Discovery and kinetic evaluation of 6-substituted 4-benzylthio-1,3,5- triazin-2(1H)-ones as inhibitors of cathepsin B

European Journal of Medicinal Chemistry

Volumn 46, Issue 9, 2011, Pages 4648-4656

  Sosič, Izidor ^a   Mirković, Bojana ^a   Turk, Samo ^a   Štefane, Bogdan ^a,b   Kos, Janko ^a,c   Gobec, Stanislav ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b EN FIST CENTRE OF EXCELLENCE   (Slovenia)

^c JO EF STEFAN INSTITUTE   (Slovenia)

Author keywords

1,3,5 Triazine 2(1H) ones; Cathepsin B; Cysteine protease; Noncovalent inhibitors; Partial mixed type inhibition

Indexed keywords

4 (BENZYLTHIO) 6 (2 CHLOROBENZYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (2 CYANOBENZYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (2 FLUORO 4 CYANOBENZYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (2 FLUOROBENZYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (2 METHOXYBENZYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (2 NITROBENZYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (3 CHLOROBENZYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (3 CYANOBENZYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (3 FLUOROBENZYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (3 METHOXYBENZYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (3 NITROBENZYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (4 CHLOROBENZYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (4 CYANOBENZYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (4 FLUOROBENZYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (4 METHOXYBENZYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (4 NITROBENZYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (BUTYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (CARBOXYMETHYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (CYANOMETHYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (CYCLOPROPYLMETHYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (ETHYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 (PROPYLTHIO) 1,3,5 TRIAZIN 2(1H) ONE; 4 (BENZYLTHIO) 6 MERCAPTO 1,3,5 TRIAZIN 2(1H) ONE; 4 BENZYLTHIO 1,3,5 TRIAZIN 2(1H) ONE DERIVATIVE; CATHEPSIN B; CATHEPSIN B INHIBITOR; CATHEPSIN H; CATHEPSIN L; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; DRUG BINDING SITE; DRUG PROTEIN BINDING; DRUG SYNTHESIS; ENZYME INHIBITION; MOLECULAR DOCKING; SUBSTITUTION REACTION;

CATHEPSIN B; ENZYME INHIBITORS; HUMANS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TRIAZINES;

EID: 80052937349     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.08.005     Document Type: Article

References (35)

