Critical comparison of shake-flask, potentiometric and chromatographic methods for lipophilicity evaluation (log Po/w) of neutral, acidic, basic, amphoteric, and zwitterionic drugs

In the present study three different procedures have been compared for the determination of the lipophilicity of the unionized species (log Po/w) of neutral, acidic, basic, amphoteric, and zwitterionic drugs. Shake-flask, potentiometric and chromatographic approaches have been assayed in a set of 66...

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Autores: Port, Ariadna, Bordas, Magda, Enrech, Raquel, Pascual, Rosalía, Rosés Pascual, Martí, Ràfols Llach, Clara, Subirats i Vila, Xavier, Bosch, Elisabeth
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2018
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/127667
Acceso en línea:https://hdl.handle.net/2445/127667
Access Level:acceso abierto
Palabra clave:Lipofília
Cromatografia de líquids
Potenciòmetres
Concentració dels ions d'hidrogen
Lipophilicity
Liquid chromatography
Potentiometer
Hydrogen-ion concentration
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spelling Critical comparison of shake-flask, potentiometric and chromatographic methods for lipophilicity evaluation (log Po/w) of neutral, acidic, basic, amphoteric, and zwitterionic drugsPort, AriadnaBordas, MagdaEnrech, RaquelPascual, RosalíaRosés Pascual, MartíRàfols Llach, ClaraSubirats i Vila, XavierBosch, ElisabethLipofíliaCromatografia de líquidsPotenciòmetresConcentració dels ions d'hidrogenLipophilicityLiquid chromatographyPotentiometerHydrogen-ion concentrationIn the present study three different procedures have been compared for the determination of the lipophilicity of the unionized species (log Po/w) of neutral, acidic, basic, amphoteric, and zwitterionic drugs. Shake-flask, potentiometric and chromatographic approaches have been assayed in a set of 66 representative compounds in different phases of advanced development. An excellent equivalence has been found between log Po/w values obtained by shake-flask and potentiometry, while the chromatographic approach is less accurate but very convenient for screening purposes when a high-throughput is required. In the case of zwitterionic and amphoteric compounds, either for shake-flask and chromatographic methods, the pH has to be accurately selected in order to ensure the compound to be in its neutral form.Elsevier B.V.2018info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttps://hdl.handle.net/2445/127667Articles publicats en revistes (Enginyeria Química i Química Analítica)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésVersió postprint del document publicat a: https://doi.org/10.1016/j.ejps.2018.07.010European Journal of Pharmaceutical Sciences, 2018, vol. 122, p. 331-340https://doi.org/10.1016/j.ejps.2018.07.010cc-by-nc-nd (c) Elsevier B.V., 2018http://creativecommons.org/licenses/by-nc-nd/3.0/esinfo:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1276672026-05-27T06:46:51Z
dc.title.none.fl_str_mv Critical comparison of shake-flask, potentiometric and chromatographic methods for lipophilicity evaluation (log Po/w) of neutral, acidic, basic, amphoteric, and zwitterionic drugs
title Critical comparison of shake-flask, potentiometric and chromatographic methods for lipophilicity evaluation (log Po/w) of neutral, acidic, basic, amphoteric, and zwitterionic drugs
spellingShingle Critical comparison of shake-flask, potentiometric and chromatographic methods for lipophilicity evaluation (log Po/w) of neutral, acidic, basic, amphoteric, and zwitterionic drugs
Port, Ariadna
Lipofília
Cromatografia de líquids
Potenciòmetres
Concentració dels ions d'hidrogen
Lipophilicity
Liquid chromatography
Potentiometer
Hydrogen-ion concentration
title_short Critical comparison of shake-flask, potentiometric and chromatographic methods for lipophilicity evaluation (log Po/w) of neutral, acidic, basic, amphoteric, and zwitterionic drugs
title_full Critical comparison of shake-flask, potentiometric and chromatographic methods for lipophilicity evaluation (log Po/w) of neutral, acidic, basic, amphoteric, and zwitterionic drugs
title_fullStr Critical comparison of shake-flask, potentiometric and chromatographic methods for lipophilicity evaluation (log Po/w) of neutral, acidic, basic, amphoteric, and zwitterionic drugs
title_full_unstemmed Critical comparison of shake-flask, potentiometric and chromatographic methods for lipophilicity evaluation (log Po/w) of neutral, acidic, basic, amphoteric, and zwitterionic drugs
title_sort Critical comparison of shake-flask, potentiometric and chromatographic methods for lipophilicity evaluation (log Po/w) of neutral, acidic, basic, amphoteric, and zwitterionic drugs
dc.creator.none.fl_str_mv Port, Ariadna
Bordas, Magda
Enrech, Raquel
Pascual, Rosalía
Rosés Pascual, Martí
Ràfols Llach, Clara
Subirats i Vila, Xavier
Bosch, Elisabeth
author Port, Ariadna
author_facet Port, Ariadna
Bordas, Magda
Enrech, Raquel
Pascual, Rosalía
Rosés Pascual, Martí
Ràfols Llach, Clara
Subirats i Vila, Xavier
Bosch, Elisabeth
author_role author
author2 Bordas, Magda
Enrech, Raquel
Pascual, Rosalía
Rosés Pascual, Martí
Ràfols Llach, Clara
Subirats i Vila, Xavier
Bosch, Elisabeth
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Lipofília
Cromatografia de líquids
Potenciòmetres
Concentració dels ions d'hidrogen
Lipophilicity
Liquid chromatography
Potentiometer
Hydrogen-ion concentration
topic Lipofília
Cromatografia de líquids
Potenciòmetres
Concentració dels ions d'hidrogen
Lipophilicity
Liquid chromatography
Potentiometer
Hydrogen-ion concentration
description In the present study three different procedures have been compared for the determination of the lipophilicity of the unionized species (log Po/w) of neutral, acidic, basic, amphoteric, and zwitterionic drugs. Shake-flask, potentiometric and chromatographic approaches have been assayed in a set of 66 representative compounds in different phases of advanced development. An excellent equivalence has been found between log Po/w values obtained by shake-flask and potentiometry, while the chromatographic approach is less accurate but very convenient for screening purposes when a high-throughput is required. In the case of zwitterionic and amphoteric compounds, either for shake-flask and chromatographic methods, the pH has to be accurately selected in order to ensure the compound to be in its neutral form.
publishDate 2018
dc.date.none.fl_str_mv 2018
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/2445/127667
url https://hdl.handle.net/2445/127667
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.ejps.2018.07.010
European Journal of Pharmaceutical Sciences, 2018, vol. 122, p. 331-340
https://doi.org/10.1016/j.ejps.2018.07.010
dc.rights.none.fl_str_mv cc-by-nc-nd (c) Elsevier B.V., 2018
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., 2018
http://creativecommons.org/licenses/by-nc-nd/3.0/es
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 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:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300719

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