Vitamin E-poly(2-oxazolin)-ciprofloxacin conjugates that enter bacterial cells via their efflux pumps

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dc.contributor.authorRomanovska, Alina
dc.contributor.authorTophoven, Jonas
dc.contributor.authorBrandt, Volker
dc.contributor.authorBreisch, Marina
dc.contributor.authorTiller, Joerg C.
dc.date.accessioned2025-09-08T13:27:58Z
dc.date.available2025-09-08T13:27:58Z
dc.date.issued2024-08-26
dc.description.abstractRendering established antibiotics by derivatization or formulation is a promising way to quickly obtain higher active antibiotics and to address antibiotic resistant bacterial strains. The antibiotic ciprofloxacin (CIP) conjugated with amphiphilic blockcopoly(2-oxazoline)s (POx) shows greatly enhanced antimicrobial activity, reduces resistance formation, and is active against CIP-resistant bacterial cells with overexpressed efflux pumps. In order to design CIP conjugates with comparable performance, but higher biocompatibility, the hydrophobic POx-block was substituted by a modified α-Tocopherol (VitE), which is predominantly referred to as vitamin E. Modification of VitE with 4-bromomethylbenzoyl bromide leads to a highly active initiator for POx synthesis. Using this initiator for the living cationic polymerization of 2-methyl-2-oxazoline leads to fully end-group functionalized PMOx. Conjugation of these polymers with CIP results in non-cytotoxic conjugates with improved CIP activity. These VitE-PMOx-EDA-xCIP conjugates enter E. coli cells via their efflux pumps. In case of E. coli with overexpressed efflux pumps (typical for resistant bacteria), the molar activity of the novel CIP conjugates is up to 100 times higher than free CIP, indicating potential of polymer conjugation with antibiotics to overcome bacterial resistances.en
dc.identifier.urihttp://hdl.handle.net/2003/43941
dc.language.isoen
dc.relation.ispartofseriesJournal of bioactive and compatible polymers; 39(6)
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subjectα-Tocopherolen
dc.subjectPoly(2-oxazolines)en
dc.subjectPolymer initiatoren
dc.subjectLiving polymerizationen
dc.subjectCiprofloxacinen
dc.subjectBacterial resistancesen
dc.subjectEfflux pumpsen
dc.subject.ddc660
dc.titleVitamin E-poly(2-oxazolin)-ciprofloxacin conjugates that enter bacterial cells via their efflux pumpsen
dc.typeText
dc.type.publicationtypeResearchArticle
dcterms.accessRightsopen access
eldorado.doi.registerfalse
eldorado.secondarypublicationtrue
eldorado.secondarypublication.primarycitationRomanovska A, Tophoven J, Brandt V, Breisch M, Tiller JC. Vitamin E-poly(2-oxazolin)-ciprofloxacin conjugates that enter bacterial cells via their efflux pumps. Journal of Bioactive and Compatible Polymers. 2024;39(6):536-550. doi:10.1177/08839115241267807
eldorado.secondarypublication.primaryidentifierhttps://doi.org/10.1177/08839115241267807

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