Discussing Endogenous NO•/HNO Interconversion Aided by Phenolic Drugs and Vitamins

The reduction of NO• to HNO/NO- under biologically compatible conditions has always been thought as unlikely, mostly because of the negative reduction potential: E°(NO•,H+/HNO) = -0.55 V vs NHE at physiological pH. Nonetheless, during the past decade, several works hinted at the possible NO-to-HNO c...

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Autores principales: Suarez, Sebastian, Martí, Marcelo Adrián, Doctorovich, Fabio Ariel
Publicado: 2015
Materias:
acetylsalicylic acid
alpha tocopherol
free radical
nitrogen oxide
nitroxyl
phenol derivative
chemical structure
chemistry
Aspirin
Free Radicals
Molecular Structure
Nitrogen Oxides
Phenols
Vitamin E
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00201669_v54_n19_p9342_Hamer
http://hdl.handle.net/20.500.12110/paper_00201669_v54_n19_p9342_Hamer
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_00201669_v54_n19_p9342_Hamer
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spelling paper:paper_00201669_v54_n19_p9342_Hamer2023-06-08T14:40:43Z Discussing Endogenous NO•/HNO Interconversion Aided by Phenolic Drugs and Vitamins Suarez, Sebastian Martí, Marcelo Adrián Doctorovich, Fabio Ariel acetylsalicylic acid alpha tocopherol free radical nitrogen oxide nitroxyl phenol derivative chemical structure chemistry Aspirin Free Radicals Molecular Structure Nitrogen Oxides Phenols Vitamin E The reduction of NO• to HNO/NO- under biologically compatible conditions has always been thought as unlikely, mostly because of the negative reduction potential: E°(NO•,H+/HNO) = -0.55 V vs NHE at physiological pH. Nonetheless, during the past decade, several works hinted at the possible NO-to-HNO conversion mediated by moderate biological reductants. Very recently, we have shown that the reaction of NO• with ascorbate and aromatic alcohols occurs through a proton-coupled nucleophilic attack (PCNA) of the alcohol to NO•, yielding an intermediate RO-N(H)O• species, which further decomposes to release HNO. For the present work, we decided to inspect whether other common biological aromatic alcohols obtained from foods, such as Vitamin E, or used as over-the-counter drugs, like aspirin, are able to undergo the reaction. The positive results suggest that the conversion of NO to HNO could occur far more commonly than previously expected. Taking these as the starting point, we set to review our and other groups' previous reports on the possible NO-to-HNO conversion mediated by biological compounds including phenolic drugs and vitamins, as well as several thiol-bearing compounds. Analysis of revised data prompted us to ask ourselves the following key questions: What are the most likely physio/pathological conditions for NO•-to-HNO conversion to take place? Which effects usually attributed to NO• are indeed mediated by HNO? These inquiries are discussed in the context of 2 decades of NO and HNO research. © 2015 American Chemical Society. Fil:Suarez, S.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Marti, 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_00201669_v54_n19_p9342_Hamer http://hdl.handle.net/20.500.12110/paper_00201669_v54_n19_p9342_Hamer
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic acetylsalicylic acid
alpha tocopherol
free radical
nitrogen oxide
nitroxyl
phenol derivative
chemical structure
chemistry
Aspirin
Free Radicals
Molecular Structure
Nitrogen Oxides
Phenols
Vitamin E
spellingShingle acetylsalicylic acid
alpha tocopherol
free radical
nitrogen oxide
nitroxyl
phenol derivative
chemical structure
chemistry
Aspirin
Free Radicals
Molecular Structure
Nitrogen Oxides
Phenols
Vitamin E
Suarez, Sebastian
Martí, Marcelo Adrián
Doctorovich, Fabio Ariel
Discussing Endogenous NO•/HNO Interconversion Aided by Phenolic Drugs and Vitamins
topic_facet acetylsalicylic acid
alpha tocopherol
free radical
nitrogen oxide
nitroxyl
phenol derivative
chemical structure
chemistry
Aspirin
Free Radicals
Molecular Structure
Nitrogen Oxides
Phenols
Vitamin E
description The reduction of NO• to HNO/NO- under biologically compatible conditions has always been thought as unlikely, mostly because of the negative reduction potential: E°(NO•,H+/HNO) = -0.55 V vs NHE at physiological pH. Nonetheless, during the past decade, several works hinted at the possible NO-to-HNO conversion mediated by moderate biological reductants. Very recently, we have shown that the reaction of NO• with ascorbate and aromatic alcohols occurs through a proton-coupled nucleophilic attack (PCNA) of the alcohol to NO•, yielding an intermediate RO-N(H)O• species, which further decomposes to release HNO. For the present work, we decided to inspect whether other common biological aromatic alcohols obtained from foods, such as Vitamin E, or used as over-the-counter drugs, like aspirin, are able to undergo the reaction. The positive results suggest that the conversion of NO to HNO could occur far more commonly than previously expected. Taking these as the starting point, we set to review our and other groups' previous reports on the possible NO-to-HNO conversion mediated by biological compounds including phenolic drugs and vitamins, as well as several thiol-bearing compounds. Analysis of revised data prompted us to ask ourselves the following key questions: What are the most likely physio/pathological conditions for NO•-to-HNO conversion to take place? Which effects usually attributed to NO• are indeed mediated by HNO? These inquiries are discussed in the context of 2 decades of NO and HNO research. © 2015 American Chemical Society.
author Suarez, Sebastian
Martí, Marcelo Adrián
Doctorovich, Fabio Ariel
author_facet Suarez, Sebastian
Martí, Marcelo Adrián
Doctorovich, Fabio Ariel
author_sort Suarez, Sebastian
title Discussing Endogenous NO•/HNO Interconversion Aided by Phenolic Drugs and Vitamins
title_short Discussing Endogenous NO•/HNO Interconversion Aided by Phenolic Drugs and Vitamins
title_full Discussing Endogenous NO•/HNO Interconversion Aided by Phenolic Drugs and Vitamins
title_fullStr Discussing Endogenous NO•/HNO Interconversion Aided by Phenolic Drugs and Vitamins
title_full_unstemmed Discussing Endogenous NO•/HNO Interconversion Aided by Phenolic Drugs and Vitamins
title_sort discussing endogenous no•/hno interconversion aided by phenolic drugs and vitamins
publishDate 2015
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00201669_v54_n19_p9342_Hamer
http://hdl.handle.net/20.500.12110/paper_00201669_v54_n19_p9342_Hamer
work_keys_str_mv AT suarezsebastian discussingendogenousnohnointerconversionaidedbyphenolicdrugsandvitamins
AT martimarceloadrian discussingendogenousnohnointerconversionaidedbyphenolicdrugsandvitamins
AT doctorovichfabioariel discussingendogenousnohnointerconversionaidedbyphenolicdrugsandvitamins
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