Novel 3-(6-methylpyridin-2-yl)coumarin-based chalcones as selective inhibitors of cancer-related carbonic anhydrases IX and XII endowed with anti-proliferative activity

References

• Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767–77.
   PubMed Web of Science ®Google Scholar
• Le Duc Y, Licsandru E, Vullo D, et al. Carbonic anhydrases activation with 3-amino-1H-1,2,4-triazole-1-carboxamides: discovery of subnanomolar isoform II activators. Bioorg Med Chem 2017;25:1681–6.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrase inhibitors: an update on experimental agents for the treatment and imaging of hypoxic tumors. Expert Opin Invest Drugs 2021;30:1197–1208.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Emerging role of carbonic anhydrase inhibitors. Clin Sci 2021;135:1233–49.
   PubMed Web of Science ®Google Scholar
• Mishra CB, Tiwari M, Supuran CT. Progress in the development of human carbonic anhydrase inhibitors and their pharmacological applications: where are we today? Med Res Rev 2020;40:2485–565.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrase inhibition and the management of hypoxic tumors. Metabolites 2017;7:48.
   PubMed Web of Science ®Google Scholar
• Shaldam M, Nocentini A, Elsayed ZM, et al. Development of novel quinoline-based sulfonamides as selective cancer-associated carbonic anhydrase isoform IX inhibitors. Int J Mol Sci 2021;22:11119.
   PubMed Web of Science ®Google Scholar
• Tafreshi NK, Lloyd MC, Proemsey JB, et al. Evaluation of CAIX and CAXII expression in breast cancer at varied O2 levels: CAIX is the superior surrogate imaging biomarker of tumor hypoxia. Mol Imaging Biol 2016;18:219–31.
   PubMed Web of Science ®Google Scholar
• Okuno K, Matsubara T, Nakamura T, et al. Carbonic anhydrase IX enhances tumor cell proliferation and tumor progression in osteosarcoma. Oncotargets Ther 2018;11:6879–86.
   PubMed Web of Science ®Google Scholar
• Mussi S, Rezzola S, Chiodelli P, et al. Antiproliferative effects of sulphonamide carbonic anhydrase inhibitors C18, SLC-0111 and acetazolamide on bladder, glioblastoma and pancreatic cancer cell lines. J Enzyme Inhib Med Chem 2022;37:280–6.
   PubMed Web of Science ®Google Scholar
• Lomelino CL, Supuran CT, McKenna R. Non-classical inhibition of carbonic anhydrase. Int J Mol Sci 2016;17:1150.
   PubMed Web of Science ®Google Scholar
• Aimene Y, Eychenne R, Rodriguez F, et al. Synthesis, crystal structure, inhibitory activity and molecular docking of coumarins/sulfonamides containing triazolyl pyridine moiety as potent selective carbonic anhydrase IX and XII inhibitors. Crystals 2021;11:1076.
   Web of Science ®Google Scholar
• Lomelino CL, Supuran CT, McKenna R. Non-classical inhibition of carbonic anhydrase. Int J Mol Sci 2016;17:1150.
   PubMed Web of Science ®Google Scholar
• Al-Sanea MM, Chilingaryan G, Abelyan N, et al. Identification of non-classical hCA XII inhibitors using combination of computational approaches for drug design and discovery. Sci Rep 2021;11:15516.
   PubMed Web of Science ®Google Scholar
• Wu Y, Xu J, Liu Y, et al. A review on anti-tumor mechanisms of coumarins. Front Oncol 2020;10:592853.
   PubMed Web of Science ®Google Scholar
• Al-Warhi T, Sabt A, Elkaeed EB, Eldehna WM. Recent advancements of coumarin-based anticancer agents: an up-to-date review. Bioorg Chem 2020;103:104163.
   PubMed Web of Science ®Google Scholar
• Maresca A, Temperini C, Vu H, et al. Non-zinc mediated inhibition of carbonic anhydrases: coumarins are a new class of suicide inhibitors. J Am Chem Soc 2009;131:3057–62.
   PubMed Web of Science ®Google Scholar
• Maresca A, Supuran CT. Coumarins incorporating hydroxy- and chloro-moieties selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II. Bioorg Med Chem Lett 2010;20:4511–4.
   PubMed Web of Science ®Google Scholar
• Thacker PS, Alvala M, Arifuddin M, et al. Design, synthesis and biological evaluation of coumarin-3-carboxamides as selective carbonic anhydrase IX and XII inhibitors. Bioorg Chem 2019;86:386–92.
   PubMed Web of Science ®Google Scholar
• Zengin Kurt B, Sonmez F, Ozturk D, et al. Synthesis of coumarin-sulfonamide derivatives and determination of their cytotoxicity, carbonic anhydrase inhibitory and molecular docking studies. Eur J Med Chem 2019;183:111702.
   PubMed Web of Science ®Google Scholar
• Ertmer A, Huber V, Gilch S, et al. The anticancer drug imatinib induces cellular autophagy. Leukemia 2007;21:936–42.
