Modelling the anti-methicillin-resistant staphylococcus aureus (MRSA) activity of cannabinoids: a QSAR and Docking study

dc.creatorEliceo Cortes, Eliceo
dc.creatorMora, José
dc.creatorMárquez, Edgar
dc.date2020-10-27T22:44:53Z
dc.date2020-10-27T22:44:53Z
dc.date2020-08-11
dc.date.accessioned2023-10-03T20:07:21Z
dc.date.available2023-10-03T20:07:21Z
dc.identifier2073-4352
dc.identifierhttps://hdl.handle.net/11323/7177
dc.identifierdoi:10.3390/cryst10080692
dc.identifierCorporación Universidad de la Costa
dc.identifierREDICUC - Repositorio CUC
dc.identifierhttps://repositorio.cuc.edu.co/
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/9174370
dc.descriptionTwenty-four cannabinoids active against MRSA SA1199B and XU212 were optimized at WB97XD/6-31G(d,p), and several molecular descriptors were obtained. Using a multiple linear regression method, several mathematical models with statistical significance were obtained. The robustness of the models was validated, employing the leave-one-out cross-validation and Y-scrambling methods. The entire data set was docked against penicillin-binding protein, iso-tyrosyl tRNA synthetase, and DNA gyrase. The most active cannabinoids had high affinity to penicillin-binding protein (PBP), whereas the least active compounds had low affinities for all of the targets. Among the cannabinoid compounds, Cannabinoid 2 was highlighted due to its suitable combination of both antimicrobial activity and higher scoring values against the selected target; therefore, its docking performance was compared to that of oxacillin, a commercial PBP inhibitor. The 2D figures reveal that both compounds hit the protein in the active site with a similar type of molecular interaction, where the hydroxyl groups in the aromatic ring of cannabinoids play a pivotal role in the biological activity. These results provide some evidence that the anti-Staphylococcus aureus activity of these cannabinoids may be related to the inhibition of the PBP protein; besides, the robustness of the models along with the docking and Quantitative Structure–Activity Relationship (QSAR) results allow the proposal of three new compounds; the predicted activity combined with the scoring values against PBP should encourage future synthesis and experimental testing.
dc.formatapplication/pdf
dc.languageeng
dc.publisherCorporación Universidad de la Costa
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dc.rightsCC0 1.0 Universal
dc.rightshttp://creativecommons.org/publicdomain/zero/1.0/
dc.rightsinfo:eu-repo/semantics/openAccess
dc.rightshttp://purl.org/coar/access_right/c_abf2
dc.sourcecrystals
dc.sourcehttps://www.mdpi.com/2073-4352/10/8/692
dc.subjectCannabinoids
dc.subjectAnti-MRSA
dc.subjectQSAR
dc.subjectMolecular docking
dc.subjectDFT
dc.titleModelling the anti-methicillin-resistant staphylococcus aureus (MRSA) activity of cannabinoids: a QSAR and Docking study
dc.typeArtículo de revista
dc.typehttp://purl.org/coar/resource_type/c_6501
dc.typeText
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:eu-repo/semantics/publishedVersion
dc.typehttp://purl.org/redcol/resource_type/ART
dc.typeinfo:eu-repo/semantics/acceptedVersion
dc.typehttp://purl.org/coar/version/c_ab4af688f83e57aa


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