Antifungal activity of eugenol analogues. Influence of different substituents and studies on mechanism of action

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dc.contributor.authorCarrasco, Héctor
dc.contributor.authorRaimondi, Marcela
dc.contributor.authorSvetaz, Laura
dc.contributor.authorDi Liberto, Melina
dc.contributor.authorRodriguez, María V.
dc.contributor.authorEspinoza, Luis
dc.contributor.authorMadrid, Alejandro
dc.contributor.authorZacchino, Susana
dc.date.accessioned2023-07-20T16:37:29Z
dc.date.available2023-07-20T16:37:29Z
dc.date.issued2012-01
dc.descriptionIndexación: Scopuses
dc.description.abstractTwenty one phenylpropanoids (including eugenol and safrole) and synthetic analogues, thirteen of them new compounds, were evaluated for antifungal properties, first with non-targeted assays against a panel of human opportunistic pathogenic fungi. Some structure-activity relationships could be observed, mainly related to the influence of an allyl substituent at C-4, an OH group at C-1 and an OCH 3 at C-2 or the presence of one or two NO2 groups in different positions of the benzene ring. All active compounds were tested in a second panel of clinical isolates of C. albicans and non-albicans Candida spp., Cryptococcus neoformans and dermatophytes. The eugenol derivative 4-allyl-2-methoxy- 5-nitrophenol (2) was the most active structure against all strains tested, and therefore it was submitted to targeted assays. These studies showed that the antifungal activity of 2 was not reversed in the presence of an osmotic support such as sorbitol, suggesting that it does not act by inhibiting the fungal cell wall synthesis or assembly. On the other hand, the Ergosterol Assay showed that 2 did not bind to the main sterol of the fungal membrane up to 250 μg mL -1. In contrast, a 22% of fungal membrane damage was observed at concentrations = 1 × MIC and 71% at 4× MIC, when 2 was tested in the Cellular Leakage assay. The comparison of log P and MICs for all compounds revealed that the antifungal activity of the eugenol analogues would not to be related to lipophilicity. © 2012 by the authors.es
dc.description.urihttps://www.mdpi.com/1420-3049/17/1/1002
dc.identifier.citationMolecules Volume 17, Issue 1, Pages 1002 - 1024January 2012es
dc.identifier.doi10.3390/molecules17011002
dc.identifier.issn1420-3049
dc.identifier.urihttps://repositorio.unab.cl/xmlui/handle/ria/51842
dc.language.isoenes
dc.publisherMDPIes
dc.rights.licenseAttribution 3.0 Unported (CC BY 3.0)
dc.rights.urihttps://creativecommons.org/licenses/by/3.0/
dc.subjectAntifungal activityes
dc.subjectEugenol derivativeses
dc.subjectLipophilicityes
dc.subjectMechanism of antifungal actiones
dc.subjectSARes
dc.titleAntifungal activity of eugenol analogues. Influence of different substituents and studies on mechanism of actiones
dc.typeArtículoes
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