1. N.D. Rawlings, A.J. Barrett, and A. Bateman Nucleic Acids Res. 38 2010 227 233
2. A.J. Barrett, and H. Kirschke Methods Enzymol. 80 1981 535 561
3. C. Illy, O. Quraishi, J. Wang, E. Purisima, T. Vernet, and J.S. Mort J. Biol. Chem. 272 1997 1197 1202
4. D. Musil, D. Zucic, D. Turk, R.A. Engh, I. Mayr, R. Huber, T. Popovic, V. Turk, T. Towatari, N. Katunuma, and W. Bode EMBO J. 10 1991 2321 2330
5. P.C. Almeida, I.L. Nantes, J.R. Chagas, C.C. Rizzi, A. Faljoni-Alario, E. Carmona, L. Juliano, H.B. Nader, and I.L. Tersariol Biol. Chem. 276 2001 944 951
6. D.K. Nägler, A.C. Storer, F.C. Portaro, E. Carmona, L. Juliano, and R. Ménard Biochemistry 36 1997 12608 12615
7. A. Pavlova, J.C. Krupa, J.S. Mort, M. Abrahamson, and I. Björk FEBS Lett. 487 2000 156 160
8. I. Redzynia, A. Ljunggren, M. Abrahamson, J.S. Mort, J.C. Krupa, M. Jaskolski, and G. Bujacz J. Biol. Chem. 283 2008 22815 22825
9. P.A. Hill, D.J. Buttle, S.J. Jones, A. Boyde, M. Murata, J.J. Reynolds, and M.C. Meikle J. Cell. Biochem. 56 1994 118 130
10. S. Jordans, S. Jenko-Kokalj, N.M. Kühl, S. Tedelind, W. Sendt, D. Brömme, D. Turk, and K. Brix BMC Biochem. 10 2009 23
11. T. Zhang, Y. Maekawa, J. Hanba, T. Dainichi, B.F. Nashed, H. Hisaeda, T. Sakai, T. Asao, K. Himeno, R.A. Good, and N. Katunuma Immunology 100 2000 13 20
12. H. Büth, P. Luigi Buttigieg, R. Ostafe, M. Rehders, S.R. Dannenmann, N. Schaschke, H.J. Stark, P. Boukamp, and K. Brix Eur. J. Cell Biol. 86 2007 747 761
13. M.M. Mohamed, and B.F. Sloane Nat. Rev. Cancer 6 2006 764 775
14. R. Frlan, and S. Gobec Curr. Med. Chem. 13 2006 2309 2327
15. B. Turk Nat. Rev. Drug Discov. 5 2006 785 799
16. B.T. Mott, R.S. Ferreira, A. Simeonov, A. Jadhav, K.K. Ang, W. Leister, M. Shen, J.T. Silveira, P.S. Doyle, M.R. Arkin, J.H. McKerrow, J. Inglese, C.P. Austin, C.J. Thomas, B.K. Shoichet, and D.J. Maloney J. Med. Chem. 53 2010 52 60
17. J.P. Mallari, A.A. Shelat, A. Kosinski, C.R. Caffrey, M. Connely, F. Zhu, J.H. McKerrow, and R.K. Guy J. Med. Chem. 52 2009 6489 6493
18. I. Sosič, B. Štefane, A. Kovač, S. Turk, D. Blanot, and S. Gobec Heterocycles 81 2010 91 115
19. B. Mirković, M. Renko, S. Turk, I. Sosič, Z. Jevnikar, N. Obermajer, D. Turk, S. Gobec, and J. Kos ChemMedChem 6 2011 1351 1356
20. J. Goerdeler, and J. Neuffer Chem. Ber. 104 1971 1606
21. D. Turk, and G. Gunčar Acta Cryst. D59 2003 203 213
22. O. Vasiljeva, T. Reinheckel, C. Peters, D. Turk, V. Turk, and B. Turk Curr. Pharm. Des. 13 2007 387 403
23. S.D. Mason, and J.A. Joyce Trends Cell. Biol. 21 2011 228 237
24. C. Bincoletto, I.L.S. Tersariol, C.R. Oliveira, S. Dreher, D.M. Fausto, M.A. Soufen, F.D. Nascimento, and A.C.F. Caires Bioorg. Med. Chem. 13 2005 3047 3055
25. D. Watanabe, A. Yamamoto, K. Tomoo, K. Matsumoto, M. Murata, K. Kitamura, and T. Ishida J. Mol. Biol. 362 2006 979 993
26. K. Tomoo Curr. Top. Med. Chem. 10 2010 696 707
27. P.D. Greenspan, C.L. Clark, R.A. Tomassi, S.D. Cowen, L.W. Mcquire, D.L. Farley, J.H. Duzer, R.L. Goldberg, H. Zhou, Z. Du, J.J. Fitt, D.E. Coppa, Z. Fang, W. Macchia, L. Zhu, M.P. Capparelli, R. Goldstein, A.M. Wigg, J. Doughty, R.S. Bohacek, and A.K. Knap J. Med. Chem. 44 2001 4524 4534
28. P.D. Greenspan, C.L. Clark, S.D. Cowen, L.W. Mcquire, R.A. Tomassi, D.L. Farley, E. Quadros, D.E. Coppa, Z. Du, Z. Fang, H. Zhou, J. Doughty, K.T. Toscano, A.M. Wigg, and S. Zhou Bioorg. Med. Chem. Lett. 13 2003 4121 4124
29. M. Rarey, B. Kramer, T. Lengauer, and G. Klebe J. Mol. Biol. 261 1996 470 489
30. L.L.C. Schrödinger The PyMOL Molecular Graphics System, Version 1.3r1 2010
31. M. Frizler, M. Stirnberg, M.T. Sisay, and M. Gütschow Curr. Top. Med. Chem. 10 2010 294 322
32. R. Kuhelj, M. Dolinar, J. Pungercar, and V. Turk Eur. J. Biochem. 229 2 1995 533 539
33. A. Schweiger, B. Stabuc, T. Popović, V. Turk, and J. Kos J. Immunol. Methods 201 1997 165 172
34. M. Dolinar, D.B. Maganja, and V. Turk Biol. Chem. Hoppe-Seyler 376 1995 385 388
35. B.Y. Feng, and B.K. Shoichet Nat. Protoc. 1 2006 550 553