Ascorbyl palmitate interaction with phospholipid monolayers: electrostatic and rheological preponderancy

Autores
Mottola, Milagro; Wilke, Natalia; Benedini, Luciano Alejandro; Oliveira, Rafael Gustavo; Fanani, Maria Laura
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Ascorbyl palmitate (ASC16) is an anionic amphiphilicmolecule of pharmacological interest due to its antioxidant properties. We found that ASC16 strongly interacted with model membranes. ASC16 penetrated phospholipid monolayers, with a cutoff near the theoretical surface pressure limit. The presence of a lipid filmat the interface favored ASC16 insertion compared with a bare air/water surface. The adsorption and penetration time curves showed a biphasic behavior: the first rapid peak evidenced a fast adsorption of charged ASC16 molecules to the interface that promoted a lowering of surface pH, thus partially neutralizing and compacting the film. The second rise represented an approach to the equilibrium between the ASC16 molecules in the subphase and the surface monolayer, whose kinetics depended on the ionization state of the film. Based on the Langmuir DMPC + ASC16 monolayer data, we estimated an ASC16 partition coefficient to DMPC monolayers of 1.5 × 105 30 Q2 and a ΔGp = −6.7 kcal·mol 31 −1. The rheological properties of the host membrane were determinant for ASC16 penetration kinetics: a fluid membrane, as provided by Chol, disrupted the liquid-condensed ASC16-enriched domains and favored ASC16 penetration. Subphase pH conditions affected ASC16 aggregation in bulk: the smaller structures at acidic pHs showed a faster equilibrium with the surface film than large lamellar ones. Our results revealed that the ASC16 interaction withmodelmembranes has a highly complex regulation. The polymorphism in the ASC16 bulk aggregation added complexity to the equilibrium between the surface and subphase form of ASC16, whose understanding may shed light on the pharmacological function of this drug.
Fil: Mottola, Milagro. Universidad Nacional de Córdoba; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Química Biológica de Córdoba (p); Argentina
Fil: Wilke, Natalia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones En Química Biológica de Córdoba (p); Argentina. Universidad Nacional de Córdoba; Argentina
Fil: Benedini, Luciano Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur; Argentina
Fil: Oliveira, Rafael Gustavo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones En Química Biológica de Córdoba (p); Argentina. Universidad Nacional de Córdoba; Argentina
Fil: Fanani, Maria Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones En Química Biológica de Córdoba (p); Argentina. Universidad Nacional de Córdoba; Argentina
Materia
Gibbs Monolayers
Brewster Angle Microscopy
Liquid-Condensed Domains
Vitamin C Derivatives
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/5542
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/5542
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Ascorbyl palmitate interaction with phospholipid monolayers: electrostatic and rheological preponderancyMottola, MilagroWilke, NataliaBenedini, Luciano AlejandroOliveira, Rafael GustavoFanani, Maria LauraGibbs MonolayersBrewster Angle MicroscopyLiquid-Condensed DomainsVitamin C Derivativeshttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1Ascorbyl palmitate (ASC16) is an anionic amphiphilicmolecule of pharmacological interest due to its antioxidant properties. We found that ASC16 strongly interacted with model membranes. ASC16 penetrated phospholipid monolayers, with a cutoff near the theoretical surface pressure limit. The presence of a lipid filmat the interface favored ASC16 insertion compared with a bare air/water surface. The adsorption and penetration time curves showed a biphasic behavior: the first rapid peak evidenced a fast adsorption of charged ASC16 molecules to the interface that promoted a lowering of surface pH, thus partially neutralizing and compacting the film. The second rise represented an approach to the equilibrium between the ASC16 molecules in the subphase and the surface monolayer, whose kinetics depended on the ionization state of the film. Based on the Langmuir DMPC + ASC16 monolayer data, we estimated an ASC16 partition coefficient to DMPC monolayers of 1.5 × 105 30 Q2 and a ΔGp = −6.7 kcal·mol 31 −1. The rheological properties of the host membrane were determinant for ASC16 penetration kinetics: a fluid membrane, as provided by Chol, disrupted the liquid-condensed ASC16-enriched domains and favored ASC16 penetration. Subphase pH conditions affected ASC16 aggregation in bulk: the smaller structures at acidic pHs showed a faster equilibrium with the surface film than large lamellar ones. Our results revealed that the ASC16 interaction withmodelmembranes has a highly complex regulation. The polymorphism in the ASC16 bulk aggregation added complexity to the equilibrium between the surface and subphase form of ASC16, whose understanding may