Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal properties

Autores
Masman, Marcelo Fabricio; Rodriguez, Ana Maria; Svetaz, Laura Andrea; Zacchino, Susana Alicia Stella; Somlai, Csaba; Csizmadia, Imre Gyula; Penke, Botond; Enriz, Ricardo Daniel
Año de publicación
2006
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The synthesis, in vitro evaluation, and conformational study of His-Phe-Arg-Trp-NH2 and related derivatives acting as antifungal agents are reported. Among them, His-Phe-Arg-Trp-NH2 and His-Tyr-Arg-Trp-NH2 exhibited antifungal activity against Cryptococcus neoformans. Antifungal activity of these compounds appears to be closely related to the α-MSH effect. A conformational and electronic study allows us to propose a biologically relevant conformation for these tetrapeptides acting as antifungal agents. In addition, these theoretical calculations permit us to determine the minimal structural requirements to produce the antifungal response and may provide a guide for the design of compounds with this biological activity.
Fil: Masman, Marcelo Fabricio. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Rodriguez, Ana Maria. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina
Fil: Svetaz, Laura Andrea. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Somlai, Csaba. Szegedi Tudományegyetem; Hungría
Fil: Csizmadia, Imre Gyula. Szegedi Tudományegyetem; Hungría
Fil: Penke, Botond. Szegedi Tudományegyetem; Hungría
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina
Materia
ANTIFUNGAL ACTIVITIES
CONFORMATIONAL AND ELECTRONIC STUDY
HIS-PHE-ARG-TRP-NH2
SMALL PEPTIDES
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:11336/139366
Acceder
id CONICETDig_6f77c42ece0c40d43c9b9529d2b3c8cb
oai_identifier_str oai:ri.conicet.gov.ar:11336/139366
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal propertiesMasman, Marcelo FabricioRodriguez, Ana MariaSvetaz, Laura AndreaZacchino, Susana Alicia StellaSomlai, CsabaCsizmadia, Imre GyulaPenke, BotondEnriz, Ricardo DanielANTIFUNGAL ACTIVITIESCONFORMATIONAL AND ELECTRONIC STUDYHIS-PHE-ARG-TRP-NH2SMALL PEPTIDEShttps://purl.org/becyt/ford/3.1https://purl.org/becyt/ford/3The synthesis, in vitro evaluation, and conformational study of His-Phe-Arg-Trp-NH2 and related derivatives acting as antifungal agents are reported. Among them, His-Phe-Arg-Trp-NH2 and His-Tyr-Arg-Trp-NH2 exhibited antifungal activity against Cryptococcus neoformans. Antifungal activity of these compounds appears to be closely related to the α-MSH effect. A conformational and electronic study allows us to propose a biologically relevant conformation for these tetrapeptides acting as antifungal agents. In addition, these theoretical calculations permit us to determine the minimal structural requirements to produce the antifungal response and may provide a guide for the design of compounds with this biological activity.Fil: Masman, Marcelo Fabricio. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Rodriguez, Ana Maria. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; ArgentinaFil: Svetaz, Laura Andrea. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Somlai, Csaba. Szegedi Tudományegyetem; HungríaFil: Csizmadia, Imre Gyula. Szegedi Tudományegyetem; HungríaFil: Penke, Botond. Szegedi Tudományegyetem; HungríaFil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; ArgentinaPergamon-Elsevier Science Ltd2006-11-15info: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/11336/139366Masman, Marcelo Fabricio; Rodriguez, Ana Maria; Svetaz, Laura Andrea; Zacchino, Susana Alicia Stella; Somlai, Csaba; et al.; Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal properties; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry; 14; 22; 15-11-2006; 7604-76140968-0896CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0968089606005621info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmc.2006.07.007info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:09:20Zoai:ri.conicet.gov.ar:11336/139366instacron: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 10:09:20.493CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal properties
title Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal properties
spellingShingle Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal properties
Masman, Marcelo Fabricio
ANTIFUNGAL ACTIVITIES
CONFORMATIONAL AND ELECTRONIC STUDY
HIS-PHE-ARG-TRP-NH2
SMALL PEPTIDES
title_short Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal properties
