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dc.creatorJovanović, Miloš
dc.creatorRadivojević, Jelena
dc.creatorO'Connor, Kevin
dc.creatorBlagojević, Stevan
dc.creatorBegović, Biljana
dc.creatorLukić, Vera
dc.creatorNikodinović-Runić, Jasmina
dc.creatorSavić, Vladimir
dc.date.accessioned2019-09-02T12:10:54Z
dc.date.available2019-09-02T12:10:54Z
dc.date.issued2019
dc.identifier.issn0045-2068
dc.identifier.urihttp://farfar.pharmacy.bg.ac.rs/handle/123456789/3335
dc.description.abstractRhamnolipids are biodegradable low toxic biosurfactants which exert antimicrobial and anti-biofilm properties. They have attracted much attention recently due to potential applications in areas of bioremediation, therapeutics, cosmetics and agriculture, however, the full potential of these versatile molecules is yet to be explored. Based on the facts that many naturally occurring lipopeptides are potent antimicrobials, our study aimed to explore the potential of replacing rhamnose in rhamnolipids with amino acids thus creating lipopeptides that would mimic or enhance properties of the parent molecule. This would allow not only for more economical and greener production but also, due to the availability of structurally different amino acids, facile manipulation of physico-chemical and biological properties. Our synthetic efforts produced a library of 43 lipopeptides revealing biologically more potent molecules. The structural changes significantly increased, in particular, anti-biofilm properties against Candida albicans, although surface activity of the parent molecule was almost completely abolished. Our findings show that the most active compounds are leucine derivatives of 3-hydroxy acids containing benzylic ester functionality. The SAR study demonstrated a further increase in activity with aliphatic chain elongation. The most promising lipopeptides 15, 23 and 36 at 12.5 mu g/mL concentration allowed only 14.3%, 5.1% and 11.2% of biofilm formation, respectively after 24 h. These compounds inhibit biofilm formation by preventing adhesion of C. albicans to abiotic and biotic surfaces.en
dc.publisherAcademic Press Inc Elsevier Science, San Diego
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172009/RS//
dc.rightsrestrictedAccess
dc.sourceBioorganic Chemistry
dc.subjectAdhesionen
dc.subjectBiofilmen
dc.subjectCandida albicansen
dc.subjectLipopeptidesen
dc.subjectRhamnolipidsen
dc.titleRhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicansen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractБлагојевић, Стеван; Лукић, Вера; Никодиновић-Рунић, Јасмина; Радивојевић, Јелена; О'Цоннор, Кевин; Савић, Владимир; Беговић, Биљана; Јовановић, Милош;
dc.citation.volume87
dc.citation.spage209
dc.citation.epage217
dc.citation.other87: 209-217
dc.citation.rankM21
dc.identifier.wos000469026400023
dc.identifier.doi10.1016/j.bioorg.2019.03.023
dc.identifier.pmid30901676
dc.identifier.scopus2-s2.0-85063032776
dc.identifier.rcubconv_4387
dc.type.versionpublishedVersion


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