Selective inhibition of human carbonic anhydrases by novel amide derivatives of probenecid: Synthesis, biological evaluation and molecular modelling studies

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 15, 2014, Pages 3982-3988

  D'Ascenzio, Melissa ^a   Carradori, Simone ^a   Secci, Daniela ^a   Vullo, Daniela ^b   Ceruso, Mariangela ^b   Akdemir, Atilla ^c   Supuran, Claudiu T ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF FLORENCE   (Italy)

^c BEZMIALEM VAKIF UNIVERSITY   (Turkey)

Author keywords

Probenecid; Selective carbonic anhydrase IX inhibitors; Selective carbonic anhydrase XII inhibitors; Tertiary sulfonamides

Indexed keywords

4 (DIPROPYLSULFAMOYL) N METHYLBENZAMIDE; 4 (DIPROPYLSULFAMOYL) N PHENYLBENZAMIDE; 4 (N,N DIPROPYLSULFAMOYL) N (1,3,4 THIADIAZOL 2 YL)BENZAMIDE; 4 (N,N DIPROPYLSULFAMOYL) N (2 AMINOPHENYL)BENZAMIDE; 4 (N,N DIPROPYLSULFAMOYL) N (2 METHYLCYCLOHEXYL)BENZAMIDE; 4 (N,N DIPROPYLSULFAMOYL) N (2 MORPHOLINOETHYL)BENZAMIDE; 4 (N,N DIPROPYLSULFAMOYL) N (2 NITROPHENYL)BENZAMIDE; 4 (N,N DIPROPYLSULFAMOYL) N (3 NITROPHENYL)BENZAMIDE; 4 (N,N DIPROPYLSULFAMOYL) N (PYRIDIN 2 YL)BENZAMIDE; ACETAZOLAMIDE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IX; CARBONATE DEHYDRATASE XII; N (3 CHLOROPHENYL) 4 (DIPROPYLSULFAMOYL)BENZAMIDE; N (4 CHLOROPHENYL) 4 (DIPROPYLSULFAMOYL)BENZAMIDE; N CYCLOHEXYL 4 (N,N DIPROPYLSULFAMOYL)BENZAMIDE; PROBENECID; UNCLASSIFIED DRUG; ZINC ION; AMIDE; CA13 PROTEIN, HUMAN; PROTEIN BINDING; SULFONAMIDE;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DERIVATIZATION; DRUG BINDING; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME BINDING; ENZYME INHIBITION; HYDROGEN BOND; MOLECULAR DOCKING; MOLECULAR INTERACTION; PROTEIN EXPRESSION; PROTEIN INTERACTION; ANTAGONISTS AND INHIBITORS; BINDING SITE; CHEMISTRY; HUMAN; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMIDES; BINDING SITES; CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; CATALYTIC DOMAIN; HUMANS; MOLECULAR DOCKING SIMULATION; PROBENECID; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 84905087830     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.06.003     Document Type: Article

References (45)

