Synthesis and use of iodinated nonsteroidal antiinflammatory drug analogs as crystallographic probes of the prostaglandin H2 synthase cyclooxygenase active site

Biochemistry

Volumn 35, Issue 23, 1996, Pages 7330-7340

  Loll, Patrick J ^a   Picot, Daniel ^b   Ekabo, Opinya ^c   Garavito, R Michael ^c,d  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b INST DE BIOLOGIE PHYSICO CHIMIQUE   (France)

^c UNIVERSITY OF CHICAGO   (United States)

^d Michigan State University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLURBIPROFEN; INDOMETACIN; INDOMETACIN DERIVATIVE; IODOSUPROFEN; NONSTEROID ANTIINFLAMMATORY AGENT; PROSTAGLANDIN SYNTHASE; SUPROFEN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; DRUG PROTEIN BINDING; DRUG SYNTHESIS; ENZYME ACTIVE SITE; IODINATION; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; CYCLOOXYGENASE INHIBITORS; FLURBIPROFEN; INDOMETHACIN; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; PROTEIN STRUCTURE, SECONDARY; THIOPHENES;

EID: 0030010696     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi952776w     Document Type: Article

References (37)

1. Abdallah, M. A., Biellmann, J. F., Nordstrom. B., & Branden, C. I. (1975) Eur. J. Biochem. 50, 475-481.
2. Abdallah, M. A., Adams, M. J., Archibald, I. G., Biellmann, J. F., Helliwell, J. R., & Jenkins. S. E. (1979) Eur. J. Biochem. 98, 121-130.
3. Bhattacharyya, D. K., Lecomte, M., Rieke, C. J., Garavito, R. M., & Smith, W. L. (1996) J. Biol. Chem. 271, 2179-2184.
4. Brunger, A. T. (1992) X-PLOR Manual, Version 3.1. Yale University Press, New Haven, CT.
5. Collaborative Computational Project, No.4. (1994) Acta Crystallogr. D50, 760-763.
6. Evans, S. V. (1993) J. Mol. Graphics 11, 134-138.
7. Garavito, R. M., Picot, D., & Loll, P. J . (1994) Curr. Opin. Struct. Biol. 4, 529-535.
8. Garavito, R. M., Picot, D., & Loll, P. J. (1995) J. Biomembr. Bioenerg. 28, 13-27.
9. Gund, P., & Shen, T. Y. (1977) J. Med. Chem. 20, 1146-1152.
10. Herschman, H. R. (1994) Cancer Metastasis Rev. 13, 241-256.
11. Hla, T., Ristimäki, A., Appleby, S., & Barriocanal, J. G. (1993) Ann. N.Y. Acad. Sci. 696, 197-204.
12. Hoogsteen, K., & Trenner, N. R. (1970) J. Org. Chem. 35, 521-523.
13. Isakson, P., Seibert, K., Masferrer, J., Salvemini, D., Lee, L., & Needleman, P. (1995) Adv. Prostaglandin, Thromboxane, Leukotriene Res. 23, 49-54.
14. Kabsch, W. (1988) J. Appl. Crystallogr. 21, 916-924.
15. Kistenmacher. T. J., & Marsh, R. E. (1972) J. Am. Chem. Soc. 94, 1340-1345.
16. Kraulis, P. J. (1991) J. Appl. Crystallogr. 24, 946-950.
17. Kulmacz, R. J., & Lands, W. E. M. (1985) J. Biol. Chem. 260, 12572-12578.
18. Kulmacz, R. J., & Lands, W. E. M. (1987) in Prostaglandins and Related Substances, A Practical Approach (Benedetto, C, McDonald-Gibson, R. G., Nigam, S., & Slater, T. F., Eds.) pp 209-227, IRL Press, Washington, DC.
19. Loll, P. J., & Garavito, R. M. (1994) Exp. Opin. Invest. Drugs 3, 1171-1180.
20. Loll, P. J., Picot, D., & Garavito, R. M. (1995a) Nat. Struct. Biol. 2, 637-643.
21. Loll, P. J., Carrell, C. J., Carrell, H. L., & Garavito, R. M. (1995b) Acta Crystallogr. C (in press).
22. Mantri, P., & Witiak, D. T. (1994) Curr. Med. Chem. 1, 328-355.
23. Messerschmidt, A., & Pflugrath, J. W. (1987) J. Appl. Crystallogr. 20,306-315.
24. Mevkh, A. T., Sud'ina, G. F., Golub. N. B., & Varfolomeev, S. D. (1985) Anal. Biochem. 150, 91-96.
25. Morrison, J. F., & Walsh, C. T. (1988) Adv. Enzymol. 61, 201-300.
26. Nyburg, S. C., & Faerman, C. H. (1985) Acta Crystallogr. B41, 274-279.
27. Olsen, K. W., Garavito, R. M., Sabesan, M. N., & Rossmann, M. G. (1976) J. Mol. Biol. 107, 577-584.
28. Peelers, O. M., Blaton, N. M., & De Ranter, C. J. (1983) Bull. Soc. Chim. Belg. 92, 191-192.
29. Picot, D., Loll, P. J., & Garavito, R. M. (1994) Nature 367, 243-249.
30. Shen, T. Y. (1979) in Handbook of Experimental Pharmacology, Vol. 50/11: Anti-Inflammatory Drugs (Vane, J. R., & Ferreira, S. H., Eds.) pp. 316-347, Springer-Verlag, New York.
31. Singh, J., Thornton, J. M., Snarey, M., & Campbell, S. F. (1987) FEBS Lett. 224, 161-171.
32. Smith, W. L., & Marnett, L. J. (1994) in Metal Ions in Biological Systems (Sigal, H., & Sigal, A., Eds.) pp 163-199, Marcel Dekker, Inc., New York.
33. Smith, W. L., Meade, E. A., & DeWitt, D. L. (1994) Ann. N.Y. Acad. Sci. 744, 50-57.
34. Vane, J. R., & Botting, R. M. (1995) Adv. Prostaglandin, Thromboxane, Leukotriene Res. 23, 41-48.
35. Weitkamp, W. A., & Hamilton, C. S. (1937) J. Am. Chem. Soc. 59, 2699-2702.
36. Yamamoto, H. (1967) Chem. Pharm. Bull. 16, 17-19.
37. Yamamoto, H. (1968) J. Org. Chem. 32, 3693-3695.