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Oligoglycol carbonate prodrugs of 5-modified 2'-deoxyuridines: synthesis and antibacterial activity

Sergey Dmitrievich Negrya 1
Sergey Dmitrievich Negrya
, 
Maxim Vladimirovich Jasko 1
Maxim Vladimirovich Jasko
, 
Dmitriy Aleksandrovich Makarov 1
Dmitriy Aleksandrovich Makarov
, 
Inna Leonidovna Karpenko 1
Inna Leonidovna Karpenko
,  , 
Vladimir Olegovich Chekhov 1
Vladimir Olegovich Chekhov
, 
Olga Vladimirovna Efremenkova 2
Olga Vladimirovna Efremenkova
, 
Byasilya F Vasilieva 2
Byasilya F Vasilieva
, 
Tatiana Aleksandrovna Efimenko 2
Tatiana Aleksandrovna Efimenko
, 
Sergei Nikolaevich Kochetkov 1
Sergei Nikolaevich Kochetkov
, 
Liudmila Aleksandrovna Alexandrova 1
Liudmila Aleksandrovna Alexandrova
10.1016/j.mencom.2022.07.002
Published 2022-07-01
Communication , Volume 32, Issue 4, 433-435
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Negrya S. D. et al. Oligoglycol carbonate prodrugs of 5-modified 2'-deoxyuridines: synthesis and antibacterial activity // Mendeleev Communications. 2022. Vol. 32. No. 4. pp. 433-435.
GOST all authors (up to 50) Copy
Negrya S. D., Jasko M. V., Makarov D. A., Karpenko I. L., Solyev P. N., Chekhov V. O., Efremenkova O. V., Vasilieva B. F., Efimenko T. A., Kochetkov S. N., Alexandrova L. A. Oligoglycol carbonate prodrugs of 5-modified 2'-deoxyuridines: synthesis and antibacterial activity // Mendeleev Communications. 2022. Vol. 32. No. 4. pp. 433-435.
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TY - JOUR
DO - 10.1016/j.mencom.2022.07.002
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.07.002
TI - Oligoglycol carbonate prodrugs of 5-modified 2'-deoxyuridines: synthesis and antibacterial activity
T2 - Mendeleev Communications
AU - Negrya, Sergey Dmitrievich
AU - Jasko, Maxim Vladimirovich
AU - Makarov, Dmitriy Aleksandrovich
AU - Karpenko, Inna Leonidovna
AU - Solyev, Pavel Nikolayevich
AU - Chekhov, Vladimir Olegovich
AU - Efremenkova, Olga Vladimirovna
AU - Vasilieva, Byasilya F
AU - Efimenko, Tatiana Aleksandrovna
AU - Kochetkov, Sergei Nikolaevich
AU - Alexandrova, Liudmila Aleksandrovna
PY - 2022
DA - 2022/07/01
PB - Mendeleev Communications
SP - 433-435
IS - 4
VL - 32
ER -
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@article{2022_Negrya,
author = {Sergey Dmitrievich Negrya and Maxim Vladimirovich Jasko and Dmitriy Aleksandrovich Makarov and Inna Leonidovna Karpenko and Pavel Nikolayevich Solyev and Vladimir Olegovich Chekhov and Olga Vladimirovna Efremenkova and Byasilya F Vasilieva and Tatiana Aleksandrovna Efimenko and Sergei Nikolaevich Kochetkov and Liudmila Aleksandrovna Alexandrova},
title = {Oligoglycol carbonate prodrugs of 5-modified 2'-deoxyuridines: synthesis and antibacterial activity},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.07.002},
number = {4},
pages = {433--435},
doi = {10.1016/j.mencom.2022.07.002}
}
MLA
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Negrya, Sergey Dmitrievich, et al. “Oligoglycol carbonate prodrugs of 5-modified 2'-deoxyuridines: synthesis and antibacterial activity.” Mendeleev Communications, vol. 32, no. 4, Jul. 2022, pp. 433-435. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.07.002.

Keywords

Antibacterial activity
bioavailability
cytotoxicity
glycol carbonates
hydrolysis
modified nucleosides
prodrugs
solubility

Abstract

In order to develop a new generation of antibacterial nucleosides, a representative set of novel 3'- and 5'-tri- or tetraethylene glycol prodrug forms of 5-alkyloxymethyl-2'- deoxyuridines was synthesized. These compounds were at least two orders of magnitude more soluble than the parent nucleosides, possessed significant inhibitory activity against a set of bacteria including resistant strains of Staphylococcus aureus and Mycobacterium smegmatis, and showed low cytotoxicity. The obtained data indicate that glycol carbonates are convenient and prospective for usage in prodrugs of nucleoside derivatives with antibacterial activity.

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