The discovery of VLA-4 antagonists

Current Topics in Medicinal Chemistry

Volumn 4, Issue 14, 2004, Pages 1509-1523

  Tilley, Jefferson W ^a   Chen, Li ^a   Sidduri, Achyutharao ^a   Fotouhi, Nader ^a  

^a HOFFMANN LA ROCHE INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARGINYLGLYCYLASPARTIC ACID; ASPARTIC ACID; BLOCKING AGENT; CYCLOPEPTIDE; PHENYLALANINE DERIVATIVE; PROLINE; TYROSINE; VERY LATE ACTIVATION ANTIGEN 4;

BINDING SITE; DRUG BINDING; DRUG CONFORMATION; DRUG MECHANISM; DRUG POTENCY; DRUG RESEARCH; HUMAN; PROCESS OPTIMIZATION; REVIEW; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

HUMANS; INHIBITORY CONCENTRATION 50; INTEGRIN ALPHA4BETA1; MOLECULAR MIMICRY; PEPTIDES, CYCLIC; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 4844231191     PISSN: 15680266     EISSN: None     Source Type: Journal    
DOI: 10.2174/1568026043387502     Document Type: Review

References (34)

1. Weg, V. B.; Williams, T. J.; Lobb, R. R.; Nourshargh, S. A Monclonal Antibody Recognizing Very Late Antigen-4 Inhibits Eosinophil Accumulation In Vivo. J. Exp. Med. 1993, 177, 561-566.
2. Chisholm, P. L.; Williams, C. A.; Lobb, R. R. Monoclonal Antibodies to the Integrin α-4 subunit Inhibit the Murine Contact Hypersensitivity Response. Eur. J. Immunol. 1993, 23, 682-688.
3. Elices, M. J.; Tamraz, S.; Tollefson, V.; Vollger, L. W. The integrin VLA-4 mediates leukocyte recruitment to skin inflammatory sites in vivo. Clin. Exp. Rheumatology 1993, 11 (Suppl. 8), S77-S80.
4. Nakajima, H.; Sano, H.; Nishimura, T.; Yoshida, S.; Iwamoto, I. Role of VCAM-VLA-4 and ICAM/LFA-1 Interactions in Antigen-induced Eosinophil and T Cell Recruitment into the Tissue. J. Exp. Med. 1994, 179, 1145-1154.
5. Issekutz, A. C.; Issekutz, T. B. Monocyte Migration to Arthritis in the Rat Utilizes both CD11/CD18 and Very Late Activation Antigen 4 Integrin Mechanisms. J. Exp. Med. 1995, 181, 1197-1203.
6. Barbadillo, C.; G-Arroyo, A.; Salas, C.; Mulero, J.; Sanchez-Madrid, F.; Andreu, J. L. Anti-integrin Immunotherapy in Rheumatoid Arthritis: Protective Effect of Anti-α4 Antibody in Adjuvant Arthritis. Springer Semin. Immunopathol. 1995, 16, 427-436.
7. Seiffge, D. Protective Effects of Monoclonal Antibody to VLA-4 on Leukocyte Adhesion and Course of Disease in Adjuvant Arthritis in Rats. J. Rheumatol. 1996, 23, 2086-2091.
8. Richards, I. M.; Kolbasa, K. P.; Hatfield, C. A.; Winterrowd, G. E.; Vonderfecht, S. L.; Fidler, S. F.; Griffin, R. L.; Brasher, J. R.; Krzesicki, R. F.; Sly, L. M.; Ready, K. A.; Staite, N. D.; Chin, J. E. Role of Very Late Activation Antigen-4 in the Lungs and Airway Lumen of Sensitized Brown Norway Rats. Am.J Respir Cell Mol Biol. 1996, 15, 172-183.
