Novel small molecule protein arginine deiminase 4 (PAD4) inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 3, 2013, Pages 715-719

  Bozdag, Murat ^a   Dreker, Tobias ^b   Henry, Christophe ^b   Tosco, Paolo ^c   Vallaro, Maura ^c   Fruttero, Roberta ^c   Scozzafava, Andrea ^a   Carta, Fabrizio ^a   Supuran, Claudiu T ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b 4SC AG   (Germany)

^c UNIVERSITY OF TURIN   (Italy)

Author keywords

CA inhibitors; Cancer; PAD inhibitors; Rheumatoid arthritis

Indexed keywords

ACETAZOLAMIDE; CIMETIDINE; GUANIDINE DERIVATIVE; HYDROLASE INHIBITOR; PHENOL; PROTEIN ARGININE DEIMINASE; PROTEIN ARGININE DEIMINASE 4; PROTEIN ARGININE DEIMINASE 4 INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CHEMICAL INTERACTION; COMPETITIVE INHIBITION; DRUG SCREENING; ENZYME ACTIVITY; ENZYME SUBSTRATE; HYDROGEN BOND; MOLECULAR DOCKING; PATHOPHYSIOLOGY; REGULATORY MECHANISM; STRUCTURE ACTIVITY RELATION;

ENZYME ACTIVATION; ENZYME INHIBITORS; GUANINE; HUMANS; HYDROLASES; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 84872319546     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.11.102     Document Type: Article

References (48)

