The carolactam strategy is ineffective: synthesis and biological evaluation of carolactam
| العنوان: | The carolactam strategy is ineffective: synthesis and biological evaluation of carolactam |
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| المؤلفون: | Nico S. Stumpp, Thomas Schmidt, Jonas Ammermann, Jannik Donner, Meike Stiesch, Irene Wagner-Döbler, Andreas Kirschning, Michael Reck, Marly Dalton |
| المصدر: | Org. Biomol. Chem.. 15:8553-8558 |
| بيانات النشر: | Royal Society of Chemistry (RSC), 2017. |
| سنة النشر: | 2017 |
| مصطلحات موضوعية: | Molecular Conformation, Microbial Sensitivity Tests, Secondary metabolite, 010402 general chemistry, medicine.disease_cause, 01 natural sciences, Biochemistry, Microbiology, Streptococcus mutans, Structure-Activity Relationship, chemistry.chemical_compound, Streptococcus pneumoniae, medicine, Physical and Theoretical Chemistry, Sorangium cellulosum, Dose-Response Relationship, Drug, biology, 010405 organic chemistry, Organic Chemistry, Biofilm, Biological activity, biology.organism_classification, Anti-Bacterial Agents, 0104 chemical sciences, chemistry, Biofilms, Lactam, Macrolides, Bacteria, medicine.drug |
| الوصف: | 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 and Streptococcus pneumoniae. It is known that macrolactam derivatives can show improved pharmacological properties compared to the corresponding macrolactons (lactam strategy). Therefore, we here report the total synthesis and biological activity of the lactam derivative of carolacton ("carolactam"). Carolactam was inactive against planktonic cultures of S. pneumoniae and caused damage of S. mutans biofilms at high concentrations only (above 10 μM). Preliminary modeling studies indicate substantial conformational differences between carolacton and carolactam. |
| تدمد: | 1477-0539 1477-0520 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::86ba7bf5c74f4b4e6271cd88a3280246 https://doi.org/10.1039/c7ob02060k |
| رقم الأكسشن: | edsair.doi.dedup.....86ba7bf5c74f4b4e6271cd88a3280246 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 14770539 14770520 |
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