Analogues of methotrexate in rheumatoid arthritis. 1. Effects of 10- deazaaminopterin analogues on type II collagen-induced arthritis in mice

Journal of Medicinal Chemistry

Volumn 40, Issue 3, 1997, Pages 370-376

  DeGraw, Joseph I ^a   Colwell, William T ^a   Crase, Jac ^a   Smith, R Lane ^b   Piper, James R ^c   Waud, William R ^c   Sirotnak, Francis M ^d  

^a SRI INTERNATIONAL   (United States)

^b STANFORD UNIVERSITY MEDICAL CENTER   (United States)

^c SOUTHERN RESEARCH INSTITUTE   (United States)

^d MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METHOTREXATE; METHOTREXATE DERIVATIVE; N [5 [1 [(2,4 DIAMINO 6 PTERIDINYL)METHYL]PROPYL] 2 THENOYL]GLUTAMIC ACID; N [5 [2 (2,4 DIAMINO 6 PTERIDINYL)ETHYL] 2 THENOYL]GLUTAMIC ACID; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; DRUG CONFORMATION; DRUG EFFECT; DRUG EFFICACY; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; RHEUMATOID ARTHRITIS; STRUCTURE ACTIVITY RELATION;

AMINOPTERIN; ANIMALS; ANTIRHEUMATIC AGENTS; ARTHRITIS, RHEUMATOID; CELL LINE; CELL SURVIVAL; COLLAGEN; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; METHOTREXATE; MICE; MOLECULAR STRUCTURE; TUMOR CELLS, CULTURED;

EID: 0031059696     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9505526     Document Type: Article

References (34)

