Lipophilicity of some GABAergic phenols and related compounds determined by HPLC and partition coefficients in different systems

Autores
Reiner, Gabriela de Las Nieves; Labuckas, Diana Ondina; Garcia, Daniel Asmed
Año de publicación
2009
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Some phenolic compounds, like propofol and thymol, have been shown to act on the GABAA receptor. Taking into account the hydrophobicity of these compounds, their interaction with the membrane surrounding the receptor and consequent non-specific effect on receptor modulation cannot be neglected. In the present work, we determined and correlated several lipophilic parameters for both GABAergic agents and three other related phenolic compounds (eugenol, carvacrol and chlorothymol), including log Po/w, retention data in high performance liquid chromatography (HPLC) by using C18 and immobilized artificial membrane (IAM) columns at different temperatures, and partition coefficients determined in phospholipid liposomes. The correlation results demonstrated the high capacity of the compounds assayed to interact with phospholipid membrane phases, which can be predicted by simple model systems as log Po/w or HPLC. The values obtained by HPLC using a fast screening IAM column were the quantitatively closest to the partition coefficients determined in liposome systems, due to the capacity of this column to permit the establishment of molecular interactions like those found in phospholipid membranes. Finally, the fact that all the compounds studied are able to interact with membranes would suggest the participation of some alteration of the GABAA receptor lipid environment as part of the receptor modulation exerted by phenolic compounds.
Fil: Reiner, Gabriela de Las Nieves. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Patagonia Norte. Instituto de Investigaciones en Biodiversidad y Medioambiente. Universidad Nacional del Comahue. Centro Regional Universidad Bariloche. Instituto de Investigaciones en Biodiversidad y Medioambiente; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Departamento de Química; Argentina
Fil: Labuckas, Diana Ondina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Departamento de Química; Argentina
Fil: Garcia, Daniel Asmed. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones Biológicas y Tecnológicas. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Instituto de Investigaciones Biológicas y Tecnológicas; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Departamento de Química; Argentina
Materia
Correlation Analysis
Gabaergic Phenols
Iam-Hplc
Lipophilicity
Liposomes
Partition Coefficient
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/58414
Acceder
id CONICETDig_fb7e8f8cb90839822751442f31282cfa
oai_identifier_str oai:ri.conicet.gov.ar:11336/58414
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Lipophilicity of some GABAergic phenols and related compounds determined by HPLC and partition coefficients in different systemsReiner, Gabriela de Las NievesLabuckas, Diana OndinaGarcia, Daniel AsmedCorrelation AnalysisGabaergic PhenolsIam-HplcLipophilicityLiposomesPartition Coefficienthttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1Some phenolic compounds, like propofol and thymol, have been shown to act on the GABAA receptor. Taking into account the hydrophobicity of these compounds, their interaction with the membrane surrounding the receptor and consequent non-specific effect on receptor modulation cannot be neglected. In the present work, we determined and correlated several lipophilic parameters for both GABAergic agents and three other related phenolic compounds (eugenol, carvacrol and chlorothymol), including log Po/w, retention data in high performance liquid chromatography (HPLC) by using C18 and immobilized artificial membrane (IAM) columns at different temperatures, and partition coefficients determined in phospholipid liposomes. The correlation results demonstrated the high capacity of the compounds assayed to interact with phospholipid membrane phases, which can be predicted by simple model systems as log Po/w or HPLC. The values obtained by HPLC using a fast screening IAM column were the quantitatively closest to the partition coefficients determined in liposome systems, due to the capacity of this column to permit the establishment of molecular interactions like those found in phospholipid membranes. Finally, the fact that all the compounds studied are able to interact with membranes would suggest the participation of some alteration of the GABAA receptor lipid environment as part of the receptor modulation exerted by phenolic compounds.Fil: Reiner, Gabriela de Las Nieves. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Patagonia Norte. Instituto de Investigaciones en Biodiversidad y Medioambiente. Universidad Nacional del Comahue. Centro Regional Universidad Bariloche. Instituto de Investigaciones en Biodiversidad y Medioambiente; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Departamento de Química; ArgentinaFil: Labuckas, Diana Ondina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Departamento de Química; ArgentinaFil: Garcia, Daniel Asmed. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones Biológicas y Tecnológicas. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Instituto de Investigaciones Biológicas y Tecnológicas; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Departamento de Química; ArgentinaElsevier Science2009-04-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/58414Reiner, Gabriela de Las Nieves; Labuckas, Diana Ondina; Garcia, Daniel Asmed; Lipophilicity of some GABAergic phenols and related compounds determined by HPLC and partition coefficients in different systems; Elsevier Science; Journal of Pharmaceutical and Biomedical Analysis; 49; 3; 5-4-2009; 686-6910731-7085CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0731708509000028info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jpba.2008.12.040info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:31:39Zoai:ri.conicet.gov.ar:11336/58414instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:31:39.622CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Lipophilicity of some GABAergic phenols and related compounds determined by HPLC and partition coefficients in different systems
title Lipophilicity of some GABAergic phenols and related compounds determined by HPLC and partition coefficients in different systems
