Open Access
Antimicrobial Agents and Chemotherapy, volume 54, issue 12, pages 4961-4970
Binding and Action of CEM-101, a New Fluoroketolide Antibiotic That Inhibits Protein Synthesis
Llano-Sotelo Beatriz
1
,
Dunkle Jack
2
,
Klepacki Dorota
1
,
Zhang Wen
2
,
Fernandes, Prabhavathi
3
,
Cate Jamie H. D.
2, 4
,
Mankin Alexander S
1
1
Center for Pharmaceutical Biotechnology, University of Illinois, Chicago, Illinois 60607
|
2
Departments of Molecular and Cell Biology and Chemistry, University of California at Berkeley, Berkeley, California 94720
|
3
Cempra Pharmaceuticals, 6340 Quadrangle Drive, Suite 100, Chapel Hill, North Carolina 27517
|
Publication type: Journal Article
Publication date: 2010-12-06
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 4.9
ISSN: 00664804, 10986596
PubMed ID:
20855725
Pharmacology
Infectious Diseases
Pharmacology (medical)
Abstract
ABSTRACT We characterized the mechanism of action and the drug-binding site of a novel ketolide, CEM-101, which belongs to the latest class of macrolide antibiotics. CEM-101 shows high affinity for the ribosomes of Gram-negative (Escherichia coli) and Gram-positive (Staphylococcus aureus) bacteria. The ketolide shows high selectivity in its inhibitory action and readily interferes with synthesis of a reporter protein in the bacterial but not eukaryotic cell-free translation system. Binding of CEM-101 to its ribosomal target site was characterized biochemically and by X-ray crystallography. The X-ray structure of CEM-101 in complex with the E. coli ribosome shows that the drug binds in the major macrolide site in the upper part of the ribosomal exit tunnel. The lactone ring of the drug forms hydrophobic interactions with the walls of the tunnel, the desosamine sugar projects toward the peptidyl transferase center and interacts with the A2058/A2509 cleft, and the extended alkyl-aryl arm of the drug is oriented down the tunnel and makes contact with a base pair formed by A752 and U2609 of the 23S rRNA. The position of the CEM-101 alkyl-aryl extended arm differs from that reported for the side chain of the ketolide telithromycin complexed with either bacterial (Deinococcus radiodurans) or archaeal (Haloarcula marismortui) large ribosomal subunits but closely matches the position of the side chain of telithromycin complexed to the E. coli ribosome. A difference in the chemical structure of the side chain of CEM-101 in comparison with the side chain of telithromycin and the presence of the fluorine atom at position 2 of the lactone ring likely account for the superior activity of CEM-101. The results of chemical probing suggest that the orientation of the CEM-101 extended side chain observed in the E. coli ribosome closely resembles its placement in Staphylococcus aureus ribosomes and thus likely accurately reflects interaction of CEM-101 with the ribosomes of the pathogenic bacterial targets of the drug. Chemical probing further demonstrated weak binding of CEM-101, but not of erythromycin, to the ribosome dimethylated at A2058 by the action of Erm methyltransferase.
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5
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5
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Llano-Sotelo B. et al. Binding and Action of CEM-101, a New Fluoroketolide Antibiotic That Inhibits Protein Synthesis // Antimicrobial Agents and Chemotherapy. 2010. Vol. 54. No. 12. pp. 4961-4970.
GOST all authors (up to 50)
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Llano-Sotelo B., Dunkle J., Klepacki D., Zhang W., Fernandes, P., Cate J. H. D., Mankin A. S. Binding and Action of CEM-101, a New Fluoroketolide Antibiotic That Inhibits Protein Synthesis // Antimicrobial Agents and Chemotherapy. 2010. Vol. 54. No. 12. pp. 4961-4970.
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RIS
Copy
TY - JOUR
DO - 10.1128/AAC.00860-10
UR - https://doi.org/10.1128%2FAAC.00860-10
TI - Binding and Action of CEM-101, a New Fluoroketolide Antibiotic That Inhibits Protein Synthesis
T2 - Antimicrobial Agents and Chemotherapy
AU - Llano-Sotelo, Beatriz
AU - Dunkle, Jack
AU - Klepacki, Dorota
AU - Zhang, Wen
AU - Fernandes,, Prabhavathi
AU - Cate, Jamie H. D.
AU - Mankin, Alexander S
PY - 2010
DA - 2010/12/06 00:00:00
PB - American Society for Microbiology
SP - 4961-4970
IS - 12
VL - 54
PMID - 20855725
SN - 0066-4804
SN - 1098-6596
ER -
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@article{2010_Llano-Sotelo,
author = {Beatriz Llano-Sotelo and Jack Dunkle and Dorota Klepacki and Wen Zhang and Prabhavathi Fernandes, and Jamie H. D. Cate and Alexander S Mankin},
title = {Binding and Action of CEM-101, a New Fluoroketolide Antibiotic That Inhibits Protein Synthesis},
journal = {Antimicrobial Agents and Chemotherapy},
year = {2010},
volume = {54},
publisher = {American Society for Microbiology},
month = {dec},
url = {https://doi.org/10.1128%2FAAC.00860-10},
number = {12},
pages = {4961--4970},
doi = {10.1128/AAC.00860-10}
}
Cite this
MLA
Copy
Llano-Sotelo, Beatriz, et al. “Binding and Action of CEM-101, a New Fluoroketolide Antibiotic That Inhibits Protein Synthesis.” Antimicrobial Agents and Chemotherapy, vol. 54, no. 12, Dec. 2010, pp. 4961-4970. https://doi.org/10.1128%2FAAC.00860-10.