Crystal structure of human factor VIIa/tissue factor in complex with peptide mimetic inhibitor

Biochemical and Biophysical Research Communications

Volumn 324, Issue 4, 2004, Pages 1227-1233

  Kadono, Shojiro ^a   Sakamoto, Akihisa ^a   Kikuchi, Yasufumi ^a   Oh Eda, Masayoshi ^a   Yabuta, Naohiro ^a   Koga, Takaki ^a   Hattori, Kunihiro ^a   Shiraishi, Takuya ^a   Haramura, Masayuki ^a   Kodama, Hirofumi ^a   Esaki, Toru ^a   Sato, Haruhiko ^a   Watanabe, Yoshiaki ^a   Itoh, Susumu ^a   Ohta, Masateru ^a   Kozono, Toshiro ^a  

^a CHUGAI PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Antithrombotic; Blood coagulation; Drug design; Factor VIIa; Serine protease; X ray crystallography

Indexed keywords

BLOOD CLOTTING FACTOR 7A; BLOOD CLOTTING FACTOR 7A INHIBITOR; BLOOD CLOTTING INHIBITOR; DEXTRO THREONINE; METHIONINE; PEPTIDE MIMETIC INHIBITOR; PROPYLSULFONAMIDE DEXTRO THREONYLMETHIONINE 4 AMINOBENZAMIDINE; THREONINE; THROMBIN; THROMBIN INHIBITOR; THROMBOPLASTIN; UNCLASSIFIED DRUG; ANTICOAGULANT AGENT; BENZAMIDINE DERIVATIVE; DIPEPTIDE; PEPTIDE; PROPYLSULFONAMIDE THREONYL METHIONYL 4 AMINOBENZAMIDINE; PROPYLSULFONAMIDE-THREONYL-METHIONYL-4-AMINOBENZAMIDINE;

ARTICLE; CRYSTAL STRUCTURE; DRUG SELECTIVITY; DRUG STRUCTURE; HYDROPHOBICITY; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN INTERACTION; PROTEIN STRUCTURE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN;

ANTICOAGULANTS; BENZAMIDINES; CRYSTALLOGRAPHY, X-RAY; DIPEPTIDES; FACTOR VIIA; HUMANS; MODELS, MOLECULAR; PEPTIDES; THROMBIN; THROMBOPLASTIN;

EID: 10644283454     PISSN: 0006291X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbrc.2004.09.182     Document Type: Article

References (40)

