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Abstract:

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.

Registro:

Documento: Artículo
Título:The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: Azanone donors at biological pH
Autor:Sirsalmath, K.; Suárez, S.A.; Bikiel, D.E.; Doctorovich, F.
Filiación:Departamento de Quimica Inorganica, Analitica y Quimica Fisica/INQUIMAE-CONICET, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires (C1428EHA), Argentina
Palabras clave: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
Año:2013
Volumen:118
Página de inicio:134
Página de fin:139
DOI: http://dx.doi.org/10.1016/j.jinorgbio.2012.10.008
Título revista:Journal of Inorganic Biochemistry
Título revista abreviado:J. Inorg. Biochem.
ISSN:01620134
CODEN:JIBID
CAS:porphyrin, 24869-67-8
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01620134_v118_n_p134_Sirsalmath

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Citas:

---------- APA ----------
Sirsalmath, K., Suárez, S.A., Bikiel, D.E. & Doctorovich, F. (2013) . The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: Azanone donors at biological pH. Journal of Inorganic Biochemistry, 118, 134-139.
http://dx.doi.org/10.1016/j.jinorgbio.2012.10.008
---------- CHICAGO ----------
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" . Journal of Inorganic Biochemistry 118 (2013) : 134-139.
http://dx.doi.org/10.1016/j.jinorgbio.2012.10.008
---------- MLA ----------
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" . Journal of Inorganic Biochemistry, vol. 118, 2013, pp. 134-139.
http://dx.doi.org/10.1016/j.jinorgbio.2012.10.008
---------- VANCOUVER ----------
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. J. Inorg. Biochem. 2013;118:134-139.
http://dx.doi.org/10.1016/j.jinorgbio.2012.10.008