Kinetics of Azanone (HNO) Reactions with Thiols: Effect of pH

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 s...

Descripción completa

Detalles Bibliográficos
Autores principales: Smulik-Izydorczyk, Renata, Dębowska, Karolina, Rostkowski, Michał, Adamus, Jan, Michalski, Radosław, Sikora, Adam
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer US 2021
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8558164/
https://www.ncbi.nlm.nih.gov/pubmed/33950351
http://dx.doi.org/10.1007/s12013-021-00986-x
_version_ 1784592495122841600
author Smulik-Izydorczyk, Renata
Dębowska, Karolina
Rostkowski, Michał
Adamus, Jan
Michalski, Radosław
Sikora, Adam
author_facet Smulik-Izydorczyk, Renata
Dębowska, Karolina
Rostkowski, Michał
Adamus, Jan
Michalski, Radosław
Sikora, Adam
author_sort Smulik-Izydorczyk, Renata
collection PubMed
description 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 O(2). 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.
format Online
Article
Text
id pubmed-8558164
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher Springer US
record_format MEDLINE/PubMed
spelling pubmed-85581642021-11-15 Kinetics of Azanone (HNO) Reactions with Thiols: Effect of pH Smulik-Izydorczyk, Renata Dębowska, Karolina Rostkowski, Michał Adamus, Jan Michalski, Radosław Sikora, Adam Cell Biochem Biophys Original Paper 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 O(2). 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. Springer US 2021-05-05 2021 /pmc/articles/PMC8558164/ /pubmed/33950351 http://dx.doi.org/10.1007/s12013-021-00986-x Text en © The Author(s) 2021 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Original Paper
Smulik-Izydorczyk, Renata
Dębowska, Karolina
Rostkowski, Michał
Adamus, Jan
Michalski, Radosław
Sikora, Adam
Kinetics of Azanone (HNO) Reactions with Thiols: Effect of pH
title Kinetics of Azanone (HNO) Reactions with Thiols: Effect of pH
title_full Kinetics of Azanone (HNO) Reactions with Thiols: Effect of pH
title_fullStr Kinetics of Azanone (HNO) Reactions with Thiols: Effect of pH
title_full_unstemmed Kinetics of Azanone (HNO) Reactions with Thiols: Effect of pH
title_short Kinetics of Azanone (HNO) Reactions with Thiols: Effect of pH
title_sort kinetics of azanone (hno) reactions with thiols: effect of ph
topic Original Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8558164/
https://www.ncbi.nlm.nih.gov/pubmed/33950351
http://dx.doi.org/10.1007/s12013-021-00986-x
work_keys_str_mv AT smulikizydorczykrenata kineticsofazanonehnoreactionswiththiolseffectofph
AT debowskakarolina kineticsofazanonehnoreactionswiththiolseffectofph
AT rostkowskimichał kineticsofazanonehnoreactionswiththiolseffectofph
AT adamusjan kineticsofazanonehnoreactionswiththiolseffectofph
AT michalskiradosław kineticsofazanonehnoreactionswiththiolseffectofph
AT sikoraadam kineticsofazanonehnoreactionswiththiolseffectofph

Ejemplares similares