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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. / Krasavin, Mikhail; Shetnev, Anton; Sharonova, Tatyana; Baykov, Sergey; Kalinin, Stanislav; Nocentini, Alessio; Sharoyko, Vladimir; Poli, Giulio; Tuccinardi, Tiziano; Presnukhina, Sofia; Tennikova, Tatiana B.; Supuran, Claudiu T.

In: European Journal of Medicinal Chemistry, Vol. 164, 15.02.2019, p. 92-105.

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

Harvard

Krasavin, M, Shetnev, A, Sharonova, T, Baykov, S, Kalinin, S, Nocentini, A, Sharoyko, V, Poli, G, Tuccinardi, T, Presnukhina, S, Tennikova, TB & Supuran, CT 2019, '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, vol. 164, pp. 92-105. https://doi.org/10.1016/j.ejmech.2018.12.049

APA

Krasavin, M., Shetnev, A., Sharonova, T., Baykov, S., Kalinin, S., Nocentini, A., Sharoyko, V., Poli, G., Tuccinardi, T., Presnukhina, S., Tennikova, T. B., & Supuran, C. T. (2019). 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, 164, 92-105. https://doi.org/10.1016/j.ejmech.2018.12.049

Vancouver

Krasavin M, Shetnev A, Sharonova T, Baykov S, Kalinin S, Nocentini A 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 Feb 15;164:92-105. https://doi.org/10.1016/j.ejmech.2018.12.049

Author

Krasavin, Mikhail ; Shetnev, Anton ; Sharonova, Tatyana ; Baykov, Sergey ; Kalinin, Stanislav ; Nocentini, Alessio ; Sharoyko, Vladimir ; Poli, Giulio ; Tuccinardi, Tiziano ; Presnukhina, Sofia ; Tennikova, Tatiana B. ; Supuran, Claudiu T. / 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. In: European Journal of Medicinal Chemistry. 2019 ; Vol. 164. pp. 92-105.

BibTeX

@article{8850bab558cd4e7e95b78ac303148cab,
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",
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.",
keywords = "1,2,4-Oxadiazole, Cancer cells, Carbonic anhydrase, Hypoxic environment, Isoform-selective inhibitors, Isosteric replacement, Periphery groups, Primary sulfonamides, Subnanomolar inhibition, AMIDOXIMES, TRANSMEMBRANE, SULFOCHLORINATION, AGENT, E7070, IN-VITRO, POTENT, PROFILE, BENZENESULFONAMIDES, DERIVATIVES",
author = "Mikhail Krasavin and Anton Shetnev and Tatyana Sharonova and Sergey Baykov and Stanislav Kalinin and Alessio Nocentini and Vladimir Sharoyko and Giulio Poli and Tiziano Tuccinardi and Sofia Presnukhina and Tennikova, {Tatiana B.} and Supuran, {Claudiu T.}",
year = "2019",
month = feb,
day = "15",
doi = "10.1016/j.ejmech.2018.12.049",
language = "English",
volume = "164",
pages = "92--105",
journal = "European Journal of Medicinal Chemistry",
issn = "0223-5234",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Continued exploration of 1,2,4-oxadiazole periphery for carbonic anhydrase-targeting primary arene sulfonamides

T2 - Discovery of subnanomolar inhibitors of membrane-bound hCA IX isoform that selectively kill cancer cells in hypoxic environment

AU - Krasavin, Mikhail

AU - Shetnev, Anton

AU - Sharonova, Tatyana

AU - Baykov, Sergey

AU - Kalinin, Stanislav

AU - Nocentini, Alessio

AU - Sharoyko, Vladimir

AU - Poli, Giulio

AU - Tuccinardi, Tiziano

AU - Presnukhina, Sofia

AU - Tennikova, Tatiana B.

AU - Supuran, Claudiu T.

PY - 2019/2/15

Y1 - 2019/2/15

N2 - 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.

AB - 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.

KW - 1,2,4-Oxadiazole

KW - Cancer cells

KW - Carbonic anhydrase

KW - Hypoxic environment

KW - Isoform-selective inhibitors

KW - Isosteric replacement

KW - Periphery groups

KW - Primary sulfonamides

KW - Subnanomolar inhibition

KW - AMIDOXIMES

KW - TRANSMEMBRANE

KW - SULFOCHLORINATION

KW - AGENT

KW - E7070

KW - IN-VITRO

KW - POTENT

KW - PROFILE

KW - BENZENESULFONAMIDES

KW - DERIVATIVES

UR - http://www.scopus.com/inward/record.url?scp=85058993622&partnerID=8YFLogxK

U2 - 10.1016/j.ejmech.2018.12.049

DO - 10.1016/j.ejmech.2018.12.049

M3 - Article

AN - SCOPUS:85058993622

VL - 164

SP - 92

EP - 105

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

SN - 0223-5234

ER -

ID: 37145047