Pharmacological cross-reactivity between 5-lipoxygenase-activating protein, 5-lipoxygenase, and leukotriene C4 synthase

Canadian Journal of Physiology and Pharmacology

Volumn 75, Issue 10-11, 1997, Pages 1212-1219

  Gupta, Namrata ^a   Nicholson, Donald W ^b   Ford Hutchinson, Anthony W ^b  

^a MCGILL UNIVERSITY   (Canada)

^b MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

5 Lipopxygenase activating protein; 5 Lipoxygenase; Inhibitors; LTC4 synthase

Indexed keywords

ARACHIDONATE 5 LIPOXYGENASE; ARACHIDONATE 5 LIPOXYGENASE ACTIVATING PROTEIN; ENZYME INHIBITOR; INDOLE DERIVATIVE; L 691816; L 693283; L 695514; L 699333; L 702561; L 702640; LEUKOTRIENE; LEUKOTRIENE C4; LEUKOTRIENE C4 SYNTHASE; LEUKOTRIENE RECEPTOR; LIPOXYGENASE INHIBITOR; MEMBRANE PROTEIN; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; BIOSYNTHESIS; ENZYME BINDING; HUMAN; HUMAN CELL; MONOCYTE; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURE ACTIVITY RELATION;

ARACHIDONATE 5-LIPOXYGENASE; CARRIER PROTEINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENZYME ACTIVATION; GLUTATHIONE TRANSFERASE; HUMANS; LIPOXYGENASE INHIBITORS; MEMBRANE PROTEINS; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0031468552     PISSN: 00084212     EISSN: None     Source Type: Journal    
DOI: 10.1139/cjpp-75-10-11-1212     Document Type: Article

References (47)

