Nitric Oxide Is Reduced to HNO by Proton-Coupled Nucleophilic Attack by Ascorbate, Tyrosine, and Other Alcohols. A New Route to HNO in Biological Media?

The role of NO in biology is well established. However, an increasing body of evidence suggests that azanone (HNO), could also be involved in biological processes, some of which are attributed to NO. In this context, one of the most important and yet unanswered questions is whether and how HNO is pr...

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Autores principales:	Suarez, Sebastian, Bikiel, Damian Ezequiel, Martí, Marcelo Adrián, Doctorovich, Fabio Ariel
Publicado:	2015
Materias:	Nitric oxide Alkoxyl radicals Biological media Biological process Enzymatic reduction In-vivo Nucleophilic attack Reducing capacity Amino acids alcohol derivative ascorbic acid azanone inducible nitric oxide synthase nitric oxide nitric oxide donor tyrosine unclassified drug alkoxyl radical nitrogen oxide nitroxyl animal cell aqueous solution Article Bovinae controlled study decomposition dimerization electron spin resonance endothelium cell immunocompetent cell in vitro study kinetics macrophage nerve cell nonhuman nuclear magnetic resonance spectroscopy nucleophilicity oxidation reduction potential proton coupled nucleophilic attack proton transport reaction analysis reduction tautomer animal bovine chemistry metabolism oxidation reduction reaction Alcohols Animals Ascorbic Acid Cattle Endothelial Cells Nitric Oxide Nitrogen Oxides Oxidation-Reduction Tyrosine
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00027863_v137_n14_p4720_Suarez http://hdl.handle.net/20.500.12110/paper_00027863_v137_n14_p4720_Suarez
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00027863_v137_n14_p4720_Suarez
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spelling	paper:paper_00027863_v137_n14_p4720_Suarez2023-06-08T14:22:53Z Nitric Oxide Is Reduced to HNO by Proton-Coupled Nucleophilic Attack by Ascorbate, Tyrosine, and Other Alcohols. A New Route to HNO in Biological Media? Suarez, Sebastian Bikiel, Damian Ezequiel Martí, Marcelo Adrián Doctorovich, Fabio Ariel Nitric oxide Alkoxyl radicals Biological media Biological process Enzymatic reduction In-vivo Nucleophilic attack Reducing capacity Amino acids alcohol derivative ascorbic acid azanone inducible nitric oxide synthase nitric oxide nitric oxide donor tyrosine unclassified drug alcohol derivative alkoxyl radical ascorbic acid nitric oxide nitrogen oxide nitroxyl tyrosine animal cell aqueous solution Article Bovinae controlled study decomposition dimerization electron spin resonance endothelium cell immunocompetent cell in vitro study kinetics macrophage nerve cell nonhuman nuclear magnetic resonance spectroscopy nucleophilicity oxidation reduction potential proton coupled nucleophilic attack proton transport reaction analysis reduction tautomer animal bovine chemistry metabolism oxidation reduction reaction Alcohols Animals Ascorbic Acid Cattle Endothelial Cells Nitric Oxide Nitrogen Oxides Oxidation-Reduction Tyrosine The role of NO in biology is well established. However, an increasing body of evidence suggests that azanone (HNO), could also be involved in biological processes, some of which are attributed to NO. In this context, one of the most important and yet unanswered questions is whether and how HNO is produced in vivo. A possible route concerns the chemical or enzymatic reduction of NO. In the present work, we have taken advantage of a selective HNO sensing method, to show that NO is reduced to HNO by biologically relevant alcohols with moderate reducing capacity, such as ascorbate or tyrosine. The proposed mechanism involves a nucleophilic attack to NO by the alcohol, coupled to a proton transfer (PCNA: proton-coupled nucleophilic attack) and a subsequent decomposition of the so-produced radical to yield HNO and an alkoxyl radical. (Graph Presented). © 2015 American Chemical Society. Fil:Suarez, S.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Bikiel, D.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Martí, M.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Doctorovich, F. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2015 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00027863_v137_n14_p4720_Suarez http://hdl.handle.net/20.500.12110/paper_00027863_v137_n14_p4720_Suarez
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Nitric oxide Alkoxyl radicals Biological media Biological process Enzymatic reduction In-vivo Nucleophilic attack Reducing capacity Amino acids alcohol derivative ascorbic acid azanone inducible nitric oxide synthase nitric oxide nitric oxide donor tyrosine unclassified drug alcohol derivative alkoxyl radical ascorbic acid nitric oxide nitrogen oxide nitroxyl tyrosine animal cell aqueous solution Article Bovinae controlled study decomposition dimerization electron spin resonance endothelium cell immunocompetent cell in vitro study kinetics macrophage nerve cell nonhuman nuclear magnetic resonance spectroscopy nucleophilicity oxidation reduction potential proton coupled nucleophilic attack proton transport reaction analysis reduction tautomer animal bovine chemistry metabolism oxidation reduction reaction Alcohols Animals Ascorbic Acid Cattle Endothelial Cells Nitric Oxide Nitrogen Oxides Oxidation-Reduction Tyrosine
