Brown Eric M, Grace James P, Ranasinghe Arachchige Nimesh P R, Bowden Ned B
W425 Chemistry Building, Department of Chemistry, University of Iowa, Iowa City, Iowa 52242 United States.
ACS Omega. 2023 Jul 19;8(30):27576-27584. doi: 10.1021/acsomega.3c03258. eCollection 2023 Aug 1.
Hydrogen sulfide has emerged as a key gasotransmitter in humans and in plants, and the addition of exogenous hydrogen sulfide has many beneficial effects and . A challenge in investigating the effect of exogenous hydrogen sulfide is tracking the location of exogenous hydrogen sulfide on an organism and cellular level. In this article, we report the synthesis of three key chemicals (cysteine trisulfide, glutathione trisulfide, and GYY-4137) that release radiolabeled S as hydrogen sulfide. The synthesis started with the reduction of NaSO mixed with NaSO to generate hydrogen sulfide gas that was trapped with aq NaOH to yield radiolabeled NaS. The NaS was converted in one step to GYY-4137 at 65% yield. It was also converted to bis(tributyltin) sulfide that readily reacted with -bromophthalimide to yield a monosulfur transfer reagent. Trisulfides were synthesized by reaction with the monosulfur transfer reagent and the corresponding thiols. The levels of radioactivity of the final products could be varied on a per gram basis to alter the radioactivity for applications that require different loadings of hydrogen sulfide donors.
硫化氢已成为人类和植物中的一种关键气体信号分子，添加外源性硫化氢具有许多有益作用。研究外源性硫化氢作用的一个挑战是在生物体和细胞水平上追踪外源性硫化氢的位置。在本文中，我们报告了三种关键化学物质（三硫化半胱氨酸、三硫化谷胱甘肽和GYY-4137）的合成，这些物质会释放出作为硫化氢的放射性标记硫。合成过程始于将NaSO与NaSO混合还原以产生硫化氢气体，该气体用氢氧化钠水溶液捕获以生成放射性标记的NaS。NaS一步转化为GYY-4137，产率为65%。它还被转化为双（三丁基锡）硫化物，该物质 readily reacted with -bromophthalimide（此处“readily reacted with -bromophthalimide”表述有误，推测可能是“readily reacted with N-bromophthalimide”，即与N-溴代邻苯二甲酰亚胺）以产生单硫转移试剂。通过与单硫转移试剂和相应的硫醇反应合成三硫化物。最终产物的放射性水平可以按每克进行变化，以改变用于需要不同硫化氢供体负载量的应用的放射性。
