Synthesis and inhibition potency of novel ureido benzenesulfonamides incorporating GABA as tumor-associated carbonic anhydrase IX and XII inhibitors

References

• Supuran CT. Carbonic anhydrases. Bioorg Med Chem 2013;21:1377–8
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81
   PubMed Web of Science ®Google Scholar
• Esbaugh AJ, Tufts BL. The structure and function of carbonic anhydrase isozymes in the respiratory system of vertebrates. Respir Physiol Neurobiol 2006;154:185–98
   PubMed Web of Science ®Google Scholar
• Supuran CT. Structure-based drug discovery of carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2012;27:759–72
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2010;20:3467–74
   PubMed Web of Science ®Google Scholar
• Neri D, Supuran CT. Interfering with pH regulation in tumors as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767–77
   PubMed Web of Science ®Google Scholar
• Švastová E, Hulíková A, Rafajová M, et al. Hypoxia activates the capacity of tumor-associated carbonic anhydrase IX to acidify extracellular pH. FEBS Lett 2004;577:439–45
   PubMed Web of Science ®Google Scholar
• McIntyre A, Patiar S, Wigfield S, et al. Carbonic anhydrase IX promotes tumor growth and necrosis in vivo and inhibition enhances anti-VEGF therapy. Clin Cancer Res 2012;18:3100–11
   PubMed Web of Science ®Google Scholar
• Hussain SA, Ganesan R, Reynolds G, et al. Hypoxia-regulated carbonic anhydrase IX expression is associated with poor survival in patients with invasive breast cancer. Br J Cancer 2007;96:104–9
   PubMed Web of Science ®Google Scholar
• Proescholdt MA, Merrill MJ, Stoerr EM, et al. Function of carbonic anhydrase IX in glioblastoma multiforme. Neurooncology 2012;14:1357–66
   PubMed Web of Science ®Google Scholar
• Barnett DH, Sheng S, Charn TH, et al. Estrogen receptor regulation of carbonic anhydrase XII through a distal enhancer in breast cancer. Cancer Res 2008;68:3505–15
   PubMed Web of Science ®Google Scholar
• Haapasalo J, Hilvo M, Nordfors K, et al. Identification of an alternatively spliced isoform of carbonic anhydrase XII in diffusely infiltrating astrocytic gliomas. Neuro-Oncology 2008;10:131–8
   PubMed Web of Science ®Google Scholar
• Said HM, Hagemann C, Carta F, et al. Hypoxia induced CA9 inhibitory targeting by two different sulfonamide derivatives including acetazolamide in human glioblastoma. Bioorg Med Chem 2013;21:3949–57
   PubMed Web of Science ®Google Scholar
• Dubois L, Lieuwes NG, Maresca A, et al. Imaging of CA IX with fluorescent labelled sulphonamides distinguishes hypoxic and (re)-oxygenated cells in a xenograft tumor model. Radiother Oncol 2009;92:423–8
   PubMed Web of Science ®Google Scholar
• Alterio V, Hilvo M, Di Fiore A, et al. Crystal structure of the catalytic domain of the tumor-associated human carbonic anhydrase IX. Proc Natl Acad Sci USA 2009;106:16233–8
   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
• Alterio V, Di Fiore A, D'Ambrosio K, et al. Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms? Chem Rev 2012;112:4421–68
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrase inhibitors and activators for novel therapeutic applications. Future Med Chem 2011;3:1165–80
   PubMed Web of Science ®Google Scholar
• De Simone G, Alterio V, Supuran CT. Exploiting the hydrophobic and hydrophilic binding sites for designing carbonic anhydrase inhibitors. Expert Opin Drug Discov 2013;8:793–810
   PubMed Web of Science ®Google Scholar
• Supuran CT, McKenna R. Carbonic anhydrase inhibitors drug design. In: McKenna R, Frost S, eds. Carbonic anhydrase: mechanism, regulation, links to disease, and industrial applications. Heidelberg: Springer Verlag; 2014:291–323
   Google Scholar
• Pacchiano F, Carta F, McDonald PC, et al. Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis. J Med Chem 2011;54:1896–902
   PubMed Web of Science ®Google Scholar
• Carta F, Scozzafava A, Supuran CT. Sulfonamides (RSO2NH2): a patent review 2008–2012. Expert Opin Ther Pat 2012;22:747–58
   PubMed Web of Science ®Google Scholar
• Cecchi A, Hulikova A, Pastorek J, et al. Carbonic anhydrase inhibitors. Sulfonamides inhibit isozyme IX mediated acidification of hypoxic tumors. Fluorescent sulphonamides design as probes of membrane-bound carbonic anhydrase isozymes involvement in tumorigenesis. J Med Chem 2005;48:4834–41
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrases: off-targets, add-on activities, or emerging novel targets? In: Peters JU, ed. Polypharmacology in drug discovery. Hoboken: Wiley; 2012:457–89
   Google Scholar
• Ceruso M, Antel S, Vullo D, et al. Inhibition studies of new ureido-substituted sulfonamides incorporating a GABA moiety against human carbonic anhydrase isoforms I-XIV. J Med Chem 2014;22:6768–75
   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
• Supuran CT, Mincione F, Scozzafava A, et al. Carbonic anhydrase inhibitors. Part 52. Metal complexes of heterocyclic sulfonamides: a new class of strong topical intraocular pressure-lowering agents with potential use as antiglaucoma drugs. Eur J Med Chem 1998;33:247–54
   Web of Science ®Google Scholar
• Wilkinson BL, Bornaghi LF, Houston TA, et al. Carbonic anhydrase inhibitors: inhibition of isozymes I, II and IX with triazole-linked O-glycosides of benzene sulphonamides. J Med Chem 2007;50:1651–7
   PubMed Web of Science ®Google Scholar
• Supuran CT, Mincione F, Scozzafava A, et al. Carbonic anhydrase inhibitors. Part 52. Metal complexes of heterocyclic sulfonamides: a new class of strong topical intraocular pressure-lowering agents with potential use as antiglaucoma drugs. Eur J Med Chem 1998;33:247–54
   Web of Science ®Google Scholar
• Ceruso M, Del Prete S, Alothman Z, et al. Sulfonamides with potent inhibitory action and selectivity against the α-carbonic anhydrase from Vibrio cholera. ACS Med Chem Lett 2014;5:826–30
   PubMed Web of Science ®Google Scholar
• Ceruso M, Bragagni M, AlOthman Z, et al. New series of sulfonamides containing amino acid moiety act as effective and selective inhibitors of tumor-associated carbonic anhydrase XII. J Enzyme Inhib Med Chem 2014. [Epub ahead of print]. doi: 10.3109/14756366.2014.942659
   Google Scholar