Multiple binding modes of inhibitors to carbonic anhydrases: How to design specific drugs targeting 15 different isoforms?(452 views) Alterio V, Di Fiore A, D'Ambrosio K, Supuran CT, De Simone G
Keywords: Active Site, Binding Modes, Close Proximity, Crystallographic Studies, Enzyme Active Sites, Esterase Activities, Inorganic Anions, Isoforms, State Of The Art, Structural Feature, Structural Studies, Zinc Ions, Binding Energy, Carbonic Anhydrase, Carbonate Dehydratase, Carbonate Dehydratase Inhibitor, Isoenzyme, Amino Acid Sequence, Animal, Chemistry, Drug Antagonism, Drug Design, Human, Metabolism, Molecular Genetics, Protein Binding, Review, Carbonic Anhydrase Inhibitors, Molecular Sequence Data,
Affiliations: *** IBB - CNR ***
Istituto di Biostrutture e Bioimmagini-CNR, via Mezzocannone 16, 80134 Napoli, Italy
Università Degli Studi di Firenze, Laboratorio di Chimica Bioinorganica, Via della Lastruccia 3, I-50019 Sesto Fiorentino, Firenze, Italy
Universit Degli Studi di Firenze, Laboratorio di Chimica Bioinorganica, Via della Lastruccia 3, I-50019 Sesto Fiorentino, Firenze, Italy
Supuran, C.T., (2008) Nat. Rev. Drug Discovery, 7, p. 168
Supuran, C.T., Winum, J.-Y., (2009) Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications, , Eds. Wiley: Hoboken, NJ, Part II
Tripp, B.C., Smith, K., Ferry, J.G., (2001) J. Biol. Chem., 276, p. 48615
Ferry, J.F., (2010) Biochim. Biophys. Acta, 1804, p. 374
Clare, B.W., Supuran, C.T., (2006) Expert Opin. Drug Metab. Toxicol., 2, p. 113
Lindskog, S., (1997) Pharmacol. Ther., 74, p. 1
Pastorekova, S., Parkkila, S., Pastorek, J., Supuran, C.T., (2004) J. Enzyme Inhib. Med. Chem, 19, p. 199
Scozzafava, A., Mastrolorenzo, A., Supuran, C.T., (2006) Expert. Opin. Ther. Pat., 16, p. 1627
Winum, J.-Y., Scozzafava, A., Montero, J.-L., Supuran, C.T., (2006) Mini Rev. Med. Chem., 6, p. 921
Temperini, C., Scozzafava, A., Supuran, C.T., (2009) Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications, p. 473. , Supuran, C. T. Winum, J.-Y. Wiley: Hoboken, NJ
De Simone, G., Di Fiore, A., Supuran, C.T., (2008) Curr. Pharm. Des., 14, p. 655
De Simone, G., Supuran, C.T., (2007) Curr. Top. Med. Chem., 7, p. 879
Supuran, C.T., Di Fiore, A., De Simone, G., (2008) Expert Opin. Emerg. Drugs, 13, p. 383
Winum, J.-Y., Rami, M., Scozzafava, A., Montero, J.-L., Supuran, C.T., (2008) Med. Res. Rev., 28, p. 445
Guler, O.O., De Simone, G., Supuran, C.T., (2010) Curr. Med. Chem., 17, p. 1516
Thiry, A., Dogné, J.M., Supuran, C.T., Masereel, B., (2008) Curr. Pharm. Des., 14, p. 661
Hen, N., Bialer, M., Yagen, B., Maresca, A., Aggarwal, M., Robbins, A.H., McKenna, R., Supuran, C.T., (2011) J. Med. Chem., 54, p. 3977
Gao, B.B., Clermont, A., Rook, S., Fonda, S.J., Srinivasan, V.J., Wojtkowski, M., Fujimoto, J.G., Feener, E.P., (2007) Nat. Med., 13, p. 181
Mincione, F., Scozzafava, A., Supuran, C.T., (2008) Curr. Pharm. Des., 14, p. 649
De Simone, G., Scozzafava, A., Supuran, C.T., (2009) Chem. Biol. Drug Des., 74, p. 317
Basnyat, B., Gertsch, J.H., Johnson, E.W., Castro-Marin, F., Inoue, Y., Yeh, C., (2003) High Alt. Med. Biol., 4, p. 45
Swenson, E.R., Teppema, L.J., (2007) J. Appl. Physiol., 102, p. 1305
Barreiro, E., Hussain, S.N.A., (2010) Antioxid. Redox Signal., 12, p. 417
Ruusuvuori, E., Li, H., Huttu, K., Palva, J.M., Smirnov, S., Rivera, C., Kaila, K., Voipio, J., (2004) J. Neurosci., 24, p. 2699
Aspatwar, A., Tolvanen, M.E., Ortutay, C., Parkkila, S., (2010) Curr. Pharm. Des., 16, p. 3264
Nishimori, I., (2004) Carbonic Anhydrase: Its Inhibitors and Activators, p. 25. , Supuran, C. T. Scozzafava, A. Conway, J. CRC Press: Boca Raton, FL
Battke, C., Kremmer, E., Mysliwietz, J., Gondi, G., Dumitru, C., Brandau, S., Lang, S., Zeidler, R., (2011) Cancer Immunol. Immunother., 60, p. 649
Liao, S.Y., Ivanov, S., Ivanova, A., Ghosh, S., Cote, M.A., Keefe, K., Coca-Prados, M., Lerman, M.I., (2003) J. Med. Genet., 40, p. 257
Lehtonen, J., Shen, B., Vihinen, M., Casini, A., Scozzafava, A., Supuran, C.T., Parkkila, A.K., Parkkila, S., (2004) J. Biol. Chem., 279, p. 2719
Shah, G.N., Ulmasov, B., Waheed, A., Becker, T., Makani, S., Svichar, N., Chesler, M., Sly, W.S., (2005) Proc. Natl. Acad. Sci.U.S.A., 102, p. 16771
Ogilvie, J.M., Ohlemiller, K.K., Shah, G.N., Ulmasov, B., Becker, T.A., Waheed, A., Hennig, A.K., Sly, W.S., (2007) Proc. Natl. Acad. Sci. U.S.A., 104, p. 8514
Alterio, V., Di Fiore, A., D'Ambrosio, K., Supuran, C.T., De Simone, G., (2009) Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications, p. 73. , Supuran, C. T. Winum, J.-Y. Wiley: Hoboken, NJ
Kannan, K.K., Ramanadham, M., Jones, T.A., (1984) Ann. N.Y. Acad. Sci., 429, p. 49
Eriksson, A.E., Kylsten, P.M., Jones, T.A., Liljas, A., (1988) Proteins, 4, p. 283
Eriksson, A.E., Liljas, A., (1993) Proteins, 16, p. 29
Boriack-Sjodin, P.A., Heck, R.W., Laipis, P.J., Silverman, D.N., Christianson, D.W., (1995) Proc. Natl. Acad. Sci. U.S.A., 92, p. 10949
