New chemotypes acting as isozyme-selective carbonic anhydrase inhibitors with low affinity for the offtarget cytosolic isoform II

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 6, 2012, Pages 2182-2185

  Carta, Fabrizio ^a   Vullo, Daniela ^a   Maresca, Alfonso ^a   Scozzafava, Andrea ^a   Supuran, Claudiu T ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

2 Hydroxyquinoline; Carbonic anhydrase; Coumaphos; Coumarin oxime; Offtarget isoform

Indexed keywords

2 HYDROXYQUINOLINE OXIME DERIVATIVE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE III; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IV; CARBONATE DEHYDRATASE IX; CARBONATE DEHYDRATASE V; CARBONATE DEHYDRATASE VA; CARBONATE DEHYDRATASE VB; CARBONATE DEHYDRATASE VI; CARBONATE DEHYDRATASE VII; CARBONATE DEHYDRATASE XII; CARBONATE DEHYDRATASE XIII; CARBONATE DEHYDRATASE XIV; COUMARIN DERIVATIVE; LACTONE DERIVATIVE; OXIME DERIVATIVE; PYRIDINE N OXIDE 2 THIOPHENOL; SULFAMIC ACID DERIVATIVE; SULFONAMIDE; THIOBENZOIC ACID; THIOMERSAL; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG STRUCTURE; ENZYME INHIBITION;

ANIMALS; CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; CATTLE; COUMARINS; HUMANS; ISOENZYMES; MOLECULAR TARGETED THERAPY; PHENOLS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 84857918967     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.01.129     Document Type: Article

References (47)

