Feasibility of the estimation of octanol-water distribution coefficients of acidic drugs by microemulsion electrokinetic chromatography

Previous studies have shown that a microemulsion electrokinetic chromatography (MEEKC) system can estimate the logarithm of the octanol-water partition coefficient (log Po/w) of neutral solutes. In the present work, the applicability of the method to partially and fully ionized acids has been evalua...

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Autores: Fernández-Pumarega, Alejandro, Amézqueta, Susana, Fuguet i Jordà, Elisabet, Rosés Pascual, Martí
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2018
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/161986
Acceso en línea:https://hdl.handle.net/2445/161986
Access Level:acceso abierto
Palabra clave:Electroforesi capil·lar
Lipofília
Capillary electrophoresis
Lipophilicity
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spelling Feasibility of the estimation of octanol-water distribution coefficients of acidic drugs by microemulsion electrokinetic chromatographyFernández-Pumarega, AlejandroAmézqueta, SusanaFuguet i Jordà, ElisabetRosés Pascual, MartíElectroforesi capil·larLipofíliaCapillary electrophoresisLipophilicityPrevious studies have shown that a microemulsion electrokinetic chromatography (MEEKC) system can estimate the logarithm of the octanol-water partition coefficient (log Po/w) of neutral solutes. In the present work, the applicability of the method to partially and fully ionized acids has been evaluated. Naproxen, a monoprotic acid, has been used as test solute. The retention factor (k) of this compound has been measured in MEEKC at several values of pH and the retention factor-pH profile has been established. As log Po/w correlates with log kMEEKC for neutral compounds, this correlation has been used to estimate the logarithm of the octanol-water partition coefficient of the neutral (log Po/w(HA)), and the fully ionized (log P o/w(A-)) forms of naproxen. Then, the logarithm of the octanol-water distribution coefficient (log Do/w) of the partially ionized form of the acid has been estimated. The comparison of the estimated values with the ones obtained experimentally using the classical procedures, such as the shake-flask method, shows differences under 0.4 log Do/w units either if the acid is partially ionized or in its neutral form in the most part of the pH range. However, the method overestimates the log Do/w of the highly (>99.5 %) or fully ionized form of naproxenIAPC Publishing2020202020182020info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersion6 p.application/pdfhttps://hdl.handle.net/2445/161986Articles publicats en revistes (Enginyeria Química i Química Analítica)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésReproducció del document publicat a: https://doi.org/10.5599/admet.6.1.510ADMET & DMPK, 2018, vol. 6, num. 1, p. 55-60https://doi.org/10.5599/admet.6.1.510cc-by (c) Fernández-Pumarega, Alejandro et al., 2018http://creativecommons.org/licenses/by/3.0/esinfo:eu-repo/semantics/openAccessoai:recercat.cat:2445/1619862026-05-29T05:05:01Z
dc.title.none.fl_str_mv Feasibility of the estimation of octanol-water distribution coefficients of acidic drugs by microemulsion electrokinetic chromatography
title Feasibility of the estimation of octanol-water distribution coefficients of acidic drugs by microemulsion electrokinetic chromatography
spellingShingle Feasibility of the estimation of octanol-water distribution coefficients of acidic drugs by microemulsion electrokinetic chromatography
Fernández-Pumarega, Alejandro
Electroforesi capil·lar
Lipofília
Capillary electrophoresis
Lipophilicity
title_short Feasibility of the estimation of octanol-water distribution coefficients of acidic drugs by microemulsion electrokinetic chromatography
title_full Feasibility of the estimation of octanol-water distribution coefficients of acidic drugs by microemulsion electrokinetic chromatography
title_fullStr Feasibility of the estimation of octanol-water distribution coefficients of acidic drugs by microemulsion electrokinetic chromatography
title_full_unstemmed Feasibility of the estimation of octanol-water distribution coefficients of acidic drugs by microemulsion electrokinetic chromatography
title_sort Feasibility of the estimation of octanol-water distribution coefficients of acidic drugs by microemulsion electrokinetic chromatography
dc.creator.none.fl_str_mv Fernández-Pumarega, Alejandro
Amézqueta, Susana
Fuguet i Jordà, Elisabet
Rosés Pascual, Martí
author Fernández-Pumarega, Alejandro
author_facet Fernández-Pumarega, Alejandro
Amézqueta, Susana
Fuguet i Jordà, Elisabet
Rosés Pascual, Martí
author_role author
author2 Amézqueta, Susana
Fuguet i Jordà, Elisabet
Rosés Pascual, Martí
author2_role author
author
author
dc.subject.none.fl_str_mv Electroforesi capil·lar
Lipofília
Capillary electrophoresis
Lipophilicity
topic Electroforesi capil·lar
Lipofília
Capillary electrophoresis
Lipophilicity
description Previous studies have shown that a microemulsion electrokinetic chromatography (MEEKC) system can estimate the logarithm of the octanol-water partition coefficient (log Po/w) of neutral solutes. In the present work, the applicability of the method to partially and fully ionized acids has been evaluated. Naproxen, a monoprotic acid, has been used as test solute. The retention factor (k) of this compound has been measured in MEEKC at several values of pH and the retention factor-pH profile has been established. As log Po/w correlates with log kMEEKC for neutral compounds, this correlation has been used to estimate the logarithm of the octanol-water partition coefficient of the neutral (log Po/w(HA)), and the fully ionized (log P o/w(A-)) forms of naproxen. Then, the logarithm of the octanol-water distribution coefficient (log Do/w) of the partially ionized form of the acid has been estimated. The comparison of the estimated values with the ones obtained experimentally using the classical procedures, such as the shake-flask method, shows differences under 0.4 log Do/w units either if the acid is partially ionized or in its neutral form in the most part of the pH range. However, the method overestimates the log Do/w of the highly (>99.5 %) or fully ionized form of naproxen
publishDate 2018
dc.date.none.fl_str_mv 2018
2020
2020
2020
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/161986
url https://hdl.handle.net/2445/161986
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Reproducció del document publicat a: https://doi.org/10.5599/admet.6.1.510
ADMET & DMPK, 2018, vol. 6, num. 1, p. 55-60
https://doi.org/10.5599/admet.6.1.510
dc.rights.none.fl_str_mv cc-by (c) Fernández-Pumarega, Alejandro et al., 2018
http://creativecommons.org/licenses/by/3.0/es
info:eu-repo/semantics/openAccess
rights_invalid_str_mv cc-by (c) Fernández-Pumarega, Alejandro et al., 2018
http://creativecommons.org/licenses/by/3.0/es
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 6 p.
application/pdf
dc.publisher.none.fl_str_mv IAPC Publishing
publisher.none.fl_str_mv IAPC Publishing
dc.source.none.fl_str_mv Articles publicats en revistes (Enginyeria Química i Química Analítica)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,81155

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