Stams, T., Nair, S.K., Okuyama, T., Waheed, A., Sly, W.S., Christianson, D.W., (1996) Proc. Natl. Acad. Sci. U.S.A., 93, p. 13589
Whittington, D.A., Waheed, A., Ulmasov, B., Shah, G.N., Grubb, J.H., Sly, W.S., Christianson, D.W., (2001) Proc. Natl. Acad. Sci. U.S.A., 98, p. 9545
Duda, D.M., Tu, C., Fisher, S.Z., An, H., Yoshioka, C., Govindasamy, L., Laipis, P.J., McKenna, R., (2005) Biochemistry, 44, p. 10046
Di Fiore, A., Monti, S.M., Hilvo, M., Parkkila, S., Romano, V., Scaloni, A., Pedone, C., De Simone, G., (2008) Proteins, 74, p. 164
Alterio, V., Hilvo, M., Di Fiore, A., Supuran, C.T., Pan, P., Parkkila, S., Scaloni, A., De Simone, G., (2009) Proc. Natl. Acad. Sci. U.S.A., 106, p. 16233
Di Fiore, A., Truppo, E., Supuran, C.T., Alterio, V., Dathan, N., Bootorabi, F., Parkkila, S., De Simone, G., (2010) Bioorg. Med. Chem. Lett., 20, p. 5023
Hakansson, K., Carlsson, M., Svensson, L.A., Liljas, A., (1992) J. Mol. Biol., 227, p. 1192
Stams, T., Christianson, D.W., (2000) The Carbonic Anhydrases. New Horizons, p. 159. , Chegwidden, W. R. Carter, N. D. Edwards, Y. H. Birkhäuser Verlag: Basel, Switzerland
Sjöblom, B., Polentarutti, M., Djinovic-Carugo, K., (2009) Proc. Natl. Acad. Sci. U.S.A., 106, p. 10609
Domsic, J.F., Avvaru, B.S., Kim, C.U., Gruner, S.M., Agbandje-Mckenna, M., Silverman, D.N., McKenna, R., (2008) J. Biol. Chem., 283, p. 30766
Merz, Jr.K.M., (1991) J. Am. Chem. Soc., 113, p. 406
Briganti, F., Mangani, S., Scozzafava, A., Vernaglione, G., Supuran, C.T., (1999) J. Biol. Inorg. Chem., 4, p. 528
Guerri, A., Briganti, F., Scozzafava, A., Supuran, C.T., Mangani, S., (2000) Biochemistry, 39, p. 12391
Pocker, Y., Dickerson, D.G., (1968) Biochemistry, 7, p. 1995
Pocker, Y., Meany, J.E., (1967) Biochemistry, 6, p. 239
Pocker, Y., Stone, J.T., (1967) Biochemistry, 6, p. 668
Verpoorte, J.A., Mehta, S., Edsall, J.T., (1967) J. Biol. Chem., 242, p. 4221
Kaiser, E.T., Lo, K.W., (1969) J. Am. Chem. Soc., 91, p. 4912
Temperini, C., Innocenti, A., Scozzafava, A., Supuran, C.T., (2006) Bioorg. Med. Chem. Lett., 16, p. 4316
Scolnick, L.R., Clements, A.M., Liao, J., Crenshaw, L., Hellberg, M., May, J., Dean, T.R., Christianson, D.W., (1997) J. Am. Chem. Soc., 119, p. 850
Wildfeuer, A., (1970) Arzneimittelforschung, 20, p. 824
Lius, V., Sennerfeldt, P., (1979) Lakartidningen, 76, p. 39
Goeth, H., Wildfeuer, A., (1969) Arzneimittelforschung, 19, p. 1298
Iyer, R., Barrese III, A.A., Parakh, S., Parker, C.N., Tripp, B.C., (2006) J. Biomol. Screen., 11, p. 782
Barrese III, A.A., Genis, C., Fisher, S.Z., Orwenyo, J.N., Kumara, M.T., Dutta, S.K., Phillips, E., Tripp, B.C., (2008) Biochemistry, 47, p. 3174
Elleby, B., Sjoblom, B., Lindskog, S., (1999) Eur. J. Biochem., 262, p. 516
Schulze Wischeler, J., Innocenti, A., Vullo, D., Agrawal, A., Cohen, S.M., Heine, A., Supuran, C.T., Klebe, G., (2010) ChemMedChem, 5, p. 1609
Liljas, A., Hakansson, K., Jonsson, B.H., Xue, Y., (1994) Eur. J. Biochem., 219, p. 1
Mangani, S., Hakansson, K., (1992) Eur. J. Biochem., 210, p. 867
Jönsson, B.M., Hakansson, K., Liljas, A., (1993) FEBS Lett., 322, p. 186
Abbate, F., Supuran, C.T., Scozzafava, A., Orioli, P., Stubbs, M.T., Klebe, G., (2002) J. Med. Chem., 45, p. 3583
Eriksson, A.E., Jones, T.A., Liljas, A., (1988) Proteins, 4, p. 274
Keilin, D., Mann, T., (1940) Biochem. J., 34, p. 1163
Winum, J.-Y., Monter, J.-L., Scozzafava, A., Supuran, C.T., (2009) Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications, p. 39. , Supuran, C. T. Winum, J.-Y. Wiley: Hoboken, NJ
Lindahl, M., Vidgren, J., Eriksson, E., Habash, J., Harrop, S., Helliwell, J., Liljas, A., Walker, N., (1991) Carbonic Anhydrase: From Biochemistry and Genetics to Physiology and Clinical Medicine, p. 111. , Botre, F. Gros, G. Storey, B. T. VCH: Weinheim, Germany
Supuran, C.T., Casini, A., Scozzafava, A., (2004) Carbonic Anhydrase: Its Inhibitors and Activators, p. 67. , Supuran, C. T. Scozzafava, A. Conway, J. CRC Press: Boca Raton, FL
Beasley, Y.M., Overell, B.G., Petrow, V., Stephenson, O., (1958) J. Pharm. Pharmacol., 10, p. 696
Supuran, C.T., (1994) Carbonic Anhydrase and Modulation of Physiological and Pathologic Processes in the Organism, p. 29. , Puscas, I. Helicon: Timisoara
Carta, F., Pothen, B., Maresca, A., Tiwari, M., Singh, V., Supuran, C.T., (2009) Chem. Biol. Drug Des., 74, p. 196
Ilies, M.A., Vullo, D., Pastorek, J., Scozzafava, A., Ilies, M., Caproiu, M.T., Pastorekova, S., Supuran, C.T., (2003) J. Med. Chem., 46, p. 2187
Scott, A.D., Phillips, C., Alex, A., Flocco, M., Bent, A., Randall, A., O'Brien, R., Jones, L.H., (2009) ChemMedChem, 4, p. 1985
Mincione, F., Starnotti, M., Menabuoni, L., Scozzafava, A., Casini, A., Supuran, C.T., (2001) Bioorg. Med. Chem. Lett., 11, p. 1787
Jain, A., Whitesides, G.M., Alexander, R.S., Christianson, D.W., (1994) J. Med. Chem., 37, p. 2100
Gao, J., Qiao, S., Whitesides, G.M., (1995) J. Med. Chem., 38, p. 2292
Gao, J., Cheng, X., Chen, R., Sigal, G.B., Bruce, J.E., Schwartz, B.L., Hofstadler, S.A., Whitesides, G.M., (1996) J. Med. Chem., 39, p. 1949
