Combinatorial chemical approaches as an efficient tool for discovering GPIIb/IIIa antagonists

Drugs of the Future

Volumn 22, Issue 12, 1997, Pages 1367-1373

  Hayashi, Yoshio ^a   Harada, Takeo ^a   Katada, Jun ^a   Uno, Isao ^a  

^a NIPPON STEEL CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 [3 (4 AMIDINOBENZAMIDO) 2,2 DIMETHYL 3 PHENYLPROPIONYL]PIPERIDINE 4 ACETIC ACID; ANTICOAGULANT AGENT; ARGINYLGLYCYLASPARTIC ACID; FIBRINOGEN RECEPTOR; FIBRINOGEN RECEPTOR ANTAGONIST; INTEGRIN; UNCLASSIFIED DRUG;

DRUG DEVELOPMENT; DRUG SYNTHESIS; HUMAN; REVIEW; STRUCTURE ACTIVITY RELATION; TECHNIQUE;

EID: 0031404346     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (73)

1. Turitto, V.T., Baumgartner, H.R. Platelet-surface interactions. In: Hemostasis and Thrombosis, Basic Principles and Clinical Practice. Colmam, R.W., Hirsh, J., Marder, V.J., Salzmann, E.W. (Eds.). J.B. Lippincott Co.: Philadelphia 1982, 364-79.
2. Leonard, E.F., Turitto, V.T., Vroman, L. (Eds.). Blood in contact with natural and artificial surfaces. Ann NY Acad Sci 1987, 516: 1-688.
3. Coller, B.S. Platelets and thrombolytic therapy. New Engl J Med 1990, 322: 33-42.
4. Scharf, R.E., Harker, L.A. Thrombosis and atherosclerosis: Regulatory role of interactions among blood components and endothelium. Blut 1987, 55: 131-44.
5. Falk, E. Unstable angina with fatal outcome: Dynamic coronary thrombosis leading to infarction and/or sudden death. Autopsy evidence of recurrent mural thrombosis with peripheral embolization culminating in total vascular occlusion. Circulation 1985, 71: 699-708.
6. Ip, J.H., Stein, B., Fuster, V., Badimon, L. Antithrombotic therapy in cardiovascular diseases. Ann NY Acad Sci 1991, 614: 289-311.
7. Meyer, D., Fressinaud, E., Sakariassen, K.S., Baumgartner, H.R., Girma, J.P. Role of von Willebrand factor in platelet vesselwall interactions. Ann NY Acad Sci 1987, 509: 118-30.
8. Savage, B., Shattil, S. J., Ruggeri, Z.M. Modulation of platelet function through adhesion receptors. J Biol Chem 1992, 267: 11300-6.
9. Badimon, L., Badimon, J.J., Chesebro, J.H., Fuster, V. von Willebrand factor and cardiovascular disease. Thromb Haemostas 1993, 70: 111-8.
10. Phillips, D.R., Charo, I.F., Parise, L.V., Fitzgerald, L.A. The platelet membrane glycoprotein IIb-IIIa complex. Blood 1988, 71: 831-43.
11. Ruoslahti, E., Pierschbacher, M.D. New perspectives in cell adhesion: RGD and integrins. Science 1987, 238: 491-7.
12. Kroll, M.H., Schafer, A.I. Biochemical mechanisms of platelet activation. Blood 1989, 74: 1181-95.
13. Hawiger, J. Formation and regulation of platelet and fibrin hemostatic plug. Hum Pathol 1987, 18: 111-22.
14. Coller, B.S., Scudder, L.E., Beer, J. et al. Monoclonal antibodies to platelet glycoprotein IIb/IIIa as antithrombotic agents. Ann NY Acad Sci 1991, 614: 193-213.
15. The EPIC Investigators. Use of a monoclonal antibody directed against the platelet glycoprotein IIb/IIIa receptor in high-risk coronary angioplasty. New Engl J Med 1994, 330: 956-61.
