Penetratin and derivatives acting as antibacterial agents

Autores
Garro, Adriana; Olivella, Mónica S.; Bombasaro, José Abel; Lima, Beatriz Viviana; Tapia, Aníbal Alejandro; Feresin, Gabriela Egly; Perczel, Andras; Somlai, Csaba; Penke, Botond; López Cascales, Javier; Rodriguez, Ana Maria; Enriz, Ricardo Daniel
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The synthesis, in vitro evaluation and conformational study of penetratin and structurally related derivatives acting as antibacterial agents are reported. Among the compounds evaluated here, two methionine sulphoxide derivatives (RQIKIWFQNRRM[O]KWKK-NH2 and RQIKIFFQNRRM[O]KFKK-NH2) exhibited the strongest antibacterial effect in this series. In order to better understand the antimicrobial activity obtained for these peptides, we performed an exhaustive conformational analysis using different approaches. Molecular dynamics simulations were performed using two different media (water and trifluoroethanol/water). The results of these theoretical calculations were corroborated using experimental CD measurements. The electronic study for these peptides was carried out using molecular electrostatic potentials obtained from RHF/6-31G(d) calculations. In addition, the non-apeptide RQIRRWWQR-NH2 showed strong inhibitory action against the Gram-negative and Gram-positive bacteria tested in this study.
Fil: Garro, Adriana. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Olivella, Mónica S.. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica; Argentina
Fil: Bombasaro, José Abel. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica; Argentina
Fil: Lima, Beatriz Viviana. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina
Fil: Tapia, Aníbal Alejandro. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina
Fil: Feresin, Gabriela Egly. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina
Fil: Perczel, Andras. Eötvös Loránd University. Institute of Chemistry. Protein Modeling Group HAS-ELTE; Hungría
Fil: Somlai, Csaba. University of Szeged. Department of Medical Chemistry; Hungría
Fil: Penke, Botond. University of Szeged. Department of Medical Chemistry; Hungría
Fil: López Cascales, Javier. Universidad Politécnica de Cartagena. Grupo de Bioinformática y Macromoléculas (BioMac); España
Fil: Rodriguez, Ana Maria. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Enriz, Ricardo Daniel. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Materia
Penetratin
Methionine Sulfoxide Derivatives
Small-Size Peptides
Antibacterial Activity
Conformational Study
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:11336/4385
Acceder
id CONICETDig_8ff1d86b631279755e106bf9016b6575
oai_identifier_str oai:ri.conicet.gov.ar:11336/4385
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Penetratin and derivatives acting as antibacterial agentsGarro, AdrianaOlivella, Mónica S.Bombasaro, José AbelLima, Beatriz VivianaTapia, Aníbal AlejandroFeresin, Gabriela EglyPerczel, AndrasSomlai, CsabaPenke, BotondLópez Cascales, JavierRodriguez, Ana MariaEnriz, Ricardo DanielPenetratinMethionine Sulfoxide DerivativesSmall-Size PeptidesAntibacterial ActivityConformational Studyhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The synthesis, in vitro evaluation and conformational study of penetratin and structurally related derivatives acting as antibacterial agents are reported. Among the compounds evaluated here, two methionine sulphoxide derivatives (RQIKIWFQNRRM[O]KWKK-NH2 and RQIKIFFQNRRM[O]KFKK-NH2) exhibited the strongest antibacterial effect in this series. In order to better understand the antimicrobial activity obtained for these peptides, we performed an exhaustive conformational analysis using different approaches. Molecular dynamics simulations were performed using two different media (water and trifluoroethanol/water). The results of these theoretical calculations were corroborated using experimental CD measurements. The electronic study for these peptides was carried out using molecular electrostatic potentials obtained from RHF/6-31G(d) calculations. In addition, the non-apeptide RQIRRWWQR-NH2 showed strong inhibitory action against the Gram-negative and Gram-positive bacteria tested in this study.Fil: Garro, Adriana. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Olivella, Mónica S.. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica; ArgentinaFil: Bombasaro, José Abel. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica; ArgentinaFil: Lima, Beatriz Viviana. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; ArgentinaFil: Tapia, Aníbal Alejandro. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; ArgentinaFil: Feresin, Gabriela Egly. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; ArgentinaFil: Perczel, Andras. Eötvös Loránd University. Institute of Chemistry. Protein Modeling Group HAS-ELTE; HungríaFil: Somlai, Csaba. University of Szeged. Department of Medical Chemistry; HungríaFil: Penke, Botond. University of Szeged. Department of Medical Chemistry; HungríaFil: López Cascales, Javier. Universidad Politécnica de Cartagena. Grupo de Bioinformática y Macromoléculas (BioMac); EspañaFil: Rodriguez, Ana Maria. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Enriz, Ricardo Daniel. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaWiley2013-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/4385Garro, Adriana; Olivella, Mónica S.; Bombasaro, José Abel; Lima, Beatriz Viviana; Tapia, Aníbal Alejandro; et al.; Penetratin and derivatives acting as antibacterial agents; Wiley; Chemical Biology & Drug Design; 82; 2; 6-2013; 167-1771747-0277enginfo:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1111/cbdd.12143/abstractinfo:eu-repo/semantics/altIdentifier/issn/1747-0277info:eu-repo/semantics/altIdentifier/doi/DOI:10.1111/cbdd.12143info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:27:44Zoai:ri.conicet.gov.ar:11336/4385instacron: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 11:27:44.335CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Penetratin and derivatives acting as antibacterial agents
title Penetratin and derivatives acting as antibacterial agents
spellingShingle Penetratin and derivatives acting as antibacterial agents
Garro, Adriana
Penetratin
Methionine Sulfoxide Derivatives
Small-Size Peptides
Antibacterial Activity
Conformational Study
title_short Penetratin and derivatives acting as antibacterial agents
title_full Penetratin and derivatives acting as antibacterial agents
title_fullStr Penetratin and derivatives acting as antibacterial agents
title_full_unstemmed Penetratin and derivatives acting as antibacterial agents
title_sort Penetratin and derivatives acting as antibacterial agents
dc.creator.none.fl_str_mv Garro, Adriana
Olivella, Mónica S.
