Design and Evaluation of Bispidine-Based SARS-CoV-2 Main Protease Inhibitors
Dmitriy N. Shcherbakov
1, 2
,
Dmitriy Shcherbakov
1, 2
,
Dmitry S. Baev
3
,
Dmitriy Baev
3
,
Mikhail A Kalinin
4, 5
,
Mikhail Kalinin
4, 5
,
Alexander Dalinger
5
,
Varvara Chirkova
2
,
Svetlana Belenkaya
1, 6
,
Aleksei Khvostov
5
,
D P Krutko
5
,
Dmitry Krutko
5
,
Ekaterina Volosnikova
1
,
Elena Sharlaeva
2
,
Daniil Shanshin
1
,
Tatyana Tolstikova
3
,
Olga I. Yarovaya
3
,
Irina V Kolosova
1
,
Rinat Maksyutov
1
,
Nariman Salakhutdinov
3
,
Publication type: Journal Article
Publication date: 2021-09-29
scimago Q1
wos Q2
SJR: 0.805
CiteScore: 5.8
Impact factor: 4.0
ISSN: 19485875
PubMed ID:
35043075
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
For the first time, derivatives of 3,7-diazabicyclo[3.3.1]nonane (bispidine) were proposed as potential inhibitors of the SARS-CoV-2 main viral protease (3-chymotrypsin-like, 3CLpro). Based on the created pharmacophore model of the active site of the protease, a group of compounds were modeled and tested for activity against 3CLpro. The 3CLpro activity was measured using the fluorogenic substrate Dabcyl-VNSTLQSGLRK(FAM)MA; the efficiency of the proposed approach was confirmed by comparison with literature data for ebselen and disulfiram. The results of the experiments performed with bispidine compounds showed that 14 compounds exhibited activity in the concentration range 1–10 μM, and 3 samples exhibited submicromolar activity. The structure–activity relationship studies showed that the molecules containing a carbonyl group in the ninth position of the bicycle exhibited the maximum activity. Based on the experimental and theoretical results obtained, further directions for the development of this topic were proposed.
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48
Total citations:
48
Citations from 2024:
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Shcherbakov D. N. et al. Design and Evaluation of Bispidine-Based SARS-CoV-2 Main Protease Inhibitors // ACS Medicinal Chemistry Letters. 2021. Vol. 13. No. 1. pp. 140-147.
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Shcherbakov D. N., Shcherbakov D., S. Baev D., Baev D., Kalinin M. A., Kalinin M., Dalinger A., Chirkova V., Belenkaya S., Khvostov A., Krutko D. P., Krutko D., Medvedko A. V., Volosnikova E., Sharlaeva E., Shanshin D., Tolstikova T., Yarovaya O. I., Kolosova I. V., Maksyutov R., Salakhutdinov N. F., Salakhutdinov N., Vatsadze S. Z. Design and Evaluation of Bispidine-Based SARS-CoV-2 Main Protease Inhibitors // ACS Medicinal Chemistry Letters. 2021. Vol. 13. No. 1. pp. 140-147.
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TY - JOUR
DO - 10.1021/acsmedchemlett.1c00299
UR - https://pubs.acs.org/doi/10.1021/acsmedchemlett.1c00299
TI - Design and Evaluation of Bispidine-Based SARS-CoV-2 Main Protease Inhibitors
T2 - ACS Medicinal Chemistry Letters
AU - Shcherbakov, Dmitriy N.
AU - Shcherbakov, Dmitriy
AU - S. Baev, Dmitry
AU - Baev, Dmitriy
AU - Kalinin, Mikhail A
AU - Kalinin, Mikhail
AU - Dalinger, Alexander
AU - Chirkova, Varvara
AU - Belenkaya, Svetlana
AU - Khvostov, Aleksei
AU - Krutko, D P
AU - Krutko, Dmitry
AU - Medvedko, Alexey V
AU - Volosnikova, Ekaterina
AU - Sharlaeva, Elena
AU - Shanshin, Daniil
AU - Tolstikova, Tatyana
AU - Yarovaya, Olga I.
AU - Kolosova, Irina V
AU - Maksyutov, Rinat
AU - Salakhutdinov, Nariman F.
AU - Salakhutdinov, Nariman
AU - Vatsadze, Sergey Z.
PY - 2021
DA - 2021/09/29
PB - American Chemical Society (ACS)
SP - 140-147
IS - 1
VL - 13
PMID - 35043075
SN - 1948-5875
ER -
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@article{2021_Shcherbakov,
author = {Dmitriy N. Shcherbakov and Dmitriy Shcherbakov and Dmitry S. Baev and Dmitriy Baev and Mikhail A Kalinin and Mikhail Kalinin and Alexander Dalinger and Varvara Chirkova and Svetlana Belenkaya and Aleksei Khvostov and D P Krutko and Dmitry Krutko and Alexey V Medvedko and Ekaterina Volosnikova and Elena Sharlaeva and Daniil Shanshin and Tatyana Tolstikova and Olga I. Yarovaya and Irina V Kolosova and Rinat Maksyutov and Nariman F. Salakhutdinov and Nariman Salakhutdinov and Sergey Z. Vatsadze},
title = {Design and Evaluation of Bispidine-Based SARS-CoV-2 Main Protease Inhibitors},
journal = {ACS Medicinal Chemistry Letters},
year = {2021},
volume = {13},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://pubs.acs.org/doi/10.1021/acsmedchemlett.1c00299},
number = {1},
pages = {140--147},
doi = {10.1021/acsmedchemlett.1c00299}
}
Cite this
MLA
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Shcherbakov, Dmitriy N., et al. “Design and Evaluation of Bispidine-Based SARS-CoV-2 Main Protease Inhibitors.” ACS Medicinal Chemistry Letters, vol. 13, no. 1, Sep. 2021, pp. 140-147. https://pubs.acs.org/doi/10.1021/acsmedchemlett.1c00299.