1. E.W. Davie, K. Fujikawa, and W. Kisiel The coagulation cascade: initiation, maintenance, and regulation Biochemistry 30 1991 10363 10370
2. D.S. Houston Tissue factor-a therapeutic target for thrombotic disorders Expert Opin. Ther. Targets 6 2002 159 174
3. T.J. Girard, and N.S. Nicholson The role of tissue factor/factor VIIa in the pathophysiology of acute thrombotic formation Curr. Opin. Pharmacol. 1 2001 159 163
4. M.S. Bajaj, J.J. Birktoft, S.A. Steer, and S.P. Bajaj Structure and biology of tissue factor pathway inhibitor Thromb. Haemost. 86 2001 959 972
5. E. Braunwald, R.M. Califf, C.P. Cannon, K.A. Fox, V. Fuster, W.B. Gibler, R.A. Harrington, S.B. Kingrd, N.S. Kleiman, P. Theroux, E.J. Topol, F. Van de Werf, H.D. White, and J.T. Willerson Redefining medical treatment in the management of unstable angina Am. J. Med. 108 2000 41 53
6. J.P. Vacca New advances in the discovery of thrombin and factor Xa inhibitors Curr. Opin. Chem. Biol. 4 2000 394 400
7. P.E. Sanderson Small, noncovalent serine protease inhibitors Med. Res. Rev. 19 1999 179 197
8. P.E.J. Sanderson Anticoagulants: inhibitors of thrombin and factor Xa Annu. Rep. Med. Chem. 36 2001 79 88
9. J.M. Fevig, and R.R. Wexler Anticoagulants: thrombin and factor Xa inhibitors Annu. Rep. Med. Chem. 34 1999 81 100
10. A. Betz Recent advances in factor Xa inhibitors Expert Opin. Ther. Pattern 11 2001 1007 1017
11. B.Y. Zhu, and R.M. Scarborough Factor Xa inhibitors: recent advances in anticoagulant agents Annu. Rep. Med. Chem. 35 2000 83 102
12. W.R. Ewing, H.W. Pauls, and A.P. Spada Progress in the design of inhibitors of coagulation Factor Xa Drug Future 24 1999 771 787
13. J.A. Szalony, B.B. Taite, T.J. Girard, N.S. Nicholson, and R.M. LaChance Pharmacological intervention at disparate sites in the coagulation cascade: comparison of anti-thrombotic efficacy vs. bleeding propensity in a rat model of acute arterial thrombosis J. Thromb. Thrombolysis 14 2002 113 121
14. P. Zoldhelyi, J. McNatt, H.S. Shelat, Y. Yamamoto, Z.Q. Chen, and J.T. Willerson Thromboresistance of balloon-injured porcine carotid arteries after local gene transfer of human tissue factor pathway inhibitor Circulation 101 2000 289 295
15. J. Himber, D. Kirchhofer, M. Riederer, T.B. Tschopp, B. Steiner, and S.P. Roux Dissociation of antithrombotic effect and bleeding time prolongation in rabbits by inhibiting tissue factor function Thromb. Haemostasis 78 1997 1142 1149
16. L.A. Harker, S.R. Hanson, J.N. Wilcox, and A.B. Kelly Antithrombotic and antilesion benefits without hemorrhagic risks by inhibiting tissue factor pathway Haemostasis 26 Suppl. 1 1996 76 82
17. O. Klingler, H. Matter, M. Schudok, S.P. Bajaj, J. Czech, M. Lorenz, H.P. Nestler, H. Schreuder, and P. Wildgoose Design, synthesis, and structure-activity relationship of a new class of amidinophenylurea-based factor VIIa inhibitors Bioorg. Med. Chem. Lett. 13 2003 1463 1467
18. J.J. Parlow, B.L. Case, T.A. Dice, R.L. Fenton, M.J. Hayes, D.E. Jones, W.L. Neumann, R.S. Wood, R.M. Lachance, T.J. Girard, N.S. Nicholson, M. Clare, R.A. Stegeman, A.M. Stevens, W.C. Stallings, R.G. Kurumbail, and M.S. South Design, parallel synthesis, and crystal structures of pyrazinone antithrombotics as selective inhibitors of the tissue factor VIIa complex J. Med. Chem. 46 2003 4050 4062
19. J.J. Parlow, T.A. Dice, R.M. Lachance, T.J. Girard, A.M. Stevens, R.A. Stegeman, W.C. Stallings, R.G. Kurumbail, and M.S. South Polymer-assisted solution-phase library synthesis and crystal structure of alpha-ketothiazoles as tissue factor VIIa inhibitors J. Med. Chem. 46 2003 4043 4049
20. J.J. Parlow, R.G. Kurumbail, R.A. Stegeman, A.M. Stevens, W.C. Stallings, and M.S. South Synthesis and X-ray crystal structures of substituted fluorobenzene and benzoquinone inhibitors of the tissue factor VIIa complex Bioorg. Med. Chem. Lett. 13 2003 3721 3725
21. J.J. Parlow, R.G. Kurumbail, R.A. Stegeman, A.M. Stevens, W.C. Stallings, and M.S. South Design, synthesis, and crystal structure of selective 2-pyridone tissue factor VIIa inhibitors J. Med. Chem. 46 2003 4696 4701
22. J.J. Parlow, A.M. Stevens, R.A. Stegeman, W.C. Stallings, R.G. Kurumbail, and M.S. South Synthesis and crystal structures of substituted benzenes and benzoquinones as tissue factor VIIa inhibitors J. Med. Chem. 46 2003 4297 4312
