Stereoselective effects of monoterpenes on the microviscosity and curvature of model membranes assessed by fluorescence anisotropy and light scattering analysis.

Autores
Zunino, María Paula; Turina, Anahi del Valle; Zygadlo, Julio Alberto; Perillo, Maria Angelica
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Here, we evaluated stereoselectivity in monoterpenes (MTs) ability to disturb membrane dynamics. Correlations between molecular structure and physicochemical properties of pinenes, menthols, and carvones enantiomers were investigated through cluster and principal component analysis. Therefore, MTs' concentration-dependent changes in light scattering and diphenylhexatriene (DPH) fluorescence polarization induced by MTs were measured on large unilamellar vesicles (LUVs) of dipalmitoylphosphatidylcholine. The behavior of the less polar compounds (hydrocarbons) was characterized by a membrane expansion (increase in light scattering), detectable within the low-concentration range. They remained in the membrane up to the highest concentrations tested exhibiting a concentration-dependent anisotropy decrease. Within the more polar terpenes (alcohols) prevailed a budding phenomenon with the production of small LUVs with roughly constant curvature (more evident at medium and high concentrations), which explains the slight change in microviscosity (DPH fluorescence anisotropy). These behaviors were compatible with the deeper localization within the membrane core of the formers compared with the latters as predicted from the corresponding polar charge distribution in their molecular structures. The enantioselectivity was expressed by neomenthol at low concentration and carvone at medium concentration. Inhibition and potentiation were evidenced, within the low-concentration range, by the racemic mixtures in neomenthol and β-pinenes, respectively.
Fil: Zunino, María Paula. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; Argentina
Fil: Turina, Anahi del Valle. Universidad Nacional de Cordoba. Facultad de Cs.exactas Fisicas y Naturales. Departamento de Quimica. Catedra de Quimica Biologica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba; Argentina
Fil: Zygadlo, Julio Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; Argentina
Fil: Perillo, Maria Angelica. Universidad Nacional de Cordoba. Facultad de Cs.exactas Fisicas y Naturales. Departamento de Quimica. Catedra de Quimica Biologica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba; Argentina
Materia
Dph Fluorescence Anisotropy
Stereoisomers
Terpenes
Membrane Organization
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:11336/13139
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/13139
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Stereoselective effects of monoterpenes on the microviscosity and curvature of model membranes assessed by fluorescence anisotropy and light scattering analysis.Zunino, María PaulaTurina, Anahi del ValleZygadlo, Julio AlbertoPerillo, Maria AngelicaDph Fluorescence AnisotropyStereoisomersTerpenesMembrane Organizationhttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1https://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1Here, we evaluated stereoselectivity in monoterpenes (MTs) ability to disturb membrane dynamics. Correlations between molecular structure and physicochemical properties of pinenes, menthols, and carvones enantiomers were investigated through cluster and principal component analysis. Therefore, MTs' concentration-dependent changes in light scattering and diphenylhexatriene (DPH) fluorescence polarization induced by MTs were measured on large unilamellar vesicles (LUVs) of dipalmitoylphosphatidylcholine. The behavior of the less polar compounds (hydrocarbons) was characterized by a membrane expansion (increase in light scattering), detectable within the low-concentration range. They remained in the membrane up to the highest concentrations tested exhibiting a concentration-dependent anisotropy decrease. Within the more polar terpenes (alcohols) prevailed a budding phenomenon with the production of small LUVs with roughly constant curvature (more evident at medium and high concentrations), which explains the slight change in microviscosity (DPH fluorescence anisotropy). These behaviors were compatible with the deeper localization within the membrane core of the formers compared with the latters as predicted from the corresponding polar charge distribution in their molecular structures. The enantioselectivity was expressed by neomenthol at low concentration and carvone at medium concentration. Inhibition and potentiation were evidenced, within the low-concentration range, by the racemic mixtures in neomenthol and β-pinenes, respectively.Fil: Zunino, María Paula. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; ArgentinaFil: Turina, Anahi del Valle. Universidad Nacional de Cordoba. Facultad de Cs.exactas Fisicas y Naturales. Departamento de Quimica. Catedra de Quimica Biologica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba; ArgentinaFil: Zygadlo, Julio Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; ArgentinaFil: Perillo, Maria Angelica. Universidad Nacional de Cordoba. Facultad de Cs.exactas Fisicas y Naturales. Departamento de Quimica. Catedra de Quimica Biologica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba; ArgentinaWiley2011-11info: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/11336/13139Zunino, María Paula; Turina, Anahi del Valle; Zygadlo, Julio Alberto; Perillo, Maria Angelica; Stereoselective effects of monoterpenes on the microviscosity and curvature of model membranes assessed by fluorescence anisotropy and light scattering analysis.; Wiley; Chirality; 23; 10; 11-2011; 867-8770899-00421520-636Xenginfo:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/chir.20998/abstractinfo:eu-repo/semantics/altIdentifier/doi/10.1002/chir.20998info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:11:30Zoai:ri.conicet.gov.ar:11336/13139instacron: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:34982025-10-22 11:11:30.462CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Stereoselective effects of monoterpenes on the microviscosity and curvature of model membranes assessed by fluorescence anisotropy and light scattering analysis.
title Stereoselective effects of monoterpenes on the microviscosity and curvature of model membranes assessed by fluorescence anisotropy and light scattering analysis.
spellingShingle Stereoselective effects of monoterpenes on the microviscosity and curvature of model membranes assessed by fluorescence anisotropy and light scattering analysis.