1. Abramovitz, M., Wong, E., Cox, M.E., Richardson, C.D., Li, C., and Vickers, P.J. 1993. 5-Lipoxygenase activating protein stimulates the utilization of arachidonic acid by 5-lipoxygenase. Eur. J. Biochem. 215: 105-111.
2. Byrum, R.S., Goulet, J.L., Griffiths, R.J., and Koller, B.H. 1997. Role of 5-lipoxygenase-activating protein (FLAP) in murine acute inflammatory responses. J. Exp. Med. 185: 1065-1075.
3. Carrier, D.J., Bogri, T., Cosentino, G.P., Guse, I., Rakhit, S., and Singh, K. 1988. HPLC studies on leukotriene A4 obtained from the hydrolysis of its methyl ester. Prostaglandins Leukot. Essent. Fatty Acids, 34: 27-30.
4. Chung, K.F. 1995. Leukotriene receptor antagonists and biosynthesis inhibitors: potential breakthrough in asthma therapy. Eur. Respir. J. 8: 1203-1213.
5. Clark, J.D., Lin, L.L., Kriz, R.W., Ramesha, C.S., Sultzman, L.A., Lin, A.Y., Milona, N., and Knopf, J.L. 1991. A novel arachidonic acid-selective cytosolic PLA2 contains a Ca(2+)-dependent translocation domain with homology to PKC and GAP. Cell, 65: 1043-1051.
6. Delorme, D., Dube, D., Ducharme, Y., Fortin, R., Girard, Y., Hamel, P., Lepine, C., Scheigetz, J., and Therien, M. 1994. Synthesis of substituted lignans: inhibitors of the 5-lipoxygenase enzyme. Presented at Gordon Research Conference on Heterocyclic Compounds at New Hampton, N.H., July 10-15, 1994.
7. Dixon, R.A.F., Diehl, R.E., Opas, E., Rands, E., Vickers, P.J., Evans, J.F., Gillard, J.W., and Miller, D.K. 1990. Requirement of a 5-lipoxygenase-activating protein for leukotriene synthesis. Nature (London), 343: 282-284.
8. Falgueyret, J.P., Hutchinson, J.H., and Riendeau, D. 1993. Criteria for the identification of non-redox inhibitors of 5-lipoxygenase. Biochem. Pharmacol. 45: 978-981.
9. 4 in inflammation. Crit. Rev. Immunol. 10: 1-12.
10. Ford-Hutchinson, A.W. 1991. FLAP: a novel drug target for inhibiting the synthesis of leukotrienes. Trends Pharmacol. Sci. 12: 68-70.
11. Ford-Hutchinson, A.W., and Rodger, I.W. 1996. Receptor site blockers. In Therapeutic immunology. Edited by K.F. Austen, S.J. Burakoff, F.S. Rosen, and T.B. Stein. Blackwell Science Inc., Boston, Mass. pp. 132-151.
12. Gillard, J., Ford-Hutchinson, A.W., Chan, C., Charleson, S., Denis, D., Foster, A., Fortin, R., Leger, S., McFarlane, C.S., Morton, H. et al. 1989. L-663,536 (MK-886) (3-[1-(4-chlorobenzyl)-3-t-butyl-thio-5-isopropylindol-2-yl]-2,2- dimethylpropanoic acid), a novel, orally active leukotriene biosynthesis inhibitor. Can. Physiol. Pharmacol. 67: 456-464.
13. Hart, F.D. 1974. Clinical experience with aspirin and indomethacin in rheumatoid arthritis: potential significance of prostaglandins and their blockade. In Prostaglandin synthetase inhibitors. Their effects on physiological functions and pathological states. Edited by H.J. Robinson and J.R. Vane. Raven Press, New York. pp. 219-222.
14. Hughes, D.L., Bergan, J.J., Amato, J.S., Reider, P.J., and Grabowski, E.J.J. 1989. Synthesis of chiral dithioacetals: a chemoenzymic synthesis of a novel LTD4 antagonist. J. Org. Chem. 54: 1787-1788.
15. Hutchinson, J.H., Prasit, P., Choo, L.Y., Riendeau, D., Charleson, S., Evans, J.F., Piechuta, H., and Ball, R.G. 1992. Development of L-689,065, the prototype of a new class of potent 5-lipoxygenase inhibitors. Bioorg. Med. Chem. Lett. 2: 1699-1702.
16. Hutchinson, J.H., Riendeau, D., Brideau, C., Chan, C., Falgueyret, J.P., Guay, J., Jones, T.R., Lepine, C., Macdonald, D., McFarlane, C.S., Piechuta, H., Scheigetz, J., Tagari, P., Therien, M., and Girard, Y. 1994. Thiopyrano(2,3,4-c,d)indoles as 5-lipoxygenase inhibitors: synthesis, biological profile, and resolution of 2-(2-(1-(4-chlorobenzyl)-4-methyl-6-((5-phenylpyridin-2-yl)methoxy)-4,5-dihydro- 1H-thiopyrano(2,3,4-c,d)indol-2-yl)ethoxy)butanoic acid. J. Med. Chem. 37: 1153-1164.