   PubMed Web of Science ®Google Scholar
• Sprinzl MF, Reisinger F, Puschnik A, et al. Sorafenib perpetuates cellular anticancer effector functions by modulating the crosstalk between macrophages and natural killer cells. Hepatology 2013;57:2358–68.
   PubMed Web of Science ®Google Scholar
• Byrd JC, Woyach JA, Furman RR, et al. Acalabrutinib in treatment-naive chronic lymphocytic leukemia. Blood 2021;137:3327–38.
   PubMed Web of Science ®Google Scholar
• Ansari MF, Idrees D, Hassan MI, et al. Design, synthesis and biological evaluation of novel pyridine-thiazolidinone derivatives as anticancer agents: targeting human carbonic anhydrase IX. Eur J Med Chem 2018;144:544–56.
   PubMed Web of Science ®Google Scholar
• Xu F, Li W, Shuai W, et al. Design, synthesis and biological evaluation of pyridine-chalcone derivatives as novel microtubule-destabilizing agents. Eur J Med Chem 2019;173:1–14.
   PubMed Web of Science ®Google Scholar
• Peerzada MN, Khan P, Ahmad K, et al. Synthesis, characterization and biological evaluation of tertiary sulfonamide derivatives of pyridyl-indole based heteroaryl chalcone as potential carbonic anhydrase IX inhibitors and anticancer agents. Eur J Med Chem 2018;155:13–23.
   PubMed Web of Science ®Google Scholar
• Eldehna WM, Altoukhy A, Mahrous H, Abdel-Aziz HA. Design, synthesis and QSAR study of certain isatin-pyridine hybrids as potential anti-proliferative agents. Eur J Med Chem 2015;90:684–94.
   PubMed Web of Science ®Google Scholar
• Vijesh AM, Isloor AM, Prabhu V, et al. Synthesis, characterization and anti-microbial studies of some novel 2,4-disubstituted thiazoles. Eur J Med Chem 2010;45:5460–4.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Skehan P, Storeng R, Scudiero D, et al. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 1990;82:1107–12.
   PubMed Web of Science ®Google Scholar
• Huo X-S, Jian X-E, Ou-Yang J, et al. Discovery of highly potent tubulin polymerization inhibitors: design, synthesis, and structure-activity relationships of novel 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidines. Eur J Med Chem 2021;220:1–13.
   Web of Science ®Google Scholar
• Al-Mousawi S, John E, Abdelkhalik MM, Elnagdi MH. Enaminones as building blocks in heterocyclic syntheses: a new approach to polyfunctionally substituted cyclohexenoazines. J Heterocyc Chem 2003;40:689–95.
   Web of Science ®Google Scholar
• Alafeefy AM, Abdel-Aziz HA, Vullo D, et al. Inhibition of human carbonic anhydrase isozymes I, II, IX and XII with a new series of sulfonamides incorporating aroylhydrazone-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazinyl- or 2-(cyanophenylmethylene)-1,3,4-thiadiazol-3(2H)-yl moieties. J Enzyme Inhib Med Chem 2015;30:52–6.
   PubMed Web of Science ®Google Scholar
• Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55–63.
   PubMed Web of Science ®Google Scholar
• Eldehna WM, Abdelrahman MA, Nocentini A, et al. Synthesis, biological evaluation and in silico studies with 4-benzylidene-2-phenyl-5(4H)-imidazolone-based benzenesulfonamides as novel selective carbonic anhydrase IX inhibitors endowed with anticancer activity. Bioorg Chem 2019;90:103102.
   PubMed Web of Science ®Google Scholar
• Eldehna WM, Taghour MS, Al-Warhi T, et al. Discovery of 2,4-thiazolidinedione-tethered coumarins as novel selective inhibitors for carbonic anhydrase IX and XII isoforms. J Enzyme Inhib Med Chem 2022;37:531–41.
   PubMed Web of Science ®Google Scholar
• Eldehna WM, Salem R, Elsayed ZM, et al. Development of novel benzofuran-isatin conjugates as potential antiproliferative agents with apoptosis inducing mechanism in colon cancer. J Enzyme Inhib Med Chem 2021;36:1424–35.
   PubMed Web of Science ®Google Scholar
• Al-Warhi T, Abo-Ashour MF, Almahli H, et al. Novel [(N-alkyl-3-indolylmethylene)hydrazono]oxindoles arrest cell cycle and induce cell apoptosis by inhibiting CDK2 and Bcl-2: synthesis, biological evaluation and in silico studies. J Enzyme Inhib Med Chem 2020;35:1300–9.
   PubMed Web of Science ®Google Scholar
• Elbadawi MM, Eldehna WM, Wang W, et al. Discovery of 4-alkoxy-2-aryl-6,7-dimethoxyquinolines as a new class of topoisomerase I inhibitors endowed with potent in vitro anticancer activity. Eur J Med Chem 2021;215:113261.
   PubMed Web of Science ®Google Scholar