Role of Guanidyl Moiety in the Insertion of Arginine and N α -Benzoyl- l -argininate Ethyl Ester Chloride in Lipid Membranes

Autores
Fonseca, A. C.; Frías, M. A.; Bouchet, Ana María; Jarmelo, S.; Simoes, P. N.; Fausto, R.; Gil, M. H.; Lairion, Fabiana Norma; Disalvo, Edgardo Anibal
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Guanidyl moieties of both arginine (Arg) and NR-benzoyl-L-argininate ethyl ester chloride (BAEE) are protonated in all environments studied, i.e., dry solid state, D2O solutions, and dry and hydrated lipids as suggested by DFT(B3LYP)/6-31+G(d,p) calculations. Arg and BAEE are able to insert in the lipid interphase of both DMPC and DOPC monolayers as revealed by the observed decrease in the membrane dipole potential they induce. The larger decrease in the dipole potential induced by BAEE, compared to Arg, can be explained partially by the higher affinity of the hydrophobic benzoyl and ethyl groups for the membrane phase, which allows an easier insertion of this molecule. FTIR studies indicate that the guanidyl moiety of Arg is with all probability facing the hydrophobic part of the lipids, whereas in BAEE this group is facing the water phase. Zeta potential measurements provide a direct evidence that Arg orients in the lipid interphase of phosphatidylcholine (PC) bilayers with the negative charged carboxylate group (-COO-) toward the aqueous phase.
Fil: Fonseca, A. C.. Universidad de Coimbra; Portugal
Fil: Frías, M. A.. Universidad de Buenos Aires; Argentina
Fil: Bouchet, Ana María. Universidad de Buenos Aires; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Jarmelo, S.. Universidad de Coimbra; Portugal
Fil: Simoes, P. N.. Universidad de Coimbra; Portugal
Fil: Fausto, R.. Universidad de Coimbra; Portugal
Fil: Gil, M. H.. Universidad de Coimbra; Portugal
Fil: Lairion, Fabiana Norma. Universidad de Buenos Aires; Argentina
Fil: Disalvo, Edgardo Anibal. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires; Argentina
Materia
ARGININE
BAEE
LIPID INTERPHASES
ZETA POTENTIAL
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:11336/240084
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/240084
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Role of Guanidyl Moiety in the Insertion of Arginine and N α -Benzoyl- l -argininate Ethyl Ester Chloride in Lipid MembranesFonseca, A. C.Frías, M. A.Bouchet, Ana MaríaJarmelo, S.Simoes, P. N.Fausto, R.Gil, M. H.Lairion, Fabiana NormaDisalvo, Edgardo AnibalARGININEBAEELIPID INTERPHASESZETA POTENTIALhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Guanidyl moieties of both arginine (Arg) and NR-benzoyl-L-argininate ethyl ester chloride (BAEE) are protonated in all environments studied, i.e., dry solid state, D2O solutions, and dry and hydrated lipids as suggested by DFT(B3LYP)/6-31+G(d,p) calculations. Arg and BAEE are able to insert in the lipid interphase of both DMPC and DOPC monolayers as revealed by the observed decrease in the membrane dipole potential they induce. The larger decrease in the dipole potential induced by BAEE, compared to Arg, can be explained partially by the higher affinity of the hydrophobic benzoyl and ethyl groups for the membrane phase, which allows an easier insertion of this molecule. FTIR studies indicate that the guanidyl moiety of Arg is with all probability facing the hydrophobic part of the lipids, whereas in BAEE this group is facing the water phase. Zeta potential measurements provide a direct evidence that Arg orients in the lipid interphase of phosphatidylcholine (PC) bilayers with the negative charged carboxylate group (-COO-) toward the aqueous phase.Fil: Fonseca, A. C.. Universidad de Coimbra; PortugalFil: Frías, M. A.. Universidad de Buenos Aires; ArgentinaFil: Bouchet, Ana María. Universidad de Buenos Aires; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Jarmelo, S.. Universidad de Coimbra; PortugalFil: Simoes, P. N.. Universidad de Coimbra; PortugalFil: Fausto, R.. Universidad de Coimbra; PortugalFil: Gil, M. H.. Universidad de Coimbra; PortugalFil: Lairion, Fabiana Norma. Universidad de Buenos Aires; ArgentinaFil: Disalvo, Edgardo Anibal. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires; ArgentinaAmerican Chemical Society2010-03info: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/11336/240084Fonseca, A. C.; Frías, M. A.; Bouchet, Ana María; Jarmelo, S.; Simoes, P. N.; et al.; Role of Guanidyl Moiety in the Insertion of Arginine and N α -Benzoyl- l -argininate Ethyl Ester Chloride in Lipid Membranes; American Chemical Society; Journal of Physical Chemistry B; 114; 17; 3-2010; 5946-59521520-6106CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jp101007binfo:eu-repo/semantics/altIdentifier/doi/10.1021/jp101007binfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:48:08Zoai:ri.conicet.gov.ar:11336/240084instacron: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 14:48:08.715CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Role of Guanidyl Moiety in the Insertion of Arginine and N α -Benzoyl- l -argininate Ethyl Ester Chloride in Lipid Membranes
title Role of Guanidyl Moiety in the Insertion of Arginine and N α -Benzoyl- l -argininate Ethyl Ester Chloride in Lipid Membranes
spellingShingle Role of Guanidyl Moiety in the Insertion of Arginine and N α -Benzoyl- l -argininate Ethyl Ester Chloride in Lipid Membranes
Fonseca, A. C.