9. Sagara, H., Matsuda, H., Wada, N.; Yagita, H.; Fukuda, T.; Okumura, K.; Makino, S.; Ra, C. A Monoclonal Antibody Against Very Late Activation Antigen-4 Inhibits Eosinophil Accumulation and Late Asthmatic Response In a Guinea Pig Model of Asthma. Int Arch Allergy Immunol. 1997, 112, 287-294.
10. Hesterberg, P. E.; Winsor-Hines, D.; Briskin, M. J.; Soler-Ferran, D.; Merrill, C.; MacKay, C. R.; Newman, W.; Ringler, D. J. Rapid resolution of chronic colitis in the cotton-top tamarin with an antibody to a gut-homing integrin α4β7. Gastroenterology, 1996, 111, 1373-1380.
11. Powrie, F.; Leach, M. W. Genetic and Spontaneious Models of Inflammatory Bowel Disease in Rodents: Evidence for Abnormalities in Muscosal Immune Regulation. Ther. Immunol. 1995, 2, 115-123.
12. Arrhenius, T.; Chiem, A.; Elices, M.; He, Y.-B.; Jia, L.; Maewal, A.; Muller, D. Graeta, F. Small Molecule Inhibitors Of The Leukocyte Interin VLA-4. Pept: Chem, Struct. Biol., Proc. Am. Pept. Symp., 14th 1996, 337-339.
13. Wahl, S. M.; Allen, J. B.; Hines, K. L.; Imamichi, T.; Wahl, A. M.; Furcht, L. T.; McCarthy, J. B. Synthetic Fibronectin Peptides Suppress Arthritis in Rats by Interupting Leukocyte Adhesion and Recruitment. J. Clin. Invest. 1994, 94, 655-662.
14. Ghosh, S.; Goldin, E.; Gordon, F. H.; Malchow, H. A. et al. New England J. Med. 2003, 348, 24-32.
15. Miller, David H.; Khan, Omar A.; Sheremata, William A.; Blumhardt, L. D.; et al. New England J. Med. 2003, 348, 15-23.
16. Lobl, T. J.; Chiang, S.-L.; Cardarelli, P. M. Preparation of cyclic cell adhesion modulation compounds. World Patent WO 92/00995, 1992.
17. Chiang, S.-L. N.; Cardarelli, P. M.; Lobl, T. J. Preparation of peptide inhibitors of cell adhesion as drugs and diagnostic agents. World Patent WO 94/15958, 1994.
18. Cardarelli, P. M.; Cobb, R. R.; Nowlin, D. M.; Scholz, W.; Gorcsan, F.; Moscinski, M.; Yasuhara, M.; Chiang, S.-L.; Lobl, T. J. Cyclic RGD Peptide Inhibits α42b1 Interaction with Connecting Segment 1 and Vascular Cell Adhesion Molecule. J. Biol. Chem. 1994, 269, 18668-18673.
19. Chen, L.; Guthrie, R.; Huang, T.-N.; Hull, K.; Sidduri, A.; Tilley, J. W. N-Alkanoylphenylalanine Derivatives. WO 9910312, 1999.
20. Jackson D. Y.; Quan, C.; Artis, D. R., Rawson, T.; Blackburn, B.; Struble, M.; Fitzgerald, G.; Chan, K.; Mullins, S.; Burnier, J. P.; Fairbrother, W. J.; Clark, K.; Berisim, M.; Chui, H.; Renz, M.; Jones, S.; Fong, S. Potent α4β1 Peptide Antagonists as Potential Anti-inflammatory Agents. J. Med. Chem 1997, 40, 3359-3368.
21. Fotouhi, N.; Joshi, P.; Fry, D.; Cook, C., Tilley, J. W.; Kaplan, G.; Hanglow, A.; Rowan, K.; Schwinge, V.; Wolitzky, B. The Design and Synthesis of Potent Cyclic Peptide VCAM/VLA-4 Antagonists Incorporating An Achiral Asp-Pro Mimetic Bioorg. Med. Chem. Lett. 2000, 10, 1171-1173.