Roy, B.C., Banerjee, A.L., Swanson, M., Jia, X.G., Haldar, M.K., Mallik, S., Srivastava, D.K., (2004) J. Am. Chem. Soc., 126, p. 13206
Doyon, J.B., Jain, A., (1999) Org. Lett., 1, p. 183
Cappalonga Bunn, A.M., Alexander, R.S., Christianson, D.W., (1994) J. Am. Chem. Soc., 116, p. 5063
Jain, A., Huang, S.G., Whitesides, G.M., (1994) J. Am. Chem. Soc., 116, p. 5057
Boriack, P.A., Christianson, D.W., Kingery-Wood, J., Whitesides, G.M., (1995) J. Med. Chem., 38, p. 2286
Chin, D.N., Whitesides, G.M., (1995) J. Am. Chem. Soc., 117, p. 6153
Chin, D.N., Lau, A.Y., Whitesides, G.M., (1998) J. Org. Chem., 63, p. 938
Cecchi, A., Winum, J.-Y., Innocenti, A., Vullo, D., Montero, J.-L., Scozzafava, A., Supuran, C.T., (2004) Bioorg. Med. Chem. Lett., 14, p. 5775
Innocenti, A., Casini, A., Alcaro, M.C., Papini, A.M., Scozzafava, A., Supuran, C.T., (2004) J. Med. Chem., 47, p. 5224
Pacchiano, F., Aggarwal, M., Avvaru, B.S., Robbins, A.H., Scozzafava, A., McKenna, R., Supuran, C.T., (2010) Chem. Commun., 46, p. 8371
Alterio, V., Vitale, R.M., Monti, S.M., Pedone, C., Scozzafava, A., Cecchi, A., De Simone, G., Supuran, C.T., (2006) J. Am. Chem. Soc., 128, p. 8329
Ciani, L., Cecchi, A., Temperini, C., Supuran, C.T., Ristori, S., (2009) J. Phys. Chem. B, 113, p. 13998
Pastorekova, S., Casini, A., Scozzafava, A., Vullo, D., Pastorek, J., Supuran, C.T., (2004) Bioorg. Med. Chem. Lett., 14, p. 869
Supuran, C.T., Manole, G., Dinculescu, A., Schiketanz, A., Gheorghiu, M.D., Puscas, I., Balaban, A.T., (1992) J. Pharm. Sci., 81, p. 716
Scozzafava, A., Briganti, F., Ilies, M.A., Supuran, C.T., (2000) J. Med. Chem., 43, p. 292
Casey, J.R., Morgan, P.E., Vullo, D., Scozzafava, A., Mastrolorenzo, A., Supuran, C.T., (2004) J. Med. Chem., 47, p. 2337
Balaban, A.T., Dinculescu, A., (1980) Rev. Roum. Chim., 28, p. 1505
Menchise, V., De Simone, G., Alterio, V., Di Fiore, A., Pedone, C., Scozzafava, A., Supuran, C.T., (2005) J. Med. Chem., 48, p. 5721
Svastová, E., Hulíková, A., Rafajová, M., Zatovicová, M., Gibadulinová, A., Casini, A., Cecchi, A., Pastoreková, S., (2004) FEBS Lett., 577, p. 439
Srivastava, D.K., Jude, K.M., Banerjee, A.L., Haldar, M., Manokaran, S., Kooren, J., Mallik, S., Christianson, D.W., (2007) J. Am. Chem. Soc., 129, p. 5528
Alterio, V., De Simone, G., Monti, S.M., Scozzafava, A., Supuran, C.T., (2007) Bioorg. Med. Chem. Lett., 17, p. 4201
Abbate, F., Casini, A., Owa, T., Scozzafava, A., Supuran, C.T., (2004) Bioorg. Med. Chem. Lett., 14, p. 217
Casini, A., Abbate, F., Scozzafava, A., Supuran, C.T., (2003) Bioorg. Med. Chem. Lett., 13, p. 2759
Mincione, F., Menabuoni, L., Supuran, C.T., (2004) Carbonic Anhydrase, Its Inhibitors and Activators, p. 243. , Supuran, C. T. Scozzafava, A. Conway, J. CRC Press: Boca Raton, FL
Tawil, R., McDermott, M.P., Brown, Jr.R., Shapiro, B.C., Ptacek, L.J., McManis, P.G., Dalakas, M.C., Griggs, R.C., (2000) Ann. Neurol., 47, p. 46
Pastoreková, S., Závadová, Z., Kostál, M., Babusíková, O., Závada, J., (1992) Virology, 187, p. 620
Türeci, O., Sahin, U., Vollmar, E., Siemer, S., Göttert, E., Seitz, G., Parkkila, A.K., Sly, W.S., (1998) Proc. Natl. Acad. Sci. U.S.A., 95, p. 7608
Ivanov, S.V., Kuzmin, I., Wei, M.H., Pack, S., Geil, L., Johnson, B.E., Stanbridge, E.J., Lerman, M.I., (1998) Proc. Natl. Acad. Sci. U.S.A., 95, p. 12596
Pastoreková, S., Pastorek, J., (2004) Carbonic Anhydrase: Its Inhibitors and Activators, p. 255. , Supuran, C. T. Scozzafava, A. Conway, J. CRC Press: Boca Raton, FL
Aaron, J.A., Chambers, J.M., Jude, K.M., Di Costanzo, L., Dmochowski, I.J., Christianson, D.W., (2008) J. Am. Chem. Soc., 130, p. 6942
Cecchi, A., Hulikova, A., Pastorek, J., Pastoreková, S., Scozzafava, A., Winum, J.-Y., Montero, J.-L., Supuran, C.T., (2005) J. Med. Chem., 48, p. 4834
Elbaum, D., Nair, S.K., Patchan, M.W., Thompson, R.B., Christianson, D.W., (1996) J. Am. Chem. Soc., 118, p. 8381
Marsh, D., Horváth, L.I., (1989) Advanced EPR. Applications in Biology and Biochemistry, p. 707. , Hoff, A. J. Elsevier: Amsterdam
Schröder, L., Lowery, T.J., Hilty, C., Wemmer, D.E., Pines, A., (2006) Science, 314, p. 446
Chambers, J.M., Hill, P.A., Aaron, J.A., Han, Z., Christianson, D.W., Kuzma, N.N., Dmochowski, I.J., (2009) J. Am. Chem. Soc., 131, p. 563
Bodor, N., Buchwald, P., (2003) Burger's Medicinal Chemistry Drug Discovery and Development, p. 533. , Abraham, D. J. Ed
John Wiley and Sons, New York
Denny, W.A., (2004) Cancer Invest., 22, p. 604
De Simone, G., Vitale, R.M., Di Fiore, A., Pedone, C., Scozzafava, A., Montero, J.-L., Winum, J.-Y., Supuran, C.T., (2006) J. Med. Chem., 49, p. 5544
D'ambrosio, K., Vitale, R.M., Dogné, J.M., Masereel, B., Innocenti, A., Scozzafava, A., De Simone, G., Supuran, C.T., (2008) J. Med. Chem., 51, p. 3230
Saczewski, F., Sawinski, J., Kornicka, A., Brzozowski, Z., Pomarnacka, E., Innocenti, A., Scozzafava, A., Supuran, C.T., (2006) Bioorg. Med. Chem. Lett., 16, p. 4846
Davenport, H.W., (1945) J. Biol. Chem., 158, p. 567
