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Research Papers

Selective inhibition of carbonic anhydrase IX by sulphonylated 1,2,3-triazole incorporated benzenesulphonamides capable of inducing apoptosis

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Pages 1454-1463 | Received 29 Mar 2022, Accepted 09 May 2022, Published online: 26 May 2022

References

  • Bray F, Laversanne M, Weiderpass E, Soerjomataram I. The ever‐increasing importance of cancer as a leading cause of premature death worldwide. Cancer 2021;127:1454–30.
  • Sung H, Ferlay J, Siegel RL, et al. Global cancer statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J Clin 2021;71:209–49.
  • Warburg O. On the origin of cancer cells. Science 1956;123:309–14.
  • Angeli A, Carta F, Nocentini A, et al. Carbonic anhydrase inhibitors targeting metabolism and tumor microenvironment. Metabolites 2020;10:412.
  • Nocentini A, Supuran CT. Carbonic anhydrase inhibitors as antitumor/antimetastatic agents: a patent review (2008–2018). Expert Opin Ther Pat 2018;28:729–40.
  • Nocentini A, Supuran CT. Advances in the structural annotation of human carbonic anhydrases and impact on future drug discovery. Expert Opin Drug Discov 2019;14:1175–97.
  • Supuran CT. Structure-based drug discovery of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012;27:759–72.
  • Supuran CT. Carbonic anhydrases-an overview. Curr Pharm Des 2008;14:603–14.
  • Supuran CT. Structure and function of carbonic anhydrases. Biochem J 2016;473:2023–32.
  • D’Ambrosio K, De Simone G, Supuran CT. Human carbonic anhydrases: catalytic properties, structural features, and tissue distribution. In: Carbonic anhydrases as biocatalysts. Amsterdam, Netherlands: Elsevier; 2015:17–30.
  • Vats L, Kumar R, Bua S, et al. Continued exploration and tail approach synthesis of benzenesulfonamides containing triazole and dual triazole moieties as carbonic anhydrase I, II, IV and IX inhibitors. Eur J Med Chem 2019;183:111698.
  • Supuran CT, Alterio V, Di Fiore A, et al. Inhibition of carbonic anhydrase IX targets primary tumors, metastases, and cancer stem cells: three for the price of one. Med Res Rev 2018;38:1799–836.
  • Supuran CT. Carbonic anhydrase inhibition and the management of hypoxic tumors. Metabolites 2017;7:48.
  • Pfeffer CM, Singh ATK. Apoptosis: a target for anticancer therapy. Int J Mol Sci 2018;19:448.
  • Carneiro BA, El-Deiry WS. Targeting apoptosis in cancer therapy. Nat Rev Clin Oncol 2020;17:395–417.
  • Kumar R, Vats L, Bua S, et al. Design and synthesis of novel benzenesulfonamide containing 1, 2, 3-triazoles as potent human carbonic anhydrase isoforms I, II, IV and IX inhibitors. Eur J Med Chem 2018;155:545–51.
  • Dheer D, Singh V, Shankar R. Medicinal attributes of 1,2,3-triazoles: current developments. Bioorg Chem 2017;71:30–54.
  • Kumar R, Sharma V, Bua S, et al. Synthesis and biological evaluation of benzenesulphonamide-bearing 1,4,5-trisubstituted-1,2,3-triazoles possessing human carbonic anhydrase I, II, IV, and IX inhibitory activity. J Enzyme Inhib Med Chem 2017;32:1187–94.
  • Vats L, Sharma V, Angeli A, et al. Synthesis of novel 4-functionalized 1, 5-diaryl-1, 2, 3-triazoles containing benzenesulfonamide moiety as carbonic anhydrase I, II, IV and IX inhibitors. Eur J Med Chem 2018;150:678–86.
  • Sharma V, Kumar R, Bua S, et al. Synthesis of novel benzenesulfonamide bearing 1,2,3-triazole linked hydroxy-trifluoromethylpyrazolines and hydrazones as selective carbonic anhydrase isoforms IX and XII inhibitors. Bioorg Chem 2019;85:198–208.
  • Khalifah RG. The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Biol Chem 1971;246:2561–73.
  • Bhardwaj JK, Kumari P, Saraf P, Yadav AS. Antiapoptotic effects of vitamins C and E against cypermethrin-induced oxidative stress and spermatogonial germ cell apoptosis. J Biochem Mol Toxicol 2018;32:e22174.
  • Bhardwaj JK, Panchal H. Quercetin mediated attenuation of cadmium-induced oxidative toxicity and apoptosis of spermatogenic cells in caprine testes in vitro. Environ Mol Mutagen 2021;62:374–84.
  • Pearse A, Histochemistry: theoretical and applied, Churchill Livingstone. Edinburgh: London Press; 1968.
  • Kasibhatla S, Amarante-Mendes GP, Finucane D, et al. Acridine orange/ethidium bromide (AO/EB) staining to detect apoptosis. Cold Spring Harb Protoc 2006;2006:pdb.prot4493.
  • Buege JA, Aust SD. Microsomal lipid peroxidation. Methods Enzymol 1978;52:302–10.
  • Benzie IF, Strain JJ. Ferric reducing/antioxidant power assay: direct measure of total antioxidant activity of biological fluids and modified version for simultaneous measurement of total antioxidant power and ascorbic acid concentration. Methods Enzymol 1999;299:15–27.
  • Wildeman J, Van Leusen AM. Convenient alternative synthesis of sulfones in aprotic medium using phase-transfer catalysis. Synthesis 1979; 1979:733–4.
  • Saraiva MT, Costa GP, Seus N, et al. Room-temperature organocatalytic cycloaddition of azides with β-keto sulfones: toward sulfonyl-1,2,3-triazoles. Org Lett 2015;17:6206–6209.