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Pyridazinone-substituted benzenesulfonamides display potent inhibition of membrane-bound human carbonic anhydrase IX and promising antiproliferative activity against cancer cell lines. / Krasavin, Mikhail; Shetnev, Anton; Baykov, Sergey; Kalinin, Stanislav; Nocentini, Alessio; Sharoyko, Vladimir; Poli, Giulio; Tuccinardi, Tiziano; Korsakov, Mikhail; Tennikova, Tatiana B.; Supuran, Claudiu T.

In: European Journal of Medicinal Chemistry, Vol. 168, 15.04.2019, p. 301-314.

Research output: Contribution to journal › Article › peer-review

Harvard

Krasavin, M, Shetnev, A, Baykov, S, Kalinin, S, Nocentini, A, Sharoyko, V, Poli, G, Tuccinardi, T, Korsakov, M, Tennikova, TB & Supuran, CT 2019, 'Pyridazinone-substituted benzenesulfonamides display potent inhibition of membrane-bound human carbonic anhydrase IX and promising antiproliferative activity against cancer cell lines', European Journal of Medicinal Chemistry, vol. 168, pp. 301-314. https://doi.org/10.1016/j.ejmech.2019.02.044

APA

Krasavin, M., Shetnev, A., Baykov, S., Kalinin, S., Nocentini, A., Sharoyko, V., Poli, G., Tuccinardi, T., Korsakov, M., Tennikova, T. B., & Supuran, C. T. (2019). Pyridazinone-substituted benzenesulfonamides display potent inhibition of membrane-bound human carbonic anhydrase IX and promising antiproliferative activity against cancer cell lines. European Journal of Medicinal Chemistry, 168, 301-314. https://doi.org/10.1016/j.ejmech.2019.02.044

Vancouver

Krasavin M, Shetnev A, Baykov S, Kalinin S, Nocentini A, Sharoyko V et al. Pyridazinone-substituted benzenesulfonamides display potent inhibition of membrane-bound human carbonic anhydrase IX and promising antiproliferative activity against cancer cell lines. European Journal of Medicinal Chemistry. 2019 Apr 15;168:301-314. https://doi.org/10.1016/j.ejmech.2019.02.044

Author

Krasavin, Mikhail ; Shetnev, Anton ; Baykov, Sergey ; Kalinin, Stanislav ; Nocentini, Alessio ; Sharoyko, Vladimir ; Poli, Giulio ; Tuccinardi, Tiziano ; Korsakov, Mikhail ; Tennikova, Tatiana B. ; Supuran, Claudiu T. / Pyridazinone-substituted benzenesulfonamides display potent inhibition of membrane-bound human carbonic anhydrase IX and promising antiproliferative activity against cancer cell lines. In: European Journal of Medicinal Chemistry. 2019 ; Vol. 168. pp. 301-314.

BibTeX

@article{d71ceebc10634420a60736efe12aeb9f,
title = "Pyridazinone-substituted benzenesulfonamides display potent inhibition of membrane-bound human carbonic anhydrase IX and promising antiproliferative activity against cancer cell lines",
abstract = "An expanded set of pyridazine-containing benzene sulfonamides was investigated for inhibition of four human carbonic anhydrase isoforms, which revealed a pronounced inhibition trend toward hCA IX, a cancer-related, membrane-bound isoform of the enzyme. Comparison of antiproliferative effects of these compounds against cancer (PANC-1) and normal (ARPE-19) cells at 50 μM concentration narrowed the selection of compounds to the eight which displayed selective growth inhibition toward the cancer cells. More detailed investigation in concentration-dependent mode against normal (ARPE-19) and two cancer cell lines (PANC-1 and SK-MEL-2) identified two lead compounds one of which displayed a notable cytotoxicity toward pancreatic cancer cells while the other targeted the melanoma cells. These findings significantly expand the knowledge base concerning the hCA IX inhibitors whose inhibitory potency against a recombinant enzyme translates into selective anticancer activity under hypoxic conditions which are aimed to model the environment of a growing tumor.",
keywords = "Cancer cells, carbonic anhydrase, Growth inhibition assay, Hypoxic environment, Isoform-selective inhibitors, Periphery groups, Phthalazinone, Primary sulfonamides, Pyridazinone, Subnanomolar inhibition, Humans, Structure-Activity Relationship, Cell Survival/drug effects, Carbonic Anhydrase IX/antagonists & inhibitors, Dose-Response Relationship, Drug, Carbonic Anhydrase Inhibitors/chemical synthesis, Molecular Structure, Sulfonamides/chemical synthesis, Cell Proliferation/drug effects, Cell Line, Pyridazines/chemistry, Models, Molecular, Antineoplastic Agents/chemical synthesis, Ligands, Antigens, Neoplasm/metabolism, SULFONAMIDES, SULFOCHLORINATION, PROFILE, BIOLOGICAL EVALUATION, PANEL, ANALOGS",
author = "Mikhail Krasavin and Anton Shetnev and Sergey Baykov and Stanislav Kalinin and Alessio Nocentini and Vladimir Sharoyko and Giulio Poli and Tiziano Tuccinardi and Mikhail Korsakov and Tennikova, {Tatiana B.} and Supuran, {Claudiu T.}",
year = "2019",
month = apr,
day = "15",
doi = "10.1016/j.ejmech.2019.02.044",
language = "English",
volume = "168",
pages = "301--314",
journal = "European Journal of Medicinal Chemistry",
issn = "0223-5234",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Pyridazinone-substituted benzenesulfonamides display potent inhibition of membrane-bound human carbonic anhydrase IX and promising antiproliferative activity against cancer cell lines