Miller, W.H., Dessert, A.M., Roblin, Jr.R.O., (1950) J. Am. Chem. Soc., 72, p. 4893
Roblin, Jr.R.O., Clapp, J.W., (1950) J. Am. Chem. Soc., 72, p. 4890
Barnish, I.T., Cross, P.E., Dickinson, R.P., Parry, M.J., Randall, M.J., (1981) J. Med. Chem., 24, p. 959
Maren, T.H., (1995) J. Glaucoma, 4, p. 492
Vidgren, J., Liljas, A., Walker, N.P.C., (1990) Int. J. Biol. Macromol., 12, p. 342
Vaughan, J.R., Eichler, J.A., Anderson, G.W., (1956) J. Org. Chem., 21, p. 700
Young, R.W., Wood, K.H., Vaughan, J.R., Anderson, G.W., (1956) J. Am. Chem. Soc., 78, p. 4649
Supuran, C.T., Ilies, M.A., Scozzafava, A., (1998) Eur. J. Med. Chem., 33, p. 739
Scozzafava, A., Menabuoni, L., Mincione, F., Briganti, F., Mincione, G., Supuran, C.T., (2000) J. Med. Chem., 43, p. 4542
Chow, K., Lai, R., Holmes, J.M., Wijono, M., Wheeler, L.A., Garst, M.E., (1996) Eur. J. Med. Chem., 31, p. 175
Maren, T.H., (1982) Orphan Drugs, p. 89. , Karch, F. E. Dekker: New York
De Leval, X., Ilies, M., Casini, A., Dogné, J.M., Scozzafava, A., Masini, E., Mincione, F., Supuran, C.T., (2004) J. Med. Chem., 47, p. 2796
Kim, C.Y., Whittington, D.A., Chang, J.S., Liao, J., May, J.A., Christianson, D.W., (2002) J. Med. Chem., 45, p. 888
Struijker-Boudier, H.A., (2007) Am. J. Hypertension, 20, pp. 15S
Patel, A., MacMahon, S., Chalmers, J., Neal, B., Woodward, M., Billot, L., Harrap, S., Williams, B., (2007) Lancet, 370, p. 829
Temperini, C., Cecchi, A., Scozzafava, A., Supuran, C.T., (2008) Bioorg. Med. Chem. Lett., 18, p. 2567
Vullo, D., Innocenti, A., Supuran, C.T., (2009) Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications, p. 155. , Supuran, C. T. Winum, J.-Y. Wiley: Hoboken, NJ
Maren, T.H., Conroy, C.W., (1993) J. Biol. Chem., 268, p. 26233
Fisher, S.Z., Govindasamy, L., Boyle, N., Agbandje-Mckenna, M., Silverman, D.N., Blackburn, G.M., McKenna, R., (2006) Acta Crystallogr., Sect. F., 62, p. 618
Lo, Y.S., Nolan, J.C., Maren, T.H., Welstead, Jr.W.J., Gripshover, D.F., Shamblee, D.A., (1992) J. Med. Chem., 35, p. 4790
Maryanoff, B.E., Nortey, S.O., Gardocki, J.F., Shank, R.P., Dodgson, S.P., (1987) J. Med. Chem., 30, p. 880
Briganti, F., Pierattelli, R., Scozzafava, A., Supuran, C.T., (1996) Eur. J. Med. Chem., 31, p. 1001
Winum, J.-Y., Vullo, D., Casini, A., Montero, J.-L., Scozzafava, A., Supuran, C.T., (2003) J. Med. Chem., 46, p. 2197
Winum, J.-Y., Pastorekova, S., Jakubickova, L., Montero, J.-L., Scozzafava, A., Pastorek, J., Vullo, D., Supuran, C.T., (2005) Bioorg. Med. Chem. Lett., 15, p. 579
Vitale, R.M., Alterio, V., Innocenti, A., Winum, J.-Y., Monti, S.M., De Simone, G., Supuran, C.T., (2009) J. Med. Chem., 52, p. 5990
Reed, M.J., Purohit, A., Newman, S.P., Potter, B.V.L., (2005) Endocr. Rev., 26, p. 171
Stanway, S.J., Purohit, A., Woo, L.W.L., Sufi, S., Vigushin, D., Ward, R., Wilson, R., Coombs, R.C., (2006) Clin. Cancer Res., 12, p. 1585
Ireson, C.R., Chander, S.K., Purohit, A., Parish, D.A., Woo, L.W.L., Potter, B.V.L., Reed, M.J., (2004) Br. J. Cancer, 91, p. 1399
Abbate, F., Winum, J.Y., Potter, B.V.L., Casini, A., Montero, J.L., Scozzafava, A., Supuran, C.T., (2004) Bioorg. Med. Chem. Lett., 14, p. 231
Lloyd, M.D., Pederick, R.L., Natesh, R., Woo, L.W.L., Purohit, A., Reed, M.J., Acharya, K.R., Potter, B.V.L., (2005) Biochem. J., 385, p. 715
Leese, M.P., Leblond, B., Smith, A., Newman, S.P., Di Fiore, A., De Simone, G., Supuran, C.T., Potter, B.V., (2006) J. Med. Chem., 49, p. 7683
Leese, M.P., Jourdan, F.L., Gaukroger, K., Mahon, M.F., Newman, S.P., Foster, P.A., Stengel, C., Potter, B.V., (2008) J. Med. Chem., 51, p. 1295
Woo, L.W.L., Fischer, D.S., Sharland, C.M., Trusselle, M., Foster, P.A., Chander, S.K., Di Fiore, A., Potter, B.V.L., (2008) Mol. Cancer Ther., 7, p. 2435
Woo, L.W., Jackson, T., Putey, A., Cozier, G., Leonard, P., Acharya, K.R., Chander, S.K., Potter, B.V., (2010) J. Med. Chem., 53, p. 2155
Gülcin, I., Bursal, E., Sehitoglu, M.H., Bilsel, M., Gören, A.C., (2010) Food Chem. Toxicol., 48, p. 2227
Mabry, H., Harborne, J.B., Mabry, T.J., (1975) The Flavonoids, , Eds. Chapman and Hall: London
Köksal, E., Gülcin, I., Beyza, S., Sarikaya, O., Bursal, E., (2009) J. Enzyme Inhib. Med. Chem., 24, p. 395
Huseini, H.F., Larijani, B., Heshmat, R., Fakhrzadeh, H., Radjabipour, B., Toliat, T., Raza, M., (2006) Phytother. Res., 20, p. 1036
Ak, T., Gülcin, I., (2008) Chem. Biol. Interact., 174, p. 27
Huang, M.T., Newmark, H.L., Frenkel, K., (1997) J. Cell Biochem., 27, p. 26
Merz, K.M., (1990) J. Mol. Biol., 214, p. 799
Khalifah, R.G., Rogers, J.I., (1988) FASEB J, 2, p. 1118
Innocenti, A., Gülcin, I., Scozzafava, A., Supuran, C.T., (2010) Bioorg. Med. Chem. Lett., 20, p. 5050
Innocenti, A., Beyza Oztürk Sarikaya, S., Gülcin, I., Supuran, C.T., (2010) Bioorg. Med. Chem., 18, p. 2159
Sarikaya, S.B., Gülcin, I., Supuran, C.T., (2010) Chem. Biol. Drug Des., 75, p. 515
Ilies, M., Banciu, M.D., Ilies, M.A., Scozzafava, A., Caproiu, M.T., Supuran, C.T., (2002) J. Med. Chem., 45, p. 504