16. Weller, T., Alig, L., Hürzeler, M., Müller, M., Kouns, W.C., Steiner, B. Fibrinogen receptor antagonists - A novel class of promising antithrombotics. Drugs Fut 1994, 19: 461-76.
17. Cook, N.S., Kottirsch, G., Zerwes, H.-G. Platelet glycoprotein IIb/IIIa antagonists. Drugs Fut 1994, 19: 135-59.
18. Austel, V., Himmelsbach, F., Müller, T. Nonpeptidic fibrinogen receptor antagonists. Drugs Fut 1994, 19: 757-64.
19. Qjima, I., Chakravarty, S., Dong, Q. Antithrombotic agents: From RGD to peptide mimetics. Bioorg Med Chem 1995, 3: 337-60.
20. Samanen, J. GPIIb/IIIa antagonists. Annu Rep Med Chem 1996, 31: 91-100.
21. Pierschbacher, M.D., Ruoslahti, E. Cell attachment activity of fibronectin can be duplicated by small synthetic fragments of the molecule. Nature 1984, 309: 30-3.
22. Merrifield, R.B. Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J Am Chem Soc 1963, 85: 2149-54.
23. Geysen, H.M., Rodda, S.J., Mason, T.J. A priori delineation of a peptide which mimics a discontinuous antigenic determinant. Mol Immunol 1986, 23: 709-15.
24. a) Furka, A., Sebestyén. F., Asgedom, M., Dibó, G. Cornucopia of peptides by synthesis. 14th Int Cong Biochem (Prague) 1988, 5: Abst 47.
25. b) Furka, A., Sebestyén, F., Asgedom, M., Dibó, G. More peptides by less labour. 10th Int Symp Med Chem (Budapest) 1988. Abst 288.
26. c) Furka, A., Sebestyén, F., Asgedom, M., Dibó, G. General method for rapid synthesis of multicomponent peptide mixtures. Int J Pept Protein Res 1991, 37: 487-93.
27. a) Gallop, M.A., Barrett, R.W., Dower, W.J., Fodor, S.P.A., Gordon, E.M. Applications of combinatorial technologies to drug discovery. 1. Background and peptide combinatorial libraries. J Med Chem 1994, 37: 1233-51.
28. b) Gordon, E.M., Barrett, R.W., Dower, W.J., Fodor, S.P.A., Gallop, M.A. Applications of combinatorial technologies to drug discovery. 2. Combinatorial organic synthesis, library screening strategies, and future directions. J Med Chem 1994, 37: 1385-401.
29. Furka, A. History of combinatorial chemistry. Drug Dev Res 1995, 36: 1-12.
30. Thompson, L.A., Ellman, J.A. Synthesis and applications of small molecule libraries. Chem Rev 1996, 96: 555-600.
31. Hermkens, P.H.H.,. Ottenheijm, H.C.J., Rees, D. Solid-phase organic reactions. A review of the recent literature. Tetrahedron 1996, 52: 4527-54.
32. a) Qabar, M., Urban, J., Sia, C., Klein, M., Kahn, M. Peptide secondary structure mimetics: Applications to vaccines and pharmaceuticals. Farmaco 1996, 51: 87-96.
33. b) Kahn, M. Peptide secondary structure mimetics: Recent advances and future challenges. Syn Lett 1993, 3: 821-6.
34. Humphries, M.J. The molecular basis and specificity of integrin-ligand interactions. J Cell Sci 1990, 97: 585-92.
35. Hynes, R.O. Integrins: A family of cell surface receptors. Cell 1987, 48: 549-54.
36. Yamada, K.M. Adhesion recognition sequences. J Biol Chem 1991, 266: 12809-12.
37. Plow, E.F., Pierschbacher, M.D., Ruoslahti, E., Marguerie, G.A., Ginsberg, M.H. The effect of Arg-Gly-Asp-containing peptides on fibrinogen and von Willebrand factor binding to platelets. Proc Natl Acad Sci USA 1985, 82: 8057-61.