1. V. Alterio, A. Di Fiore, K. D'Ambrosio, C.T. Supuran, and G. De Simone Chem. Rev. 112 2012 4421
2. C.T. Supuran Nat. Rev. Drug Disc. 7 2008 168
3. M. Hilvo, A. Innocenti, S.M. Monti, G. De Simone, C.T. Supuran, and S. Parkkila Curr. Pharm. Des. 14 2008 672
4. C.T. Supuran, A. Scozzafava, and A. Casini Med. Res. Rev. 23 2003 146
5. C.T. Supuran, and A. Scozzafava Expert Opin. Ther. Pat. 10 2000 575
6. P. Swietach, S. Wigfield, P. Cobden, C.T. Supuran, A.L. Harris, and R.D. Vaughan-Jones J. Biol. Chem. 283 2008 20473
7. C.T. Supuran Expert Opin. Ther. Pat. 23 2013 677
8. C.T. Supuran Future Med. Chem. 3 2011 1165
9. S. Pastorekova, S. Parkkila, J. Pastorek, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 19 2004 199
10. C.E. Weber, and P.C. Kuo Surg. Oncol. 21 2012 172
11. O. Warburg Science 124 1956 269
12. O. Warburg, F. Wind, and E. Negelein J. Gen. Physiol. 8 1927 519
13. R.A. Gatenby, and R.J. Gillies Nat. Rev. Cancer 4 2004 891
14. B.A. Webb, M. Chimenti, M.P. Jacobson, and D.L. Barber Nat. Rev. Cancer 11 2011 671
15. R.A. Gatenby, K. Smallbone, P.K. Maini, F. Rose, J. Averill, R.B. Nagle, L. Worrall, and R.J. Gillies Br. J. Cancer 97 2007 646
16. C.V. Dang, and G.L. Semenza Trends Biochem. Sci. 24 1999 68
17. G.L. Semenza Crit. Rev. Biochem. Mol. Biol. 35 2000 71
18. S.K. Parks, J. Chiche, and J. Pouysségur Nat. Rev. Cancer 13 2013 611
19. F.E. Lock, P.C. McDonald, Y. Lou, I. Serrano, S.C. Chafe, C. Ostlund, S. Aparicio, J.Y. Winum, C.T. Supuran, and S. Dedhar Oncogene 32 2013 5210
20. C. Ward, S.P. Langdon, P. Mullen, A.L. Harris, D.J. Harrison, C.T. Supuran, and I.H. Kunkler Cancer Treat. Rev. 39 2013 171
21. C.P.S. Potter, and A.L. Harris Br. J. Cancer 89 2003 2
22. P.C. McDonald, J.Y. Winum, C.T. Supuran, and S. Dedhar Oncotarget 3 2012 84
23. Y. Lou, P.C. McDonald, A. Oloumi, S.K. Chia, C. Ostlund, A. Ahmadi, A. Kyle, U. AufdemKeller, 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
24. N. Lounnas, C. Rosilio, M. Nebout, D. Mary, E. Griessinger, Z. Neffati, H. Spits, T. Hagenbeek, V. Asnafi, S.A. Poulsen, C.T. Supuran, J.F. Peyron, and V. Imbert Cancer Lett. 333 2013 76
25. D. Neri, and C.T. Supuran Nat. Rev. Drug Disc. 10 2011 767
26. J.Y. Winum, F. Carta, C. Ward, P. Mullen, D. Harrison, S.P. Langdon, A. Cecchi, A. Scozzafava, I. Kunkler, and C.T. Supuran Bioorg. Med. Chem. Lett. 22 2012 4681
27. P. Ebbesen, E.O. Pettersen, T.A. Gorr, G. Jobst, K. Williams, J. Kieninger, R.H. Wenger, S. Pastorekova, L. Dubois, P. Lambin, B.G. Wouters, T. Van Den Beucken, 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
28. N.K. Tafreshi, M.M. Bui, K. Bishop, M.C. Lloyd, S.A. Enkemann, A.S. Lopez, D. Abrahams, B.W. Carter, J. Vagner, S.R. Grobmyer, R.T. Gillies, and D.C. Morse Clin. Cancer Res. 18 2012 207
29. R.G. Gieling, and K.J. Williams Bioorg. Med. Chem. 21 2013 1470
30. J. Borras, A. Scozzafava, L. Menabuoni, F. Mincione, F. Briganti, G. Mincione, and C.T. Supuran Bioorg. Med. Chem. 7 1999 2397
31. H.M. Said, C.T. Supuran, C. Hageman, A. Staab, B. Polat, A. Katzer, A. Scozzafava, J. Anacker, M. Flentje, and D. Vordermark Curr. Pharm. Des. 16 2010 3288
32. C.T. Supuran, F. Mincione, A. Scozzafava, F. Briganti, G. Mincione, and M.A. Ilies Eur. J. Med. Chem. 33 1998 247
33. R. Demirdaǧ, V. ÇomaklI, M. Şentürk, D. Ekinci, Ö. İrfan Küfrevioǧlu, and C.T. Supuran Bioorg. Med. Chem. 21 2013 1522
34. F. Briganti, R. Pierattelli, A. Scozzafava, and C.T. Supuran Eur. J. Med. Chem. 1001 1996 31
35. T. Rogez-Florent, S. Meignan, C. Foulon, P. Six, A. Gros, C. Bal-Mahieu, C.T. Supuran, A. Scozzafava, R. Frédérick, B. Masereel, P. Depreuxa, A. Lansiauxa, J.F. Goossensa, S. Gluszoka, and L. Goossens Bioorg. Med. Chem. 21 2013 1451
36. V. Alterio, A. Di Fiore, K. D'Ambrosio, C.T. Supuran, and G. De Simone C.T. Supuran, J.-Y. Winum, Drug Design of Zinc-Enzyme Inhibitors 2009 John Wiley & Sons 138
37. 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
38. C. Alp, A. Maresca, N.A. Alp, M.S. Gültekin, D. Ekinci, A. Scozzafava, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 28 2013 294
39. B. Métayer, A. Martin-Mingot, D. Vullo, C.T. Supuran, and S. Thibaudeau Org. Biomol. Chem. 11 2013 7540
40. B. Métayer, A. Mingot, D. Vullo, C.T. Supuran, and S. Thibaudeau Chem. Commun. 49 2013 6015
41. M. D'Ascenzio, S. Carradori, C. De Monte, D. Secci, M. Ceruso, and C.T. Supuran Bioorg. Med. Chem. 22 2014 1821
42. A. Akdemir, C. De Monte, S. Carradori, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 2014 10.3109/14756366.2014.892936
43. S. Carradori, C. De Monte, M. D'Ascenzio, D. Secci, G. Celik, M. Ceruso, D. Vullo, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 23 2013 6759
44. I. Puscas, M. Coltau, and R. Pasca J. Pharmacol. Exp. Ther. 277 1996 1464
45. H.C. Cheng J. Pharmacol. Toxicol. Methods 46 2001 61