ARGININE
BAEE
LIPID INTERPHASES
ZETA POTENTIAL
title_short Role of Guanidyl Moiety in the Insertion of Arginine and N α -Benzoyl- l -argininate Ethyl Ester Chloride in Lipid Membranes
title_full Role of Guanidyl Moiety in the Insertion of Arginine and N α -Benzoyl- l -argininate Ethyl Ester Chloride in Lipid Membranes
title_fullStr Role of Guanidyl Moiety in the Insertion of Arginine and N α -Benzoyl- l -argininate Ethyl Ester Chloride in Lipid Membranes
title_full_unstemmed Role of Guanidyl Moiety in the Insertion of Arginine and N α -Benzoyl- l -argininate Ethyl Ester Chloride in Lipid Membranes
title_sort Role of Guanidyl Moiety in the Insertion of Arginine and N α -Benzoyl- l -argininate Ethyl Ester Chloride in Lipid Membranes
dc.creator.none.fl_str_mv Fonseca, A. C.
Frías, M. A.
Bouchet, Ana María
Jarmelo, S.
Simoes, P. N.
Fausto, R.
Gil, M. H.
Lairion, Fabiana Norma
Disalvo, Edgardo Anibal
author Fonseca, A. C.
author_facet Fonseca, A. C.
Frías, M. A.
Bouchet, Ana María
Jarmelo, S.
Simoes, P. N.
Fausto, R.
Gil, M. H.
Lairion, Fabiana Norma
Disalvo, Edgardo Anibal
author_role author
author2 Frías, M. A.
Bouchet, Ana María
Jarmelo, S.
Simoes, P. N.
Fausto, R.
Gil, M. H.
Lairion, Fabiana Norma
Disalvo, Edgardo Anibal
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv ARGININE
BAEE
LIPID INTERPHASES
ZETA POTENTIAL
topic ARGININE
BAEE
LIPID INTERPHASES
ZETA POTENTIAL
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Guanidyl moieties of both arginine (Arg) and NR-benzoyl-L-argininate ethyl ester chloride (BAEE) are protonated in all environments studied, i.e., dry solid state, D2O solutions, and dry and hydrated lipids as suggested by DFT(B3LYP)/6-31+G(d,p) calculations. Arg and BAEE are able to insert in the lipid interphase of both DMPC and DOPC monolayers as revealed by the observed decrease in the membrane dipole potential they induce. The larger decrease in the dipole potential induced by BAEE, compared to Arg, can be explained partially by the higher affinity of the hydrophobic benzoyl and ethyl groups for the membrane phase, which allows an easier insertion of this molecule. FTIR studies indicate that the guanidyl moiety of Arg is with all probability facing the hydrophobic part of the lipids, whereas in BAEE this group is facing the water phase. Zeta potential measurements provide a direct evidence that Arg orients in the lipid interphase of phosphatidylcholine (PC) bilayers with the negative charged carboxylate group (-COO-) toward the aqueous phase.
Fil: Fonseca, A. C.. Universidad de Coimbra; Portugal
Fil: Frías, M. A.. Universidad de Buenos Aires; Argentina
Fil: Bouchet, Ana María. Universidad de Buenos Aires; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Jarmelo, S.. Universidad de Coimbra; Portugal
Fil: Simoes, P. N.. Universidad de Coimbra; Portugal
Fil: Fausto, R.. Universidad de Coimbra; Portugal
Fil: Gil, M. H.. Universidad de Coimbra; Portugal
Fil: Lairion, Fabiana Norma. Universidad de Buenos Aires; Argentina
Fil: Disalvo, Edgardo Anibal. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires; Argentina
description Guanidyl moieties of both arginine (Arg) and NR-benzoyl-L-argininate ethyl ester chloride (BAEE) are protonated in all environments studied, i.e., dry solid state, D2O solutions, and dry and hydrated lipids as suggested by DFT(B3LYP)/6-31+G(d,p) calculations. Arg and BAEE are able to insert in the lipid interphase of both DMPC and DOPC monolayers as revealed by the observed decrease in the membrane dipole potential they induce. The larger decrease in the dipole potential induced by BAEE, compared to Arg, can be explained partially by the higher affinity of the hydrophobic benzoyl and ethyl groups for the membrane phase, which allows an easier insertion of this molecule. FTIR studies indicate that the guanidyl moiety of Arg is with all probability facing the hydrophobic part of the lipids, whereas in BAEE this group is facing the water phase. Zeta potential measurements provide a direct evidence that Arg orients in the lipid interphase of phosphatidylcholine (PC) bilayers with the negative charged carboxylate group (-COO-) toward the aqueous phase.
publishDate 2010
dc.date.none.fl_str_mv 2010-03
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/11336/240084
Fonseca, A. C.; Frías, M. A.; Bouchet, Ana María; Jarmelo, S.; Simoes, P. N.; et al.; Role of Guanidyl Moiety in the Insertion of Arginine and N α -Benzoyl- l -argininate Ethyl Ester Chloride in Lipid Membranes; American Chemical Society; Journal of Physical Chemistry B; 114; 17; 3-2010; 5946-5952
1520-6106
CONICET Digital
CONICET
url http://hdl.handle.net/11336/240084
identifier_str_mv Fonseca, A. C.; Frías, M. A.; Bouchet, Ana María; Jarmelo, S.; Simoes, P. N.; et al.; Role of Guanidyl Moiety in the Insertion of Arginine and N α -Benzoyl- l -argininate Ethyl Ester Chloride in Lipid Membranes; American Chemical Society; Journal of Physical Chemistry B; 114; 17; 3-2010; 5946-5952
1520-6106
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://pubs.acs.org/doi/10.1021/jp101007b
info:eu-repo/semantics/altIdentifier/doi/10.1021/jp101007b
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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
_version_ 1846083000130863104
score 13.22299

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