Anti-breast cancer action of carbonic anhydrase IX inhibitor 4-[4-(4-Benzo[1,3]dioxol-5-ylmethyl-piperazin-1-yl)-benzylidene-hydrazinocarbonyl]-benzenesulfonamide (BSM-0004): in vitro and in vivo studies

References

• Momenimovahe Z, Salehiniya H. Epidemiological characteristics of and risk factors for breast cancer in the world. Breast Cancer 2019;11:151–64.
   PubMed Web of Science ®Google Scholar
• Hussain A, Yong C, Tkaczuk KHR, et al. Prevalence and risk of skeletal complications and use of radiation therapy in elderly women diagnosed with metastatic breast cancer. PLOS One 2018;13:e0193661.
   PubMed Web of Science ®Google Scholar
• Fahad UM. Breast cancer: current perspectives on the disease status. Adv Exp Med Biol 2019;1152:51–64.
   PubMed Web of Science ®Google Scholar
• Harbeck N, Penault-Llorca F, Cortes J, et al. Breast cancer. Nat Rev Dis Primers 2019;5:66.
   PubMed Web of Science ®Google Scholar
• Sun YS, Zhao Z, Yang ZN, et al. Risk factors and preventions of breast cancer. Int J Biol Sci 2017;13:1387–97.
   PubMed Web of Science ®Google Scholar
• Veronesi U, Boyle P, Goldhirsch A, et al. Breast cancer. Lancet 2005;365:1727–41.
   PubMed Web of Science ®Google Scholar
• Moo TA, Sanford R, Dang C, Morrow M. Overview of breast cancer therapy. PET Clin 2018;13:339–54.
   PubMed Web of Science ®Google Scholar
• Peart O. Breast intervention and breast cancer treatment options. Radiol Technol 2015;86:535M–58M.
   PubMedGoogle Scholar
• Redig AJ, McAllister SS. Breast cancer as a systemic disease: a view of metastasis. J Intern Med 2013;274:113–26.
   PubMed Web of Science ®Google Scholar
• Borniger JC. Central regulation of breast cancer growth and metastasis. J Cancer Metastasis Treat 2019;5:23.
   PubMedGoogle Scholar
• Mishra CB, Kumari S, Angeli A, et al. Discovery of benzenesulfonamide derivatives as carbonic anhydrase inhibitors with effective anticonvulsant action: design, synthesis, and pharmacological evaluation. J Med Chem 2018;61:3151–65.
   PubMed Web of Science ®Google Scholar
• Mishra CB, Kumari S, Angeli A, et al. Discovery of benzenesulfonamides with potent human carbonic anhydrase inhibitory and effective anticonvulsant action: design, synthesis, and pharmacological assessment. J Med Chem 2017;60:2456–69.
   PubMed Web of Science ®Google Scholar
• Mishra CB, Kumari S, Angeli A, et al. Discovery of potent anti-convulsant carbonic anhydrase inhibitors: design, synthesis, in vitro and in vivo appraisal. Eur J Med Chem 2018;156:430–43.
   PubMed Web of Science ®Google Scholar
• Mishra CB, Kumari S, Angeli A, et al. Design, synthesis and biological evaluation of N-(5-methyl-isoxazol-3-yl/1,3,4-thiadiazol-2-yl)-4-(3-substitutedphenylureido) benzenesulfonamides as human carbonic anhydrase isoenzymes I, II, VII and XII inhibitors. J Enzyme Inhib Med Chem 2016;31:174–9.
   PubMed Web of Science ®Google Scholar
• Rotondi G, Guglielmi P, Carradori S, et al. Design, synthesis and biological activity of selective hCAs inhibitors based on 2-(benzylsulfinyl)benzoic acid scaffold. J Enzyme Inhib Med Chem 2019;34:1400–13.
   PubMed Web of Science ®Google Scholar
• Uslu AG, Gür Maz T, Nocentini A, et al. Benzimidazole derivatives as potent and isoform selective tumor-associated carbonic anhydrase IX/XII inhibitors. Bioorg Chem 2020;95:103544.
   PubMed Web of Science ®Google Scholar
• Scozzafava A, Mastrolorenzo A, Supuran CT. Modulation of carbonic anhydrase activity and its applications in therapy. Exp Opin Ther Pat 2004;14:667–702.
   Web of Science ®Google Scholar
• Supuran CT, Scozzafava A. Carbonic anhydrase inhibitors and their therapeutic potential. Exp Opin Ther Patents 2000;10:575–600.
   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
• Guler OO, De Simone G, Supuran CT. Drug design studies of the novel antitumor targets carbonic anhydrase IX and XII. Curr Med Chem 2010;17:1516–26.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrase inhibition and the management of hypoxic tumors. Metabolites 2017;7:E48.
