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dc.contributor.authorNocedo Mena, Deyani
dc.contributor.authorArrasate Gil, Sonia
dc.contributor.authorGarza González, Elvira
dc.contributor.authorRivas Galindo, Verónica M.
dc.contributor.authorRomo-Mancillas, Antonio
dc.contributor.authorMunteanu, Cristian R.
dc.contributor.authorSotomayor Anduiza, María Nuria
dc.contributor.authorLete Expósito, María Esther
dc.contributor.authorBarbolla Cuadrado, Iratxe
dc.contributor.authorMartín Plágaro, César Augusto
dc.contributor.authorCamacho Corona, María del Rayo
dc.date.accessioned2023-11-24T12:36:29Z
dc.date.available2023-11-24T12:36:29Z
dc.date.issued2021-02-18
dc.identifier.citationBioorganic Chemistry 109 : (2021) // 104745es_ES
dc.identifier.issn0045-2068
dc.identifier.issn1090-2120
dc.identifier.urihttp://hdl.handle.net/10810/63146
dc.description.abstractThe developing of antibacterial resistance is becoming in crisis. In this sense, natural products play a fundamental role in the discovery of antibacterial agents with diverse mechanisms of action. Phytochemical investigation of Cissus incisa leaves led to isolation and characterization of the ceramides mixture (1): (8E)-2-(tritriacont-9-enoyl amino)-1,3,4-octadecanetriol-8-ene (1-I); (8E)-2-(2´,3´-dihydroxyoctacosanoyl amino)- 1,3,4-octadecanetriol-8-ene (1-II); (8E)-2-(2´-hydroxyheptacosanoyl amino)-1,3,4- octadecanetriol-8-ene (1-III); and (8E)-2-(-2´-hydroxynonacosanoyl amino)-1,3,4- octadecanetriol-8-ene (1-IV). Until now, this is the first report of the ceramides (1-I), (1-II), and (1-III). The structures were elucidated using NMR and mass spectrometry analyses. Antibacterial activity of ceramides (1) and acetylated derivates (2) was evaluated against nine multidrug-resistant bacteria by Microdilution method. (1) showed the best results against Gram-negatives, mainly against carbapenems-resistant Acinetobacter baumannii with MIC=50 μg/mL. Structure-activity analysis and molecular docking revealed interactions between plant ceramides with membrane proteins, and enzymes associated with biological membranes of Gram-negative bacteria, through hydrogen bonding of functional groups. Vesicular contents release assay showed the capacity of (1) to disturb membrane permeability detected by an increase of fluorescence probe over time. The membrane disruption is not caused for ceramides lytic action on cell membranes, according in vitro hemolytic activity results. Combining SAR analysis, bioinformatics and biophysical techniques, and also experimental tests, it was possible to explain the antibacterial action of these natural ceramides.es_ES
dc.description.sponsorshipMinisterio de Economía y Competitividad (CTQ2016-74881-P) // Gobierno Vasco (IT1045-16)es_ES
dc.language.isoenges_ES
dc.publisherElsevieres_ES
dc.relationinfo:eu-repo/grantAgreement/MINECO/CTQ2016-74881-Pes_ES
dc.rightsinfo:eu-repo/semantics/openAccesses_ES
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/es/*
dc.subjectceramidees_ES
dc.subjectantibacterial activityes_ES
dc.subjectmolecular dockinges_ES
dc.subjectAcinetobacter baumanniies_ES
dc.subjectCissus incisaes_ES
dc.subjectvesicular contents assayes_ES
dc.titleMolecular docking, SAR analysis and biophysical approaches in the study of the antibacterial activity of ceramides isolated from Cissus incisaes_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.rights.holderAtribución-NoComercial-SinDerivadas 3.0 Españaes_ES
dc.relation.publisherversionhttps://www.sciencedirect.com/science/article/pii/S004520682100122Xes_ES
dc.relation.publisherversionhttps://doi.org/10.1016/j.bioorg.2021.104745es_ES
dc.departamentoesQuímica orgánica IIes_ES
dc.departamentoeuKimika organikoa IIes_ES


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