23. M.S. South, T.A. Dice, T.J. Girard, R.M. Lachance, A.M. Stevens, R.A. Stegeman, W.C. Stallings, R.G. Kurumbail, and J.J. Parlow Polymer-assisted solution-phase (PASP) parallel synthesis of an alpha-ketothiazole library as tissue factor VIIa inhibitors Bioorg. Med. Chem. Lett. 13 2003 2363 2367
24. M.S. South, B.L. Case, R.S. Wood, D.E. Jones, M.J. Hayes, T.J. Girard, R.M. Lachance, N.S. Nicholson, M. Clare, A.M. Stevens, R.A. Stegeman, W.C. Stallings, R.G. Kurumbail, and J.J. Parlow Structure-based drug design of pyrazinone antithrombotics as selective inhibitors of the tissue factor VIIa complex Bioorg. Med. Chem. Lett. 13 2003 2319 2325
25. M.R. Wiley, N.Y. Chirgadze, D.K. Clawson, T.J. Craft, D.S. Gifford-Moore, N.D. Jones, J.L. Olkowski, L.C. Weir, and G.F. Smith d-Phe-Pro-p- amidinobenzylamine: a potent and highly selective thrombin inhibitor Bioorg. Med. Chem. Lett. 6 1996 2387 2392
26. D.W. Banner, A. D'Arcy, C. Chene, F.K. Winkler, A. Guha, W.H. Konigsberg, Y. Nemerson, and D. Kirchhofer The crystal structure of the complex of blood coagulation factor VIIa with soluble tissue factor Nature 380 1996 41 46
27. G. Kemball-Cook, D.J. Johnson, E.G. Tuddenham, and K. Harlos Crystal structure of active site-inhibited human coagulation factor VIIa (des-Gla) J. Struct. Biol. 127 1999 213 223
28. A.C. Pike, A.M. Brzozowski, S.M. Roberts, O.H. Olsen, and E. Persson Structure of human factor VIIa and its implications for the triggering of blood coagulation Proc. Natl. Acad. Sci. USA 96 1999 8925 8930
29. D. Kirchhofer, A. Guha, Y. Nemerson, W.H. Konigsberg, F. Vilbois, C. Chene, D.W. Banner, and A. D'Arcy Activation of blood coagulation factor VIIa with cleaved tissue factor extracellular domain and crystallization of the active complex Proteins 22 1995 419 425
30. Z. Otwinowski, and W. Minor Processing of X-ray diffraction data collected in oscillation mode Methods Enzymol. 276 1997 307 326
31. K. Sichler, D.W. Banner, A. D'Arcy, K.P. Hopfner, R. Huber, W. Bode, G.B. Kresse, E. Kopetzki, and H. Brandstetter Crystal structures of uninhibited factor VIIa link its cofactor and substrate-assisted activation to specific interactions J. Mol. Biol. 322 2002 591 603
32. C. Eigenbrot, D. Kirchhofer, M.S. Dennis, L. Santell, R.A. Lazarus, J. Stamos, and M.H. Ultsch The factor VII zymogen structure reveals reregistration of beta strands during activation Structure (Camb) 9 2001 627 636
33. W. Bode, I. Mayr, U. Baumann, R. Huber, S.R. Stone, and J. Hofsteenge The refined 1.9 Å crystal structure of human alpha-thrombin: interaction with D-Phe-Pro-Arg chloromethylketone and significance of the Tyr-Pro-Pro-Trp insertion segment EMBO J. 8 1989 3467 3475
34. W. Bode, D. Turk, and A. Karshikov The refined 1.9-Å X-ray crystal structure of d-Phe-Pro-Arg chloromethylketone-inhibited human alpha-thrombin: structure analysis, overall structure, electrostatic properties, detailed active-site geometry, and structure-function relationships Protein Sci. 1 1992 426 471
35. D.W. Banner, and P. Hadvary Crystallographic analysis at 3.0-Å resolution of the binding to human thrombin of four active site-directed inhibitors J. Biol. Chem. 266 1991 20085 20093
36. K. Padmanabhan, K.P. Padmanabhan, A. Tulinsky, C.H. Park, W. Bode, R. Huber, D.T. Blankenship, A.D. Cardin, and W. Kisiel Structure of human des(1-45) factor Xa at 2.2 Å resolution J. Mol. Biol. 232 1993 947 966
37. K.P. Hopfner, A. Lang, A. Karcher, K. Sichler, E. Kopetzki, H. Brandstetter, R. Huber, W. Bode, and R.A. Engh Coagulation factor IXa: the relaxed conformation of Tyr99 blocks substrate binding Struct. Fold Des. 7 1999 989 996
38. T. Mather, V. Oganessyan, P. Hof, R. Huber, S. Foundling, C. Esmon, and W. Bode The 2.8 Å crystal structure of Gla-domainless activated protein C EMBO J. 15 1996 6822 6831
39. X. Wang, X. Lin, J.A. Loy, J. Tang, and X.C. Zhang Crystal structure of the catalytic domain of human plasmin complexed with streptokinase Science 281 1998 1662 1665
40. D. Lamba, M. Bauer, R. Huber, S. Fischer, R. Rudolph, U. Kohnert, and W. Bode The 2.3 Å crystal structure of the catalytic domain of recombinant two-chain human tissue-type plasminogen activator J. Mol. Biol. 258 1996 117 135