Synthesis of new carolacton derivatives and their activity against biofilms of oral bacteria.
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AbstractCarolacton, 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.
CitationSynthesis of new carolacton derivatives and their activity against biofilms of oral bacteria. 2015, 13 (20):5765-74 Org. Biomol. Chem.
AffiliationHelmholtz Centre for infection research, Inhoffenstr. 7, D-38124 Braunschweig, Germany
JournalOrganic & biomolecular chemistry
The following license files are associated with this item:
- Damage of Streptococcus mutans biofilms by carolacton, a secondary metabolite from the myxobacterium Sorangium cellulosum.
- Authors: Kunze B, Reck M, Dötsch A, Lemme A, Schummer D, Irschik H, Steinmetz H, Wagner-Döbler I
- Issue date: 2010 Jul 26
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- Two-dimensional gel-based proteomic of the caries causative bacterium Streptococcus mutans UA159 and insight into the inhibitory effect of carolacton.
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- Issue date: 2011 Oct
- The biofilm inhibitor Carolacton inhibits planktonic growth of virulent pneumococci via a conserved target.
- Authors: Donner J, Reck M, Bergmann S, Kirschning A, Müller R, Wagner-Döbler I
- Issue date: 2016 Jul 11