   PubMed Web of Science ®Google Scholar
• Monti SM, Supuran CT, De Simone G. Carbonic anhydrase IX as a target for designing novel anticancer drugs. Curr Med Chem 2012;19:821–30.
   PubMed Web of Science ®Google Scholar
• D’Ascenzio M, Secci D, Carradori S, et al. 1,3-Dipolar cycloaddition, HPLC enantioseparation, and docking studies of saccharin/isoxazole and saccharin/isoxazoline derivatives as selective carbonic anhydrase IX and XII inhibitors. J Med Chem 2020;63:2470–88.
   PubMed Web of Science ®Google Scholar
• Margheri F, Ceruso M, Carta F, et al. Overexpression of the transmembrane carbonic anhydrase isoforms IX and XII in the inflamed synovium. J Enzyme Inhib Med Chem 2016;31:60–3.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Singh S, Lomelino CL, Mboge MY, et al. Cancer drug development of carbonic anhydrase inhibitors beyond the active site. Molecules 2018;23:1045.
   PubMed Web of Science ®Google Scholar
• Tafreshi NK, Lloyd MC, Bui MM, et al. Carbonic anhydrase IX as an imaging and therapeutic target for tumors and metastases. Subcell Biochem 2014;75:221–54.
   PubMedGoogle Scholar
• Supuran CT. Experimental carbonic anhydrase inhibitors for the treatment of hypoxic tumors. J Exp Pharmacol 2020;12:603–17.
   PubMedGoogle Scholar
• Angeli A, Carta F, Nocentini A, et al. Carbonic anhydrase inhibitors targeting metabolism and tumor microenvironment. Metabolites 2020;10:412.
   PubMed Web of Science ®Google Scholar
• Pastorekova S, Gillies RJ. The role of carbonic anhydrase IX in cancer development: links to hypoxia, acidosis, and beyond. Cancer Metastasis Rev 2019;38:65–77.
   PubMed Web of Science ®Google Scholar
• Pastorek J, Pastorekova S. Hypoxia-induced carbonic anhydrase IX as a target for cancer therapy: from biology to clinical use. Semin Cancer Biol 2015;31:52–64.
   PubMed Web of Science ®Google Scholar
• Zatovicova M, Jelenska L, Hulikova A, et al. Carbonic anhydrase IX as an anticancer therapy target: preclinical evaluation of internalizing monoclonal antibody directed to catalytic domain. Curr Pharm Des 2010;16:3255–63.
   PubMed Web of Science ®Google Scholar
• Winum JY, Scozzafava A, Montero JL, Supuran CT. Inhibition of carbonic anhydrase IX: a new strategy against cancer. Anticancer Agents Med Chem 2009;9:693–702.
   PubMed Web of Science ®Google Scholar
• De Simone G, Supuran CT. Carbonic anhydrase IX: biochemical and crystallographic characterization of a novel antitumor target. Biochim Biophys Acta 2010;1804:404–9.
   PubMed Web of Science ®Google Scholar
• Winum JY, Rami M, Scozzafava A, et al. Carbonic anhydrase IX: a new druggable target for the design of antitumor agents. Med Res Rev 2008;28:445–63.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Winum JY. Carbonic anhydrase IX inhibitors in cancer therapy: an update. Future Med Chem 2015;7:1407–14.
   PubMed Web of Science ®Google Scholar
• Thiry A, Dogné JM, Masereel B, Supuran CT. Targeting tumor-associated carbonic anhydrase IX in cancer therapy. Trends Pharmacol Sci 2006;27:566–73.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrase inhibitors as emerging agents for the treatment and imaging of hypoxic tumors. Expert Opin Investig Drugs 2018;27:963–70.
   PubMed Web of Science ®Google Scholar
• Monti SM, Supuran CT, De Simone G. Anticancer carbonic anhydrase inhibitors: a patent review (2008–2013). Expert Opin Ther Pat 2013;23:737–49.
   PubMed Web of Science ®Google Scholar
• Poulsen SA. Carbonic anhydrase inhibition as a cancer therapy: a review of patent literature, 2007–2009. Expert Opin Ther Pat 2010;20:795–806.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Winum JY. Designing carbonic anhydrase inhibitors for the treatment of breast cancer. Expert Opin Drug Discov 2015;6:591–7.
   Web of Science ®Google Scholar
• Lock FE, McDonald PC, Lou Y, et al. Targeting carbonic anhydrase IX depletes breast cancer stem cells within the hypoxic niche. Oncogene 2013;32:5210–9.
   PubMed Web of Science ®Google Scholar
• Güttler A, Theuerkorn K, Riemann A, et al. Cellular and radiobiological effects of carbonic anhydrase IX in human breast cancer cells. Oncol Rep 2019;41:2585–94.
