Continued exploration of 1,2,4-oxadiazole periphery for carbonic anhydrase-targeting primary arene sulfonamides: Discovery of subnanomolar inhibitors of membrane-bound hCA IX isoform that selectively kill cancer cells in hypoxic environment.
Publication type: Journal Article
Publication date: 2019-02-01
scimago Q1
wos Q1
SJR: 1.142
CiteScore: 11.3
Impact factor: 5.9
ISSN: 02235234, 17683254
PubMed ID:
30594030
Organic Chemistry
Drug Discovery
General Medicine
Pharmacology
Abstract
An expanded set of diversely substituted 1,2,4-oxadiazole-containing primary aromatic sulfonamides was synthesized and tested for inhibition of human carbonic anhydrase I, II, IX and XII isoforms. The initial biochemical profiling revealed a significantly more potent inhibition of cancer-related, membrane-bound isoform hCA IX (reaching into submicromolar range), on top of potent inhibition of hCA XII that is another cancer target. The observed structure-activity relationships have been rationalized by molecular modeling. Comparative single-concentration profiling of the carbonic anhydrase inhibitors synthesized for antiproliferative effects against normal (ARPE-19) and cancer (PANC-1) cell lines under chemically induced hypoxia conditions revealed several candidate compounds selectively targeting cancer cells. More in-depth characterization of these leads revealed two structurally related compounds that showed promising selective cytotoxicity against pancreatic cancer (PANC-1) and melanoma (SK-MEL-2) cell lines.
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62
Total citations:
62
Citations from 2024:
12
(19%)
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Krasavin M. et al. Continued exploration of 1,2,4-oxadiazole periphery for carbonic anhydrase-targeting primary arene sulfonamides: Discovery of subnanomolar inhibitors of membrane-bound hCA IX isoform that selectively kill cancer cells in hypoxic environment. // European Journal of Medicinal Chemistry. 2019. Vol. 164. pp. 92-105.
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Krasavin M., Shetnev A. A., Sharonova T., Baykov S. V., Kalinin S., Nocentini A., Sharoyko V., Poli G., Tuccinardi T., Presnukhina S., Tennikova T. B., T Supuran C. Continued exploration of 1,2,4-oxadiazole periphery for carbonic anhydrase-targeting primary arene sulfonamides: Discovery of subnanomolar inhibitors of membrane-bound hCA IX isoform that selectively kill cancer cells in hypoxic environment. // European Journal of Medicinal Chemistry. 2019. Vol. 164. pp. 92-105.
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TY - JOUR
DO - 10.1016/j.ejmech.2018.12.049
UR - https://doi.org/10.1016/j.ejmech.2018.12.049
TI - Continued exploration of 1,2,4-oxadiazole periphery for carbonic anhydrase-targeting primary arene sulfonamides: Discovery of subnanomolar inhibitors of membrane-bound hCA IX isoform that selectively kill cancer cells in hypoxic environment.
T2 - European Journal of Medicinal Chemistry
AU - Krasavin, Mikhail
AU - Shetnev, Anton A
AU - Sharonova, Tatyana
AU - Baykov, Sergey V
AU - Kalinin, Stanislav
AU - Nocentini, Alessio
AU - Sharoyko, Vladimir
AU - Poli, Giulio
AU - Tuccinardi, Tiziano
AU - Presnukhina, Sofia
AU - Tennikova, T. B.
AU - T Supuran, Claudiu
PY - 2019
DA - 2019/02/01
PB - Elsevier
SP - 92-105
VL - 164
PMID - 30594030
SN - 0223-5234
SN - 1768-3254
ER -
Cite this
BibTex (up to 50 authors)
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@article{2019_Krasavin,
author = {Mikhail Krasavin and Anton A Shetnev and Tatyana Sharonova and Sergey V Baykov and Stanislav Kalinin and Alessio Nocentini and Vladimir Sharoyko and Giulio Poli and Tiziano Tuccinardi and Sofia Presnukhina and T. B. Tennikova and Claudiu T Supuran},
title = {Continued exploration of 1,2,4-oxadiazole periphery for carbonic anhydrase-targeting primary arene sulfonamides: Discovery of subnanomolar inhibitors of membrane-bound hCA IX isoform that selectively kill cancer cells in hypoxic environment.},
journal = {European Journal of Medicinal Chemistry},
year = {2019},
volume = {164},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/j.ejmech.2018.12.049},
pages = {92--105},
doi = {10.1016/j.ejmech.2018.12.049}
}