Ilies, M., Scozzafava, A., Supuran, C.T., (2004) Carbonic Anhydrase: Its Inhibitors and Activators, p. 317. , Supuran, C. T. Scozzafava, A. Conway, J. CRC Press: Boca Raton, FL
Temperini, C., Vullo, D., Scozzafava, A., Supuran, C.T., (2006) J. Med. Chem., 49, p. 3019
Vu, H., Pham, N.B., Quinn, R.J., (2008) J. Biomol. Screen., 13, p. 265
Maresca, A., Scozzafava, A., Supuran, C.T., (2010) Bioorg. Med. Chem. Lett., 20, p. 7255
Maresca, A., Supuran, C.T., (2010) Bioorg. Med. Chem. Lett., 20, p. 4511
Lou, Y., McDonald, P.C., Oloumi, A., Chia, S., Ostlund, C., Ahmadi, A., Kyle, A., Dedhar, S., (2011) Cancer Res., 71, p. 3364
Cortes, S., Liao, Z.K., Watson, D., Kohn, H., (1985) J. Med. Chem., 28, p. 601
Conley, J.D., Kohn, H., (1987) J. Med. Chem., 30, p. 567
Kohn, H., Sawhney, K.N., Legall, P., Conley, J.D., Robertson, D.W., Leander, J.D., (1990) J. Med. Chem., 33, p. 919
Bardel, P., Bolanos, A., Kohn, H., (1994) J. Med. Chem., 37, p. 4567
Choi, D., Stables, J.P., Kohn, H., (1996) J. Med. Chem., 39, p. 1907
Halford, J.J., Lapointe, M., (2009) Epilepsy Curr., 9, p. 1
Davis, R.A., Innocenti, A., Poulsen, S.A., Supuran, C.T., (2010) Bioorg. Med. Chem., 18, p. 14
Winum, J.Y., Montero, J.L., Innocenti, A., Supuran, C.T., (2009) Chem. Biol. Drug. Des., 74, p. 636
Güzel, Ö., Innocenti, A., Scozzafava, A., Salman, A., Supuran, C.T., (2009) Bioorg. Med. Chem. Lett., 19, p. 3170
Asiedu, M., Ossipov, M.H., Kaila, K., Price, T.J., (2010) Pain, 148, p. 302
Pacchiano, F., Carta, F., McDonald, P.C., Lou, Y., Vullo, D., Scozzafava, A., Dedhar, S., Supuran, C.T., (2011) J. Med. Chem., 54, p. 1896
Krishnamurthy, V. M., Kaufman, G. K., Urbach, A. R., Gitlin, I., Gudiksen, K. L., Weibel, D. B., Whitesides, G. M., (2008) Chem. Rev., 108, p. 94
Supuran, C. T., (2008) Nat. Rev. Drug Discovery, 7, p. 168
Supuran, C. T., Winum, J. -Y., (2009) Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications, , Eds. Wiley: Hoboken, NJ, Part II
Supuran, C. T., Scozzafava, A., Conway, J., (2004) Carbonic Anhydrase: Its Inhibitors and Activators, , Eds. CRC Press: Boca Raton, FL
Maren, T. H., (1967) Physiol. Rev., 47, p. 595
Lane, T. W., Saito, M. A., George, G. N., Pickering, I. J., Prince, R. C., Morel, F. M., (2005) Nature, 435, p. 42
Tripp, B. C., Smith, K., Ferry, J. G., (2001) J. Biol. Chem., 276, p. 48615
Ferry, J. F., (2010) Biochim. Biophys. Acta, 1804, p. 374
Clare, B. W., Supuran, C. T., (2006) Expert Opin. Drug Metab. Toxicol., 2, p. 113
Winum, J. -Y., Scozzafava, A., Montero, J. -L., Supuran, C. T., (2006) Mini Rev. Med. Chem., 6, p. 921
Supuran, C. T., Di Fiore, A., De Simone, G., (2008) Expert Opin. Emerg. Drugs, 13, p. 383
Winum, J. -Y., Rami, M., Scozzafava, A., Montero, J. -L., Supuran, C. T., (2008) Med. Res. Rev., 28, p. 445
Guler, O. O., De Simone, G., Supuran, C. T., (2010) Curr. Med. Chem., 17, p. 1516
Thiry, A., Dogn, J. M., Supuran, C. T., Masereel, B., (2008) Curr. Pharm. Des., 14, p. 661
Gao, B. B., Clermont, A., Rook, S., Fonda, S. J., Srinivasan, V. J., Wojtkowski, M., Fujimoto, J. G., Feener, E. P., (2007) Nat. Med., 13, p. 181
Swenson, E. R., Teppema, L. J., (2007) J. Appl. Physiol., 102, p. 1305
Zimmerman, U. J., Wang, P., Zhang, X., Bogdanovich, S., Forster, R., (2004) IUBMB Life., 56, p. 343
Ochrietor, J. D., Clamp, M. F., Moroz, T. P., Grubb, J. H., Shah, G. N., Waheed, A., Sly, W. S., Linser, P. J., (2005) Exp. Eye Res., 81, p. 492
Kivel, J., Parkkila, S., Parkkila, A. K., Rajaniemi, H., (1999) Caries Res., 33, p. 178
Liao, S. Y., Ivanov, S., Ivanova, A., Ghosh, S., Cote, M. A., Keefe, K., Coca-Prados, M., Lerman, M. I., (2003) J. Med. Genet., 40, p. 257
Shah, G. N., Ulmasov, B., Waheed, A., Becker, T., Makani, S., Svichar, N., Chesler, M., Sly, W. S., (2005) Proc. Natl. Acad. Sci. U. S. A., 102, p. 16771
Ogilvie, J. M., Ohlemiller, K. K., Shah, G. N., Ulmasov, B., Becker, T. A., Waheed, A., Hennig, A. K., Sly, W. S., (2007) Proc. Natl. Acad. Sci. U. S. A., 104, p. 8514
Kannan, K. K., Ramanadham, M., Jones, T. A., (1984) Ann. N. Y. Acad. Sci., 429, p. 49
Eriksson, A. E., Kylsten, P. M., Jones, T. A., Liljas, A., (1988) Proteins, 4, p. 283
Eriksson, A. E., Liljas, A., (1993) Proteins, 16, p. 29
Boriack-Sjodin, P. A., Heck, R. W., Laipis, P. J., Silverman, D. N., Christianson, D. W., (1995) Proc. Natl. Acad. Sci. U. S. A., 92, p. 10949
Whittington, D. A., Waheed, A., Ulmasov, B., Shah, G. N., Grubb, J. H., Sly, W. S., Christianson, D. W., (2001) Proc. Natl. Acad. Sci. U. S. A., 98, p. 9545
Duda, D. M., Tu, C., Fisher, S. Z., An, H., Yoshioka, C., Govindasamy, L., Laipis, P. J., McKenna, R., (2005) Biochemistry, 44, p. 10046
Pilka, E. S., Kochan, G., Oppermann, U., Yue, W. W., (2012) Biochem. Biophys. Res. Commun., 419, p. 485
Sj blom, B., Polentarutti, M., Djinovic-Carugo, K., (2009) Proc. Natl. Acad. Sci. U. S. A., 106, p. 10609
Domsic, J. F., Avvaru, B. S., Kim, C. U., Gruner, S. M., Agbandje-Mckenna, M., Silverman, D. N., McKenna, R., (2008) J. Biol. Chem., 283, p. 30766
Merz, Jr. K. M., (1991) J. Am. Chem. Soc., 113, p. 406