   PubMed Web of Science ®Google Scholar
• Ward C, Meehan J, Gray M, et al. Carbonic anhydrase IX (CAIX), cancer, and radiation responsiveness. Metabolites 2018;8:13.
   PubMed Web of Science ®Google Scholar
• Robertson N, Potter C, Harris AL. Role of carbonic anhydrase IX in human tumor cell growth, survival, and invasion. Cancer Res 2004;64:6160–5.
   PubMed Web of Science ®Google Scholar
• Eldehna WM, Nocentini A, Elsayed ZM, et al. Benzofuran-based carboxylic acids as carbonic anhydrase inhibitors and antiproliferative agents against breast cancer. ACS Med Chem Lett 2020;11:1022–7.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Shaldam M, Eldehna WM, Nocentini A, et al. Development of novel benzofuran-based SLC-0111 analogs as selective cancer-associated carbonic anhydrase isoform IX inhibitors. Eur J Med Chem 2021;216:113283.
   PubMed Web of Science ®Google Scholar
• Peppicelli S, Andreucci E, Ruzzolini J, et al. The carbonic anhydrase IX inhibitor SLC-0111 as emerging agent against the mesenchymal stem cell-derived pro-survival effects on melanoma cells. J Enzyme Inhib Med Chem 2020;35:1185–93.
   PubMed Web of Science ®Google Scholar
• van Kuijk SJA, Parvathaneni NK, Niemans R, et al. New approach of delivering cytotoxic drugs towards CAIX expressing cells: a concept of dual-target drugs. Eur J Med Chem 2017;127:691–702.
   PubMed Web of Science ®Google Scholar
• Mishra CB, Mongre RK, Kumari S, et al. Novel triazole-piperazine hybrid molecules induce apoptosis via activation of the mitochondrial pathway and exhibit antitumor efficacy in osteosarcoma xenograft nude mice model. ACS Chem Biol 2017;12:753–68.
   PubMed Web of Science ®Google Scholar
• Mongre RK, Mishra CB, Prakash A, et al. Novel carbazole-piperazine hybrid small molecule induces apoptosis by targeting BCL-2 and inhibits tumor progression in lung adenocarcinoma in vitro and xenograft mice model. Cancers (Basel) 2019;11:1245.
   Web of Science ®Google Scholar
• Mongre RK, Mishra CB, Jung S, et al. Exploring the role of TRIP-Brs in human breast cancer: an investigation of expression, clinicopathological significance, and prognosis. Mol Ther Oncol 2020;19:105–26.
   PubMed Web of Science ®Google Scholar
• Mishra CB, Mongre RK, Kumari S, et al. Synthesis, in vitro and in vivo anticancer activity of novel 1-(4-imino-1-substituted-1H-pyrazolo[3,4-d]pyrimidin-5(4H)-yl)urea derivatives. RSC Adv 2016;6:24491–500.
   Web of Science ®Google Scholar
• Maeda H, Khatami M. Analyses of repeated failures in cancer therapy for solid tumors: poor tumor-selective drug delivery, low therapeutic efficacy and unsustainable costs. Clin Transl Med 2018;7:11.
   PubMed Web of Science ®Google Scholar
• Zhang Z, Zhou L, Xie N, et al. Overcoming cancer therapeutic bottleneck by drug repurposing. Signal Transduct Target Ther 2020;5:113.
   PubMed Web of Science ®Google Scholar
• Logozzi M, Capasso C, Di Raimo R, et al. Prostate cancer cells and exosomes in acidic condition show increased carbonic anhydrase IX expression and activity. J Enzyme Inhib Med Chem 2019;34:272–8.
   PubMed Web of Science ®Google Scholar
• Fiaschi T, Giannoni E, Taddei ML, et al. Carbonic anhydrase IX from cancer-associated fibroblasts drives epithelial–mesenchymal transition in prostate carcinoma cells. Cell Cycle 2013;12:1791–801.
   PubMed Web of Science ®Google Scholar
• Otto T, Sicinski P. Cell cycle proteins as promising targets in cancer therapy. Nat Rev Cancer 2017;17:93–115.
   PubMed Web of Science ®Google Scholar
• Pfeffer CM, Singh ATK. Apoptosis: a target for anticancer therapy. Int J Mol Sci 2018;19:448.
   PubMed Web of Science ®Google Scholar
• Shamas-Din A, Kale J, Leber B, Andrews DW. Mechanisms of action of Bcl-2 family proteins. Cold Spring Harb Perspect Biol 2013;5:a008714.
   PubMed Web of Science ®Google Scholar
• Obexer P, Ausserlechner MJ. X-linked inhibitor of apoptosis protein – a critical death resistance regulator and therapeutic target for personalized cancer therapy. Front Oncol 2014;4:197.
   PubMedGoogle Scholar