Estimation of the octanol-water distribution coefficient of acidic compounds by microemulsion electrokinetic chromatography

The feasibility of extending the determination of the lipophilicity of partially ionized acids (log Do/w) by microemulsion electrokinetic chromatography (MEEKC) is tested. Theoretical considerations predict that a linear log Do/w vs. log k correlation can be obtained only when the neutral and ionic...

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Autores: Fernández-Pumarega, Alejandro, Amézqueta, Susana, Fuguet i Jordà, Elisabet, Rosés Pascual, Martí
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2019
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:2445/161991
Acceso en línea:https://hdl.handle.net/2445/161991
Access Level:acceso abierto
Palabra clave:Lipofília
Cromatografia
Micel·les
Lipophilicity
Chromatography
Micelles
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spelling Estimation of the octanol-water distribution coefficient of acidic compounds by microemulsion electrokinetic chromatographyFernández-Pumarega, AlejandroAmézqueta, SusanaFuguet i Jordà, ElisabetRosés Pascual, MartíLipofíliaCromatografiaMicel·lesLipophilicityChromatographyMicellesThe feasibility of extending the determination of the lipophilicity of partially ionized acids (log Do/w) by microemulsion electrokinetic chromatography (MEEKC) is tested. Theoretical considerations predict that a linear log Do/w vs. log k correlation can be obtained only when the neutral and ionic forms of an acid follow the same correlation equation and the slope of the correlation is unity. In practice, since the lipophilicity of the neutral acid is much higher than that of the ionic form and the correlation slope is not very different from 1, the general linear correlation for neutral compounds can be applied across most of the ionization range of the acid. The linear correlation between log Po/w and log k of 20 neutral solutes (calibration curve) has been established and extended to 6 acids used as models, tested across their full ionization range. log Do/w-pH, and log k-pH profiles have been obtained for these 6 acids, and plotted log Do/w against log k for any acid at any degree of ionization. Furthermore, the log Do/w of the acids has been estimated from the calibration curve and log k-pH profile, and compared to values in the literature determined using reference methods such as the shake-flask one. Accurate values have been obtained using the MEEKC method when the acids are in their neutral form or partially ionized (ionization degree, α < 0.995). However, this parameter is overestimated when the acids are highly or fully ionized (α ≈ 1). Finally, in order to test the applicability of this method, we have applied the same procedure to estimate log Do/w at pH = 7.4 (blood physiological pH) of a set of 30 additional compounds (including partially and fully ionized acids). The results at this pH folloElsevier B.V.2020202120192020info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion36 p.application/pdfhttps://hdl.handle.net/2445/161991Articles 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)InglésVersió postprint del document publicat a: https://doi.org/10.1016/j.jpba.2019.112981Journal of Pharmaceutical and Biomedical Analysis, 2019, vol. 179, p. 112981https://doi.org/10.1016/j.jpba.2019.112981cc-by-nc-nd (c) Elsevier B.V., 2019http://creativecommons.org/licenses/by-nc-nd/3.0/esinfo:eu-repo/semantics/openAccessoai:recercat.cat:2445/1619912026-05-29T05:05:01Z
dc.title.none.fl_str_mv Estimation of the octanol-water distribution coefficient of acidic compounds by microemulsion electrokinetic chromatography
title Estimation of the octanol-water distribution coefficient of acidic compounds by microemulsion electrokinetic chromatography
spellingShingle Estimation of the octanol-water distribution coefficient of acidic compounds by microemulsion electrokinetic chromatography
Fernández-Pumarega, Alejandro
Lipofília
Cromatografia
Micel·les
Lipophilicity
Chromatography
Micelles
title_short Estimation of the octanol-water distribution coefficient of acidic compounds by microemulsion electrokinetic chromatography
title_full Estimation of the octanol-water distribution coefficient of acidic compounds by microemulsion electrokinetic chromatography
title_fullStr Estimation of the octanol-water distribution coefficient of acidic compounds by microemulsion electrokinetic chromatography
title_full_unstemmed Estimation of the octanol-water distribution coefficient of acidic compounds by microemulsion electrokinetic chromatography
title_sort Estimation of the octanol-water distribution coefficient of acidic compounds 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 Lipofília
Cromatografia
Micel·les
Lipophilicity
Chromatography
Micelles
topic Lipofília
Cromatografia
Micel·les
Lipophilicity
Chromatography
Micelles
description The feasibility of extending the determination of the lipophilicity of partially ionized acids (log Do/w) by microemulsion electrokinetic chromatography (MEEKC) is tested. Theoretical considerations predict that a linear log Do/w vs. log k correlation can be obtained only when the neutral and ionic forms of an acid follow the same correlation equation and the slope of the correlation is unity. In practice, since the lipophilicity of the neutral acid is much higher than that of the ionic form and the correlation slope is not very different from 1, the general linear correlation for neutral compounds can be applied across most of the ionization range of the acid. The linear correlation between log Po/w and log k of 20 neutral solutes (calibration curve) has been established and extended to 6 acids used as models, tested across their full ionization range. log Do/w-pH, and log k-pH profiles have been obtained for these 6 acids, and plotted log Do/w against log k for any acid at any degree of ionization. Furthermore, the log Do/w of the acids has been estimated from the calibration curve and log k-pH profile, and compared to values in the literature determined using reference methods such as the shake-flask one. Accurate values have been obtained using the MEEKC method when the acids are in their neutral form or partially ionized (ionization degree, α < 0.995). However, this parameter is overestimated when the acids are highly or fully ionized (α ≈ 1). Finally, in order to test the applicability of this method, we have applied the same procedure to estimate log Do/w at pH = 7.4 (blood physiological pH) of a set of 30 additional compounds (including partially and fully ionized acids). The results at this pH follo
publishDate 2019
dc.date.none.fl_str_mv 2019
2020
2020
2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/161991
url https://hdl.handle.net/2445/161991
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: https://doi.org/10.1016/j.jpba.2019.112981
Journal of Pharmaceutical and Biomedical Analysis, 2019, vol. 179, p. 112981
https://doi.org/10.1016/j.jpba.2019.112981
dc.rights.none.fl_str_mv cc-by-nc-nd (c) Elsevier B.V., 2019
http://creativecommons.org/licenses/by-nc-nd/3.0/es
info:eu-repo/semantics/openAccess
rights_invalid_str_mv cc-by-nc-nd (c) Elsevier B.V., 2019
http://creativecommons.org/licenses/by-nc-nd/3.0/es
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 36 p.
application/pdf
dc.publisher.none.fl_str_mv Elsevier B.V.
publisher.none.fl_str_mv Elsevier B.V.
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
_version_ 1869409309597630464
score 15.811543

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