spellingShingle	Nitric oxide Alkoxyl radicals Biological media Biological process Enzymatic reduction In-vivo Nucleophilic attack Reducing capacity Amino acids alcohol derivative ascorbic acid azanone inducible nitric oxide synthase nitric oxide nitric oxide donor tyrosine unclassified drug alcohol derivative alkoxyl radical ascorbic acid nitric oxide nitrogen oxide nitroxyl tyrosine animal cell aqueous solution Article Bovinae controlled study decomposition dimerization electron spin resonance endothelium cell immunocompetent cell in vitro study kinetics macrophage nerve cell nonhuman nuclear magnetic resonance spectroscopy nucleophilicity oxidation reduction potential proton coupled nucleophilic attack proton transport reaction analysis reduction tautomer animal bovine chemistry metabolism oxidation reduction reaction Alcohols Animals Ascorbic Acid Cattle Endothelial Cells Nitric Oxide Nitrogen Oxides Oxidation-Reduction Tyrosine Suarez, Sebastian Bikiel, Damian Ezequiel Martí, Marcelo Adrián Doctorovich, Fabio Ariel Nitric Oxide Is Reduced to HNO by Proton-Coupled Nucleophilic Attack by Ascorbate, Tyrosine, and Other Alcohols. A New Route to HNO in Biological Media?
topic_facet	Nitric oxide Alkoxyl radicals Biological media Biological process Enzymatic reduction In-vivo Nucleophilic attack Reducing capacity Amino acids alcohol derivative ascorbic acid azanone inducible nitric oxide synthase nitric oxide nitric oxide donor tyrosine unclassified drug alcohol derivative alkoxyl radical ascorbic acid nitric oxide nitrogen oxide nitroxyl tyrosine animal cell aqueous solution Article Bovinae controlled study decomposition dimerization electron spin resonance endothelium cell immunocompetent cell in vitro study kinetics macrophage nerve cell nonhuman nuclear magnetic resonance spectroscopy nucleophilicity oxidation reduction potential proton coupled nucleophilic attack proton transport reaction analysis reduction tautomer animal bovine chemistry metabolism oxidation reduction reaction Alcohols Animals Ascorbic Acid Cattle Endothelial Cells Nitric Oxide Nitrogen Oxides Oxidation-Reduction Tyrosine
description	The role of NO in biology is well established. However, an increasing body of evidence suggests that azanone (HNO), could also be involved in biological processes, some of which are attributed to NO. In this context, one of the most important and yet unanswered questions is whether and how HNO is produced in vivo. A possible route concerns the chemical or enzymatic reduction of NO. In the present work, we have taken advantage of a selective HNO sensing method, to show that NO is reduced to HNO by biologically relevant alcohols with moderate reducing capacity, such as ascorbate or tyrosine. The proposed mechanism involves a nucleophilic attack to NO by the alcohol, coupled to a proton transfer (PCNA: proton-coupled nucleophilic attack) and a subsequent decomposition of the so-produced radical to yield HNO and an alkoxyl radical. (Graph Presented). © 2015 American Chemical Society.
author	Suarez, Sebastian Bikiel, Damian Ezequiel Martí, Marcelo Adrián Doctorovich, Fabio Ariel
author_facet	Suarez, Sebastian Bikiel, Damian Ezequiel Martí, Marcelo Adrián Doctorovich, Fabio Ariel
author_sort	Suarez, Sebastian
title	Nitric Oxide Is Reduced to HNO by Proton-Coupled Nucleophilic Attack by Ascorbate, Tyrosine, and Other Alcohols. A New Route to HNO in Biological Media?
title_short	Nitric Oxide Is Reduced to HNO by Proton-Coupled Nucleophilic Attack by Ascorbate, Tyrosine, and Other Alcohols. A New Route to HNO in Biological Media?
title_full	Nitric Oxide Is Reduced to HNO by Proton-Coupled Nucleophilic Attack by Ascorbate, Tyrosine, and Other Alcohols. A New Route to HNO in Biological Media?
title_fullStr	Nitric Oxide Is Reduced to HNO by Proton-Coupled Nucleophilic Attack by Ascorbate, Tyrosine, and Other Alcohols. A New Route to HNO in Biological Media?
title_full_unstemmed	Nitric Oxide Is Reduced to HNO by Proton-Coupled Nucleophilic Attack by Ascorbate, Tyrosine, and Other Alcohols. A New Route to HNO in Biological Media?
title_sort	nitric oxide is reduced to hno by proton-coupled nucleophilic attack by ascorbate, tyrosine, and other alcohols. a new route to hno in biological media?
publishDate	2015
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00027863_v137_n14_p4720_Suarez http://hdl.handle.net/20.500.12110/paper_00027863_v137_n14_p4720_Suarez
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_version_	1768543922481528832

Nitric Oxide Is Reduced to HNO by Proton-Coupled Nucleophilic Attack by Ascorbate, Tyrosine, and Other Alcohols. A New Route to HNO in Biological Media?

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