Combining the tail and the ring approaches for obtaining potent and isoform-selective carbonic anhydrase inhibitors: Solution and X-ray crystallographic studies

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 1, 2014, Pages 334-340

  Bozdag, Murat ^a   Ferraroni, Marta ^a   Nuti, Elisa ^b   Vullo, Daniela ^a   Rossello, Armando ^b   Carta, Fabrizio ^a   Scozzafava, Andrea ^a   Supuran, Claudiu T ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b UNIVERSITY OF PISA   (Italy)

Author keywords

Carbonic anhydrase; Inhibitor; Sulfonamide; Tosylureido; X ray crystallography

Indexed keywords

4 TOSYLUREIDO BENZENESULFONAMIDE; 5 (3 TOSYLUREIDO)PYRIDINE 2 SULFONAMIDE; BENZENE DERIVATIVE; BENZENE SULFONAMIDE DERIVATIVE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE III; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IV; CARBONATE DEHYDRATASE IX; CARBONATE DEHYDRATASE VI; CARBONATE DEHYDRATASE XII; CARBONIC ANHYDRASE VA; CARBONIC ANHYDRASE VII; CARBONIC ANHYDRASE XIII; CARBONIC ANHYDRASE XIV; ISOENZYME; PYRIDINE DERIVATIVE; SULFONAMIDE; UNCLASSIFIED DRUG; ZINC ION;

ARTICLE; BINDING KINETICS; CHEMICAL MODIFICATION; DRUG DEVELOPMENT; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; ENZYME ACTIVE SITE; ENZYME BINDING; ENZYME INHIBITION; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

CARBONIC ANHYDRASE; INHIBITOR; SULFONAMIDE; TOSYLUREIDO; X-RAY CRYSTALLOGRAPHY;

CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; CRYSTALLOGRAPHY, X-RAY; HUMANS; MODELS, MOLECULAR; PROTEIN ISOFORMS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84891481971     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.11.016     Document Type: Article

References (75)