title_full Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal properties
title_fullStr Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal properties
title_full_unstemmed Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal properties
title_sort Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal properties
dc.creator.none.fl_str_mv Masman, Marcelo Fabricio
Rodriguez, Ana Maria
Svetaz, Laura Andrea
Zacchino, Susana Alicia Stella
Somlai, Csaba
Csizmadia, Imre Gyula
Penke, Botond
Enriz, Ricardo Daniel
author Masman, Marcelo Fabricio
author_facet Masman, Marcelo Fabricio
Rodriguez, Ana Maria
Svetaz, Laura Andrea
Zacchino, Susana Alicia Stella
Somlai, Csaba
Csizmadia, Imre Gyula
Penke, Botond
Enriz, Ricardo Daniel
author_role author
author2 Rodriguez, Ana Maria
Svetaz, Laura Andrea
Zacchino, Susana Alicia Stella
Somlai, Csaba
Csizmadia, Imre Gyula
Penke, Botond
Enriz, Ricardo Daniel
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv ANTIFUNGAL ACTIVITIES
CONFORMATIONAL AND ELECTRONIC STUDY
HIS-PHE-ARG-TRP-NH2
SMALL PEPTIDES
topic ANTIFUNGAL ACTIVITIES
CONFORMATIONAL AND ELECTRONIC STUDY
HIS-PHE-ARG-TRP-NH2
SMALL PEPTIDES
purl_subject.fl_str_mv https://purl.org/becyt/ford/3.1
https://purl.org/becyt/ford/3
dc.description.none.fl_txt_mv The synthesis, in vitro evaluation, and conformational study of His-Phe-Arg-Trp-NH2 and related derivatives acting as antifungal agents are reported. Among them, His-Phe-Arg-Trp-NH2 and His-Tyr-Arg-Trp-NH2 exhibited antifungal activity against Cryptococcus neoformans. Antifungal activity of these compounds appears to be closely related to the α-MSH effect. A conformational and electronic study allows us to propose a biologically relevant conformation for these tetrapeptides acting as antifungal agents. In addition, these theoretical calculations permit us to determine the minimal structural requirements to produce the antifungal response and may provide a guide for the design of compounds with this biological activity.
Fil: Masman, Marcelo Fabricio. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Rodriguez, Ana Maria. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina
Fil: Svetaz, Laura Andrea. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Somlai, Csaba. Szegedi Tudományegyetem; Hungría
Fil: Csizmadia, Imre Gyula. Szegedi Tudományegyetem; Hungría
Fil: Penke, Botond. Szegedi Tudományegyetem; Hungría
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia; Argentina
description The synthesis, in vitro evaluation, and conformational study of His-Phe-Arg-Trp-NH2 and related derivatives acting as antifungal agents are reported. Among them, His-Phe-Arg-Trp-NH2 and His-Tyr-Arg-Trp-NH2 exhibited antifungal activity against Cryptococcus neoformans. Antifungal activity of these compounds appears to be closely related to the α-MSH effect. A conformational and electronic study allows us to propose a biologically relevant conformation for these tetrapeptides acting as antifungal agents. In addition, these theoretical calculations permit us to determine the minimal structural requirements to produce the antifungal response and may provide a guide for the design of compounds with this biological activity.
publishDate 2006
dc.date.none.fl_str_mv 2006-11-15
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/11336/139366
Masman, Marcelo Fabricio; Rodriguez, Ana Maria; Svetaz, Laura Andrea; Zacchino, Susana Alicia Stella; Somlai, Csaba; et al.; Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal properties; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry; 14; 22; 15-11-2006; 7604-7614
0968-0896
CONICET Digital
CONICET
url http://hdl.handle.net/11336/139366
identifier_str_mv Masman, Marcelo Fabricio; Rodriguez, Ana Maria; Svetaz, Laura Andrea; Zacchino, Susana Alicia Stella; Somlai, Csaba; et al.; Synthesis and conformational analysis of His-Phe-Arg-Trp-NH2 and analogues with antifungal properties; Pergamon-Elsevier Science Ltd; Bioorganic & Medicinal Chemistry; 14; 22; 15-11-2006; 7604-7614
0968-0896
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://www.sciencedirect.com/science/article/abs/pii/S0968089606005621
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmc.2006.07.007
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 Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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 13.070432

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