1. Harris, E. D., Jr. Pathogenesis of rheumatoid arthritis. In Textbook of Rheumatology; Kelly, W. N., Harris, E. D., Jr., Ruddy, S., Sledge, C. B., Eds.; W. B. Saunders: Philadelphia, 1985.
2. Dinarello, C. A. Interleukin 1 and the pathogenesis of the acute-phase response. New Engl. J. Med. 1984, 311, 1413-1418.
3. Smith, R. L.; Schurman, D. J. Comparison of cartilage destruction between infectious and adjuvant arthritis. J. Orthop. Res. 1983, 1, 136-143.
4. (a) Gross, D.; Enderlin, M. Beitrag zur Behandlung der progredient chronischen Polyarthritis mit Antimetaboliten und Zytostatika. (Communication on the treatment of advanced chronic polyarthritis with antimetabolites and cytostatics.) Z. Rheumaforsch. 1967, 26, 26-35.
5. (b) Gross, D.; Enderlin, M.; Fehr, K. Die immunosuppressive Behandlung der progredient chronischen Polyarthritis mit antimetaboliten und Zytostatika. (The immunosuppressive treatment of advanced chronic polyarthritis with antimetabolites and cytostatics.) Schweiz Med. Wochenschr. 1967, 97, 1301-1307.
6. Csuka, M. E.; Carrera, G. F.; McCarty, D. J. Treatment of intractable rheumatoid arthritis with combined cyclophosphamide, azathioprine and hydroxychloroquine. A follow-up study. J. Am. Med. Assoc. 1986, 255, 2315-2319.
7. Bitter, T. Combined disease-modifying chemotherapy for intractable rheumatoid arthritis. Clin. Rheum. Dis. 1984, 10, 417-428.
8. Kremer, J. The changing face of therapy for rheumatoid arthritis. Rheum. Dis. Clin. North Am. 1995, 21, 845-852.
9. Weinblatt, M. E. The controlled trial experience of methotrexate in rheumatoid arthritis. In Methotrexate Therapy in Rheumatic Disease; Wilke, W. S., Ed.; Marcel Dekker: New York/Basel, 1989; pp 45-56.
10. Andersen, P. A.; West, S. G.; O'Dell, J. R.; Via, C. S.; Claypool, R. G.; Kotzin, B. L. Weekly pulse methotrexate in rheumatoid arthritis; Clinical and immunological effects in a randomized double-blind study. Ann. Intern. Med. 1985, 103, 489-496.
11. Weinblatt, M. E.; Coblyn, J. S.; Fox, D. A.; Fraser, P. A.; Holdsworth, D. E.; Glass, D. N.; Trentham, D. E. Efficacy of low dose methotrexate in rheumatoid arthritis. New. Engl. J. Med. 1985, 312, 818-822.
12. Williams, H. J.; Wilkens, R. F.; Samuelson, C. O., Jr.; Alarcon, G. S.; Guttadaura, M.; Yarboro, C.; Polisson, R. P.; Weiner, S. R.; Luggen, M. E.; Billingsley, L. M.; Dahl, S. L.; Egger, M. J.; Reading, J. C.; Ward, J. R. Comparison of low-dose oral pulse methotrexate and placebo in the treatment of rheumatoid arthritis: a controlled clinical trial. Arthritis Rheum. 1985, 28, 721-730.
13. Thompson, R. N.; Watts, C.; Edelman, J.; Esdaile, J.; Russel, A. S. A controlled two-center trial of parenteral methotrexate therapy for refractory rheumatoid arthritis. J. Rheumatol. 1984, 11, 760-763.
14. Kremer, J. M.; Galivan, J. Mechanisms of hepatic toxicity of methotrexate. See ref 8, pp 219-241.
15. Galivan, J.; Rehder, M. C.; Kerwar, S. Methotrexate in adjuvant arthritis. In Chemistry and Biology of Pteridines; Cooper, B. A., Whitehead, V. M., Eds.; DeGruyter: Berlin, 1986; pp 847-849.
16. Krumdieck, C. L.; Casteneda, O.; Alareon, G.; Koopman, W. J.; Nair, M. G. 10-Deazaaminopterin for treatment of rheumatoid arthritis. U.S. Patent 5,030,634, July 9, 1991.
17. Sirotnak, F. M.; DeGraw, J. I.; Moccio, D. M.; Dorick, D. M. Antitumor properties of a new folate analog, 10-deazaaminopterin, in mice. Cancer Treat. Rep. 1978, 62, 1047-1052.
18. DeGraw, J. I.; Brown, V. H.; Tagawa, H.; Kisliuk, R. L.; Gaumont, Y.; Sirotnak, F. M. Synthesis and antitumor activity of 10-alkyl-10-deazaaminopterins. A convenient synthesis of 10-deazaaminopterin. J. Med. Chem. 1982, 25, 1227-1230.
19. Baggott, J. E.; Morgan, S. L.; Freeberg, L. E.; Hudson, B. B.; Vaughn, W. H.; Nair, M. G.; Krumdieck, C. L.; Koopman, W. J.; Gay, R. E.; Gay, S. Long-term treatment of the MRL/lpr mouse with methotrexate and 10-deazaaminopterin. Agents Actions 1992, 35, 104-111.
20. DeGraw, J. I.; Colwell, W. T.; Piper, J. R.; Sirotnak, F. M. Synthesis and antitumor activity of 10-propargyl-10-deazaaminopterin. J. Med. Chem. 1993, 36, 2228-2231.
21. DeGraw, J. I.; Christie, P. H.; Brown, E. G.; Kelly, L. F.; Kisliuk, R. L.; Gaumont, Y.; Sirotnak, F. M. Synthesis and antifolate properties of 10-alkyl-8,10-dideazaaminopterins. J. Med. Chem. 1984, 27, 376-380.
22. Courtenay, J. S.; Dallman, M. J.; Dayan, A. D.; Martin, A.; Mosedale, B. Immunization against heterologous type II collagen induces arthritis in mice. Nature 1980, 283, 666-668.
23. Chang, R. S. Continuous subcultivation of epithelial-like cells from normal human tissues. Proc. Soc. Exptl. Biol. Med. 1954, 87, 440-443.
24. Wooley, P. H.; Luthra, H. S.; Griffiths, M. M.; Stuart, J. M.; Huse, A.; David, C. S. Type II collagen-induced arthritis in mice. 4. Variations in immunogenetic regulation provide evidence for multiple arthritogenic epitopes on the collagen molecule. J. Immunol. 1985, 135, 2443-2451.
25. Terato, K.; Hasty, K. A.; Cremer, M. A.; Stuart, J. M.; Townes, A. S.; Kang, A. H. Collagen induced arthritis in mice. Localization of an arthritogenic determinant to a fragment of the type-II collagen molecule. J. Exp. Med. 1985, 162, 637-646.
26. Watson, W. C.; Townes, A. S. Genetic susceptibility to murine collagen II autoimmune arthritis: Proposed relationship to the IgG2 auto antibody subclass response, complement C5, major histocompatibility complex and non-(MHC)loci. J. Exp. Med. 1985, 162, 1878-1891.
27. Stuart, J. M.; Townes, A. S.; Kang, A. H. Nature and specificity of the immune response to collagen in type II collagen induced arthritis in mice. J. Clin. Invest. 1982, 69, 673-683.
28. Dallman, M.; Fathman, C. G. Type II collagen-reactive T-cell clones from mice with collagen-induced arthritis. J. Immunol. 1985, 135, 1113-1118.
29. Wooley, P. H.; Luthra, H. S.; Lafuse, W. P.; Huse, A.; Stuart, J. M.; David, C. S. Type II collagen-induced arthritis in mice. III. Suppression of arthritis by using monoclonal and polyclonal anti-IA antisera. J. Immunol. 1985, 134, 2366-2374.
30. Weinblatt, M. E. Efficacy of methotrexate in rheumatoid arthritis. Br. J. Rheum. 1995, 34 (Suppl. 2), 43-48.
31. Flynn, J. A.; Hellmann, D. B. Methotrexate in rheumatoid arthritis: when NSAIDs fail. Cleveland Clin. J. Med. 1995, 62, 351-359.
32. Obtained from Chemodynamics Co., Garfield, NJ.
33. Desai, A.; Nair, M. G. Evaluation of the anti-arthritic activity and an alternate synthesis of a thiophene-substituted 10-deazaaminopterin. In Chemistry and Biology of Pteridines; Ayling, J., Nair, M. G., Baugh, C. M., Eds.; Plenum: New York, 1993; pp 425-428.
34. Skeith, K. J.; Romos-Remus, C.; Russell, A. S. Comparative efficacy and toxicity of 10-ethyl-10-deazaaminopterin and methotrexate in a mycobacterial rat arthritis model. J. Rheumatol. 1994, 21, 473-475.