1. C.T. Supuran, A. Scozzafava, and A. Casini Med. Res. Rev. 23 2003 146
2. C.T. Supuran Nat. Rev. Drug Discov. 7 2008 168
3. C.T. Supuran Bioorg. Med. Chem. Lett. 20 2010 3467
4. V. Alterio, R.M. Vitale, S.M. Monti, C. Pedone, A. Scozzafava, A. Cecchi, G. De Simone, and C.T. Supuran J. Am. Chem. Soc. 128 2006 8329
5. A. Weber, A. Casini, A. Heine, D. Kuhn, C.T. Supuran, A. Scozzafava, and G. Klebe J. Med. Chem. 47 2004 550
6. A. Di Fiore, S.M. Monti, M. Hilvo, S. Parkkila, V. Romano, A. Scaloni, C. Pedone, A. Scozzafava, C.T. Supuran, and G. De Simone Proteins 74 2009 164
7. J.Y. Winum, C. Temperini, K. El Cheikh, A. Innocenti, D. Vullo, S. Ciattini, J.L. Montero, A. Scozzafava, and C.T. Supuran J. Med. Chem. 49 2006 7024
8. A. Innocenti, A. Casini, M.C. Alcaro, A.M. Papini, A. Scozzafava, and C.T. Supuran J. Med. Chem. 47 2004 5224
9. F. Carta, C.T. Supuran, and A. Scozzafava Exper. Opin. Ther. Pat. 22 2012 79
10. F. Abbate, J.Y. Winum, B.V.L. Potter, A. Casini, J.L. Montero, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 14 2004 231
11. I. Nishimori, D. Vullo, A. Innocenti, A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran J. Med. Chem. 48 2005 7860
12. M. Bialer, S.I. Johannessen, H.J. Kupferberg, R.H. Levy, P. Loiseau, and E. Perucca Epilepsy Res. 43 2001 11
13. D. Neri, and C.T. Supuran Nat. Rev. Drug Discov. 10 2011 767
14. P. Ebbesen, E.O. Pettersen, T.A. Gorr, G. Jobst, K. Williams, J. Kienninger, R.H. Wenger, S. Pastorekova, L. Dubois, P. Lambin, B.G. Wouters, C.T. Supuran, L. Poellinger, P. Ratcliffe, A. Kanopka, A. Görlach, M. Gasmann, A.L. Harris, P. Maxwell, and A. Scozzafava J. Enzyme Inhib. Med. Chem. 24 2009 1
15. E. Švastová, A. Hulíková, M. Rafajová, M. Zat'ovičová, A. Gibadulinová, A. Casini, A. Cecchi, A. Scozzafava, C. Supuran, and J. Pastorek FEBS Lett. 577 2004 439
16. L. Dubois, N.G. Lieuwes, A. Maresca, A. Thiry, C.T. Supuran, A. Scozzafava, B.G. Wouters, and P. Lambin Radiother. Oncol. 92 2009 423
17. P. Swietach, S. Wigfield, P. Cobden, C.T. Supuran, A.L. Harris, and R.D. Vaughan-Jones J. Biol. Chem. 283 2008 20473
18. F. Pacchiano, F. Carta, P.C. McDonald, Y. Lou, D. Vullo, A. Scozzafava, S. Dedhar, and C.T. Supuran J. Med. Chem. 2011 1896 54
19. L.R. Scolnick, A.M. Clements, J. Liao, L. Crenshaw, M. Hellberg, J. May, T.R. Dean, and D.W. Christianson J. Am. Chem. Soc. 119 1997 850
20. F. Carta, C. Temperini, A. Innocenti, A. Scozzafava, K. Kaila, and C.T. Supuran J. Med. Chem. 53 2010 5511
21. A. Maresca, C. Temperini, H. Vu, N.B. Pham, S.A. Poulsen, A. Scozzafava, R.J. Quinn, and C.T. Supuran J. Am. Chem. Soc. 131 2009 3057
22. A. Maresca, C. Temperini, L. Pochet, B. Masereel, A. Scozzafava, and C.T. Supuran J. Med. Chem. 53 2010 335
23. A. Maresca, and C.T. Supuran Bioorg Med. Chem. Lett. 20 2010 4511 4514
24. A. Maresca, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 20 2010 7255
25. R.A. Davis, A. Innocenti, S.A. Poulsen, and C.T. Supuran Bioorg. Med. Chem. 18 2010 14
26. A. Innocenti, D. Vullo, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 18 2008 1583
27. A. Innocenti, D. Vullo, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. 16 2008 7424
28. Y. Lou, P.C. McDonald, A. Oloumi, S.K. Chia, C. Ostlund, A. Ahmadi, A. Kyle, U. Auf dem Keller, S. Leung, D.G. Huntsman, B. Clarke, B.W. Sutherland, D. Waterhouse, M.B. Bally, C.D. Roskelley, C.M. Overall, A. Minchinton, F. Pacchiano, F. Carta, A. Scozzafava, N. Touisni, J.Y. Winum, C.T. Supuran, and S. Dedhar Cancer Res. 71 2011 3364
29. N. Touisni, A. Maresca, P.C. McDonald, Y. Lou, A. Scozzafava, S. Dedhar, J.-Y. Winum, and C.T. Supuran J. Med. Chem. 54 2011 8271
30. S.K. Nair, P.A. Ludwig, and D.W. Christianson J. Am. Chem. Soc. 116 1994 3659
31. R.A. Davis, A. Hofmann, A. Osman, R.A. Hall, F.A. Mühlschlegel, D. Vullo, A. Innocenti, C.T. Supuran, and S.A. Poulsen J. Med. Chem. 54 2011 1682
32. J.G. Dorea Neurochem. Res. 36 2011 927
33. D.A. Geier, L.K. Sykes, and M.R. Geier J. Toxicol. Environ. Health B. Crit. Rev. 10 2007 575
34. W. Mao, M.A. Schuler, and M.R. Berenbaum Proc. Natl. Acad. Sci. U.S.A. 108 2011 12657
35. M. Del Carlo, A. Pepe, M. Sergi, M. Mascini, A. Tarentini, and D. Compagnone Talanta 81 2010 76
36. M.D. Maggi, S.R. Ruffinengo, N. Damiani, N.H. Sardella, and M.J. Eguaras Exp. Appl. Acarol. 47 2009 317
37. C. Temperini, A. Innocenti, A. Scozzafava, S. Parkkila, and C.T. Supuran J. Med. Chem. 53 2010 850
38. I. Nishimori, T. Minakuchi, S. Onishi, D. Vullo, A. Cecchi, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. 15 2007 7229
39. I. Nishimori, T. Minakuchi, S. Onishi, D. Vullo, A. Cecchi, A. Scozzafava, and C.T. Supuran J. Enz. Inhib. Med. Chem. 24 2009 70
40. F. Carta, A. Maresca, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 22 2012 267
41. C.T. Supuran, and A. Scozzafava Bioorg. Med. Chem. 15 2007 4336
42. C. Temperini, A. Cecchi, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 18 2008 2567
43. C.T. Supuran Curr. Pharm. Des. 14 2008 603
44. C. Temperini, A. Cecchi, A. Scozzafava, and C.T. Supuran Org. Biomol. Chem. 6 2008 2499
45. C. Temperini, A. Cecchi, A. Scozzafava, and C.T. Supuran J. Med. Chem. 52 2009 322
46. C. Temperini, A. Cecchi, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. 17 2009 1214
47. V. Alterio, M. Hilvo, A. Di Fiore, C.T. Supuran, P. Pan, S. Parkkila, A. Scaloni, J. Pastorek, S. Pastorekova, C. Pedone, A. Scozzafava, S.M. Monti, and G. De Simone Proc. Natl. Acad. Sci. U.S.A. 106 2009 16233