Carbonic anhydrase inhibitors. Comparison of aliphatic sulfamate/bis- sulfamate adducts with isozymes II and IX as a platform for designing tight-binding, more isoform-selective inhibitors
Carbonic anhydrase inhibitors. Comparison of aliphatic sulfamate/bis- sulfamate adducts with isozymes II and IX as a platform for designing tight-binding, more isoform-selective inhibitors(462 views) Vitale RM, Alterio V, Innocenti A, Winum JY, Monti SM, De Simone G, Supuran CT
J Med Chem (ISSN: 0022-2623, 1520-4804, 0022-2623print), 2009 Oct 8; 52(19): 5990-5998.
Keywords: Aliphatic Compound, Bis Sulfamate, Carbonate Dehydratase, Carbonate Dehydratase Inhibitor, Isoenzyme, Sulfamic Acid, Sulfonamide, Sulfonic Acid Derivative, Unclassified Drug, Article, Binding Affinity, Crystal Structure, Drug Design, Drug Structure, Antigens, Neoplasm, Carbonic Anhydrase Ii, Carbonic Anhydrase Inhibitors, Catalytic Domain, Humans, Models, Molecular, Protein Binding, Structure-Activity Relationship,
Affiliations: *** IBB - CNR ***
Istituto di Chimica Biomolecolare - CNR, Via Campi Flegrei 34, 80078, Pozzuoli, Italy
Istituto di Biostrutture e Bioimmagini - CNR, Via Mezzocannone 16, 80134 Napoli, Italy
Laboratorio di Chimica Bioinorganica, Università degli Studi di Firenze, Via della Lastruccia 3, I-50019 Sesto Fiorentino, Firenze, Italy
Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS-UM1-UM2, Ecole Nationale Supérieure de Chimie de Montpellier, 8 Rue de l'Ecole Normale, 34296 Montpellier Cedex, France
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Winum, J. -Y., Vullo, D., Casini, A., Montero, J. -L., Scozzafava, A., Supuran, C. T., Carbonic anhydrase inhibitors. Inhibition of cytosolic isozymes I and II and transmembrane, tumor-associated isozyme IX with sulfamates including EMATE also acting as steroid sulfatase inhibitors (2003) J. Med. Chem., 46, pp. 2197-2204
Winum, J. -Y., Pastorekova, S., Jakubickova, L., Montero, J. -L., Scozzafava, A., Pastorek, J., Vullo, D., Supuran, C. T., Carbonic anhydrase inhibitors: Synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II and IX with bis-sulfamates (2005) Bioorg. Med. Chem. Lett., 15, pp. 579-584
Supuran, C. T., Diuretics: From classical carbonic anhydrase inhibitors to novel applications of the sulfonamides (2008) Curr. Pharm. Des., 14, pp. 641-648
Supuran, C. T., Scozzafava, A., Conway, J., (2004) Carbonic Anhydrase. Its Inhibitors and Activators, pp. 1-363. , CRC Press: Boca Raton, FL
Thiry, A., Dogn, J. M., Masereel, B., Supuran, C. T., Targeting tumor-associated carbonic anhydrase IX in cancer therapy (2006) Trends Pharmacol. Sci., 27, pp. 566-573
Winum, J. Y., Montero, J. L., Scozzafava, A., Supuran, C. T., New zinc binding motifs in the design of selective carbonic anhydrase inhibitors (2006) Mini-Rev. Med. Chem., 6, pp. 921-936
Krishnamurthy, V. M., Kaufman, G. K., Urbach, A. R., Gitlin, I., Gudiksen, K. L., Weibel, D. B., Whitesides, G. M., Carbonic anhydrase as a model for biophysical and physical-organic studies of proteins and protein-ligand binding (2008) Chem. Rev., 108, pp. 946-1051
Supuran, C. T., Di Fiore, A., De Simone, G., Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity (2008) Expert Opinion on Emerging Drugs, 13 (2), pp. 383-392. , DOI 10. 1517/14728214. 13. 2. 383
Khalifah, R. G., The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C (1971) J. Biol. Chem., 246, pp. 2561-2573
Eriksson, A. E., Jones, T. A., Liljas, A., Refined structure of human carbonic anhydrase II at 2. 0 resolution (1988) Proteins: Struct. Funct., 4, pp. 274-282
Brunger, A. T., Adams, P. D., Clore, G. M., De Lano, W. L., Gros, P., Grosse-Kunstleve, R. W., Jiang, J. S., Warren, G. L., Crystallography & NMR system: A new software suite for macromolecular structure determination (1998) Acta Crystallogr., Sect. D, 54, pp. 905-921
Jones, T. A., Zou, J. Y., Cowan, S. W., Kjeldgaard, M., Improved methods for building protein models in electron density maps and the location of errors in these models (1991) Acta Crystallogr., Sect. A, 47, pp. 110-119
Allen, F. H., The Cambridge Structural Database: A quarter of a million crystal structures and rising (2002) Acta Crystallogr., Sect. B, 58, pp. 380-388
Laskowski, R. A., MacArthur, M. W., Moss, D. S., Thornton, J. M., PROCHECK, a program to check the stereochemical quality of protein structures (1993) J. Appl. Crystallogr., 26, pp. 283-291
Whittington, D. A., Grubb, J. H., Waheed, A., Shah, G. N., Sly, W. S., Christianson, D. W., Expression, assay, and structure of the extracellular domain of murine carbonic anhydrase XIV: Implications for selective inhibition of membrane-associated isozymes (2004) J. Biol. Chem., 279, pp. 7223-7228
Bowie, J. U., Luthy, R., Eisenberg, D., A method to identify protein sequences that fold into a known three-dimensional structure (1991) Science, 253 (5016), pp. 164-170
Case, D. A., Darden, T. A., Cheatham III, T. E., Simmerling, C. L., Wang, J., Duke, R. E., Luo, R., Kollman, P. A., (2006) AMBER 9, , University of California: San Francisco, CA
Bayly, C. I., Cieplak, P., Cornell, W. D., Kollman, P. A., A well-behaved electrostatic potential based method using charge restraints for determining atom-centered charges: The RESP model (1993) J. Phys. Chem., 97, pp. 10269-10280
Schmidt, M. W., Baldridge, K. K., Boatz, J. A., Elbert, S. T., Gordon, M. S., Jensen, J. J., Koseki, S., Montgomery, J. A., General atomic and molecular electronic structure system (1993) J. Comput. Chem., 14, pp. 1347-1363
Hoops, S. C., Anderson, K. W., Merz Jr., K. M., Force field design for metalloproteins (1991) J. Am. Chem. Soc., 113, pp. 8262-8270
Ryckaert, J. -P., Ciccotti, G., Berendsen, H. J. C., Numerical integration of the Cartesian equations of motion of a system with constraints: Molecular dynamics of n-alkanes (1997) J. Comput. Phys., 23, pp. 327-341
Carbonic anhydrase inhibitors. Comparison of aliphatic sulfamate/bis- sulfamate adducts with isozymes II and IX as a platform for designing tight-binding, more isoform-selective inhibitors
Carbonic anhydrase inhibitors. Comparison of aliphatic sulfamate/bis- sulfamate adducts with isozymes II and IX as a platform for designing tight-binding, more isoform-selective inhibitors
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Carbonic anhydrase inhibitors. Comparison of aliphatic sulfamate/bis- sulfamate adducts with isozymes II and IX as a platform for designing tight-binding, more isoform-selective inhibitors