1. C.T. Supuran Bioorg. Med. Chem. 21 2013 1377
2. C.T. Supuran, A. Scozzafava, and A. Casini Med. Res. Rev. 23 2003 146
3. V. Alterio, A. Di Fiore, K. D'Ambrosio, C.T. Supuran, and G. De Simone Chem. Rev. 112 2012 4421
4. C.T. Supuran Nat. Rev. Drug Disc. 7 2008 168
5. C.T. Supuran, and A. Scozzafava Bioorg. Med. Chem. 15 2007 4336
6. G. De Simone, V. Alterio, and C.T. Supuran Expert Opin. Drug Discovery 8 2013 793
7. C.T. Supuran J. Enzyme Inhib. Med. Chem. 27 2012 759
8. M. Aggarwal, B. Kondeti, and R. McKenna Expert Opin. Ther. Pat. 23 2013 717
9. M. Aggarwal, C.D. Boone, B. Kondeti, and R. McKenna J. Enzyme Inhib. Med. Chem. 28 2013 267
10. M. Aggarwal, B. Kondeti, and R. McKenna Bioorg. Med. Chem. 21 2013 1526
11. V. Garaj, L. Puccetti, G. Fasolis, J.Y. Winum, J.L. Montero, A. Scozzafava, D. Vullo, A. Innocenti, and C.T. Supuran Bioorg. Med. Chem. Lett. 14 2004 5427
12. V. Garaj, L. Puccetti, G. Fasolis, J.Y. Winum, J.L. Montero, A. Scozzafava, D. Vullo, A. Innocenti, and C.T. Supuran Bioorg. Med. Chem. Lett. 15 2005 3102
13. F. Carta, V. Garaj, A. Maresca, J. Wagner, B.S. Avvaru, A.H. Robbins, A. Scozzafava, R. McKenna, and C.T. Supuran Bioorg. Med. Chem. 19 2011 3105
14. J.K.J. Ahlskog, C.E. Dumelin, S. Trüssel, J. Marlind, and D. Neri Bioorg. Med. Chem. Lett. 19 2009 4851
15. 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
16. C.T. Supuran Bioorg. Med. Chem. Lett. 20 2010 3467
17. L. Baranauskiene, M. Hilvo, J. Matuliene, D. Golovenko, E. Manakova, V. Dudutiene, V. Michailoviene, J. Torresan, J. Jachno, S. Parkkila, A. Maresca, C.T. Supuran, S. Grazulis, and D. Matulis J. Enzyme Inhib. Med. Chem. 25 2010 863
18. T. Mann, and D. Keilin Nature 146 1940 164
19. C.T. Supuran, and A. Scozzafava J. Enzyme Inhib. 14 1999 343
20. A. Scozzafava, and C.T. Supuran Eur. J. Med. Chem. 35 2000 299
21. A. Scozzafava, and C.T. Supuran Eur. J. Pharm. Sci. 10 2000 29
22. M. Ilies, M.D. Banciu, A. Scozzafava, M.A. Ilies, M.T. Caproiu, and C.T. Supuran Bioorg. Med. Chem. 11 2003 2227
23. K. D'Ambrosio, R.M. Vitale, J.M. Dogné, B. Masereel, A. Innocenti, A. Scozzafava, G. De Simone, and C.T. Supuran J. Med. Chem. 51 2008 3230
24. C. Temperini, A. Cecchi, N.A. Boyle, A. Scozzafava, J.E. Cabeza, P. Wentworth, G.M. Blackburn, and C.T. Supuran Bioorg. Med. Chem. Lett. 18 2008 999
25. J.R. Casey, P.E. Morgan, D. Vullo, A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran J. Med. Chem. 47 2004 2337
26. N. Hen, M. Bialer, B. Yagen, A. Maresca, M. Aggarwal, A.H. Robbins, R. McKenna, A. Scozzafava, and C.T. Supuran J. Med. Chem. 54 2011 3977
27. C.T. Supuran, A. Di Fiore, and G. De Simone Expert Opin. Emerg. Drugs 13 2008 383
28. D. Vullo, A. Innocenti, I. Nishimori, J. Pastorek, A. Scozzafava, S. Pastorekova, and C.T. Supuran Bioorg. Med. Chem. Lett. 15 2005 963
29. I. Nishimori, D. Vullo, A. Innocenti, A. Scozzafava, A. Mastrolorenzo, and C.T. Supuran Bioorg. Med. Chem. Lett. 15 2005 3828
30. D. Vullo, J. Voipio, A. Innocenti, C. Rivera, H. Ranki, A. Scozzafava, K. Kaila, and C.T. Supuran Bioorg. Med. Chem. Lett. 15 2005 971
31. S.M. Monti, C.T. Supuran, and G. De Simone Expert Opin. Ther. Pat. 23 2013 737
32. A. Innocenti, D. Vullo, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 18 2008 1583
33. E. Masini, F. Carta, A. Scozzafava, and C.T. Supuran Expert Opin. Ther. Pat. 23 2013 705
34. F. Carta, and C.T. Supuran Expert Opin. Ther. Pat. 23 2013 681
35. C.T. Supuran Expert Opin. Ther. Pat. 23 2013 677
36. A. Scozzafava, C.T. Supuran, and F. Carta Expert Opin. Ther. Pat. 23 2013 725
37. H. Sahin, R. Aliyazicioglu, O. Yildiz, S. Kolayli, A. Innocenti, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 26 2011 440
38. P.A. Boriack, D.W. Christianson, J. Kingery-Wood, and G.M. Whitesides J. Med. Chem. 38 1995 2286
39. J.J. Baldwin, G.S. Ponticello, G.S. Anderson, M.E. Christy, M.A. Murcko, W.C. Randall, H. Schwam, M.F. Sugrue, J.B. Springer, P. Gautheron, J. Grove, P. Mallorga, M.P. Viader, B.M. McKeever, and M.A. Navia J. Med. Chem. 32 1989 2510
40. I.T. Barnish, P.E. Cross, R.P. Dickinson, M.J. Parry, and M.J. Randall J. Med. Chem. 24 1981 959
41. F. Fabrizi, F. Mincione, T. Somma, G. Scozzafava, F. Galassi, E. Masini, F. Impagnatiello, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 27 2012 138
