Journal of Medicinal Chemistry, volume 63, issue 21, pages 13031-13063
Novel Copper-Containing Cytotoxic Agents Based on 2-Thioxoimidazolones
Krasnovskaya Olga O.
1, 2
,
Guk Dmitry A.
1
,
Naumov Alexey E
1
,
Nikitina Vita N
1
,
Semkina Alevtina S.
3, 4
,
Pokrovsky Vadim S.
5, 6
,
Ryabaya Oksana O
5
,
Skvortsov Dmitry
1, 7
,
Zhirkina Irina V
1
,
Shafikov Radik R
1
,
Gorelkin Peter
2
,
Vaneev Alexander N.
1, 2
,
Mazur Dmitrii M.
1
,
Тафеенко В. А.
1
,
Pergushov Vladimir I
1
,
Soldatov Mikhail
8
,
Akasov Roman A.
2, 9
,
Gerasimov Vasily M
10
,
Sakharov Dmitry A.
10
,
Moiseeva Anna A.
1
,
Zyk Nikolay V.
1
,
Majouga Alexander G.
1, 2, 10
1
Publication type: Journal Article
Publication date: 2020-09-28
Journal:
Journal of Medicinal Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 7.3
ISSN: 00222623, 15204804
Drug Discovery
Molecular Medicine
Abstract
A series of 73 ligands and 73 of their Cu+2 and Cu+1 copper complexes with different geometries, oxidation states of the metal, and redox activities were synthesized and characterized. The aim of the study was to establish the structure-activity relationship within a series of analogues with different substituents at the N(3) position, which govern the redox potentials of the Cu+2/Cu+1 redox couples, ROS generation ability, and intracellular accumulation. Possible cytotoxicity mechanisms, such as DNA damage, DNA intercalation, telomerase inhibition, and apoptosis induction have been investigated. ROS formation in MCF-7 cells and 3D spheroids was proven using Pt-nanoelectrode. Drug accumulation and ROS formation at 40-60 µm spheroid depths was found to be the key factor for the drug efficacy in the 3D tumor model, governed by the Cu+2/Cu+1 redox potential. A nontoxic in vivo single dose evaluation for two binuclear mixed-valence Cu+1/Cu+2 redox-active coordination compounds, 72k and 61k, was evaluated.
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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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Krasnovskaya O. O. et al. Novel Copper-Containing Cytotoxic Agents Based on 2-Thioxoimidazolones // Journal of Medicinal Chemistry. 2020. Vol. 63. No. 21. pp. 13031-13063.
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Krasnovskaya O. O., Guk D. A., Naumov A. E., Nikitina V. N., Semkina A. S., Vlasova K. Y., Pokrovsky V. S., Ryabaya O. O., Karshieva S. S., Skvortsov D., Zhirkina I. V., Shafikov R. R., Gorelkin P., Vaneev A. N., Erofeev A. V., Mazur D. M., Тафеенко В. А., Pergushov V. I., Melnikov M. Y., Soldatov M., Shapovalov V. V., Soldatov A., Akasov R. A., Gerasimov V. M., Sakharov D. A., Moiseeva A. A., Zyk N. V., Beloglazkina E. K., Majouga A. G. Novel Copper-Containing Cytotoxic Agents Based on 2-Thioxoimidazolones // Journal of Medicinal Chemistry. 2020. Vol. 63. No. 21. pp. 13031-13063.
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TY - JOUR
DO - 10.1021/acs.jmedchem.0c01196
UR - https://doi.org/10.1021%2Facs.jmedchem.0c01196
TI - Novel Copper-Containing Cytotoxic Agents Based on 2-Thioxoimidazolones
T2 - Journal of Medicinal Chemistry
AU - Naumov, Alexey E
AU - Semkina, Alevtina S.
AU - Ryabaya, Oksana O
AU - Karshieva, Saida S
AU - Zhirkina, Irina V
AU - Pergushov, Vladimir I
AU - Gerasimov, Vasily M
AU - Sakharov, Dmitry A.
AU - Zyk, Nikolay V.
AU - Krasnovskaya, Olga O.
AU - Vlasova, Kseniya Yu.
AU - Mazur, Dmitrii M.
AU - Soldatov, Mikhail
AU - Akasov, Roman A.
AU - Majouga, Alexander G.
AU - Guk, Dmitry A.
AU - Nikitina, Vita N
AU - Pokrovsky, Vadim S.
AU - Skvortsov, Dmitry
AU - Shafikov, Radik R
AU - Gorelkin, Peter
AU - Vaneev, Alexander N.
AU - Erofeev, Alexander V.
AU - Тафеенко, В. А.
AU - Melnikov, Mikhail Y.
AU - Shapovalov, Viktor V.
AU - Soldatov, Alexander
AU - Moiseeva, Anna A.
AU - Beloglazkina, Elena K.
PY - 2020
DA - 2020/09/28 00:00:00
PB - American Chemical Society (ACS)
SP - 13031-13063
IS - 21
VL - 63
SN - 0022-2623
SN - 1520-4804
ER -
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@article{2020_Krasnovskaya,
author = {Alexey E Naumov and Alevtina S. Semkina and Oksana O Ryabaya and Saida S Karshieva and Irina V Zhirkina and Vladimir I Pergushov and Vasily M Gerasimov and Dmitry A. Sakharov and Nikolay V. Zyk and Olga O. Krasnovskaya and Kseniya Yu. Vlasova and Dmitrii M. Mazur and Mikhail Soldatov and Roman A. Akasov and Alexander G. Majouga and Dmitry A. Guk and Vita N Nikitina and Vadim S. Pokrovsky and Dmitry Skvortsov and Radik R Shafikov and Peter Gorelkin and Alexander N. Vaneev and Alexander V. Erofeev and В. А. Тафеенко and Mikhail Y. Melnikov and Viktor V. Shapovalov and Alexander Soldatov and Anna A. Moiseeva and Elena K. Beloglazkina},
title = {Novel Copper-Containing Cytotoxic Agents Based on 2-Thioxoimidazolones},
journal = {Journal of Medicinal Chemistry},
year = {2020},
volume = {63},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021%2Facs.jmedchem.0c01196},
number = {21},
pages = {13031--13063},
doi = {10.1021/acs.jmedchem.0c01196}
}
Cite this
MLA
Copy
Krasnovskaya, Olga O., et al. “Novel Copper-Containing Cytotoxic Agents Based on 2-Thioxoimidazolones.” Journal of Medicinal Chemistry, vol. 63, no. 21, Sep. 2020, pp. 13031-13063. https://doi.org/10.1021%2Facs.jmedchem.0c01196.