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: Sirsalmath, K., Suárez, S.A., Bikiel, D.E., Doctorovich, F.
Formato: JOUR
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:http://hdl.handle.net/20.500.12110/paper_01620134_v118_n_p134_Sirsalmath
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling todo:paper_01620134_v118_n_p134_Sirsalmath2023-10-03T15:01:28Z The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: Azanone donors at biological pH Sirsalmath, K. Suárez, S.A. Bikiel, D.E. Doctorovich, F. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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
Sirsalmath, K.
Suárez, S.A.
Bikiel, D.E.
Doctorovich, F.
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.
format JOUR
author Sirsalmath, K.
Suárez, S.A.
Bikiel, D.E.
Doctorovich, F.
author_facet Sirsalmath, K.
Suárez, S.A.
Bikiel, D.E.
Doctorovich, F.
author_sort Sirsalmath, K.
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
url http://hdl.handle.net/20.500.12110/paper_01620134_v118_n_p134_Sirsalmath
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