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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/54465
Ver los metadatos del registro completo
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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 Técnicas2025-09-03T09:47:19Zoai: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:34982025-09-03 09:47:19.345CONICET 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 |
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CONICET Digital (CONICET) |
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CONICET Digital (CONICET) |
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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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13.13397 |