42. C. Alp, S. Özsoy, N.A. Alp, D. Erdem, M.S. Gültekin, Ö.I. Küfrevioǧlu, M. Şentürk, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 27 2012 818
43. S. Singh, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 27 2012 666
44. D. Ekinci, N.I. Kurbanoglu, E. Salamci, M. Senturk, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 27 2012 845
45. F. Liu, A. Martin-Mingot, F. Lecornué, A. Maresca, S. Thibaudeau, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 27 2012 886
46. J. Leitans, A. Sprudza, M. Tanc, I. Vozny, R. Zalubovskis, K. Tars, and C.T. Supuran Bioorg. Med. Chem. 21 2013 5130
47. E. Čapkauskaite, A. Zubriene, L. Baranauskiene, G. Tamulaitiene, E. Manakova, V. Kairys, S. Gražulis, S. Tumkevičius, and D. Matulis Eur. J. Med. Chem. 51 2012 259
48. C.T. Supuran, C.W. Conroy, and T.H. Maren Eur. J. Med. Chem. 31 1996 843
49. A. Scozzafava, L. Menabuoni, F. Mincione, F. Briganti, G. Mincione, and C.T. Supuran J. Med. Chem. 42 1999 2641
50. A. Scozzafava, L. Menabuoni, F. Mincione, F. Briganti, G. Mincione, and C.T. Supuran J. Med. Chem. 43 2000 4542
51. W.T. Caldwell, and E.C. Kornfeld J. Am. Chem. Soc. 64 1942 1695 1698
52. C.T. Supuran, and A. Scozzafava Expert Opin. Ther. Pat. 10 2000 575
53. F. Carta, A. Scozzafava, and C.T. Supuran Expert Opin. Ther. Pat. 22 2012 747
54. C.T. Supuran, A. Scozzafava, and A. Casini Development of Sulfonamide Carbonic Anhydrase Inhibitors C.T. Supuran, A. Scozzafava, J. Conway, Carbonic Anhydrase - Its Inhibitors and Activators 2004 CRC Press Boca Raton 67 147
55. D.M. Duda, C. Tu, S.Z. Fisher, H. An, C. Yoshioka, L. Govindasamy, P.J. Laipis, M. Agbandje-McKenna, D.N. Silverman, and R. McKenna Biochemistry 44 2005 10046
56. R.G. Khalifah J. Biol. Chem. 246 1971 2561
57. V. Alterio, A. Di Fiore, K. D'Ambrosio, C.T. Supuran, and G. De Simone C.T. Supuran, J.Y. Winum, X-ray Crystallography of CA Inhibitors and its Importance in Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications 2009 Wiley Hoboken 73 138
58. B.S. Avvaru, J.M. Wagner, A. Maresca, A. Scozzafava, A.H. Robbins, C.T. Supuran, and R. McKenna Bioorg. Med. Chem. Lett. 20 2010 4376
59. J.M. Wagner, B.S. Avvaru, A.H. Robbins, A. Scozzafava, C.T. Supuran, and R. McKenna Bioorg. Med. Chem. 18 2010 4873
60. F. Pacchiano, M. Aggarwal, B.S. Avvaru, A.H. Robbins, A. Scozzafava, R. McKenna, and C.T. Supuran Chem. Commun. 46 2010 8371
61. K. Köhler, A. Hillebrecht, J.S. Wischeler, A. Innocenti, A. Heine, C.T. Supuran, and G. Klebe Angew. Chem., Int. Ed. 46 2007 7697
62. E. Eriksson, T.A. Jones, and A. Liljas Proteins: Struct., Funct., Genet. 4 1988 274
63. G. De Simone, R.M. Vitale, A. Di Fiore, C. Pedone, A. Scozzafava, J.L. Montero, J.Y. Winum, and C.T. Supuran J. Med. Chem. 49 2006 5544
64. S. Biswas, M. Aggarwal, O. Guzel, A. Scozzafava, R. McKenna, and C.T. Supuran Bioorg. Med. Chem. 19 2011 3732
65. V. Menchise, G. De Simone, V. Alterio, A. Di Fiore, C. Pedone, A. Scozzafava, and C.T. Supuran J. Med. Chem. 48 2005 5721
66. A.M. Marini, A. Maresca, M. Aggarwal, S. Nencetti, E. Orlandini, F. Da Settimo, S. Salerno, F. Simorini, C. La Motta, S. Taliani, E. Nuti, R. McKenna, A. Rossello, and C.T. Supuran J. Med. Chem. 55 2012 9619
67. 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
68. C. Temperini, A. Innocenti, A. Guerri, A. Scozzafava, S. Rusconi, and C.T. Supuran Bioorg. Med. Chem. Lett. 17 2007 2210
69. 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 (S1)
70. D. Neri, and C.T. Supuran Nat. Rev. Drug Disc. 10 2011 767
71. A.G.W. Leslie, and H.R. Powell Processing Diffraction Data with Mosfilm Evolving Methods for Macromolecular Crystallography 245 2007 41 51 (ISBN 978-1-4020-6314-5)
72. G.N. Murshudov, A.A. Vagin, and E.J. Dodson Acta Crystallogr., Sect. D D53 1997 240
73. P. Emsley, B. Lohkamp, W. Scott, and K. Cowtan Acta Crystallogr., Sect. D D66 2010 486
74. V.S. Lamzin, A. Perrakis, and K.S. Wilson International Tables for Crystallography M.G. Rossmann, E. Arnold, Crystallography of Biological Macromolecules Vol. F 2001 Kluwer Academic Publishers Dordrecht, The Netherlands 720 722
75. R.A. Laskowski, M.W. MacArthur, D.S. Moss, and J.M. Thornton J. Appl. Crystallogr. 26 1993 283