22. Fotouhi, N.; Joshi, P.; Tilley, J. W.; Rowan, K.; Schwinge, V.; Wolitzky, B. Cyclic thioether peptide mimetics as VCAM-VLA-4 antagonists. Bioorg. Med. Chem. Lett. 2000, 10: 1167-1169.
23. Chen, L.; Fotouhi, N.; Jackson, D. Y.; Tilley, J. W. Preparation of 5,10-diaza-6,11-dioxo-1,2-dithiacyclotridecane-4-carboxylic acids and analogs as antiinflammatory agents. World Patent, WO 0063234, 2000
24. Tilley, J. W.; Chen, L.i; Fry, D. C.; Emerson, S. D.; Powers, G. D.; Biondi, D.; Varnell, T.; Trilles, R.; Guthrie, R.; Mennona, F.; Kaplan, G.; LeMahieu, R. A.; Carson, M.; Han, R.-J.; Liu, C.-M.; Palermo, R.; Ju, G. Identification of a Small Molecule Inhibitor of the IL-2/IL-2R Receptor Interaction Which Binds to IL-2. J. Am. Chem. Soc. 1997, 119, 7589-7590.
25. Chen, L.; Tilley, J. W.; Huang, T.-N.; Miklowski, D.; Trilles, R.; Guthrie, R.W.; Luk, K.; Hanglow, A.; Rowan, K.; Schwinge, V.; Wolitzky, B. N-acyl phenylalanine analogues as potent small molecule VLA-4 antagonists. Bioorg. Med. Chem. Lett. 2000, 10, 725-727.
26. Chen, L.; Tilley, J.; Trilles, R. V.; Yun, W.; Fry, D.; Cook, C.; Rowan, K.; Schwinge, V.; Campbell, R. N-Acyl-L-phenylalanine derivatives as potent VLA-4 antagonists that mimic a cyclic peptide conformation. Bioorg. Med. Chem. Lett., 2002, 12, 137-140.
27. Chen, L.; Tilley, J. W.; Guthrie, R. W.; Mennona, F.; Huang, T.-N.; Kaplan, G.; Trilles, R., Miklowski, D.; Huby, N.; Schwinge, V.; Wolitzky, B.; Rowan, K. N-Benzylpyroglutamyl-L-phenylalanine Derivatives as VCAM/VLA-4 antagonists. Bioorg. Med. Chem. Lett. 2000, 10, 729-733.
28. Burley, S. K.; Petsko, G. A. Aromatic-aromatic interaction: a mechanism of protein structure stabilization. Burley, S. K.; Petsko, G. A. Science 1985, 229, 23-8.
29. Burley, S. K. The structure of an antisickling agent, N-phenylacetyl-L-phenylalanine monohydrate. Acta Crystal. 1987, 43, 1316-1318.
30. Chen, L.; Trilles, R.; Miklowski, D.; Huang, T.-N.; Fry, D.; Campbell, R.; Rowan, K.; Schwinge, V.; Tilley, J. W. Focused library approach for identification of new N-acylphenylalanines as VCAM/VLA-4 antagonists. Bioorg. Med. Chem. Lett., 2002, 12, in press.
31. Sidduri, A.; Tilley, J. W.; Lou, J. P.; Kaplan, G.; Mennona, F.; Campbell, R.; Huang, T.-N.; Rowan, K.; Schwinge, V.; Renzetti, L. Bioorg. Med. Chem. Lett.. 2002, 12, in press
32. Sidduri, A.; Tilley, J. W.; Lou, J. P.; Chen, L.; Kaplan, G.; Mennona, F.; Campbell, R.; Guthrie, R. W.; Rowan, K.; Schwinge, V.; Renzetti, L. M. Bioorg. Med. Chem. Lett. 2002, 12, in press
33. Tilley, J. W. VLA-4 Antagonists Exp. Opin. Therapeutic Patents, 2002, in press
34. Armour, D. R.; Brown, D.; Congreave, M. S.; Gore, P. M.; Green, D. V. S.; Holman, S.; Jack, T. I. M.; Keeling, S. P.; Mason, A. M.; Morriss, K.; Ramsden, N. G.; Ward, P. Preparation of peptides useful in the treatment of inflammatory diseases. WO 0037444, 2000.