Journal of Molecular Biology, volume 430, issue 6, pages 842-852
Binding and Action of Amino Acid Analogs of Chloramphenicol upon the Bacterial Ribosome
Tereshchenkov Andrey G
1, 2, 3
,
Sumbatyan Natalia V
1, 2, 3
,
Sergiev Petr V.
,
Stavrianidi Andrey
1, 2, 3
,
Osterman Ilya A.
,
Konevega Andrey L.
4, 5
,
Sergeeva Vasilina A
1, 2, 3
,
Polikanov Yury S
6, 7
,
Kasatsky Pavel
,
Mankin Alexander S
,
Dobosz Bartoszek Malgorzata
8
,
Marks James
7, 9
,
Rodin Igor A
,
Osterman Ilya A
10, 11
,
Kasatsky Pavel
12
,
Komarova Ekaterina S
13, 14
,
RODIN Igor
1, 2, 3
,
Sergiev Petr V.
10, 11
,
Mankin Alexander S.
7, 9
,
Bogdanov Alexey A.
1, 2, 3
2
Moscow 119992 Russia
|
5
6
Department of Biological Sciences, University of Illinois at Chicago, Chicago, IL 60607, USA
|
7
Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, Chicago, IL 60607, USA.
|
8
Dept. of Biological Sciences, Univ. of Illinois at Chicago, Chicago, IL 60607, USA.
|
9
Center for Biomolecular Sciences, University of Illinois, Chicago, IL 60607, USA
|
12
Publication type: Journal Article
Publication date: 2018-03-01
Journal:
Journal of Molecular Biology
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 5.6
ISSN: 00222836, 10898638
PubMed ID:
29410130
Molecular Biology
Structural Biology
Abstract
Antibiotic chloramphenicol (CHL) binds with a moderate affinity at the peptidyl transferase center of the bacterial ribosome and inhibits peptide bond formation. As an approach for modifying and potentially improving properties of this inhibitor, we explored ribosome binding and inhibitory activity of a number of amino acid analogs of CHL. The L-histidyl analog binds to the ribosome with the affinity exceeding that of CHL by 10 fold. Several of the newly synthesized analogs were able to inhibit protein synthesis and exhibited the mode of action that was distinct from the action of CHL. However, the inhibitory properties of the semi-synthetic CHL analogs did not correlate with their affinity and in general, the amino acid analogs of CHL were less active inhibitors of translation in comparison with the original antibiotic. The X-ray crystal structures of the Thermus thermophilus 70S ribosome in complex with three semi-synthetic analogs showed that CHL derivatives bind at the peptidyl transferase center, where the aminoacyl moiety of the tested compounds established idiosyncratic interactions with rRNA. Although still fairly inefficient inhibitors of translation, the synthesized compounds represent promising chemical scaffolds that target the peptidyl transferase center of the ribosome and potentially are suitable for further exploration.
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Tereshchenkov A. G. et al. Binding and Action of Amino Acid Analogs of Chloramphenicol upon the Bacterial Ribosome // Journal of Molecular Biology. 2018. Vol. 430. No. 6. pp. 842-852.
GOST all authors (up to 50)
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Dobosz Bartoszek M., Polikanov Y. S., Bogdanov A. A., Mankin A. S., Sumbatyan N. V., Sergiev P. V., Konevega A. L., Rodin I. A., Stavrianidi A., Komarova E. S., Kasatsky P., Sergeeva V. A., Marks J., Osterman I. A., Tereshchenkov A. G., Osterman I. A., Kasatsky P., Komarova E. S., RODIN I., Sergiev P. V., Mankin A. S., Bogdanov A. A. Binding and Action of Amino Acid Analogs of Chloramphenicol upon the Bacterial Ribosome // Journal of Molecular Biology. 2018. Vol. 430. No. 6. pp. 842-852.
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TY - JOUR
DO - 10.1016/j.jmb.2018.01.016
UR - https://doi.org/10.1016%2Fj.jmb.2018.01.016
TI - Binding and Action of Amino Acid Analogs of Chloramphenicol upon the Bacterial Ribosome
T2 - Journal of Molecular Biology
AU - Tereshchenkov, Andrey G
AU - Dobosz Bartoszek, Malgorzata
AU - Osterman, Ilya A.
AU - Marks, James
AU - Sergeeva, Vasilina A
AU - Kasatsky, Pavel
AU - Komarova, Ekaterina S.
AU - Stavrianidi, Andrey
AU - Rodin, Igor A
AU - Konevega, Andrey L.
AU - Sergiev, Petr V.
AU - Sumbatyan, Natalia V
AU - Mankin, Alexander S
AU - Bogdanov, Alexey A.
AU - Polikanov, Yury S
AU - Osterman, Ilya A
AU - Kasatsky, Pavel
AU - Komarova, Ekaterina S
AU - RODIN, Igor
AU - Sergiev, Petr V.
AU - Mankin, Alexander S.
AU - Bogdanov, Alexey A.
PY - 2018
DA - 2018/03/01 00:00:00
PB - Elsevier
SP - 842-852
IS - 6
VL - 430
PMID - 29410130
SN - 0022-2836
SN - 1089-8638
ER -
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@article{2018_Tereshchenkov,
author = {Andrey G Tereshchenkov and Malgorzata Dobosz Bartoszek and Ilya A. Osterman and James Marks and Vasilina A Sergeeva and Pavel Kasatsky and Ekaterina S. Komarova and Andrey Stavrianidi and Igor A Rodin and Andrey L. Konevega and Petr V. Sergiev and Natalia V Sumbatyan and Alexander S Mankin and Alexey A. Bogdanov and Yury S Polikanov and Ilya A Osterman and Pavel Kasatsky and Ekaterina S Komarova and Igor RODIN and Petr V. Sergiev and Alexander S. Mankin and Alexey A. Bogdanov},
title = {Binding and Action of Amino Acid Analogs of Chloramphenicol upon the Bacterial Ribosome},
journal = {Journal of Molecular Biology},
year = {2018},
volume = {430},
publisher = {Elsevier},
month = {mar},
url = {https://doi.org/10.1016%2Fj.jmb.2018.01.016},
number = {6},
pages = {842--852},
doi = {10.1016/j.jmb.2018.01.016}
}
Cite this
MLA
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Tereshchenkov, Andrey G., et al. “Binding and Action of Amino Acid Analogs of Chloramphenicol upon the Bacterial Ribosome.” Journal of Molecular Biology, vol. 430, no. 6, Mar. 2018, pp. 842-852. https://doi.org/10.1016%2Fj.jmb.2018.01.016.