Inhibition and binding studies of carbonic anhydrase isozymes I, II and IX with benzimidazo[1,2-c][1,2,3]thiadiazole-7-sulphonamides

References

• Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–181.
   PubMed Web of Science ®Google Scholar
• Krishnamurthy VM, Kaufman GK, Urbach AR, Gitlin I, Gudiksen KL, Weibel DB, Whitesides GM. Carbonic anhydrase as a model for biophysical and physical-organic studies of proteins and protein-ligand binding. Chem Rev 2008;108:946–1051.
   PubMed Web of Science ®Google Scholar
• Velazquez-Campoy A, Ohtaka H, Nezami A, Muzammil S, Freire E. Isothermal titration calorimetry. Curr Protoc Cell Biol 2004;Chapter 17:Unit 17 8.
   PubMedGoogle Scholar
• Matulis D, Kranz JK, Salemme FR, Todd MJ. Thermodynamic stability of carbonic anhydrase: measurements of binding affinity and stoichiometry using ThermoFluor. Biochemistry 2005;44:5258–5266.
   PubMed Web of Science ®Google Scholar
• Supuran CT. Carbonic anhydrases–an overview. Curr Pharm Des 2008;14:603–14.
   PubMed Web of Science ®Google Scholar
• Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 2007;15:4336–4350.
   PubMed Web of Science ®Google Scholar
• Lindskog S. Structure and mechanism of carbonic anhydrase. Pharmacol Ther 1997;74:1–20.
   PubMed Web of Science ®Google Scholar
• Hilvo M, Baranauskiene L, Salzano AM, Scaloni A, Matulis D, Innocenti A, Scozzafava A, Monti SM, Di Fiore A, De Simone G, Lindfors M, Janis J, Valjakka J, Pastorekova S, Pastorek J, Kulomaa MS, Nordlund HR, Supuran CT, Parkkila S. Biochemical characterization of CA IX, one of the most active carbonic anhydrase isozymes. J Biol Chem 2008;283:27799–27809.
   PubMed Web of Science ®Google Scholar
• Dorai T, Sawczuk IS, Pastorek J, Wiernik PH, Dutcher JP. The role of carbonic anhydrase IX overexpression in kidney cancer. Eur J Cancer 2005;41:2935–2947.
   PubMed Web of Science ®Google Scholar
• Chen J, Rocken C, Hoffmann J, Kruger S, Lendeckel U, Rocco A, Pastorekova S, Malfertheiner P, Ebert MP. Expression of carbonic anhydrase 9 at the invasion front of gastric cancers. Gut 2005;54:920–927.
   PubMed Web of Science ®Google Scholar
• Kon-no H, Ishii G, Nagai K, Yoshida J, Nishimura M, Nara M, Fujii T, Murata Y, Miyamoto H, Ochiai A. Carbonic anhydrase IX expression is associated with tumor progression and a poor prognosis of lung adenocarcinoma. Lung Cancer 2006;54:409–418.
   PubMedGoogle Scholar
• Pastorekova S, Zatovicova M, Pastorek J. Cancer-associated carbonic anhydrases and their inhibition. Curr Pharm Des 2008;14:685–698.
   PubMed Web of Science ®Google Scholar
• Dudutiene V, Baranauskiene L, Matulis D. Benzimidazo[1,2-c][1,2,3]thiadiazole-7-sulfonamides as inhibitors of carbonic anhydrase. Bioorg Med Chem Lett 2007;17:3335–3338.
   PubMed Web of Science ®Google Scholar
• Pocker Y, Stone JT. The catalytic versatility of erythrocyte carbonic anhydrase. 3. Kinetic studies of the enzyme-catalyzed hydrolysis of p-nitrophenyl acetate. Biochemistry 1967;6: 668–678.
   PubMed Web of Science ®Google Scholar
• Cimmperman P, Baranauskiene L, Jachimoviciute S, Jachno J, Torresan J, Michailoviene V, Matuliene J, Sereikaite J, Bumelis V, Matulis D. A quantitative model of thermal stabilization and destabilization of proteins by ligands. Biophys J 2008;95:3222–3231.
   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;246:2561–2573.
   PubMed Web of Science ®Google Scholar
• Nishimori I, Minakuchi T, Onishi S, Vullo D, Cecchi A, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Bioorg Med Chem 2007;15:7229–7236.
   PubMed Web of Science ®Google Scholar
• Vullo D, Voipio J, Innocenti A, Rivera C, Ranki H, Scozzafava A, Kaila K, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides. Bioorg Med Chem Lett 2005;15:971–976.
