1,3-Diaryl Triazenes Incorporating Disulfonamides Show Both Antiproliferative Activity and Effective Inhibition of Tumor-associated Carbonic Anhydrases IX and XII

  • Authors: Lolak N.1, Akocak S.2, Petreni A.3, Budak Y.4, Bozgeyik E.5, Gurdere M.6, Ceylan M.4, Supuran C.7
  • Affiliations:
    1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy,, Adıyaman University
    2. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Adıyaman University
    3. NEUROFARBA Department Sezione di Scienze Farmaceutiche, Università Degli Studi di Firenze,
    4. Department of Chemistry, Faculty of Arts and Sciences,, Gaziosmanpaşa University
    5. Department of Medical Services and Techniques, Vocational School of Health Services,, Adıyaman University,
    6. Department of Department of Chemistry, Faculty of Arts and Sciences,, Gaziosmanpaşa University
    7. NEUROFARBA Department Sezione di Scienze Farmaceutiche,, Università Degli Studi di Firenze
  • Issue: Vol 24, No 10 (2024)
  • Pages: 755-763
  • Section: Oncology
  • URL: https://snv63.ru/1871-5206/article/view/643701
  • DOI: https://doi.org/10.2174/0118715206285326240207045249
  • ID: 643701

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Full Text

Abstract

Aim:The aim of this study was to synthesize a library of novel di-sulfa drugs containing 1,3- diaryltriazene derivatives TS (1-13) by conjugation of diazonium salts of primary sulfonamides with sulfa drugs to investigate the cytotoxic effect of these new compounds in different cancer types and to determine their inhibitory activity against tumor-associated carbonic anhydrases IX and XII.

Materials and Methods:A carbonic anhydrase inhibitory activity of the obtained compounds was evaluated against four selected human carbonic anhydrase isoforms (hCA I, hCA II, hCA IX and hCA XII) by a stoppedflow CO2 hydrase assay. In addition, in vitro, cytotoxicity studies were applied by using A549 (lung cancer), BEAS-2B (normal lung), MCF-7 (breast cancer), MDA-MB-231 (breast cancer), CRL-4010 (normal breast epithelium), HT-29 (colon cancer), and HCT -116 (colon cancer) cell lines.

Results:As a result of the inhibition data, the 4-aminobenzenesulfonamide derivatives were more active than their 3-aminobenzenesulfonamide counterparts. More specifically, compounds TS-1 and TS-2, both of which have primary sulfonamides on both sides of the triazene linker, showed the best inhibitory activity against hCA IX with Ki values of 19.5 and 13.7 nM and also against hCA XII with Ki values of 6.6 and 8.3 nM, respectively. In addition, in vitro cytotoxic activity on the human breast cancer cell line MCF-7 showed that some derivatives of di-sulfa triazenes, such as TS-5 and TS-13, were more active than SLC-0111.

Conclusion:With the aim of developing more potent and isoform-selective CA inhibitors, these novel hybrid molecules containing sulfa drugs, triazene linkers, and the classical primary sulfonamide chemotype may be considered an interesting example of effective enzyme inhibitors and important anticancer agents.

About the authors

Nebih Lolak

Department of Pharmaceutical Chemistry, Faculty of Pharmacy,, Adıyaman University

Email: info@benthamscience.net

Suleyman Akocak

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Adıyaman University

Author for correspondence.
Email: info@benthamscience.net

Andrea Petreni

NEUROFARBA Department Sezione di Scienze Farmaceutiche, Università Degli Studi di Firenze,

Email: info@benthamscience.net

Yakup Budak

Department of Chemistry, Faculty of Arts and Sciences,, Gaziosmanpaşa University

Email: info@benthamscience.net

Esra Bozgeyik

Department of Medical Services and Techniques, Vocational School of Health Services,, Adıyaman University,

Email: info@benthamscience.net

Meliha Gurdere

Department of Department of Chemistry, Faculty of Arts and Sciences,, Gaziosmanpaşa University

Email: info@benthamscience.net

Mustafa Ceylan

Department of Chemistry, Faculty of Arts and Sciences,, Gaziosmanpaşa University

Email: info@benthamscience.net

Claudiu Supuran

NEUROFARBA Department Sezione di Scienze Farmaceutiche,, Università Degli Studi di Firenze

Author for correspondence.
Email: info@benthamscience.net

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