Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 14, 2012, Pages 4681-4685

  Winum, Jean Yves ^a   Carta, Fabrizio ^b   Ward, Carol ^c   Mullen, Peter ^c   Harrison, David ^d   Langdon, Simon P ^c   Cecchi, Alessandro ^b   Scozzafava, Andrea ^b   Kunkler, Ian ^c   Supuran, Claudiu T ^b  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b UNIVERSITY OF FLORENCE   (Italy)

^c UNIVERSITY OF EDINBURGH   (United Kingdom)

^d UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

Antitumor agent; Breast cancer; Carbonic anhydrase; Inhibitor; Isoform IX and XII; Sulfamate

Indexed keywords

4 AMINOPHENOL; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IX; CARBONATE DEHYDRATASE IX INHIBITOR; CARBONATE DEHYDRATASE XII; ISOCYANIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG EFFECT; DRUG SYNTHESIS; HUMAN; HUMAN CELL;

BREAST NEOPLASMS; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; CELL LINE, TUMOR; CELL PROLIFERATION; HUMANS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONIC ACIDS;

EID: 84863424129     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.05.083     Document Type: Article

References (49)

1. 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
2. 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
3. Alterio, V.; Di Fiore, A.; D'Ambrosio, K.; Supuran, C.T.; De Simone, G. Chem. Rev., in press, http://dx.doi.org/10.1021/cr200176r.
4. C.T. Supuran Nat. Rev. Drug Discov. 7 2008 168
5. K.S. Smith, C. Jakubzick, T.S. Whittam, and J.G. Ferry Proc. Natl. Acad. Sci. U.S.A. 96 1999 15184
6. S.A. Zimmerman, J.G. Ferry, and C.T. Supuran Curr. Top. Med. Chem. 7 2007 901
7. Y. Xu, L. Feng, P.D. Jeffrey, Y. Shi, and F.M. Morel Nature 452 2008 56
8. V. Alterio, E. Langella, F. Viparelli, D. Vullo, G. Ascione, N.A. Dathan, F.M.M. Morel, C.T. Supuran, G. De Simone, and S.M. Monti Biochimie 94 2012 1232
9. J.K. Ahlskog, C. Schliemann, J. Mårlind, U. Qureshi, A. Ammar, R.B. Pedleym, and D. Neri Bioorg. Med. Chem. Lett. 19 2009 4851
10. D. Neri, and C.T. Supuran Nat. Rev. Drug Discov. 10 2011 767
11. C.T. Supuran Bioorg. Med. Chem. Lett. 20 2010 3467
12. S. Pastorekova, S. Parkkila, J. Pastorek, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 19 2004 199
13. Supuran, C.T. J. Enzyme Inhib. Med. Chem. in press.
14. J.F. Domsic, B.S. Avvaru, C.U. Kim, S.M. Gruner, M. Agbandje-McKenna, D.N. Silverman, and R. McKenna J. Biol. Chem. 283 2008 30766
15. C.M. Maupin, N. Castillo, S. Taraphder, C. Tu, R. McKenna, D.N. Silverman, and G.A. Voth J. Am. Chem. Soc. 133 2011 6223
16. C.T. Supuran Carbonic Future Med. Chem. 3 2011 1165
17. C.T. Supuran, A. Scozzafava, and A. Casini Med. Res. Rev. 23 2003 146
18. 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
19. S. Huang, T. Hainzl, C. Grundström, C. Forsman, G. Samuelsson, and A.E. Sauer-Eriksson PLoS One 6 2011 e28458
20. F. Briganti, S. Mangani, P. Orioli, A. Scozzafava, G. Vernaglione, and C.T. Supuran Biochemistry 36 1997 10384
21. C. Temperini, A. Scozzafava, D. Vullo, and C.T. Supuran Chemistry 12 2006 7057