Tu, C. K., Silverman, D. N., Forsman, C., Jonsson, B. H., Lindskog, S., (1989) Biochemistry, 28, p. 7913
Fisher, S. Z., Maupin, C. M., Budayova-Spano, M., Govindasamy, L., Tu, C. K., Agbandje-Mckenna, M., Silverman, D. N., McKenna, R., (2007) Biochemistry, 46, p. 2930
Williams, T. J., Henkens, R. W., (1985) Biochemistry, 24, p. 2459
Krebs, J. F., Rana, F., Dluhy, R. A., Fierke, C. A., (1993) Biochemistry, 32, p. 4496
Liang, J. Y., Lipscomb, W. N., (1990) Proc. Natl. Acad. Sci. U. S. A., 87, p. 3675
Fierke, C. A., Calderone, T. L., Krebs, J. F., (1991) Biochemistry, 30, p. 11054
Alexander, R. S., Nair, S. K., Christianson, D. W., (1991) Biochemistry, 30, p. 11064
Nair, S. K., Calderone, T. L., Christianson, D. W., Fierke, C. A., (1991) J. Biol. Chem., 266, p. 17320
Domsic, J. F., McKenna, R., (2010) Biochim. Biophys. Acta, 1804, p. 326
Supuran, C. T., Conroy, C. W., Maren, T. H., (1997) Proteins, 27, p. 272
Verpoorte, J. A., Mehta, S., Edsall, J. T., (1967) J. Biol. Chem., 242, p. 4221
Kaiser, E. T., Lo, K. W., (1969) J. Am. Chem. Soc., 91, p. 4912
Scolnick, L. R., Clements, A. M., Liao, J., Crenshaw, L., Hellberg, M., May, J., Dean, T. R., Christianson, D. W., (1997) J. Am. Chem. Soc., 119, p. 850
J nsson, B. M., Hakansson, K., Liljas, A., (1993) FEBS Lett., 322, p. 186
Eriksson, A. E., Jones, T. A., Liljas, A., (1988) Proteins, 4, p. 274
Winum, J. -Y., Monter, J. -L., Scozzafava, A., Supuran, C. T., (2009) Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications, p. 39. , Supuran, C. T. Winum, J. -Y. Wiley: Hoboken, NJ
King, R. W., Burgen, A. S., (1970) Biochim. Biophys. Acta, 207, p. 278
Supuran, C. T., Casini, A., Scozzafava, A., (2004) Carbonic Anhydrase: Its Inhibitors and Activators, p. 67. , Supuran, C. T. Scozzafava, A. Conway, J. CRC Press: Boca Raton, FL
Beasley, Y. M., Overell, B. G., Petrow, V., Stephenson, O., (1958) J. Pharm. Pharmacol., 10, p. 696
Ilies, M. A., Vullo, D., Pastorek, J., Scozzafava, A., Ilies, M., Caproiu, M. T., Pastorekova, S., Supuran, C. T., (2003) J. Med. Chem., 46, p. 2187
Scott, A. D., Phillips, C., Alex, A., Flocco, M., Bent, A., Randall, A., O'Brien, R., Jones, L. H., (2009) ChemMedChem, 4, p. 1985
Roy, B. C., Banerjee, A. L., Swanson, M., Jia, X. G., Haldar, M. K., Mallik, S., Srivastava, D. K., (2004) J. Am. Chem. Soc., 126, p. 13206
Jude, K. M., Banerjee, A. L., Haldar, M. K., Manokaran, S., Roy, B., Mallik, S., Srivastava, D. K., Christianson, D. W., (2006) J. Am. Chem. Soc., 128, p. 3011
Doyon, J. B., Jain, A., (1999) Org. Lett., 1, p. 183
Boriack, P. A., Christianson, D. W., Kingery-Wood, J., Whitesides, G. M., (1995) J. Med. Chem., 38, p. 2286
Chin, D. N., Whitesides, G. M., (1995) J. Am. Chem. Soc., 117, p. 6153
Chin, D. N., Lau, A. Y., Whitesides, G. M., (1998) J. Org. Chem., 63, p. 938
Supuran, C. T., Manole, G., Dinculescu, A., Schiketanz, A., Gheorghiu, M. D., Puscas, I., Balaban, A. T., (1992) J. Pharm. Sci., 81, p. 716
Casey, J. R., Morgan, P. E., Vullo, D., Scozzafava, A., Mastrolorenzo, A., Supuran, C. T., (2004) J. Med. Chem., 47, p. 2337
Balaban, A. T., Dinculescu, A., (1980) Rev. Roum. Chim., 28, p. 1505
Svastov, E., Hul kov, A., Rafajov, M., Zatovicov, M., Gibadulinov, A., Casini, A., Cecchi, A., Pastorekov, S., (2004) FEBS Lett., 577, p. 439
Srivastava, D. K., Jude, K. M., Banerjee, A. L., Haldar, M., Manokaran, S., Kooren, J., Mallik, S., Christianson, D. W., (2007) J. Am. Chem. Soc., 129, p. 5528
Pastorekov, S., Z vadov, Z., Kost l, M., Babus kov, O., Z vada, J., (1992) Virology, 187, p. 620
T reci, O., Sahin, U., Vollmar, E., Siemer, S., G ttert, E., Seitz, G., Parkkila, A. K., Sly, W. S., (1998) Proc. Natl. Acad. Sci. U. S. A., 95, p. 7608
Ivanov, S. V., Kuzmin, I., Wei, M. H., Pack, S., Geil, L., Johnson, B. E., Stanbridge, E. J., Lerman, M. I., (1998) Proc. Natl. Acad. Sci. U. S. A., 95, p. 12596
Pastorekov, S., Pastorek, J., (2004) Carbonic Anhydrase: Its Inhibitors and Activators, p. 255. , Supuran, C. T. Scozzafava, A. Conway, J. CRC Press: Boca Raton, FL
Aaron, J. A., Chambers, J. M., Jude, K. M., Di Costanzo, L., Dmochowski, I. J., Christianson, D. W., (2008) J. Am. Chem. Soc., 130, p. 6942
Marsh, D., Horv th, L. I., (1989) Advanced EPR. Applications in Biology and Biochemistry, p. 707. , Hoff, A. J. Elsevier: Amsterdam
Taylor, J. S., Mushak, P., Coleman, J. E., (1970) Proc. Natl. Acad. Sci. U. S. A., 67, p. 1410
Chignell, C. F., Starkweather, D. K., Erlich, R. H., (1972) J. Med. Chem., 15, p. 876
Erlich, R. H., Starkweather, D. K., Chignell, C. F., (1973) Mol. Pharmacol., 9, p. 61
Hower, J. F., Henkens, R. W., Chesnut, D. B., (1971) J. Am. Chem. Soc., 93, p. 6665
Wee, V. T., Feldmann, R. J., Tanis, R. J., Chignell, C. F., (1976) Mol. Pharmacol., 12, p. 832
Fain, S. B., Korosec, F. R., Holmes, J. H., O'Halloran, R., Sorkness, R. L., Grist, T. M., (2007) J. Magn. Reson. Imaging, 25, p. 910
Hill, P. A., Wei, Q., Eckenhoff, R. G., Dmochowski, I. J., (2007) J. Am. Chem. Soc., 129, p. 9262
