The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: Azanone donors at biological pH

A group of Piloty's acid (N-hydroxybenzenesulfonamide) derivatives were synthesized and fully characterized in order to assess the rates and pH of HNO (azanone, nitroxyl) donation in aqueous media. The derivatives, with electron-withdrawing and -donating substituents include methyl, nitro, fluo...

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Autores principales:	Suarez, Sebastian, Bikiel, Damian Ezequiel, Doctorovich, Fabio Ariel
Publicado:	2013
Materias:	Azanone donors Nitroxyl donors Piloty's acid Ring substituents benzenesulfonamide derivative phenol derivative piloty acid derivative porphyrin unclassified drug acidity aqueous solution decomposition density functional theory electrochemical analysis electron transport enthalpy modulation pH pKa proton transport review sensor
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01620134_v118_n_p134_Sirsalmath http://hdl.handle.net/20.500.12110/paper_01620134_v118_n_p134_Sirsalmath
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_01620134_v118_n_p134_Sirsalmath
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spelling	paper:paper_01620134_v118_n_p134_Sirsalmath2023-06-08T15:13:35Z The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: Azanone donors at biological pH Suarez, Sebastian Bikiel, Damian Ezequiel Doctorovich, Fabio Ariel Azanone donors Nitroxyl donors Piloty's acid Ring substituents benzenesulfonamide derivative phenol derivative piloty acid derivative porphyrin unclassified drug acidity aqueous solution decomposition density functional theory electrochemical analysis electron transport enthalpy modulation pH pKa proton transport review sensor A group of Piloty's acid (N-hydroxybenzenesulfonamide) derivatives were synthesized and fully characterized in order to assess the rates and pH of HNO (azanone, nitroxyl) donation in aqueous media. The derivatives, with electron-withdrawing and -donating substituents include methyl, nitro, fluoro, tri-isopropyl, trifluoromethyl and methoxy groups. The most interesting modulation observed is the change in pH range in which the compounds are able to donate HNO. UV-visible kinetic measurements at different pH values were used to evaluate the decomposition rate of the donors. A novel technique based on electrochemical measurements using a Co-porphyrin sensor was used to assess the release of HNO as a function of pH, by direct measurement of [HNO]. The results were contrasted with DFT calculations in order to understand the electronic effects exerted by the ring substituents, which drastically modify the pH range of donation. For example, while Piloty's acid donates HNO from pH 9.3, the corresponding fluoro derivative starts donating at pH 4.0. © 2012 Elsevier Inc. All rights reserved. Fil:Suárez, 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:Doctorovich, F. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2013 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01620134_v118_n_p134_Sirsalmath http://hdl.handle.net/20.500.12110/paper_01620134_v118_n_p134_Sirsalmath
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Azanone donors Nitroxyl donors Piloty's acid Ring substituents benzenesulfonamide derivative phenol derivative piloty acid derivative porphyrin unclassified drug acidity aqueous solution decomposition density functional theory electrochemical analysis electron transport enthalpy modulation pH pKa proton transport review sensor
spellingShingle	Azanone donors Nitroxyl donors Piloty's acid Ring substituents benzenesulfonamide derivative phenol derivative piloty acid derivative porphyrin unclassified drug acidity aqueous solution decomposition density functional theory electrochemical analysis electron transport enthalpy modulation pH pKa proton transport review sensor Suarez, Sebastian Bikiel, Damian Ezequiel Doctorovich, Fabio Ariel The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: Azanone donors at biological pH
topic_facet	Azanone donors Nitroxyl donors Piloty's acid Ring substituents benzenesulfonamide derivative phenol derivative piloty acid derivative porphyrin unclassified drug acidity aqueous solution decomposition density functional theory electrochemical analysis electron transport enthalpy modulation pH pKa proton transport review sensor
description	A group of Piloty's acid (N-hydroxybenzenesulfonamide) derivatives were synthesized and fully characterized in order to assess the rates and pH of HNO (azanone, nitroxyl) donation in aqueous media. The derivatives, with electron-withdrawing and -donating substituents include methyl, nitro, fluoro, tri-isopropyl, trifluoromethyl and methoxy groups. The most interesting modulation observed is the change in pH range in which the compounds are able to donate HNO. UV-visible kinetic measurements at different pH values were used to evaluate the decomposition rate of the donors. A novel technique based on electrochemical measurements using a Co-porphyrin sensor was used to assess the release of HNO as a function of pH, by direct measurement of [HNO]. The results were contrasted with DFT calculations in order to understand the electronic effects exerted by the ring substituents, which drastically modify the pH range of donation. For example, while Piloty's acid donates HNO from pH 9.3, the corresponding fluoro derivative starts donating at pH 4.0. © 2012 Elsevier Inc. All rights reserved.
author	Suarez, Sebastian Bikiel, Damian Ezequiel Doctorovich, Fabio Ariel
author_facet	Suarez, Sebastian Bikiel, Damian Ezequiel Doctorovich, Fabio Ariel
author_sort	Suarez, Sebastian
title	The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: Azanone donors at biological pH
title_short	The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: Azanone donors at biological pH
title_full	The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: Azanone donors at biological pH
title_fullStr	The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: Azanone donors at biological pH
title_full_unstemmed	The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: Azanone donors at biological pH
title_sort	ph of hno donation is modulated by ring substituents in piloty's acid derivatives: azanone donors at biological ph
publishDate	2013
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01620134_v118_n_p134_Sirsalmath http://hdl.handle.net/20.500.12110/paper_01620134_v118_n_p134_Sirsalmath
work_keys_str_mv	AT suarezsebastian thephofhnodonationismodulatedbyringsubstituentsinpilotysacidderivativesazanonedonorsatbiologicalph AT bikieldamianezequiel thephofhnodonationismodulatedbyringsubstituentsinpilotysacidderivativesazanonedonorsatbiologicalph AT doctorovichfabioariel thephofhnodonationismodulatedbyringsubstituentsinpilotysacidderivativesazanonedonorsatbiologicalph AT suarezsebastian phofhnodonationismodulatedbyringsubstituentsinpilotysacidderivativesazanonedonorsatbiologicalph AT bikieldamianezequiel phofhnodonationismodulatedbyringsubstituentsinpilotysacidderivativesazanonedonorsatbiologicalph AT doctorovichfabioariel phofhnodonationismodulatedbyringsubstituentsinpilotysacidderivativesazanonedonorsatbiologicalph
_version_	1768545277825777664

The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: Azanone donors at biological pH

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