Haibin Song 1 , Sarah G Bolton 4 , Zhen Xi 1 , Michael D Pluth 4 , Long Yi 2
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H2S is a well-known toxic gas and also a gaseous signaling molecule involved in many biological processes. Advanced chemical tools that can regulate H2S levels in vivo are useful for understanding H2S biology as well as its potential therapeutic effects. To this end, we have developed a series of 7-nitro-1,2,3-benzoxadiazole (NBD) amines as potential H2S scavengers. The kinetic studies of thiolysis reactions revealed that incorporation of positively-charged groups onto the NBD amines greatly increased the rate of the H2S-specific thiolysis reaction. We demonstrate that these reactions proceed effectively, with second order rate constants (k2) of >116 M−1 s−1 at 37 °C for NBD-S8. Additionally, we demonstrate that NBD-S8 can effectively scavenge enzymatically-produced and endogenous H2S in live cells. Furthering the biological significance, we demonstrate NBD-S8 mediates scavenging of H2S in mice.
中文翻译：
通过带正电荷的 NBD 胺的硫解作用形成高效 H2S 清除剂
H 2 S是一种众所周知的有毒气体，也是参与许多生物过程的气态信号分子。能够调节体内H 2 S 水平的先进化学工具有助于了解 H 2 S 生物学及其潜在的治疗效果。为此，我们开发了一系列7-硝基-1,2,3-苯并恶二唑(NBD)胺作为潜在的H 2 S清除剂。硫解反应的动力学研究表明，将带正电荷的基团掺入NBD胺上大大提高了H 2 S特异性硫解反应的速率。我们证明这些反应有效进行， NBD-S8在 37 °C 下的二阶速率常数 ( k 2 ) >116 M -1 s -1。此外，我们证明NBD-S8可以有效清除活细胞中酶促产生的内源性 H 2 S。为了进一步发挥生物学意义，我们证明NBD-S8介导小鼠体内H 2 S的清除。
更新日期：2020-08-05
中文翻译：
通过带正电荷的 NBD 胺的硫解作用形成高效 H2S 清除剂
H 2 S是一种众所周知的有毒气体，也是参与许多生物过程的气态信号分子。能够调节体内H 2 S 水平的先进化学工具有助于了解 H 2 S 生物学及其潜在的治疗效果。为此，我们开发了一系列7-硝基-1,2,3-苯并恶二唑(NBD)胺作为潜在的H 2 S清除剂。硫解反应的动力学研究表明，将带正电荷的基团掺入NBD胺上大大提高了H 2 S特异性硫解反应的速率。我们证明这些反应有效进行， NBD-S8在 37 °C 下的二阶速率常数 ( k 2 ) >116 M -1 s -1。此外，我们证明NBD-S8可以有效清除活细胞中酶促产生的内源性 H 2 S。为了进一步发挥生物学意义，我们证明NBD-S8介导小鼠体内H 2 S的清除。
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