Molecular dynamics study of uncharged bupivacaine enantiomers in phospholipid bilayers

Autores
Martini, María Florencia; Pickholz, Mónica Andrea
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
To investigate the effects of the uncharged bupivacaine (BVC) on the properties of model membranes of 1-palmitoyl- 2-oleoyl-sn-glycero-3-phosphatidylcholine (POPC), we have performed a series of molecular dynamics simulations. A very particular characteristic of the local anesthetic BVC, that is being discuss in the recent literature, is that their enantiomers R-(þ) (R-BVC) and S-(À) (S-BVC) present different activities. In this way, we have studied both enantiomers in a POPC phospholipids bilayers at a high molar ratios [local anesthetic (LA):lipid of 1:3]. The simulations were able to capture important features of the BVC?phospholipid bilayer interactions: BVC molecules are found in the interior of the bilayer. The R-BVC enantiomerfollows a bimodal distribution with access to the water?lipid interface; while the S-BVC is found, in more uniformdistribution, at the hydrophobic region. A decrease in theacyl chain segment order parameters, SCD, compared to neatbilayers, is found. Furthermore, this behavior is morenoticeable for the R-BVC form. The found decrease in SCD isattributed to a larger accessible volume per lipid in the tailregion. Our results could help to understand the highertoxicity of this enantiomer. 
Fil: Martini, María Florencia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Tecnología Farmacéutica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Pickholz, Mónica Andrea. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Tecnología Farmacéutica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Materia
BUPIVACAINE
LIPID BILAYER
LOCAL ANESTHETICS
MOLECULAR DYNAMICS
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:11336/162029
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/162029
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Molecular dynamics study of uncharged bupivacaine enantiomers in phospholipid bilayersMartini, María FlorenciaPickholz, Mónica AndreaBUPIVACAINELIPID BILAYERLOCAL ANESTHETICSMOLECULAR DYNAMICShttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1To investigate the effects of the uncharged bupivacaine (BVC) on the properties of model membranes of 1-palmitoyl- 2-oleoyl-sn-glycero-3-phosphatidylcholine (POPC), we have performed a series of molecular dynamics simulations. A very particular characteristic of the local anesthetic BVC, that is being discuss in the recent literature, is that their enantiomers R-(þ) (R-BVC) and S-(À) (S-BVC) present different activities. In this way, we have studied both enantiomers in a POPC phospholipids bilayers at a high molar ratios [local anesthetic (LA):lipid of 1:3]. The simulations were able to capture important features of the BVC?phospholipid bilayer interactions: BVC molecules are found in the interior of the bilayer. The R-BVC enantiomerfollows a bimodal distribution with access to the water?lipid interface; while the S-BVC is found, in more uniformdistribution, at the hydrophobic region. A decrease in theacyl chain segment order parameters, SCD, compared to neatbilayers, is found. Furthermore, this behavior is morenoticeable for the R-BVC form. The found decrease in SCD isattributed to a larger accessible volume per lipid in the tailregion. Our results could help to understand the highertoxicity of this enantiomer. Fil: Martini, María Florencia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Tecnología Farmacéutica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: Pickholz, Mónica Andrea. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Tecnología Farmacéutica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaJohn Wiley & Sons Inc.2012-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/162029Martini, María Florencia; Pickholz, Mónica Andrea; Molecular dynamics study of uncharged bupivacaine enantiomers in phospholipid bilayers; John Wiley & Sons Inc.; International Journal of Quantum Chemistry; 112; 20; 9-2012; 3341-33450020-7608CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/qua.24208/pdfinfo:eu-repo/semantics/altIdentifier/doi/10.1002/qua.24208info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:09:31Zoai:ri.conicet.gov.ar:11336/162029instacron: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:34982025-09-10 13:09:32.0CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Molecular dynamics study of uncharged bupivacaine enantiomers in phospholipid bilayers
title Molecular dynamics study of uncharged bupivacaine enantiomers in phospholipid bilayers
spellingShingle Molecular dynamics study of uncharged bupivacaine enantiomers in phospholipid bilayers
Martini, María Florencia
BUPIVACAINE
LIPID BILAYER
LOCAL ANESTHETICS
MOLECULAR DYNAMICS