   PubMed Web of Science ®Google Scholar
• Nishimori I, Vullo D, Innocenti A, Scozzafava A, Mastrolorenzo A, Supuran CT. Carbonic anhydrase inhibitors: inhibition of the transmembrane isozyme XIV with sulfonamides. Bioorg Med Chem Lett 2005;15:3828–3833.
   PubMed Web of Science ®Google Scholar
• Vullo D, Innocenti A, Nishimori I, Pastorek J, Scozzafava A, Pastorekova S, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-a new target for the design of antitumor and antiglaucoma drugs? Bioorg Med Chem Lett 2005;15:963–969.
   PubMed Web of Science ®Google Scholar
• Pantoliano MW, Petrella EC, Kwasnoski JD, Lobanov VS, Myslik J, Graf E, Carver T, Asel E, Springer BA, Lane P, Salemme FR. High-density miniaturized thermal shift assays as a general strategy for drug discovery. J Biomol Screen 2001;6:429–440.
   PubMed Web of Science ®Google Scholar
• Niesen FH, Berglund H, Vedadi M. The use of differential scanning fluorimetry to detect ligand interactions that promote protein stability. Nat Protoc 2007;2:2212–2221.
   PubMed Web of Science ®Google Scholar
• Leslie AGW. The integration of macromolecular diffraction data. Acta Crystallogr D Biol Crystallogr 2006;62:48–57.
   PubMedGoogle Scholar
• Evans P. Scaling and assessment of data quality. Acta Crystallogr D Biol Crystallogr 2006;62:72–82.
   PubMedGoogle Scholar
• Srivastava DK, Jude KM, Banerjee AL, Haldar M, Manokaran S, Kooren J, Mallik S, Christianson DW. Structural analysis of charge discrimination in the binding of inhibitors to human carbonic anhydrases I and II. J Am Chem Soc 2007;129:5528–5537.
   PubMedGoogle Scholar
• Murshudov GN, Vagin AA, Dodson EJ. Refinement of macromolecular structures by the maximum-likelihood method. Acta Crystallogr D Biol Crystallogr 1997;53:240–255.
   PubMed Web of Science ®Google Scholar
• Brunger AT, Adams PD, Clore GM, DeLano WL, Gros P, Grosse-Kunstleve RW, Jiang JS, Kuszewski J, Nilges M, Pannu NS, Read RJ, Rice LM, Simonson T, Warren GL. Crystallography & NMR system: A new software suite for macromolecular structure determination. Acta Crystallogr D Biol Crystallogr 1998;54:905–921.
   PubMed Web of Science ®Google Scholar
• Kleywegt GJ, Zou JY, Kjeldgaard M, Jones TA. Crystallography of biological macromolecules. In: Rossmann MG, Arnold E, Eds. International Tables for Crystallography. Vol F. The Netherlands, Kluwer Academic Publishers 2001:L353–367.
   Google Scholar
• Collaborative Computational Project (CCP). The CCP4 suite: programs for protein crystallography. Acta Cryst D 1994;50:760–763.
   PubMedGoogle Scholar
• Hubbard SJ, Thornton JM. Department of Biochemistry and molecular biology, UCL. ‘NACCESS’, Computer Program. 1993.
   Google Scholar
• Briganti F, Pierattelli R, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Part 37. Novel classes of isozyme I and II inhibitors and their mechanism of action. Kinetic and spectroscopic investigations on native and cobalt substituted enzymes. Eur J Med Chem 1996;31:1001–1010.
   Web of Science ®Google Scholar
• Hilvo M, Salzano AM, Innocenti A, Kulomaa MS, Scozzafava A, Scaloni A, Parkkila S, Supuran CT. Cloning, expression, post-translational modifications and inhibition studies on the latest mammalian carbonic anhydrase isoform, CA XV. J Med Chem 2009;52:646–54.
   PubMed Web of Science ®Google Scholar
• Kraulis PJ. MOLSCRIPT: a program to produce both detailed and schematic plots of protein structures. J Appl Cryst 1991;24:946–950.
   Web of Science ®Google Scholar
• Merritt EA, Bacon DJ. Raster3D: Photorealistic molecular graphics. Methods Enzymol 1997;277:505–524.
   PubMed Web of Science ®Google Scholar
• Esnouf RM. Further additions to MolScript version 1.4, including reading and contouring of electron-density maps. Acta Crystallogr D Biol Crystallogr 1999;55:938–940.
   PubMedGoogle Scholar