AU - Krasavin, Mikhail

AU - Shetnev, Anton

AU - Baykov, Sergey

AU - Kalinin, Stanislav

AU - Nocentini, Alessio

AU - Sharoyko, Vladimir

AU - Poli, Giulio

AU - Tuccinardi, Tiziano

AU - Korsakov, Mikhail

AU - Tennikova, Tatiana B.

AU - Supuran, Claudiu T.

PY - 2019/4/15

Y1 - 2019/4/15

N2 - An expanded set of pyridazine-containing benzene sulfonamides was investigated for inhibition of four human carbonic anhydrase isoforms, which revealed a pronounced inhibition trend toward hCA IX, a cancer-related, membrane-bound isoform of the enzyme. Comparison of antiproliferative effects of these compounds against cancer (PANC-1) and normal (ARPE-19) cells at 50 μM concentration narrowed the selection of compounds to the eight which displayed selective growth inhibition toward the cancer cells. More detailed investigation in concentration-dependent mode against normal (ARPE-19) and two cancer cell lines (PANC-1 and SK-MEL-2) identified two lead compounds one of which displayed a notable cytotoxicity toward pancreatic cancer cells while the other targeted the melanoma cells. These findings significantly expand the knowledge base concerning the hCA IX inhibitors whose inhibitory potency against a recombinant enzyme translates into selective anticancer activity under hypoxic conditions which are aimed to model the environment of a growing tumor.

AB - An expanded set of pyridazine-containing benzene sulfonamides was investigated for inhibition of four human carbonic anhydrase isoforms, which revealed a pronounced inhibition trend toward hCA IX, a cancer-related, membrane-bound isoform of the enzyme. Comparison of antiproliferative effects of these compounds against cancer (PANC-1) and normal (ARPE-19) cells at 50 μM concentration narrowed the selection of compounds to the eight which displayed selective growth inhibition toward the cancer cells. More detailed investigation in concentration-dependent mode against normal (ARPE-19) and two cancer cell lines (PANC-1 and SK-MEL-2) identified two lead compounds one of which displayed a notable cytotoxicity toward pancreatic cancer cells while the other targeted the melanoma cells. These findings significantly expand the knowledge base concerning the hCA IX inhibitors whose inhibitory potency against a recombinant enzyme translates into selective anticancer activity under hypoxic conditions which are aimed to model the environment of a growing tumor.

KW - Cancer cells

KW - carbonic anhydrase

KW - Growth inhibition assay

KW - Hypoxic environment

KW - Isoform-selective inhibitors

KW - Periphery groups

KW - Phthalazinone

KW - Primary sulfonamides

KW - Pyridazinone

KW - Subnanomolar inhibition

KW - Humans

KW - Structure-Activity Relationship

KW - Cell Survival/drug effects

KW - Carbonic Anhydrase IX/antagonists & inhibitors

KW - Dose-Response Relationship, Drug

KW - Carbonic Anhydrase Inhibitors/chemical synthesis

KW - Molecular Structure

KW - Sulfonamides/chemical synthesis

KW - Cell Proliferation/drug effects

KW - Cell Line

KW - Pyridazines/chemistry

KW - Models, Molecular

KW - Antineoplastic Agents/chemical synthesis

KW - Ligands

KW - Antigens, Neoplasm/metabolism

KW - SULFONAMIDES

KW - SULFOCHLORINATION

KW - PROFILE

KW - BIOLOGICAL EVALUATION

KW - PANEL

KW - ANALOGS

UR - http://www.scopus.com/inward/record.url?scp=85062155225&partnerID=8YFLogxK

U2 - 10.1016/j.ejmech.2019.02.044

DO - 10.1016/j.ejmech.2019.02.044

M3 - Article

C2 - 30826507

AN - SCOPUS:85062155225

VL - 168

SP - 301

EP - 314

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

SN - 0223-5234

ER -

ID: 39973599