Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi

Autores
Leal, P. C.; Mascarello, A.; Derita, Marcos Gabriel; Zuljan, Federico Alberto; Nunes, R. J.; Zacchino, Susana Alicia Stella; Yunes, R. A.
Año de publicación
2009
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The antifungal activity of a complete series of 15 n-alkyl gallates and six analogues acting against a representative panel of opportunistic pathogenic fungi was studied in order to analyze their role in: the importance of the fungi tested, the importance of the hydroxyls, the influence of the chain length and the hydrophobicity of the compounds. It was demonstrated that dermatophytes were the most susceptible species and that hydroxyls appear to be necessary but not sufficient for the activity. When the log P of each gallate was calculated and related to the different values of MIC against Microsporum gypseum it was observed that hexyl, heptyl, octyl and nonyl gallates exhibit a significant positive deviation from the curve corresponding to a polynomial equation obtained for the other gallates. This suggests that these compounds have a further mode of action besides their hydrophobicity, possibly the inhibition of some enzyme involved in ergosterol biosynthesis. © 2009 Elsevier Ltd. All rights reserved.
Fil: Leal, P. C.. Universidade Federal de Santa Catarina; Brasil
Fil: Mascarello, A.. Universidade Federal de Santa Catarina; Brasil
Fil: Derita, Marcos Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Zuljan, Federico Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Nunes, R. J.. Universidade Federal de Santa Catarina; Brasil
Fil: Zacchino, Susana Alicia Stella. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Yunes, R. A.. Universidade Federal de Santa Catarina; Brasil
Materia
Antifungal Activity
Gallates
Lipophilicity
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:11336/54465
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungiLeal, P. C.Mascarello, A.Derita, Marcos GabrielZuljan, Federico AlbertoNunes, R. J.Zacchino, Susana Alicia StellaYunes, R. A.Antifungal ActivityGallatesLipophilicityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The antifungal activity of a complete series of 15 n-alkyl gallates and six analogues acting against a representative panel of opportunistic pathogenic fungi was studied in order to analyze their role in: the importance of the fungi tested, the importance of the hydroxyls, the influence of the chain length and the hydrophobicity of the compounds. It was demonstrated that dermatophytes were the most susceptible species and that hydroxyls appear to be necessary but not sufficient for the activity. When the log P of each gallate was calculated and related to the different values of MIC against Microsporum gypseum it was observed that hexyl, heptyl, octyl and nonyl gallates exhibit a significant positive deviation from the curve corresponding to a polynomial equation obtained for the other gallates. This suggests that these compounds have a further mode of action besides their hydrophobicity, possibly the inhibition of some enzyme involved in ergosterol biosynthesis. © 2009 Elsevier Ltd. All rights reserved.Fil: Leal, P. C.. Universidade Federal de Santa Catarina; BrasilFil: Mascarello, A.. Universidade Federal de Santa Catarina; BrasilFil: Derita, Marcos Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; ArgentinaFil: Zuljan, Federico Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; ArgentinaFil: Nunes, R. J.. Universidade Federal de Santa Catarina; BrasilFil: Zacchino, Susana Alicia Stella. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; ArgentinaFil: Yunes, R. A.. Universidade Federal de Santa Catarina; BrasilPergamon-Elsevier Science Ltd2009-03info: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/11336/54465Leal, P. C.; Mascarello, A.; Derita, Marcos Gabriel; Zuljan, Federico Alberto; Nunes, R. J.; et al.; Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi; Pergamon-Elsevier Science Ltd; Biorganic and Medicinal Chemistry Letters; 19; 6; 3-2009; 1793-17960960-894XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmcl.2009.01.061info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0960894X09000845info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:39:15Zoai:ri.conicet.gov.ar:11336/54465instacron: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 09:39:15.634CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi
title Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi
spellingShingle Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi
Leal, P. C.
