Open Access
Antibiotics, volume 10, issue 5, pages 489
Triphenilphosphonium analogs of chloramphenicol as dual-acting antimicrobial and antiproliferating agents
Pavlova Julia A
1
,
Nazarov Pavel A.
2, 3
,
Volynkina Inna A
5
,
Makarov Gennady I
6
,
Abad Etna
7
,
Murayama Somay Y.
8
,
Kajiwara Susumu
9
,
Paleskava Alena
10, 11
,
Konevega Andrey L.
10, 11, 12
,
Lyakhovich A.
13, 14
,
Osterman Ilya A
1, 4, 15
,
Bogdanov Alexey A.
1, 2
,
Sumbatyan Natalia V
1, 2
1
7
Department of Experimental and Health Sciences, Universitat Pompeu Fabra, 08003 Barcelona, Spain
|
8
Department of Chemotherapy and Mycoses, National Institute of Infectious Diseases, 1-23-1 Toyama, Shinjuku-ku, Tokyo 162-8340, Japan
|
10
14
Vall D’Hebron Institut de Recerca, 08035 Barcelona, Spain
|
Publication type: Journal Article
Publication date: 2021-04-23
PubMed ID:
33922611
Biochemistry
Microbiology (medical)
Microbiology
Infectious Diseases
Pharmacology (medical)
General Pharmacology, Toxicology and Pharmaceutics
Abstract
In the current work, in continuation of our recent research, we synthesized and studied new chimeric compounds, including the ribosome-targeting antibiotic chloramphenicol (CHL) and the membrane-penetrating cation triphenylphosphonium (TPP), which are linked by alkyl groups of different lengths. Using various biochemical assays, we showed that these CAM-Cn-TPP compounds bind to the bacterial ribosome, inhibit protein synthesis in vitro and in vivo in a way similar to that of the parent CHL, and significantly reduce membrane potential. Similar to CAM-C4-TPP, the mode of action of CAM-C10-TPP and CAM-C14-TPP in bacterial ribosomes differs from that of CHL. By simulating the dynamics of CAM-Cn-TPP complexes with bacterial ribosomes, we proposed a possible explanation for the specificity of the action of these analogs in the translation process. CAM-C10-TPP and CAM-C14-TPP more strongly inhibit the growth of the Gram-positive bacteria, as compared to CHL, and suppress some CHL-resistant bacterial strains. Thus, we have shown that TPP derivatives of CHL are dual-acting compounds targeting both the ribosomes and cellular membranes of bacteria. The TPP fragment of CAM-Cn-TPP compounds has an inhibitory effect on bacteria. Moreover, since the mitochondria of eukaryotic cells possess qualities similar to those of their prokaryotic ancestors, we demonstrate the possibility of targeting chemoresistant cancer cells with these compounds.
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Antibiotics
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Journal of Structural Chemistry
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Future Medicinal Chemistry
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1 publication, 11.11%
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1 publication, 11.11%
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1
2
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Citations by publishers
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1
2
3
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Multidisciplinary Digital Publishing Institute (MDPI)
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Multidisciplinary Digital Publishing Institute (MDPI)
3 publications, 33.33%
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Elsevier
|
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3 publications, 33.33%
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Pleiades Publishing
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2 publications, 22.22%
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Future Medicine
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Future Medicine
1 publication, 11.11%
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1
2
3
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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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Pavlova J. A. et al. Triphenilphosphonium analogs of chloramphenicol as dual-acting antimicrobial and antiproliferating agents // Antibiotics. 2021. Vol. 10. No. 5. p. 489.
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Pavlova J. A., Khairullina Z. Z., Tereshchenkov A. G., Nazarov P. A., Lukianov D. A., Volynkina I. A., Skvortsov D. A., Makarov G. I., Abad E., Murayama S. Y., Kajiwara S., Paleskava A., Konevega A. L., Antonenko Y. N., Lyakhovich A., Osterman I. A., Bogdanov A. A., Sumbatyan N. V. Triphenilphosphonium analogs of chloramphenicol as dual-acting antimicrobial and antiproliferating agents // Antibiotics. 2021. Vol. 10. No. 5. p. 489.
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TY - JOUR
DO - 10.3390/antibiotics10050489
UR - https://doi.org/10.3390%2Fantibiotics10050489
TI - Triphenilphosphonium analogs of chloramphenicol as dual-acting antimicrobial and antiproliferating agents
T2 - Antibiotics
AU - Pavlova, Julia A
AU - Nazarov, Pavel A.
AU - Skvortsov, Dmitry A.
AU - Makarov, Gennady I
AU - Murayama, Somay Y.
AU - Kajiwara, Susumu
AU - Sumbatyan, Natalia V
AU - Lukianov, Dmitrii A.
AU - Volynkina, Inna A
AU - Paleskava, Alena
AU - Bogdanov, Alexey A.
AU - Khairullina, Zimfira Z
AU - Tereshchenkov, Andrey G
AU - Abad, Etna
AU - Konevega, Andrey L.
AU - Antonenko, Yuri N.
AU - Lyakhovich, A.
AU - Osterman, Ilya A
PY - 2021
DA - 2021/04/23 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 489
IS - 5
VL - 10
PMID - 33922611
SN - 2079-6382
ER -
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@article{2021_Pavlova,
author = {Julia A Pavlova and Pavel A. Nazarov and Dmitry A. Skvortsov and Gennady I Makarov and Somay Y. Murayama and Susumu Kajiwara and Natalia V Sumbatyan and Dmitrii A. Lukianov and Inna A Volynkina and Alena Paleskava and Alexey A. Bogdanov and Zimfira Z Khairullina and Andrey G Tereshchenkov and Etna Abad and Andrey L. Konevega and Yuri N. Antonenko and A. Lyakhovich and Ilya A Osterman},
title = {Triphenilphosphonium analogs of chloramphenicol as dual-acting antimicrobial and antiproliferating agents},
journal = {Antibiotics},
year = {2021},
volume = {10},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {apr},
url = {https://doi.org/10.3390%2Fantibiotics10050489},
number = {5},
pages = {489},
doi = {10.3390/antibiotics10050489}
}
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Pavlova, Julia A., et al. “Triphenilphosphonium analogs of chloramphenicol as dual-acting antimicrobial and antiproliferating agents.” Antibiotics, vol. 10, no. 5, Apr. 2021, p. 489. https://doi.org/10.3390%2Fantibiotics10050489.