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Kinetics of Azanone (HNO) Reactions with Thiols: Effect of pH
Cell Biochemistry and Biophysics ( IF 2.6 ) Pub Date : 2021-05-05 , DOI: 10.1007/s12013-021-00986-x
Renata Smulik-Izydorczyk 1 , Karolina Dębowska 1 , Michał Rostkowski 1 , Jan Adamus 1 , Radosław Michalski 1 , Adam Sikora 1
Affiliation  

HNO (nitroxyl, IUPAC name azanone) is an electrophilic reactive nitrogen species of growing pharmacological and biological significance. Here, we present data on the pH-dependent kinetics of azanone reactions with the low molecular thiols glutathione and N-acetylcysteine, as well as with important serum proteins: bovine serum albumin and human serum albumin. The competition kinetics method used is based on two parallel HNO reactions: with RSH/RS or with O2. The results provide evidence that the reaction of azanone with the anionic form of thiols (RS) is favored over reactions with the protonated form (RSH). The data are supported with quantum mechanical calculations. A comprehensive discussion of the HNO reaction with thiolates is provided.



中文翻译:

氮杂酮 (HNO) 与硫醇反应的动力学:pH 的影响

HNO(硝酰基,IUPAC 名称 azanone)是一种具有日益增长的药理学和生物学意义的亲电活性氮物种。在这里,我们展示了氮杂酮与低分子硫醇谷胱甘肽和N-乙酰半胱氨酸以及重要的血清蛋白(牛血清白蛋白和人血清白蛋白)反应的 pH 依赖性动力学数据。使用的竞争动力学方法基于两个平行的HNO反应:与RSH / RS -或与O 2。结果提供了证据表明氮杂酮与阴离子形式的硫醇 ( RS - ) 的反应优于与质子化形式 ( RSH ) 的反应。)。数据得到量子力学计算的支持。提供了HNO与硫醇盐反应的全面讨论。

更新日期:2021-05-05
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