title_short Molecular dynamics study of uncharged bupivacaine enantiomers in phospholipid bilayers
title_full Molecular dynamics study of uncharged bupivacaine enantiomers in phospholipid bilayers
title_fullStr Molecular dynamics study of uncharged bupivacaine enantiomers in phospholipid bilayers
title_full_unstemmed Molecular dynamics study of uncharged bupivacaine enantiomers in phospholipid bilayers
title_sort Molecular dynamics study of uncharged bupivacaine enantiomers in phospholipid bilayers
dc.creator.none.fl_str_mv Martini, María Florencia
Pickholz, Mónica Andrea
author Martini, María Florencia
author_facet Martini, María Florencia
Pickholz, Mónica Andrea
author_role author
author2 Pickholz, Mónica Andrea
author2_role author
dc.subject.none.fl_str_mv BUPIVACAINE
LIPID BILAYER
LOCAL ANESTHETICS
MOLECULAR DYNAMICS
topic BUPIVACAINE
LIPID BILAYER
LOCAL ANESTHETICS
MOLECULAR DYNAMICS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv To investigate the effects of the uncharged bupivacaine (BVC) on the properties of model membranes of 1-palmitoyl- 2-oleoyl-sn-glycero-3-phosphatidylcholine (POPC), we have performed a series of molecular dynamics simulations. A very particular characteristic of the local anesthetic BVC, that is being discuss in the recent literature, is that their enantiomers R-(þ) (R-BVC) and S-(À) (S-BVC) present different activities. In this way, we have studied both enantiomers in a POPC phospholipids bilayers at a high molar ratios [local anesthetic (LA):lipid of 1:3]. The simulations were able to capture important features of the BVC?phospholipid bilayer interactions: BVC molecules are found in the interior of the bilayer. The R-BVC enantiomerfollows a bimodal distribution with access to the water?lipid interface; while the S-BVC is found, in more uniformdistribution, at the hydrophobic region. A decrease in theacyl chain segment order parameters, SCD, compared to neatbilayers, is found. Furthermore, this behavior is morenoticeable for the R-BVC form. The found decrease in SCD isattributed to a larger accessible volume per lipid in the tailregion. Our results could help to understand the highertoxicity of this enantiomer. 
Fil: Martini, María Florencia. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Tecnología Farmacéutica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Pickholz, Mónica Andrea. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Tecnología Farmacéutica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
description To investigate the effects of the uncharged bupivacaine (BVC) on the properties of model membranes of 1-palmitoyl- 2-oleoyl-sn-glycero-3-phosphatidylcholine (POPC), we have performed a series of molecular dynamics simulations. A very particular characteristic of the local anesthetic BVC, that is being discuss in the recent literature, is that their enantiomers R-(þ) (R-BVC) and S-(À) (S-BVC) present different activities. In this way, we have studied both enantiomers in a POPC phospholipids bilayers at a high molar ratios [local anesthetic (LA):lipid of 1:3]. The simulations were able to capture important features of the BVC?phospholipid bilayer interactions: BVC molecules are found in the interior of the bilayer. The R-BVC enantiomerfollows a bimodal distribution with access to the water?lipid interface; while the S-BVC is found, in more uniformdistribution, at the hydrophobic region. A decrease in theacyl chain segment order parameters, SCD, compared to neatbilayers, is found. Furthermore, this behavior is morenoticeable for the R-BVC form. The found decrease in SCD isattributed to a larger accessible volume per lipid in the tailregion. Our results could help to understand the highertoxicity of this enantiomer. 
publishDate 2012
dc.date.none.fl_str_mv 2012-09
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/11336/162029
Martini, María Florencia; Pickholz, Mónica Andrea; Molecular dynamics study of uncharged bupivacaine enantiomers in phospholipid bilayers; John Wiley & Sons Inc.; International Journal of Quantum Chemistry; 112; 20; 9-2012; 3341-3345
0020-7608
CONICET Digital
CONICET
url http://hdl.handle.net/11336/162029
identifier_str_mv Martini, María Florencia; Pickholz, Mónica Andrea; Molecular dynamics study of uncharged bupivacaine enantiomers in phospholipid bilayers; John Wiley & Sons Inc.; International Journal of Quantum Chemistry; 112; 20; 9-2012; 3341-3345
0020-7608
CONICET Digital
CONICET
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/qua.24208/pdf
info:eu-repo/semantics/altIdentifier/doi/10.1002/qua.24208
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
dc.publisher.none.fl_str_mv John Wiley & Sons Inc.
publisher.none.fl_str_mv John Wiley & Sons Inc.
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 12.993085

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