38. Pytela, R., Pierschbacher, M.D., Ginsberg, M.H., Plow, E.F., Ruoslahti, E. Platelet membrane glycoprotein IIb-IIIa: Member of a family of Arg-Gly-Asp specific adhesion receptors. Science 1986, 231: 1559-62.
39. 2+-dependent binding of a synthetic Arg-Gly-Asp (RGD) peptide to a single site on the purified platelet glycoprotein IIb-IIIa complex. J Biol Chem 1989, 264: 13102-8.
40. Gartner, T.K., Bennett, J.S. The tetrapeptide analogue of the cell attachment site of fibronectin inhibits platelet aggregation and fibrinogen binding to activated platelets. J Biol Chem 1985, 260: 11891-4.
41. Ruggeri, Z.M., Houghten, R.A., Russell, S.R., Zimmerrnan, T.S. Inhibition of platelet function with synthetic peptides designed to be high-affinity antagonists of fibrinogen binding to platelets. Proc Natl Acad Sci USA 1986, 83: 5708-12.
42. Samanen, J., Ali, F., Romoff, T. et al. Development of a small BGD peptide fibrinogen receptor antagonist with potent antiaggregatory activity in vitro. J Med Chem 1991, 34: 3114-25.
43. Gould, R.J., Polokoff, M.A., Friedman, P.A. et al. Disintegrins: A family of integrin inhibitory proteins from viper venoms. Proc Soc Exp Biol Med 1990, 195: 168-71.
44. Chen, Y., Pitzenberger, S.M., Garsky, V.M., Lumma, P.K., Sanyal, G., Baum, J. Proton NMR assignments and secondary structure of the snake venom protein echistatin. Biochemistry 1991, 30: 11625-36.
45. Adler, M., Lazarus, R.A., Dennis, M.S., Wagner, G. Solution structure of kistrin, a potent platelet aggregation inhibitor and GPIIb-IIIa antagonist. Science 1991, 253: 445-8.
46. McDowell, R.S., Dennis, M.S., Louie, A., Shuster, M., Mulkerrin, M.G., Lazarus, R.A. Mambin, a potent glycoprotein IIb-IIIa antagonist and platelet aggregation inhibitor structurally related to the short neurotoxins. Biochemistry 1992, 31: 4766-72.
47. Can, Z.-R., Gould, R.J., Jacobs, J.W., Friedman, P.A., Polokoff, M.A. Echistatin, a potent platelet aggregation inhibitor from the venom of the viper, Echis carinatus. J Biol Chem 1988, 263: 19827-32.
48. Peishoff, C.E., Ali, F.E., Bean, J.W. et al. Investigation of conformational specifi/city at GPIIb/IIIa: Evaluation of conformationally constrained RGD peptides. J Med Chem 1992, 35: 3962-9.
49. 3 antagonists. J Med Chem 1994, 37: 1-8.
50. Scarborough, R.M., Naughton, M.A., Teng, W. et al. Design of potent and specific integrin antagonists. J Biol Chem 1993, 268: 1066-73.
51. 1 integrins. J Biol Chem 1994, 269: 20233-8.
52. Müller, G., Gurrath, M., Kessler, H. Pharmacophorerefinement of gpIIb/IIIa antagonists based on comparative studies of antiadhesive cyclic and acyclic RGD peptides. J Comput Aided Mol Des 1994, 8: 709-30.
53. a) Katada, J., Hayashi, Y., Sato, Y. at al. A novel peptide motif for platelet fibrinogen receptor recognition. J Biol Chem 1997, 272: 7720-6.
54. b) Hayashi, Y., Sato, Y., Katada, J., Takiguchi, Y., Ojima, I., Uno, I. Design and synthesis of new antagonist peptides for platelet gpIIb/IIIa receptor as anti-thrombotic agents. Bioorg Med Chem Lett 1996, 6; 1351-6.