Bombasaro, José Abel
Lima, Beatriz Viviana
Tapia, Aníbal Alejandro
Feresin, Gabriela Egly
Perczel, Andras
Somlai, Csaba
Penke, Botond
López Cascales, Javier
Rodriguez, Ana Maria
Enriz, Ricardo Daniel
author Garro, Adriana
author_facet Garro, Adriana
Olivella, Mónica S.
Bombasaro, José Abel
Lima, Beatriz Viviana
Tapia, Aníbal Alejandro
Feresin, Gabriela Egly
Perczel, Andras
Somlai, Csaba
Penke, Botond
López Cascales, Javier
Rodriguez, Ana Maria
Enriz, Ricardo Daniel
author_role author
author2 Olivella, Mónica S.
Bombasaro, José Abel
Lima, Beatriz Viviana
Tapia, Aníbal Alejandro
Feresin, Gabriela Egly
Perczel, Andras
Somlai, Csaba
Penke, Botond
López Cascales, Javier
Rodriguez, Ana Maria
Enriz, Ricardo Daniel
author2_role author
author
author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Penetratin
Methionine Sulfoxide Derivatives
Small-Size Peptides
Antibacterial Activity
Conformational Study
topic Penetratin
Methionine Sulfoxide Derivatives
Small-Size Peptides
Antibacterial Activity
Conformational Study
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The synthesis, in vitro evaluation and conformational study of penetratin and structurally related derivatives acting as antibacterial agents are reported. Among the compounds evaluated here, two methionine sulphoxide derivatives (RQIKIWFQNRRM[O]KWKK-NH2 and RQIKIFFQNRRM[O]KFKK-NH2) exhibited the strongest antibacterial effect in this series. In order to better understand the antimicrobial activity obtained for these peptides, we performed an exhaustive conformational analysis using different approaches. Molecular dynamics simulations were performed using two different media (water and trifluoroethanol/water). The results of these theoretical calculations were corroborated using experimental CD measurements. The electronic study for these peptides was carried out using molecular electrostatic potentials obtained from RHF/6-31G(d) calculations. In addition, the non-apeptide RQIRRWWQR-NH2 showed strong inhibitory action against the Gram-negative and Gram-positive bacteria tested in this study.
Fil: Garro, Adriana. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Olivella, Mónica S.. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica; Argentina
Fil: Bombasaro, José Abel. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica; Argentina
Fil: Lima, Beatriz Viviana. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina
Fil: Tapia, Aníbal Alejandro. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina
Fil: Feresin, Gabriela Egly. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina
Fil: Perczel, Andras. Eötvös Loránd University. Institute of Chemistry. Protein Modeling Group HAS-ELTE; Hungría
Fil: Somlai, Csaba. University of Szeged. Department of Medical Chemistry; Hungría
Fil: Penke, Botond. University of Szeged. Department of Medical Chemistry; Hungría
Fil: López Cascales, Javier. Universidad Politécnica de Cartagena. Grupo de Bioinformática y Macromoléculas (BioMac); España
Fil: Rodriguez, Ana Maria. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Enriz, Ricardo Daniel. Universidad Nacional de San Luis. Facultad de Quimica, Bioquimica y Farmacia. Departamento de Quimica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
description The synthesis, in vitro evaluation and conformational study of penetratin and structurally related derivatives acting as antibacterial agents are reported. Among the compounds evaluated here, two methionine sulphoxide derivatives (RQIKIWFQNRRM[O]KWKK-NH2 and RQIKIFFQNRRM[O]KFKK-NH2) exhibited the strongest antibacterial effect in this series. In order to better understand the antimicrobial activity obtained for these peptides, we performed an exhaustive conformational analysis using different approaches. Molecular dynamics simulations were performed using two different media (water and trifluoroethanol/water). The results of these theoretical calculations were corroborated using experimental CD measurements. The electronic study for these peptides was carried out using molecular electrostatic potentials obtained from RHF/6-31G(d) calculations. In addition, the non-apeptide RQIRRWWQR-NH2 showed strong inhibitory action against the Gram-negative and Gram-positive bacteria tested in this study.
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/11336/4385
Garro, Adriana; Olivella, Mónica S.; Bombasaro, José Abel; Lima, Beatriz Viviana; Tapia, Aníbal Alejandro; et al.; Penetratin and derivatives acting as antibacterial agents; Wiley; Chemical Biology & Drug Design; 82; 2; 6-2013; 167-177
1747-0277
url http://hdl.handle.net/11336/4385
identifier_str_mv Garro, Adriana; Olivella, Mónica S.; Bombasaro, José Abel; Lima, Beatriz Viviana; Tapia, Aníbal Alejandro; et al.; Penetratin and derivatives acting as antibacterial agents; Wiley; Chemical Biology & Drug Design; 82; 2; 6-2013; 167-177
1747-0277
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/10.1111/cbdd.12143/abstract
info:eu-repo/semantics/altIdentifier/issn/1747-0277
info:eu-repo/semantics/altIdentifier/doi/DOI:10.1111/cbdd.12143
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
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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score 12.982451

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