Zunino, María Paula
Dph Fluorescence Anisotropy
Stereoisomers
Terpenes
Membrane Organization
title_short Stereoselective effects of monoterpenes on the microviscosity and curvature of model membranes assessed by fluorescence anisotropy and light scattering analysis.
title_full Stereoselective effects of monoterpenes on the microviscosity and curvature of model membranes assessed by fluorescence anisotropy and light scattering analysis.
title_fullStr Stereoselective effects of monoterpenes on the microviscosity and curvature of model membranes assessed by fluorescence anisotropy and light scattering analysis.
title_full_unstemmed Stereoselective effects of monoterpenes on the microviscosity and curvature of model membranes assessed by fluorescence anisotropy and light scattering analysis.
title_sort Stereoselective effects of monoterpenes on the microviscosity and curvature of model membranes assessed by fluorescence anisotropy and light scattering analysis.
dc.creator.none.fl_str_mv Zunino, María Paula
Turina, Anahi del Valle
Zygadlo, Julio Alberto
Perillo, Maria Angelica
author Zunino, María Paula
author_facet Zunino, María Paula
Turina, Anahi del Valle
Zygadlo, Julio Alberto
Perillo, Maria Angelica
author_role author
author2 Turina, Anahi del Valle
Zygadlo, Julio Alberto
Perillo, Maria Angelica
author2_role author
author
author
dc.subject.none.fl_str_mv Dph Fluorescence Anisotropy
Stereoisomers
Terpenes
Membrane Organization
topic Dph Fluorescence Anisotropy
Stereoisomers
Terpenes
Membrane Organization
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Here, we evaluated stereoselectivity in monoterpenes (MTs) ability to disturb membrane dynamics. Correlations between molecular structure and physicochemical properties of pinenes, menthols, and carvones enantiomers were investigated through cluster and principal component analysis. Therefore, MTs' concentration-dependent changes in light scattering and diphenylhexatriene (DPH) fluorescence polarization induced by MTs were measured on large unilamellar vesicles (LUVs) of dipalmitoylphosphatidylcholine. The behavior of the less polar compounds (hydrocarbons) was characterized by a membrane expansion (increase in light scattering), detectable within the low-concentration range. They remained in the membrane up to the highest concentrations tested exhibiting a concentration-dependent anisotropy decrease. Within the more polar terpenes (alcohols) prevailed a budding phenomenon with the production of small LUVs with roughly constant curvature (more evident at medium and high concentrations), which explains the slight change in microviscosity (DPH fluorescence anisotropy). These behaviors were compatible with the deeper localization within the membrane core of the formers compared with the latters as predicted from the corresponding polar charge distribution in their molecular structures. The enantioselectivity was expressed by neomenthol at low concentration and carvone at medium concentration. Inhibition and potentiation were evidenced, within the low-concentration range, by the racemic mixtures in neomenthol and β-pinenes, respectively.
Fil: Zunino, María Paula. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; Argentina
Fil: Turina, Anahi del Valle. Universidad Nacional de Cordoba. Facultad de Cs.exactas Fisicas y Naturales. Departamento de Quimica. Catedra de Quimica Biologica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba; Argentina
Fil: Zygadlo, Julio Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba. Instituto Multidisciplinario de Biología Vegetal (p); Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; Argentina
Fil: Perillo, Maria Angelica. Universidad Nacional de Cordoba. Facultad de Cs.exactas Fisicas y Naturales. Departamento de Quimica. Catedra de Quimica Biologica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Córdoba; Argentina
description Here, we evaluated stereoselectivity in monoterpenes (MTs) ability to disturb membrane dynamics. Correlations between molecular structure and physicochemical properties of pinenes, menthols, and carvones enantiomers were investigated through cluster and principal component analysis. Therefore, MTs' concentration-dependent changes in light scattering and diphenylhexatriene (DPH) fluorescence polarization induced by MTs were measured on large unilamellar vesicles (LUVs) of dipalmitoylphosphatidylcholine. The behavior of the less polar compounds (hydrocarbons) was characterized by a membrane expansion (increase in light scattering), detectable within the low-concentration range. They remained in the membrane up to the highest concentrations tested exhibiting a concentration-dependent anisotropy decrease. Within the more polar terpenes (alcohols) prevailed a budding phenomenon with the production of small LUVs with roughly constant curvature (more evident at medium and high concentrations), which explains the slight change in microviscosity (DPH fluorescence anisotropy). These behaviors were compatible with the deeper localization within the membrane core of the formers compared with the latters as predicted from the corresponding polar charge distribution in their molecular structures. The enantioselectivity was expressed by neomenthol at low concentration and carvone at medium concentration. Inhibition and potentiation were evidenced, within the low-concentration range, by the racemic mixtures in neomenthol and β-pinenes, respectively.
publishDate 2011
dc.date.none.fl_str_mv 2011-11
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/11336/13139
Zunino, María Paula; Turina, Anahi del Valle; Zygadlo, Julio Alberto; Perillo, Maria Angelica; Stereoselective effects of monoterpenes on the microviscosity and curvature of model membranes assessed by fluorescence anisotropy and light scattering analysis.; Wiley; Chirality; 23; 10; 11-2011; 867-877
0899-0042
1520-636X
url http://hdl.handle.net/11336/13139
identifier_str_mv Zunino, María Paula; Turina, Anahi del Valle; Zygadlo, Julio Alberto; Perillo, Maria Angelica; Stereoselective effects of monoterpenes on the microviscosity and curvature of model membranes assessed by fluorescence anisotropy and light scattering analysis.; Wiley; Chirality; 23; 10; 11-2011; 867-877
0899-0042
1520-636X
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/chir.20998/abstract
info:eu-repo/semantics/altIdentifier/doi/10.1002/chir.20998
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
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
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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