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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/5542
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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 Técnicas2025-09-29T10:06:23Zoai: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:34982025-09-29 10:06:23.495CONICET 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/ |
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application/pdf application/pdf application/pdf application/pdf application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
Elsevier |
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Elsevier |
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reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas |
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Consejo Nacional de Investigaciones Científicas y Técnicas |
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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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13.070432 |