spellingShingle Lipophilicity of some GABAergic phenols and related compounds determined by HPLC and partition coefficients in different systems
Reiner, Gabriela de Las Nieves
Correlation Analysis
Gabaergic Phenols
Iam-Hplc
Lipophilicity
Liposomes
Partition Coefficient
title_short Lipophilicity of some GABAergic phenols and related compounds determined by HPLC and partition coefficients in different systems
title_full Lipophilicity of some GABAergic phenols and related compounds determined by HPLC and partition coefficients in different systems
title_fullStr Lipophilicity of some GABAergic phenols and related compounds determined by HPLC and partition coefficients in different systems
title_full_unstemmed Lipophilicity of some GABAergic phenols and related compounds determined by HPLC and partition coefficients in different systems
title_sort Lipophilicity of some GABAergic phenols and related compounds determined by HPLC and partition coefficients in different systems
dc.creator.none.fl_str_mv Reiner, Gabriela de Las Nieves
Labuckas, Diana Ondina
Garcia, Daniel Asmed
author Reiner, Gabriela de Las Nieves
author_facet Reiner, Gabriela de Las Nieves
Labuckas, Diana Ondina
Garcia, Daniel Asmed
author_role author
author2 Labuckas, Diana Ondina
Garcia, Daniel Asmed
author2_role author
author
dc.subject.none.fl_str_mv Correlation Analysis
Gabaergic Phenols
Iam-Hplc
Lipophilicity
Liposomes
Partition Coefficient
topic Correlation Analysis
Gabaergic Phenols
Iam-Hplc
Lipophilicity
Liposomes
Partition Coefficient
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Some phenolic compounds, like propofol and thymol, have been shown to act on the GABAA receptor. Taking into account the hydrophobicity of these compounds, their interaction with the membrane surrounding the receptor and consequent non-specific effect on receptor modulation cannot be neglected. In the present work, we determined and correlated several lipophilic parameters for both GABAergic agents and three other related phenolic compounds (eugenol, carvacrol and chlorothymol), including log Po/w, retention data in high performance liquid chromatography (HPLC) by using C18 and immobilized artificial membrane (IAM) columns at different temperatures, and partition coefficients determined in phospholipid liposomes. The correlation results demonstrated the high capacity of the compounds assayed to interact with phospholipid membrane phases, which can be predicted by simple model systems as log Po/w or HPLC. The values obtained by HPLC using a fast screening IAM column were the quantitatively closest to the partition coefficients determined in liposome systems, due to the capacity of this column to permit the establishment of molecular interactions like those found in phospholipid membranes. Finally, the fact that all the compounds studied are able to interact with membranes would suggest the participation of some alteration of the GABAA receptor lipid environment as part of the receptor modulation exerted by phenolic compounds.
Fil: Reiner, Gabriela de Las Nieves. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Patagonia Norte. Instituto de Investigaciones en Biodiversidad y Medioambiente. Universidad Nacional del Comahue. Centro Regional Universidad Bariloche. Instituto de Investigaciones en Biodiversidad y Medioambiente; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Departamento de Química; Argentina
Fil: Labuckas, Diana Ondina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Departamento de Química; Argentina
Fil: Garcia, Daniel Asmed. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones Biológicas y Tecnológicas. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Instituto de Investigaciones Biológicas y Tecnológicas; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales. Departamento de Química; Argentina
description Some phenolic compounds, like propofol and thymol, have been shown to act on the GABAA receptor. Taking into account the hydrophobicity of these compounds, their interaction with the membrane surrounding the receptor and consequent non-specific effect on receptor modulation cannot be neglected. In the present work, we determined and correlated several lipophilic parameters for both GABAergic agents and three other related phenolic compounds (eugenol, carvacrol and chlorothymol), including log Po/w, retention data in high performance liquid chromatography (HPLC) by using C18 and immobilized artificial membrane (IAM) columns at different temperatures, and partition coefficients determined in phospholipid liposomes. The correlation results demonstrated the high capacity of the compounds assayed to interact with phospholipid membrane phases, which can be predicted by simple model systems as log Po/w or HPLC. The values obtained by HPLC using a fast screening IAM column were the quantitatively closest to the partition coefficients determined in liposome systems, due to the capacity of this column to permit the establishment of molecular interactions like those found in phospholipid membranes. Finally, the fact that all the compounds studied are able to interact with membranes would suggest the participation of some alteration of the GABAA receptor lipid environment as part of the receptor modulation exerted by phenolic compounds.
publishDate 2009
dc.date.none.fl_str_mv 2009-04-05
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/58414
Reiner, Gabriela de Las Nieves; Labuckas, Diana Ondina; Garcia, Daniel Asmed; Lipophilicity of some GABAergic phenols and related compounds determined by HPLC and partition coefficients in different systems; Elsevier Science; Journal of Pharmaceutical and Biomedical Analysis; 49; 3; 5-4-2009; 686-691
0731-7085
CONICET Digital
CONICET
url http://hdl.handle.net/11336/58414
identifier_str_mv Reiner, Gabriela de Las Nieves; Labuckas, Diana Ondina; Garcia, Daniel Asmed; Lipophilicity of some GABAergic phenols and related compounds determined by HPLC and partition coefficients in different systems; Elsevier Science; Journal of Pharmaceutical and Biomedical Analysis; 49; 3; 5-4-2009; 686-691
0731-7085
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0731708509000028
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jpba.2008.12.040
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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