Dental composite materials containing carolacton inhibit biofilm growth of Streptococcus mutans

Apel, Christian; Barg, Andree; Rheinberg, Anke; Conrads, Georg; Wagner‐Döbler, Irene

doi:10.1016/j.dental.2013.09.005

Cited by 33 publications

(29 citation statements)

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“…The small amounts of carolacton needed did not impact the mechanical properties of the material. 22 Here, we found another possibility to control the release of carolacton to the microorganisms: Remarkably, ester derivatives 5 and 7 that lack the free carboxylate group still show biofilm inhibitory activity in a similar range as carolacton 1. As demonstrated in this report for bislactone 7 and methylester 5 the activity is due to hydrolysis of the lactone ring attached to C-18 by bacterial enzymes and in both cases carolacton 1 is formed.…”

Section: Localized Releasementioning

confidence: 96%

“…21 The synthesis of advanced intermediates 8 and 9 and derivatives 11a,b and 12 are described in ref. 22 …”

Section: Methodsmentioning

confidence: 99%

“…19,20 In particular, biofilms containing the caries-and endocarditis-associated bacterium S. mutans are sensitive to this compound. 19,21,22 Our first report on carolacton 1 as well as its first total synthesis 23 covered and proved its structure including the assignment of all stereogenic centers. Carolacton 1 features a polyketide-type backbone which forms a 12-membered macrolactone with a 1,2-diol moiety with trans orientation in the open-chain conformation.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2015

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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.

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Section: Localized Releasementioning

confidence: 96%

“…21 The synthesis of advanced intermediates 8 and 9 and derivatives 11a,b and 12 are described in ref. 22 …”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2015

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“…Focusing on the prevention of S. mutans biofilm formation, the antimicrobiological effect of Carolacton incorporated into composite materials has previously been reported [Apel et al, 2013]. Carolacton is a secondary metabolite produced by the myxobacterium Sorangium cellulosum and causes membrane damage and cell death of S. mutans bacteria growing under acidic conditions [Kunze et al, 2010].…”

Section: Introductionmentioning

confidence: 99%

“…Carolacton is a secondary metabolite produced by the myxobacterium Sorangium cellulosum and causes membrane damage and cell death of S. mutans bacteria growing under acidic conditions [Kunze et al, 2010]. The Carolacton molecule seems to be active at very small concentrations (10 nM) [Kunze et al, 2010] which may not influence the mechanical properties of composite restorations [Apel et al, 2013].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Restorative Materials Containing Preventive Additives in a Secondary Caries Model in vitro

et al. 2019

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The incorporation of antibacterial agents into dental restorative materials is a promising strategy for secondary caries prevention. Previously, Carolacton affected Streptococcus mutans biofilm formation on composite materials in vitro. The present study evaluated secondary caries formation adjacent to Carolacton-containing composites and conventional restorative materials using an artificial biofilm model. Standardized cavities were prepared in bovine dentin-enamel samples (n = 175) and restored with various dental materials (Tetric EvoCeram [T], GrandioSo composite without [G] and with Carolacton [GC], Grandio Flow without [F] and with Carolacton [FC], GrandioSo containing sodium fluoride [GNaF], and Ketac Fil [K]). After artificial aging, S. mutans was grown on the samples for 7 days. The investigation of gap sizes and secondary caries formation was performed using confocal laser scanning microscopy and transversal microradiography. Median gap size in enamel was 9.4 µm (interquartile range 7.9–12.7). Compared to all other groups significant differences in gap sizes could be observed for Ketac Fil (p < 0.001; Mann-Whitney test). Only GrandioSo composite containing 30% sodium fluoride and Ketac Fil showed significantly smaller lesion areas in enamel (p < 0.001; Mann-Whitney test) than all other groups which was confirmed by the mineral loss data (p < 0.001; Mann-Whitney test). Based on the present in vitro results, it seems that Carolacton-containing composite in the current formulation within the shown simplified monoculture biofilm model is not able to prevent caries formation compared to fluoride-releasing restorative materials.

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Considerations for Designing Next-Generation Composite Dental Materials

Pfeifer

Kreth

Koley

et al. 2021

Oral Biofilms and Modern Dental Materials

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Dental composite materials containing carolacton inhibit biofilm growth of Streptococcus mutans

Cited by 33 publications

References 33 publications

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

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

Evaluation of Restorative Materials Containing Preventive Additives in a Secondary Caries Model in vitro

Considerations for Designing Next-Generation Composite Dental Materials

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