Antifungal Activity
Gallates
Lipophilicity
title_short Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi
title_full Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi
title_fullStr Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi
title_full_unstemmed Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi
title_sort Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi
dc.creator.none.fl_str_mv Leal, P. C.
Mascarello, A.
Derita, Marcos Gabriel
Zuljan, Federico Alberto
Nunes, R. J.
Zacchino, Susana Alicia Stella
Yunes, R. A.
author Leal, P. C.
author_facet Leal, P. C.
Mascarello, A.
Derita, Marcos Gabriel
Zuljan, Federico Alberto
Nunes, R. J.
Zacchino, Susana Alicia Stella
Yunes, R. A.
author_role author
author2 Mascarello, A.
Derita, Marcos Gabriel
Zuljan, Federico Alberto
Nunes, R. J.
Zacchino, Susana Alicia Stella
Yunes, R. A.
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Antifungal Activity
Gallates
Lipophilicity
topic Antifungal Activity
Gallates
Lipophilicity
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 antifungal activity of a complete series of 15 n-alkyl gallates and six analogues acting against a representative panel of opportunistic pathogenic fungi was studied in order to analyze their role in: the importance of the fungi tested, the importance of the hydroxyls, the influence of the chain length and the hydrophobicity of the compounds. It was demonstrated that dermatophytes were the most susceptible species and that hydroxyls appear to be necessary but not sufficient for the activity. When the log P of each gallate was calculated and related to the different values of MIC against Microsporum gypseum it was observed that hexyl, heptyl, octyl and nonyl gallates exhibit a significant positive deviation from the curve corresponding to a polynomial equation obtained for the other gallates. This suggests that these compounds have a further mode of action besides their hydrophobicity, possibly the inhibition of some enzyme involved in ergosterol biosynthesis. © 2009 Elsevier Ltd. All rights reserved.
Fil: Leal, P. C.. Universidade Federal de Santa Catarina; Brasil
Fil: Mascarello, A.. Universidade Federal de Santa Catarina; Brasil
Fil: Derita, Marcos Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Zuljan, Federico Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Nunes, R. J.. Universidade Federal de Santa Catarina; Brasil
Fil: Zacchino, Susana Alicia Stella. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Yunes, R. A.. Universidade Federal de Santa Catarina; Brasil
description The antifungal activity of a complete series of 15 n-alkyl gallates and six analogues acting against a representative panel of opportunistic pathogenic fungi was studied in order to analyze their role in: the importance of the fungi tested, the importance of the hydroxyls, the influence of the chain length and the hydrophobicity of the compounds. It was demonstrated that dermatophytes were the most susceptible species and that hydroxyls appear to be necessary but not sufficient for the activity. When the log P of each gallate was calculated and related to the different values of MIC against Microsporum gypseum it was observed that hexyl, heptyl, octyl and nonyl gallates exhibit a significant positive deviation from the curve corresponding to a polynomial equation obtained for the other gallates. This suggests that these compounds have a further mode of action besides their hydrophobicity, possibly the inhibition of some enzyme involved in ergosterol biosynthesis. © 2009 Elsevier Ltd. All rights reserved.
publishDate 2009
dc.date.none.fl_str_mv 2009-03
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/11336/54465
Leal, P. C.; Mascarello, A.; Derita, Marcos Gabriel; Zuljan, Federico Alberto; Nunes, R. J.; et al.; Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi; Pergamon-Elsevier Science Ltd; Biorganic and Medicinal Chemistry Letters; 19; 6; 3-2009; 1793-1796
0960-894X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/54465
identifier_str_mv Leal, P. C.; Mascarello, A.; Derita, Marcos Gabriel; Zuljan, Federico Alberto; Nunes, R. J.; et al.; Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi; Pergamon-Elsevier Science Ltd; Biorganic and Medicinal Chemistry Letters; 19; 6; 3-2009; 1793-1796
0960-894X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmcl.2009.01.061
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0960894X09000845
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 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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