1. A. Innocenti, D. Vullo, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 18 2008 1583
2. A. Innocenti, D. Vullo, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 16 2008 7424
3. F. Carta, D. Vullo, A. Maresca, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 2012 in press, and references therein
4. H. Shirai, T.L. Blundell, and K. Mizuguchi Trends Biochem. Sci. 26 2001 465
5. T. Senshu, K. Aliyama, A. Ishigami, and K. Nomura J. Dermatol. Sci. 21 1999 113
6. A. Ishida-Yamamoto, T. Senshu, R.A. Eady, H. Takahashi, H. Shimizu, M. Akiyama, and H. Iizuka J. Invest. Dermatol. 118 2002 282
7. M.A. Moscarello, L.B. Pritzker, F.G. Mastronardi, and D.D. Wood J. Neurochem. 81 2002 335
8. L.B. Pritzker, T.A. Nguyen, and M.A. Moscarello Neurosci. Lett. 266 1999 161
9. D.D. Wood, J.M. Bilbao, P. O'Connors, and M.A. Moscarello Ann. Neurol. 40 1996 18
10. T. Kanno, A. Kawada, J. Yamanouchi, C. Yosida-Noro, A. Yoshiki, M. Shiraiwa, M. Kusakabe, M. Manabe, T. Tezuka, and H. Takahara J. Invest. Dermatol. 115 2000 813
11. G. Rogers, B. Winter, C. McLaughlan, B. Powell, and T. Nesci J. Invest. Dermatol. 108 1997 700
12. K. Nakashima, T. Hagiwara, A. Ishigami, S. Nagata, H. Asaga, M. Kuramoto, T. Senshu, and M. Yamada J. Biol. Chem. 274 1999 27786
13. T. Hagiwara, K. Nakashima, H. Hirano, T. Senshu, and M. Yamada Biochem. Biophys. Res. Commun. 290 2002 979
14. K. Nakashima, T. Hagiwara, and M. Yamada J. Biol. Chem. 277 2002 49562
15. S. Chavanas, M.C. Méchin, H. Takahara, A. Kawada, R. Nachat, G. Serre, and M. Simon Gene 330 2004 19
16. P.W. Wright, L.C. Bolling, M.E. Calvert, O.F. Sarmento, E.V. Berkeley, M.C. Shea, Z. Hao, F.C. Jayes, L.A. Bush, J. Shetty, A.N. Shore, P.P. Reddi, K.S. Tung, E. Samy, M.M. Allietta, N.E. Sherman, J.C. Herr, and S.A. Coonrod Dev. Biol. 256 2003 74
17. M. Guerrin, A. Ishigami, M.C. Méchin, R. Nachat, S. Valmary, M. Sebbag, M. Simon, T. Senshu, and G. Serre Biochem. J. 370 2003 167
18. A. Ishigami, T. Ohsawa, H. Asaga, K. Akiyama, M. Kuramoto, and N. Maruyama Arch. Biochem. Biophys. 407 2002 25
19. K. Arita, H. Hashimoto, T. Shimizu, K. Nakashima, M. Yamada, and M. Sato Nat. Struct. Biol. 11 2004 777
20. R.S. Lewis Annu. Rev. Immunol. 19 2001 497
21. H. Takahara, M. Tsuchida, M. Kusubata, K. Akutsu, S. Tagami, and K. Sugawara J. Biol. Chem. 264 1989 13361
22. J.L. Slack, L.E. Jones Jr., M.M. Bhatia, and P.R. Thompson Biochemistry 50 2011 3997
23. L. Klareskog, J. Rönnelid, K. Lundberg, L. Padyukov, and L. Alfredsson Annu. Rev. Immunol. 26 2008 651
24. N. Wegner, K. Lundberg, A. Kinloch, B. Fisher, V. Malmström, M. Feldmann, and P.J. Venables Immunol. Rev. 233 2010 34
25. K. Lundberg, N. Wegner, T. Yucel-Lindberg, and P.J. Venables Nat. Rev. Rheumatol. 12 2010 727
26. P.R. Thompson, and W. Fast ACS Chem. Biol. 7 2006 433
27. J.L. Slack, C.P. Causey, and P.R. Thompson Cell Mol. 68 2011 709
28. P.L. Kearney, M. Bhatia, N.G. Jones, L. Yuan, M.C. Glascock, K.L. Catchings, M. Yamada, and P.R. Thompson Biochemistry 44 2005 10570
29. H. Yuki, T. Ohmura, H. Kawasaki, T. Yajima, and K. Saito Chem. Pharm. Bull. 29 1981 1096
30. K. Sugawara, and O. Oyama J. Biochem. 89 1981 771
31. L.A. Sternson, J.F. Stobaugh, and A.J. Repta Anal. Biochem. 144 1985 233
32. Mana, H. Ph.D. Thesis, Martin-Luther-Universität Halle-Wittenberg, November 1998.
33. Y. Luo, K. Arita, M. Bhatia, B. Knuckley, Y.H. Lee, M.R. Stallcup, M. Sato, and P.R. Thompson Biochemistry 45 2006 11727
34. B. Knuckley, C.P. Causey, P.J. Pellechia, P.F. Cook, and P.R. Thompson ChemBioChem 11 2010 161
35. S. Wang, G. Wood, C. Meades, G. Griffiths, C. Midgley, I. McNae, C. McInnes, S. Anderson, W. Jackson, M. Mezna, R. Yuill, M. Walkinshaw, and P.M. Fisher Bioorg. Med. Chem. Lett. 14 2004 4237 Compound 1
36. X. Li, and R.S. Prakash J. Labelled Compd. Radiopharm. 52 2009 355 Compound 2
37. M. Bertinaria, G. Sorba, C. Medana, C. Cena, M. Adami, G. Morini, C. Pozzoli, G. Coruzzi, and A. Gasco Helv. Chim. Acta 83 2000 287
38. M. Bertinaria, A. Di Stilo, P. Tosco, G. Sorba, E. Poli, C. Pozzoli, G. Coruzzi, R. Fruttero, and A. Gasco Bioorg. Med. Chem. Lett. 11 2003 1197
39. A. Di Stilo, C. Cena, M. Lolli, G. Sorba, A. Gasco, G. Bertaccini, C. Pozzoli, M. Adami, and G. Coruzzi Farmaco 53 1998 536
40. J. Wang, P. Cieplak, and P.A. Kollman J. Comput. Chem. 21 2000 1049
41. G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, and A.J. Olson J. Comput. Chem. 19 1998 1639
42. R.G. Khalifah J. Biol. Chem. 246 1971 2561
43. 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
44. A. Maresca, C. Temperini, L. Pochet, B. Masereel, A. Scozzafava, and C.T. Supuran J. Med. Chem. 53 2010 335
45. F. Carta, C. Temperini, A. Innocenti, A. Scozzafava, K. Kaila, and C.T. Supuran J. Med. Chem. 53 2010 5511
46. A. Di Fiore, E. Truppo, C.T. Supuran, V. Alterio, N. Dathan, F. Bootorabi, S. Parkkila, S.M. Monti, and G. De Simone Bioorg. Med. Chem. Lett. 20 2010 5023
47. M. Hilvo, L. Baranauskiene, A.M. Salzano, A. Scaloni, D. Matulis, A. Innocenti, A. Scozzafava, S.M. Monti, A. Di Fiore, G. De Simone, M. Lindfors, J. Janis, J. Valjakka, S. Pastorekova, J. Pastorek, M.S. Kulomaa, H.R. Nordlund, C.T. Supuran, and S. Parkkila J. Biol. Chem. 283 2008 27799
48. P.C. Causey, E.J. Jones, J.L. Slack, D. Kamei, L.E. Jones, V. Subramanian, B. Knuckley, P. Ebrahimi, A.A. Chumanevich, Y. Luo, H. Hashimoto, M. Sato, L.J. Hofseth, and P.R. Thompson J. Med. Chem. 54 2011 6919