55. Harada, T., Katada, J., Tachiki, A. et al. Development of the new potent non-peptide gpIIb/IIIa antagonist NSL-95301 by utilizing combinatorial technique. Bioorg Med Chem Lett 1997, 7: 209-12.
56. Kuramoto, Y., Inokuma, K., Hashimoto, K., Yazaki, A. Novel 4-quinolone derivatives as GPIIb/IIIa antagonist. 16th Symp Med Chem (Nov 27-29, Toyama) 1996, Abst 81-2.
57. Smith, P.W., Lai, J.Y.Q., Whittington, R. et al. Synthesis and biological evaluation of a library containing potentially 1600 amides/ esters. A strategy for rapid compound generation and screening. Bioorg Med Chem Lett 1994, 4: 2821-4.
58. Kloczewiak, M., Timmons, S., Lukas, T.J., Hawiger, J. Platelet receptor recognition site on human fibrinogen. Synthesis and structure-function relationship of peptides corresponding to the carboxy-terminal segment of the γ-chain. Biochemistry 1984, 23: 1767-74.
59. a) Farrell, D.H., Thiagarajan, P., Chung, D.W., Davie, E.W. Role of fibrinogen α- and γ-chain sites in platelet aggregation. Proc Natl Acad Sci USA 1992, 89: 10729-32.
60. b) Hettasch, J.M., Bolyard, M.G., Lord. S.T. The residues AGDV of recombinant γ-chains of human fibrinogen must be carboxy-terminal to support human platelet aggregation. Thromb Haemostas 1992, 68: 701-6.
61. Hoekstra, W.J., Beavers, M.P., Andrade-Gordon, P. et al. Design and evaluation of nonpeptide fibrinogen γ-chain based GPIIb/IIIa antagonists. J Med Chem 1995, 38: 1582-92.
62. Hoekstra, W.J., Maryanoff, B.E., Andrade-Gordon, P. et al. Solid-phase parallel synthesis applied to lead optimization: Discovery of potent analogues of the GPIIb/IIIa antagonist RWJ-50042. Bioorg Med Chem Lett 1996, 6: 2371-6.
63. DeWitt, S.H., Kiely, J.S., Stankovic, C.J., Schroeder, M.C., Cody, D.M.R., Pavia, M.R. Diversomers: An approach to nonpeptide, nonoligomeric chemical diversity. Proc Natl Acad Sci USA 1993, 90: 6909-13.
64. 1, to mediate spreading on fibronectin. J Cell Sci 1995, 108: 1227-38.
65. Dresner-Pollack, R., Rosenblatt, M. Blockade of osteoclastmediated bone resorption through occupancy of the integrin receptor: A potential approach to the therapy of osteoporosis. J Cell Biochem 1994, 56: 323-30.
66. 3 by osteopontin stimulates phosphatidylinositol 3-hydroxylkinase activity. Endocrinology 1995, 136: 2984-92.
67. 3 integrin inhibits bone resorption in vitro and prevents osteoporosis in vivo. J Clin Invest 1997, 99: 2284-92.
68. 3 prevents maturation of blood vessels during embryonic neovascularization. J Cell Sci 1995, 108: 2655-61.
69. 3 integrin in human melanoma cell invasion. Proc Natl Acad Sci USA 1992, 89: 1557-61.
70. 3 blocks human breast cancer growth and angiogenesis in human skin. J Clin Invest 1995, 96: 1815-22.
71. Weller, M., Wiedemann, P., Bresgen, M., Heimann, K. Vitronectin and proliferative intraocular disorders. II. Expression of cell surface receptors for fibronectin and vitronectin in periretinal membranes. Int Ophthamol 1991, 15: 103-8.
72. v integrins. Science 1995, 270: 1500-2.
73. 3 integrin antagonist library. Bioorg Med Chem Lett 1997, 7: 1371-6.