The suppression of 5-lipoxygenation of arachidonic acid in human polymorphonuclear leucocytes by the 15-lipoxygenase product (15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid: Structure-activity relationship and mechanism of action

Biochemical Journal

Volumn 314, Issue 3, 1996, Pages 911-916

  Petrich, Karen ^a   Ludwig, Peter ^a   Kühn, Hartmut ^a   Schewe, Tankred ^a  

^a CHARITÉ UNIVERSITÄTSMEDIZIN BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

15 HYDROXYICOSATETRAENOIC ACID; ARACHIDONATE 15 LIPOXYGENASE; ARACHIDONIC ACID; CALCIMYCIN; CARBON 14; LEUKOTRIENE B4; LIPOXYGENASE INHIBITOR;

ARTICLE; ENZYME SUBSTRATE; HUMAN; HUMAN CELL; MALE; NEUTROPHIL; NORMAL HUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ARACHIDONATE 15-LIPOXYGENASE; ARACHIDONATE 5-LIPOXYGENASE; ARACHIDONIC ACID; CALCIMYCIN; FATTY ACIDS, UNSATURATED; HUMANS; HYDROXYEICOSATETRAENOIC ACIDS; KINETICS; LEUKOTRIENE B4; LIPOXYGENASE INHIBITORS; NEUTROPHILS; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 0029873358     PISSN: 02646021     EISSN: None     Source Type: Journal    
DOI: 10.1042/bj3140911     Document Type: Article

References (40)

1. Samuelsson, B., Dahlén, S.-E., Lindgren, J. A., Rouzer, C. A. and Serhan, C. N. (1987) Science 237, 1171-1176
2. Samuelsson, B. and Funk, C. D. (1989) J. Biol. Chem. 264, 19469-19472
3. Yamamoto, S. (1991) Free Radical Biol. Med. 10, 149-159
4. Winkler, J. D., Sung, C.-M., Hubbard, W. C. and Chilton, F. H. (1993) Biochem. J. 291, 825-831
5. Schatz-Munding, M., Hatzelmann, A. and Ullrich, V. (1991) Eur. J. Biochem. 197, 487-493
6. Wong, A., Cook, M. N., Foley, J. J., Sarau, H., Marshall, P. and Hwang, S. M. (1991) Biochemistry 30, 9346-9354
7. Woods, J. W., Evans, J. F., Ethier, D., Scott, S., Vickers, P. J., Hearn, L., Heibein, J. A., Charleson S., and Singer, I. I. (1993) J. Exp. Med. 178, 1935-1946
8. Hatzelmann, A., Schatz, M. and Ullrich, V. (1989) Eur. J. Biochem. 180, 527-533
9. Weitzel, F. and Wendel, A. (1993) J. Biol. Chem. 268, 6288-6292
10. McDonald, P. P., McColl, S. R., Naccache, P. H. and Borgeat, P. (1992) Br. J. Pharmacol 107, 226-232
11. Vanderhoek, J. Y., Bryant, R. W. and Bailey, J. M. (1980) J. Biol. Chem. 255, 10064-10065
12. Vanderhoek, J. Y., Karmin, M. T. and Ekberg, S.-L. (1985) J. Biol. Chem. 260, 15482-15487
13. Vanderhoek, J. Y., Wilhelmi, L. L., Ekberg, S.-L. and Karmin, M. T. (1990), Eicosanoids 3, 181-185
14. Salari, H., Braquet, P. and Borgeat, P. (1984) Prostaglandins Leukotrienes Med. 13, 53-60
15. Camp, R. D. R. and Fincham, N. J. (1985) Br. J. Pharmacol 85, 837-841
16. Chang, J., Skowronek, M. D. and Lewis, A. J. (1985) Inflammation 9, 395-504
17. Cashman, J. R., Lambert, C. and Sigal, E. (1988) Biochem. Biophys. Res. Commun.155, 38-44
18. Serhan, C. N. (1989) Biochim. Biophys. Acta 1004, 158-168
19. Iversen, L., Fogh, K., Bojesen, G. and Kragballe, K. (1991) Agents Actions 33, 286-291
20. Kang, L.-T. and Vanderhoek, I. Y. (1995) Biochim. Biophys. Acta 1256, 297-304
21. Böyum, A. (1968) Scand. J. Clin. Lab. Invest. 21, 77-89
22. Denis, D., Falgueyret, J.-P., Riendeau, D. and Abramovitz, M. (1991) J. Biol. Chem. 266, 5072-5079
23. Peers, K. E. and Coxon, D. T. (1983) Chem. Phys. Lipids 32, 49-56
24. Iacazio, G., Lagrand, G., Baratti, J., Bouno, G. and Triantaphylides, C. (1990) J. Org. Chem. 55, 1690-1691
25. Kühn, H., Wiesner, R., Lankin, V. Z., Nekrasov, A., Alder, L. and Schewe, T. (1987) Anal. Biochem. 160, 24-34
26. Kühn, H. and Wiesner, R. (1990) J. Chromatogr. 520, 391-401
27. Crawford, C. G., van Alpen, G. H. W., Cook, H. W. and Lands, W. E. M. (1978) Life Sci. 23, 1255-1262
28. Hurst, J. S., Flatman, S. and McDonald-Gibson, R. G. (1987) in Prostaglandins and Related Substances: A Practical Approach (Benedetto, C., McDonald-Gibson, R. G., Nigam, S. and Slater, T. F., eds.), pp. 53-73, IRL Press, Oxford and Washington, DC
29. Gibian, M. J. and Vandenberg, P. (1987) Anal. Biochem. 163, 343-349
30. van Os, C. P. A., Rijke-Schilder, G. P. M., van Halbeck, H., Verhagen, J. and Vliegenthart, J. F. G. (1981) Biochim. Biophys. Acta 663, 177-193
31. Holzhütter, H.-G. and Colosimo, A. (1990) Comput. Applic. Biosci. 6, 23-28
32. Wilkinson, D., Hallam, C., Helmsley, P. E., Lord, G. H. and Mitchell, P. D. (1985) Biochem. Soc. Trans. 13, 180-182
33. Chavis, C. M., Godard, P., dePaulet, A. C. and Damon, M. (1992) Eicosanoids 5, 203-211
34. Kühn, H., Wiesner, R., Stender, H., Schewe, T., Lankin, V. Z., Nekrasov, A. and Rapoport, S. M. (1986) FEBS Lett. 203, 247-252
35. Percival, M., D., Denis, D., Riendeau, D. and Gresser, M. J. (1992) Eur. J. Biochem. 210, 109-117
36. Haviv, F., Ratajczyk, I. D., DeNet, R. W., Martin, Y. C., Dyer, R. D. and Carter, G. W. (1987) J. Med. Chem. 30, 254-263
37. Ford-Hutchinson, A. W. (1991) Eicosanoids 4, 65-75
38. Schewe, T. and Kühn, H. (1991) Trends Biochem. Sci. 16, 369-373
39. Powell, W. S., Gravelle, F. and Gravel. S. (1992) J. Biol. Chem. 267, 19233-19241
40. Schwenk, U., Morita, E., Engel, R. and Schröder, J.-M. (1992) J. Biol. Chem. 267, 12482-12488