Selective carbonic anhydrase IX inhibitors based on coumarin scaffold as promising antimetastatic agents: WO2012070024

Bibliography

• Eccles SA, Welch DR. Metastasis: recent discoveries and novel treatment strategies. Lancet 2007;369:1742-57
   PubMed Web of Science ®Google Scholar
• Gupta GP, Massague J. Cancer metastasis: building a framework. Cell 2006;127:679-85
   PubMed Web of Science ®Google Scholar
• Iiizumi M, Liu W, Pai SK, et al. Drug development against metastasis-related genes and their pathways: a rationale for cancer therapy. Biochim Biophys Acta 2008;1786:87-104
   PubMed Web of Science ®Google Scholar
• McDonald PC, Winum JY, Supuran CT, Dedhar S. Recent developments in targeting carbonic anhydrase IX for cancer therapeutics. Oncotarget 2012;3:84-97
   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
• Carradori S, Cristini C, Secci D, et al. Current and emerging strategies in bladder cancer. Anticancer Agents Med Chem 2012;12:589-603
   Google Scholar
• Alterio V, Hilvo M, Di Fiorea A, et al. Crystal structure of the catalytic domain of the tumor-associated human carbonic anhydrase IX. PNAS 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
• Carta F, Garaj V, Maresca A, et al. Sulfonamides incorporating 1,3,5-triazine moieties selectively and potently inhibit carbonic anhydrase transmembrane isoforms IX, XII and XIV over cytosolic isoforms I and II: solution and X-ray crystallographic studies. Bioorg Med Chem 2011;19:3105-19
   PubMed Web of Science ®Google Scholar
• 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
• Brockton NT, Klimowicz AC, Bose P, et al. High stromal carbonic anhydrase IX expression is associated with nodal metastasis and decreased survival in patients with surgically-treated oral cavity squamous cell carcinoma. Oral Oncol 2012;48:615-22
   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
• Hynninen P, Parkkila S, Huhtala H, et al. Carbonic anhydrase isozymes II, IX, and XII in uterine tumors. APMIS 2012;120:117-29
   PubMedGoogle Scholar
• Kivela AJ, Knuuttila A, Rasanen J, et al. Carbonic anhydrase IX in malignant pleural mesotheliomas: a potential target for anti-cancer therapy. Bioorg Med Chem 2012; published online 18 September 2012; doi: 10.1016/j.bmc.2012.09.018
   PubMedGoogle Scholar
• Williams E, Martin S, Moss R, et al. Co-expression of VEGF and CA9 in ovarian high-grade serous carcinoma and relationship to survival. Virchows Arch 2012;461:33-9
   PubMed Web of Science ®Google Scholar
• Ma B, Pan Y, Song Q, et al. The effect of topiramate on tumor-related angiogenesis and on serum proteome of mice bearing Lewis lung carcinoma. Eur J Pharmacol 2011;663:9-16
   PubMedGoogle Scholar
• Collier C, Petrovic S. Carbonic anhydrase IX as a target for renal cell carcinoma therapy. Nephrol Rev 2011;3:36-41
   Google Scholar
• Schoppmann SF, Jesch B, Friedrich J, et al. Phosphorylation of signal transducer and activator of transcription 3 (STAT3) correlates with Her-2 status, carbonic anhydrase 9 expression and prognosis in esophageal cancer. Clin Exp Metastasis 2012;29:615-24
   PubMedGoogle Scholar
• Battke C, Kremmer E, Mysliwietz J, et al. Generation and characterization of the first inhibitory antibody targeting tumour-associated carbonic anhydrase XII. Cancer Immunol Immunother 2011;60:649-58
   PubMed Web of Science ®Google Scholar
• Hassan MdI, Shajee B, Waheed A, et al. Structure, function and applications of carbonic anhydrase isozymes. Bioorg Med Chem 2012; published online 27 April 2012; doi: 10.1016/j.bmc.2012.04.044
   Google Scholar
• Chiche J, Ilc K, Laferriere J, et al. Hypoxia-inducible carbonic anhydrase IX and XII promote tumor cell growth by counteracting acidosis through the regulation of the intracellular pH. Cancer Res 2009;69:358-68
   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
• Gieling RG, Williams KJ. Carbonic anhydrase IX as a target for metastatic disease. Bioorg Med Chem 2012; published online 11 October 2012; doi 10.1016/j.bmc.2012.09.062
   PubMedGoogle 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
• Lock FE, McDonald PC, Lou Y, et al. Targeting carbonic anhydrase IX depletes breast cancer stem cells within the hypoxic niche. Oncogene 2012; published online 3 December 2012; doi: 10.1038/onc.2012.550
   Google Scholar
• Jogaite V, Zubriene A, Michailoviene V, et al. Characterization of human carbonic anhydrase XII stability and inhibitor binding. Bioorg Med Chem 2012; published online 27 October 2012; doi: 10.1016/j.bmc.2012.10.016
   PubMedGoogle 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, Scozzafava A. Carbonic anhydrase inhibitors and their therapeutic potential. Expert Opin Ther Pat 2000;10:575-600
   Web of Science ®Google Scholar
• Supuran CT, Scozzafava A. Applications of carbonic anhydrase inhibitors and activators in therapy. Expert Opin Ther Pat 2002;12:217-42
   Web of Science ®Google Scholar
• Scozzafava A, Mastrolorenzo A, Supuran CT. Carbonic anhydrase inhibitors and activators and their use in therapy. Expert Opin Ther Pat 2006;16:1627-64
   Web of Science ®Google Scholar
• Clare BW, Supuran CT. A perspective on quantitative structure-activity relationships and carbonic anhydrase inhibitors. Expert Opin Drug Metab Toxicol 2006;2:113-37
   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, Temperini C, Pochet L, et al. Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J Med Chem 2010;53:335-44
   PubMed Web of Science ®Google Scholar
• Balboni G, Congiu C, Onnis V, et al. Flavones and structurally related 4-chromenones inhibit carbonic anhydrases by a different mechanism of action compared to coumarins. Bioorg Med Chem Lett 2012;22:3063-6
   PubMed Web of Science ®Google Scholar
• Davis RA, Vullo D, Maresca A, et al. Natural product coumarins that inhibit human carbonic anhydrases. Bioorg Med Chem 2012; published online 23 July 2012; doi: 10.1016/j.bmc.2012.07.021
   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;20:4511-14
   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
• Lou Y, McDonald PC, Oloumi A, et al. Targeting tumor hypoxia: suppression of breast tumor growth and metastasis by novel carbonic anhydrase IX inhibitors. Cancer Res 2011;71:3364-76
   PubMed Web of Science ®Google Scholar
• Carta F, Maresca A, Scozzafava A, Supuran CT. 5- and 6-Membered (thio)lactones are prodrug type carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2012;22:267-70
   PubMed Web of Science ®Google Scholar
• Riafrecha LE, Rodriguez OM, Vullo D, et al. Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases. Bioorg Med Chem 2012; published online 11 September 2012; doi: 10.1016/j.bmc.2012.09.002
   PubMedGoogle Scholar