Synthesis of new carolacton derivatives and their activity against biofilms of oral bacteria

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dc.identifier.uri Stumpp, Nico Premnath, P. Schmidt, T. Ammermann, J. Draeger, Gerald Reck, M. Jansen, R. Stiesch, Meike Wagner-Döbler, Irene Kirschning, Andreas 2015-12-08T13:08:05Z 2016-04-13T22:05:36Z 2015-04-13
dc.identifier.citation Stumpp, N.; Premnath, P.; Schmidt, T.; Ammermann, J.; Draeger, G.; Reck, M.; Jansen, R.; Stiesch, M.; Wagner-Doebler, I.; Kirschning, A.: Synthesis of new carolacton derivatives and their activity against biofilms of oral bacteria. In: Organic & Biomolecular Chemistry 13 (2015), Nr. 20, S. 5765-5774. DOI:
dc.description.abstract Carolacton, a secondary metabolite isolated from the extracts of Sorangium cellulosum, causes membrane damage and cell death in biofilms of the caries- and endocarditis-associated bacterium Streptococcus mutans. Here, we report the total synthesis of several derivatives of carolacton. All new structural modifications introduced abolished its biological activity, including subtle ones, such as inversion of configuration at C9. However, a bicyclic bislactone derivative as well as the methyl ester of carolacton resulted in compounds with prodrug properties. Their inhibitory activity on S. mutans was proven to be based on enzymatic hydrolysis by S. mutans which provided native carolacton resulting in biofilm damage in vivo. Moreover, we demonstrate that carolacton acts also on S. gordonii, S. oralis and the periodontitis pathogen Aggregatibacter actinomycetemcomitans, causing elongated cells and growth inhibition. eng
dc.description.sponsorship ministry of Lower Saxony
dc.description.sponsorship Volkswagen Stiftung
dc.description.sponsorship BMBF/e:bio/ 031 A299
dc.language.iso eng eng
dc.publisher Cambridge : Royal Society of Chemistry
dc.relation.ispartofseries Organic & Biomolecular Chemistry 13 (2015), Nr. 20
dc.rights Es gilt deutsches Urheberrecht. Das Dokument darf zum eigenen Gebrauch kostenfrei genutzt, aber nicht im Internet bereitgestellt oder an Außenstehende weitergegeben werden. Dieser Beitrag ist aufgrund einer (DFG-geförderten) Allianz- bzw. Nationallizenz frei zugänglich.
dc.subject streptococcus-mutans eng
dc.subject pseudomonas-aeruginosa eng
dc.subject inhibitor eng
dc.subject disease eng
dc.subject host eng
dc.subject.ddc 540 | Chemie ger
dc.title Synthesis of new carolacton derivatives and their activity against biofilms of oral bacteria eng
dc.type Article
dc.type Text
dc.relation.essn 1477-0539
dc.relation.issn 1477-0520
dc.bibliographicCitation.issue 20
dc.bibliographicCitation.volume 13
dc.bibliographicCitation.firstPage 5765
dc.bibliographicCitation.lastPage 5774
dc.description.version publishedVersion
tib.accessRights frei zug�nglich

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