Details
| Original language | English |
|---|---|
| Pages (from-to) | 8553-8558 |
| Number of pages | 6 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 15 |
| Issue number | 40 |
| Publication status | Published - 2017 |
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 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.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic and Biomolecular Chemistry, Vol. 15, No. 40, 2017, p. 8553-8558.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - The carolactam strategy is ineffective
T2 - Synthesis and biological evaluation of carolactam
AU - Ammermann, Jonas
AU - Schmidt, Thomas
AU - Donner, Jannik
AU - Reck, Michael
AU - Dalton, Marly
AU - Stumpp, Nico
AU - Stiesch, Meike
AU - Wagner-Döbler, Irene
AU - Kirschning, Andreas
N1 - Funding information: This work has been carried out as an integral part of the BIOFABRICATION FOR NIFE Initiative, which is financially supported by the ministry of Lower Saxony and the Volkswagen Stiftung (NIFE is the Lower Saxony Center for Biomedical Engineering, Implant Research and Development, a joint translational research center of the Hannover Medical School, the Leibniz University Hannover, the University of Veterinary Medicine Hannover and the Laser Center Hannover).
PY - 2017
Y1 - 2017
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85031914197&partnerID=8YFLogxK
U2 - 10.1039/c7ob02060k
DO - 10.1039/c7ob02060k
M3 - Article
C2 - 28972613
AN - SCOPUS:85031914197
VL - 15
SP - 8553
EP - 8558
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 40
ER -