Lucky Switcheroo: Dramatic Potency and Selectivity Improvement of Imidazoline Inhibitors of Human Carbonic Anhydrase VII.
Stanislav Kopylov
1
,
Dmitry Dar’in
1
,
Publication type: Journal Article
Publication date: 2017-09-20
scimago Q1
wos Q2
SJR: 0.805
CiteScore: 5.8
Impact factor: 4.0
ISSN: 19485875
PubMed ID:
29057059
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A substantial improvement of potency and selectivity of imidazoline-based inhibitors of hCA VII (a promising target for the treatment of seizures and neuropathic pain) was achieved by simply switching the position of the benzenesulfonamide moiety from N1 (as in the earlier reported series) to C2. Selectivity indices vs the off-target isoforms (hCA I, I, I and IV) greater than 100 were reached, which is exceedingly rare for hCA VII inhibitors. The drastic profile improvement of the new series has been rationalized by an additional hydrogen bonding with the nonconserved Q69 residue in the active site of hCA VII (absent in the other three isoforms studied), which also results in a favorable accommodation of the inhibitor's lipophilic periphery in the nearby hydrophobic pocket. The robustness of the docking simulations was tested and confirmed by molecular dynamics simulations.
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Kalinin S. et al. Lucky Switcheroo: Dramatic Potency and Selectivity Improvement of Imidazoline Inhibitors of Human Carbonic Anhydrase VII. // ACS Medicinal Chemistry Letters. 2017. Vol. 8. No. 10. pp. 1105-1109.
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Kalinin S., Kopylov S., Tuccinardi T., Novikov A. S., Dar’in D., T Supuran C., Krasavin M. Lucky Switcheroo: Dramatic Potency and Selectivity Improvement of Imidazoline Inhibitors of Human Carbonic Anhydrase VII. // ACS Medicinal Chemistry Letters. 2017. Vol. 8. No. 10. pp. 1105-1109.
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RIS
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TY - JOUR
DO - 10.1021/acsmedchemlett.7b00300
UR - https://doi.org/10.1021/acsmedchemlett.7b00300
TI - Lucky Switcheroo: Dramatic Potency and Selectivity Improvement of Imidazoline Inhibitors of Human Carbonic Anhydrase VII.
T2 - ACS Medicinal Chemistry Letters
AU - Kalinin, Stanislav
AU - Kopylov, Stanislav
AU - Tuccinardi, Tiziano
AU - Novikov, Alexander S.
AU - Dar’in, Dmitry
AU - T Supuran, Claudiu
AU - Krasavin, Mikhail
PY - 2017
DA - 2017/09/20
PB - American Chemical Society (ACS)
SP - 1105-1109
IS - 10
VL - 8
PMID - 29057059
SN - 1948-5875
ER -
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BibTex (up to 50 authors)
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@article{2017_Kalinin,
author = {Stanislav Kalinin and Stanislav Kopylov and Tiziano Tuccinardi and Alexander S. Novikov and Dmitry Dar’in and Claudiu T Supuran and Mikhail Krasavin},
title = {Lucky Switcheroo: Dramatic Potency and Selectivity Improvement of Imidazoline Inhibitors of Human Carbonic Anhydrase VII.},
journal = {ACS Medicinal Chemistry Letters},
year = {2017},
volume = {8},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acsmedchemlett.7b00300},
number = {10},
pages = {1105--1109},
doi = {10.1021/acsmedchemlett.7b00300}
}
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MLA
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Kalinin, Stanislav, et al. “Lucky Switcheroo: Dramatic Potency and Selectivity Improvement of Imidazoline Inhibitors of Human Carbonic Anhydrase VII..” ACS Medicinal Chemistry Letters, vol. 8, no. 10, Sep. 2017, pp. 1105-1109. https://doi.org/10.1021/acsmedchemlett.7b00300.