shed light on the pharmacological function of this drug.Fil: Mottola, Milagro. Universidad Nacional de Córdoba; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Química Biológica de Córdoba (p); ArgentinaFil: Wilke, Natalia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones En Química Biológica de Córdoba (p); Argentina. Universidad Nacional de Córdoba; ArgentinaFil: Benedini, Luciano Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur; ArgentinaFil: Oliveira, Rafael Gustavo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones En Química Biológica de Córdoba (p); Argentina. Universidad Nacional de Córdoba; ArgentinaFil: Fanani, Maria Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones En Química Biológica de Córdoba (p); Argentina. Universidad Nacional de Córdoba; ArgentinaElsevier2013-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/5542Mottola, Milagro; Wilke, Natalia; Benedini, Luciano Alejandro; Oliveira, Rafael Gustavo; Fanani, Maria Laura; Ascorbyl palmitate interaction with phospholipid monolayers: electrostatic and rheological preponderancy; Elsevier; Biochimica Et Biophysica Acta - Biomembranes; 1828; 11; 6-2013; 2496-25050005-2736enginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0005273613002058info:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bbamem.2013.06.016info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:03:13Zoai:ri.conicet.gov.ar:11336/5542instacron: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:34982025-10-15 15:03:13.445CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Ascorbyl palmitate interaction with phospholipid monolayers: electrostatic and rheological preponderancy
title Ascorbyl palmitate interaction with phospholipid monolayers: electrostatic and rheological preponderancy
spellingShingle Ascorbyl palmitate interaction with phospholipid monolayers: electrostatic and rheological preponderancy
Mottola, Milagro
Gibbs Monolayers
Brewster Angle Microscopy
Liquid-Condensed Domains
Vitamin C Derivatives
title_short Ascorbyl palmitate interaction with phospholipid monolayers: electrostatic and rheological preponderancy
title_full Ascorbyl palmitate interaction with phospholipid monolayers: electrostatic and rheological preponderancy
title_fullStr Ascorbyl palmitate interaction with phospholipid monolayers: electrostatic and rheological preponderancy
title_full_unstemmed Ascorbyl palmitate interaction with phospholipid monolayers: electrostatic and rheological preponderancy
title_sort Ascorbyl palmitate interaction with phospholipid monolayers: electrostatic and rheological preponderancy
dc.creator.none.fl_str_mv Mottola, Milagro
Wilke, Natalia
Benedini, Luciano Alejandro
Oliveira, Rafael Gustavo
Fanani, Maria Laura
author Mottola, Milagro
author_facet Mottola, Milagro
Wilke, Natalia
Benedini, Luciano Alejandro
Oliveira, Rafael Gustavo
Fanani, Maria Laura
author_role author
author2 Wilke, Natalia
Benedini, Luciano Alejandro
Oliveira, Rafael Gustavo
Fanani, Maria Laura
author2_role author
author
author
author
dc.subject.none.fl_str_mv Gibbs Monolayers
Brewster Angle Microscopy
Liquid-Condensed Domains
Vitamin C Derivatives
topic Gibbs Monolayers
Brewster Angle Microscopy
Liquid-Condensed Domains
Vitamin C Derivatives
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Ascorbyl palmitate (ASC16) is an anionic amphiphilicmolecule of pharmacological interest due to its antioxidant properties. We found that ASC16 strongly interacted with model membranes. ASC16 penetrated phospholipid monolayers, with a cutoff near the theoretical surface pressure limit. The presence of a lipid filmat the interface favored ASC16 insertion compared with a bare air/water surface. The adsorption and penetration time curves showed a biphasic behavior: the first rapid peak evidenced a fast adsorption of charged ASC16 molecules to the interface that promoted a lowering of surface pH, thus partially neutralizing and compacting the film. The second rise represented an approach to the equilibrium between the ASC16 molecules in the subphase and the surface monolayer, whose kinetics depended on the ionization state of the film. Based on the Langmuir DMPC + ASC16 monolayer data, we estimated an ASC16 partition coefficient to DMPC monolayers of 1.5 × 105 30 Q2 and a ΔGp = −6.7 kcal·mol 31 −1. The rheological properties of the host membrane were determinant for ASC16 penetration kinetics: a fluid membrane, as provided by Chol, disrupted the liquid-condensed ASC16-enriched domains and favored ASC16 penetration. Subphase pH conditions affected ASC16 aggregation in bulk: the smaller structures at acidic pHs showed a faster equilibrium with the surface film than large lamellar ones. Our results revealed that the ASC16 interaction withmodelmembranes has a highly complex regulation. The polymorphism in the ASC16 bulk aggregation added complexity to the equilibrium between the surface and subphase form of ASC16, whose understanding may shed light on the pharmacological function of this drug.