22. F. Carta, M. Aggarwal, A. Maresca, A. Scozzafava, R. McKenna, and C.T. Supuran Chem. Commun. 2012 1868 48
23. S.M. Monti, A. Maresca, F. Carta, G. De Simone, F.A. Mühlschlegel, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 22 2012 859
24. F. Carta, M. Aggarwal, A. Maresca, A. Scozzafava, R. McKenna, E. Masini, and C.T. Supuran J. Med. Chem. 55 2012 1721
25. S. Kolayli, F. Karahalil, H. Sahin, B. Dincer, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 26 2011 895
26. G. De Simone, and C.T.J. Supuran Inorg. Biochem. 111 2012 117
27. S. Parkkila, D. Vullo, A. Maresca, F. Carta, A. Scozzafava, and C.T. Supuran Chem. Commun. 48 2012 3551
28. F. Carta, C. Temperini, A. Innocenti, A. Scozzafava, K. Kaila, and C.T. Supuran J. Med. Chem. 53 2010 5511
29. 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
30. A. Maresca, C. Temperini, L. Pochet, B. Masereel, A. Scozzafava, and C.T. Supuran J. Med. Chem. 53 2010 335
31. A. Maresca, and C.T. Supuran Bioorg. Med. Chem. Lett. 20 2010 4511
32. A. Maresca, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 20 2010 7255
33. 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
34. S.K. Chia, C.C. Wykoff, P.H. Watson, C. Han, R.D. Leek, J. Pastorek, K.C. Gatter, P. Ratcliffe, and A.L. Harris J. Clin. Oncol. 19 2001 3660
35. C.C. Wykoff, N.J. Beasley, P.H. Watson, K.J. Turner, J. Pastorek, A. Sibtain, G.D. Wilson, H. Turley, K.L. Talks, P.H. Maxwell, C.W. Pugh, P.J. Ratcliffe, and A.L. Harris Cancer Res. 60 2000 7075
36. N. Robertson, C. Potter, and A.L. Harris Cancer Res. 64 2004 6160
37. E. Svastova, W. Witarski, L. Csaderova, I. Kosik, L. Skvarkova, A. Hulikova, M. Zatovicova, M. Barathova, J. Kopacek, J. Pastorek, and S. Pastorekova J. Biol. Chem. 287 2012 3392
38. P. Ditte, F. Dequiedt, E. Svastova, A. Hulikova, A. Ohradanova-Repic, M. Zatovicova, L. Csaderova, J. Kopacek, C.T. Supuran, S. Pastorekova, and J. Pastorek Cancer Res. 71 2011 7558
39. L. Dubois, S. Peeters, N.G. Lieuwes, N. Geusens, A. Thiry, S. Wigfield, F. Carta, A. McIntyre, A. Scozzafava, J.M. Dogne, C.T. Supuran, A.L. Harris, B. Masereel, and P. Lambin Radiother. Oncol. 99 2011 424
40. J.Y. Winum, D. Vullo, A. Casini, J.L. Montero, A. Scozzafava, and C.T. Supuran J. Med. Chem. 46 2003 5471
41. J.Y. Winum, D. Vullo, A. Casini, J.L. Montero, A. Scozzafava, and C.T. Supuran J. Med. Chem. 46 2003 2197
42. V. Menchise, G. De Simone, V. Alterio, A. Di Fiore, C. Pedone, A. Scozzafava, and C.T. Supuran J. Med. Chem. 48 2005 5721
43. 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
44. V. Alterio, G. De Simone, S.M. Monti, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 17 2007 4201
45. 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
46. F. Pacchiano, M. Aggarwal, B.S. Avvaru, A.H. Robbins, A. Scozzafava, R. McKenna, and C.T. Supuran Chem. Commun. 46 2010 8371
47. 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
48. 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
49. C.T. Supuran Carbonic anhydrases: off-targets, add-on activities, or emerging novel targets ? J.U. Peters, Polypharmacology in Drug Discovery 2012 Wiley Hoboken 457 489