Lowery, T. J., Garcia, S., Chavez, L., Ruiz, E. J., Wu, T., Brotin, T., Dutasta, J. P., Wemmer, D. E., (2006) ChemBioChem, 7, p. 65
Schr der, L., Lowery, T. J., Hilty, C., Wemmer, D. E., Pines, A., (2006) Science, 314, p. 446
Chambers, J. M., Hill, P. A., Aaron, J. A., Han, Z., Christianson, D. W., Kuzma, N. N., Dmochowski, I. J., (2009) J. Am. Chem. Soc., 131, p. 563
Denny, W. A., (2004) Cancer Invest., 22, p. 604
Davenport, H. W., (1945) J. Biol. Chem., 158, p. 567
Miller, W. H., Dessert, A. M., Roblin, Jr. R. O., (1950) J. Am. Chem. Soc., 72, p. 4893
Roblin, Jr. R. O., Clapp, J. W., (1950) J. Am. Chem. Soc., 72, p. 4890
Barnish, I. T., Cross, P. E., Dickinson, R. P., Parry, M. J., Randall, M. J., (1981) J. Med. Chem., 24, p. 959
Maren, T. H., (1995) J. Glaucoma, 4, p. 492
Vaughan, J. R., Eichler, J. A., Anderson, G. W., (1956) J. Org. Chem., 21, p. 700
Young, R. W., Wood, K. H., Vaughan, J. R., Anderson, G. W., (1956) J. Am. Chem. Soc., 78, p. 4649
Supuran, C. T., Ilies, M. A., Scozzafava, A., (1998) Eur. J. Med. Chem., 33, p. 739
Maren, T. H., (1982) Orphan Drugs, p. 89. , Karch, F. E. Dekker: New York
Kim, C. Y., Whittington, D. A., Chang, J. S., Liao, J., May, J. A., Christianson, D. W., (2002) J. Med. Chem., 45, p. 888
Smith, G. M., Alexander, R. S., Christianson, D. W., McKeever, B. M., Ponticello, G. S., Springer, J. P., Randall, W. C., Habecker, C. N., (1994) Protein Sci., 3, p. 118
Ponticello, G. S., Freedman, M. B., Habecker, C. N., Lyle, P. A., Schwam, H., Varga, S. L., Christy, M. E., Baldwin, J. J., (1987) J. Med. Chem., 30, p. 591
Steele, R. M., Benedini, F., Biondi, S., Borghi, V., Carzaniga, L., Impagnatiello, F., Miglietta, D., Supuran, C. T., (2009) Bioorg. Med. Chem. Lett., 19, p. 6565
Nathanson, J. A., (1992) J. Pharmacol. Exp. Ther., 260, p. 956
G zel, ., Temperini, C., Innocenti, A., Scozzafava, A., Salman, A., Supuran, C. T., (2008) Bioorg. Med. Chem. Lett., 18, p. 152
G zel, O., Innocenti, A., Scozzafava, A., Salman, A., Parkkila, S., Hilvo, M., Supuran, C. T., (2008) Bioorg. Med. Chem., 16, p. 9113
Luz, C., Netto, M. C., Rocha, L. F., (2007) Mycopathologia, 164, p. 39
Martin, R. J., Robertson, A. P., Bjorn, H., (1997) Parasitology, 114, p. 111
Smith, R. E., Ashiya, M., (2007) Nat. Rev. Drug Discovery, 6, p. 597
Padilla, M. C., Armas-Hern ndez, M. J., Hern ndez, R. H., Israili, Z. H., Valasco, M., (2007) Am. J. Ther., 14, p. 154
Black, H. R., Davis, B., Barzilay, J., Nwachuku, C., Baimbridge, C., Marginean, H., Wright Jr., J. T., Thadani, U., (2008) Diabetes Care, 31, p. 353
Maren, T. H., Conroy, C. W., (1993) J. Biol. Chem., 268, p. 26233
Fisher, S. Z., Govindasamy, L., Boyle, N., Agbandje-Mckenna, M., Silverman, D. N., Blackburn, G. M., McKenna, R., (2006) Acta Crystallogr., Sect. F., 62, p. 618
Lo, Y. S., Nolan, J. C., Maren, T. H., Welstead, Jr. W. J., Gripshover, D. F., Shamblee, D. A., (1992) J. Med. Chem., 35, p. 4790
Maryanoff, B. E., Nortey, S. O., Gardocki, J. F., Shank, R. P., Dodgson, S. P., (1987) J. Med. Chem., 30, p. 880
Winum, J. -Y., Vullo, D., Casini, A., Montero, J. -L., Scozzafava, A., Supuran, C. T., (2003) J. Med. Chem., 46, p. 2197
Winum, J. -Y., Pastorekova, S., Jakubickova, L., Montero, J. -L., Scozzafava, A., Pastorek, J., Vullo, D., Supuran, C. T., (2005) Bioorg. Med. Chem. Lett., 15, p. 579
Vitale, R. M., Alterio, V., Innocenti, A., Winum, J. -Y., Monti, S. M., De Simone, G., Supuran, C. T., (2009) J. Med. Chem., 52, p. 5990
Reed, M. J., Purohit, A., Newman, S. P., Potter, B. V. L., (2005) Endocr. Rev., 26, p. 171
Stanway, S. J., Purohit, A., Woo, L. W. L., Sufi, S., Vigushin, D., Ward, R., Wilson, R., Coombs, R. C., (2006) Clin. Cancer Res., 12, p. 1585
Ireson, C. R., Chander, S. K., Purohit, A., Parish, D. A., Woo, L. W. L., Potter, B. V. L., Reed, M. J., (2004) Br. J. Cancer, 91, p. 1399
Lloyd, M. D., Pederick, R. L., Natesh, R., Woo, L. W. L., Purohit, A., Reed, M. J., Acharya, K. R., Potter, B. V. L., (2005) Biochem. J., 385, p. 715
Lloyd, M. D., Thiyagarajan, N., Ho, Y. T., Woo, L. W. L., Sutcliffe, O. B., Purohit, A., Reed, M. J., Potter, B. V. L., (2005) Biochemistry, 44, p. 6858
Leese, M. P., Leblond, B., Smith, A., Newman, S. P., Di Fiore, A., De Simone, G., Supuran, C. T., Potter, B. V., (2006) J. Med. Chem., 49, p. 7683
Leese, M. P., Jourdan, F. L., Gaukroger, K., Mahon, M. F., Newman, S. P., Foster, P. A., Stengel, C., Potter, B. V., (2008) J. Med. Chem., 51, p. 1295
Woo, L. W. L., Fischer, D. S., Sharland, C. M., Trusselle, M., Foster, P. A., Chander, S. K., Di Fiore, A., Potter, B. V. L., (2008) Mol. Cancer Ther., 7, p. 2435
Woo, L. W., Jackson, T., Putey, A., Cozier, G., Leonard, P., Acharya, K. R., Chander, S. K., Potter, B. V., (2010) J. Med. Chem., 53, p. 2155
Cozier, G. E., Leese, M. P., Lloyd, M. D., Baker, M. D., Thiyagarajan, N., Acharya, K. R., Potter, B. V., (2010) Biochemistry, 49, p. 3464
Howarth, N. M., Purohit, A., Reed, M. J., Potter, B. V. L., (1994) J. Med. Chem., 37, p. 219