Fil: Mottola, Milagro. Universidad Nacional de Córdoba; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones en Química Biológica de Córdoba (p); Argentina
Fil: Wilke, Natalia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones En Química Biológica de Córdoba (p); Argentina. Universidad Nacional de Córdoba; Argentina
Fil: Benedini, Luciano Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina. Universidad Nacional del Sur; Argentina
Fil: Oliveira, Rafael Gustavo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones En Química Biológica de Córdoba (p); Argentina. Universidad Nacional de Córdoba; Argentina
Fil: Fanani, Maria Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Centro de Investigaciones En Química Biológica de Córdoba (p); Argentina. Universidad Nacional de Córdoba; Argentina
description Ascorbyl palmitate (ASC16) is an anionic amphiphilicmolecule of pharmacological interest due to its antioxidant properties. We found that ASC16 strongly interacted with model membranes. ASC16 penetrated phospholipid monolayers, with a cutoff near the theoretical surface pressure limit. The presence of a lipid filmat the interface favored ASC16 insertion compared with a bare air/water surface. The adsorption and penetration time curves showed a biphasic behavior: the first rapid peak evidenced a fast adsorption of charged ASC16 molecules to the interface that promoted a lowering of surface pH, thus partially neutralizing and compacting the film. The second rise represented an approach to the equilibrium between the ASC16 molecules in the subphase and the surface monolayer, whose kinetics depended on the ionization state of the film. Based on the Langmuir DMPC + ASC16 monolayer data, we estimated an ASC16 partition coefficient to DMPC monolayers of 1.5 × 105 30 Q2 and a ΔGp = −6.7 kcal·mol 31 −1. The rheological properties of the host membrane were determinant for ASC16 penetration kinetics: a fluid membrane, as provided by Chol, disrupted the liquid-condensed ASC16-enriched domains and favored ASC16 penetration. Subphase pH conditions affected ASC16 aggregation in bulk: the smaller structures at acidic pHs showed a faster equilibrium with the surface film than large lamellar ones. Our results revealed that the ASC16 interaction withmodelmembranes has a highly complex regulation. The polymorphism in the ASC16 bulk aggregation added complexity to the equilibrium between the surface and subphase form of ASC16, whose understanding may shed light on the pharmacological function of this drug.
publishDate 2013
dc.date.none.fl_str_mv 2013-06
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/11336/5542
Mottola, Milagro; Wilke, Natalia; Benedini, Luciano Alejandro; Oliveira, Rafael Gustavo; Fanani, Maria Laura; Ascorbyl palmitate interaction with phospholipid monolayers: electrostatic and rheological preponderancy; Elsevier; Biochimica Et Biophysica Acta - Biomembranes; 1828; 11; 6-2013; 2496-2505
0005-2736
url http://hdl.handle.net/11336/5542
identifier_str_mv Mottola, Milagro; Wilke, Natalia; Benedini, Luciano Alejandro; Oliveira, Rafael Gustavo; Fanani, Maria Laura; Ascorbyl palmitate interaction with phospholipid monolayers: electrostatic and rheological preponderancy; Elsevier; Biochimica Et Biophysica Acta - Biomembranes; 1828; 11; 6-2013; 2496-2505
0005-2736
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0005273613002058
info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bbamem.2013.06.016
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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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