Foster, P. A., Newman, S. P., Chander, S. K., Stengel, C., Jhalli, R., Woo, L. L., Potter, B. V., Purohit, A., (2006) Clin. Cancer Res., 12, p. 5543
Fischer, D. S., Woo, L. W., Mahon, M. F., Purohit, A., Reed, M. J., Potter, B. V., (2003) Bioorg. Med. Chem., 11, p. 1685
Fischer, D. S., Chander, S. K., Woo, L. W., Fenton, J. C., Purohit, A., Reed, M. J., Potter, B. V., (2003) J. Steroid. Biochem. Mol. Biol., 84, p. 343
Wilkinson, B. L., Bornaghi, L. F., Houston, T. A., Innocenti, A., Supuran, C. T., Poulsen, S. A., (2006) J. Med. Chem., 49, p. 6539
Winum, J. -Y., Poulsen, S. -A., Supuran, C. T., (2009) Med. Res. Rev., 29, p. 419
Winum, J. -Y., Casini, A., Minzione, F., Starnotti, M., Montero, J. -L., Scozzafava, A., Supuran, C. T., (2004) Bioorg. Med. Chem. Lett., 14, p. 225
Colinas, P. A., Bravo, R. D., Vullo, D., Scozzafava, A., Supuran, C. T., (2007) Bioorg. Med. Chem. Lett., 17, p. 5086
Shank, R. P., Gardocki, J. F., Vaught, J. L., Davis, C. B., Schupsky, J. J., Raffa, R. B., Dodgson, S. J., Maryanoff, B. E., (1994) Epilepsia, 35, p. 450
Edmonds, Jr. H. L., Jiang, Y. D., Zhang, P. Y., Shank, R. P., (1996) Life Sci., 59, p. 127
Stringer, J. L., (2000) Epilepsy Res., 40, p. 147
Bourgeois, B. F., (2000) J. Child Neurol., 15, p. 27
Vitale, R. M., Pedone, C., Amodeo, P., Antel, J., Wurl, M., Scozzafava, A., Supuran, C. T., De Simone, G., (2007) Bioorg. Med. Chem., 15, p. 4152
Winum, J. -Y., Temperini, C., El Cheikh, K., Innocenti, A., Vullo, D., Ciattini, S., Montero, J. -L., Supuran, C. T., (2006) J. Med. Chem., 49, p. 7024
Maryanoff, B. E., Costanzo, M. J., Nortey, S. O., Greco, M. N., Shank, R. P., Schupsky, J. J., Ortegon, M. E., Vaught, J. L., (1998) J. Med. Chem., 41, p. 1315
Nair, S. K., Ludwig, P. A., Christianson, D. W., (1994) J. Am. Chem. Soc., 116, p. 3659
Davis, R. A., Hofmann, A., Osman, A., Hall, R. A., M hlschlegel, F. A., Vullo, D., Innocenti, A., Poulsen, S. A., (2011) J. Med. Chem., 54, p. 1682
G rlach, A., Kietzmann, T., (2007) Methods Enzymol., 435, p. 421
Belaiba, R. S., Djordjevic, T., Petry, A., Diemer, K., Bonello, S., Banfi, B., Hess, J., G rlach, A., (2007) Free Radic. Biol. Med., 42, p. 446
Bell, E. L., Klimova, T. A., Eisenbart, J., Moraes, C. T., Murphy, M. P., Budinger, G. R., Chandel, N. S., (2007) J. Cell Biol., 177, p. 1029
Bonello, S., Z hringer, C., Belaiba, R. S., Djordjevic, T., Hess, J., Michiels, C., Kietzmann, T., G rlach, A., (2007) Arterioscler. Thromb. Vasc. Biol., 27, p. 755
G lcin, I., (2006) Toxicology, 217, p. 213
G lcin, I., (2007) Amino Acids, 32, p. 431
G lcin, I., Bursal, E., Sehitoglu, M. H., Bilsel, M., G ren, A. C., (2010) Food Chem. Toxicol., 48, p. 2227
K ksal, E., G lcin, I., Beyza, S., Sarikaya, O., Bursal, E., (2009) J. Enzyme Inhib. Med. Chem., 24, p. 395
Huseini, H. F., Larijani, B., Heshmat, R., Fakhrzadeh, H., Radjabipour, B., Toliat, T., Raza, M., (2006) Phytother. Res., 20, p. 1036
Ak, T., G lcin, I., (2008) Chem. Biol. Interact., 174, p. 27
Huang, M. T., Newmark, H. L., Frenkel, K., (1997) J. Cell Biochem., 27, p. 26
Merz, K. M., (1990) J. Mol. Biol., 214, p. 799
Khalifah, R. G., Rogers, J. I., (1988) FASEB J, 2, p. 1118
Innocenti, A., G lcin, I., Scozzafava, A., Supuran, C. T., (2010) Bioorg. Med. Chem. Lett., 20, p. 5050
Sarikaya, S. B., G lcin, I., Supuran, C. T., (2010) Chem. Biol. Drug Des., 75, p. 515
Vu, H., Pham, N. B., Quinn, R. J., (2008) J. Biomol. Screen., 13, p. 265
Conley, J. D., Kohn, H., (1987) J. Med. Chem., 30, p. 567
Halford, J. J., Lapointe, M., (2009) Epilepsy Curr., 9, p. 1
Davis, R. A., Innocenti, A., Poulsen, S. A., Supuran, C. T., (2010) Bioorg. Med. Chem., 18, p. 14
Winum, J. Y., Montero, J. L., Innocenti, A., Supuran, C. T., (2009) Chem. Biol. Drug. Des., 74, p. 636
G zel, ., Innocenti, A., Scozzafava, A., Salman, A., Supuran, C. T., (2009) Bioorg. Med. Chem. Lett., 19, p. 3170
Multiple binding modes of inhibitors to carbonic anhydrases: How to design specific drugs targeting 15 different isoforms?
A description of the structural studies on α-Carbonic anhydrases (α-CA) is presented. Main structural features of the catalytically active α-CA isozymes are described and the current state of the art on complexes of hCA II with the principal classes of inhibitors is summarized. Studies have demonstrated that cyanamide acts as a weak inhibitor of the esterase activity of hCA II, interacting with the zinc ion within the enzyme active site. Crystallographic studies have shown that inorganic anions can bind within the CA II active site, either coordinating the catalytic Zn2+ ion or not coordinating it, but being located in its close proximity in a nonmetal site. The effect of the presence of a positive, negative or neutral substituent on benzenesulfonamide CAIs has been investigated to understand the effect of different charges in the CA I and CA II active sites, to discriminate the binding to these two isoforms.
Multiple binding modes of inhibitors to carbonic anhydrases: How to design specific drugs targeting 15 different isoforms?