17. Hutchinson, J.H., Charleson, S., Evans, J.F., Falgueyret, J.P., Hoogsteen, K., Jones, T.R., Kargman, S., Macdonald, D., McFarlane, C.S., Nicholson, D.W., Piechuta, H., Riendeau, D., Scheigetz, J., Therien, M., and Girard, Y. 1995. Thiopyranol[2,3,4-c,d]indoles as inhibitors of 5-lipoxygenase, 5-lipoxygenase-activating protein, and leukotriene C4 synthase. J. Med. Chem. 38: 4538-4547.
18. Jakobsson, P.-J., Mancini, J.A., and Ford-Hutchinson, A.W. 1996. Identification and characterization of a novel human microsomal glutathione S-transferase with leukotriene C4 synthase activity and significant sequence identity to 5-lipoxygenase-activating protein and leukotriene C4 synthase. J. Biol. Chem. 271: 22 203-22 210.
19. Lam, B.K., Penrose, J.F., Freeman, G.J., and Austen, K.F. 1994. Expression cloning of a cDNA for human leukotriene C4 synthase, an integral membrane protein conjugating reduced glutathione to leukotriene A4. Proc. Natl. Acad. Sci. U.S.A. 91: 7663-7667.
20. Lam, B.K., Penrose, J.F., Xu, K., Baldasaro, M.H., and Austen, K.F. 1997. Site-directed mutagenesis of human leukotriene C4 synthase. J. Biol. Chem. 272: 13 923-13 928.
21. Lau, C.K., Belanger, P.C., Scheigetz, J., Dufresne, C., Williams, H.W.R., Maycock, A.L., Guindon, Y., Bach, T., Dallob, A.L., Denis, D., Ford-Hutchinson, A.W., Gale, P.H., Hopple, S.L., Letts, G., Luell, S., McFarlane, C.S., MacIntyre, E., Meurer, R., Miller, D.K., Piechuta, H., Riendeau, D., Rokach, J., and Rouzer, C. 1989. Synthesis and structure-activity relationship of a novel class of 5-lipoxygenase inhibitors, 2-(phenylmethyl)-4 hydroxy-3,5-dialkylbenzofurans: the development of L-656,224. J. Med. Chem. 32: 1190-1197.
22. Lau, C.K., Belanger, P.C., Dufresne, C., Scheigetz, J., Therien, M., Fitzsimmons, B., Young, R.N., Ford-Hutchinson, A.W., Riendeau, D., Denis, D., Guay, J., Charleson, S., Piechuta, H., McFarlane, C.S., Chiu, S.-H.L., Eline, D., Alvaro, R.F., Miwa, G., and Walsh, J.L. 1992. Development of 2,3-dihydro-6-(3-phenoxypropyl)-2-(2-phenylethyl)-5-benzofuranol (L-670,630) as a potent and orally active inhibitor of 5-lipoxygenase. J. Med. Chem. 35: 1299-1318.
23. Lehmann, W.D. 1994. Regio- and stereochemistry of the dioxygenation reaction catalyzed by (5)-type lipoxygenases or by the cyclooxygenase activity of prostaglandin H synthases. Free Radical Biol. Med. 16: 241-253.
24. Lewis, R.A., Austen, K.F., and Soberman, R.J. 1990. Leukotrienes and other products of the 5-lipoxygenase pathway. Biochemistry and relation to pathobiology in human diseases. N. Engl. J. Med. 323: 645-655.
25. Liu, L., Cheng, H., Zhao, J., and Rogers, J.D. 1996. Stereoselective determination of montelukast and its S-enantiomer in human plasma using HPLC with column-switching. Pharm. Res. 13(9 Suppl.): S16.
26. Mancini, J.A., Abramovitz, M., Cox, M.E., Wong, E., Charleson, S., Perrier, H., Wang, Z., Prasit, P., and Vickers, P.J. 1993. 5-Lipoxygenase-activating protein is an arachidonate binding protein. FEBS Lett. 318: 277-281.
27. Miller, D.K., Gillard, J.W., Vickers, P.J., Sadowski, S., Leveille, C., Mancini, J.A., Charleson, P., Dixon, R.A.F., Ford-Hutchinson, A.W., Fortin, R., Gauthier, J.Y., Rodkey, J., Rosen, R., Rouzer, C., Sigal, I.S., Strader, C.D., and Evans, J.F. 1990. Identification and isolation of a membrane protein necessary for leukotriene production. Nature (London), 343: 278-281.
28. Nicholson, D.W., Ali, A., Klemba, M.W., Munday, N.A., Zamboni, R.J., and Ford-Hutchinson, A.W. 1992a. Human leukotriene C4 synthase expression in dimethyl sulfoxide-differentiated U937 cells. J. Biol. Chem. 267: 17 849-17 857.
29. Nicholson, D.W., Klemba, M., Rasper, D.M., Metters, K.M., Zamboni, R.J., and Ford-Hutchinson, A.W. 1992b. Purification of human leukotriene C4 synthase from dimethylsulfoxide-differentiated U937 cells. Eur. J. Biochem. 209: 725-734.
30. Nicholson, D.W., Ali, A., Vaillancourt, J.P., Calaycay, J.R., Mumford, R.A., Zamboni, R.J., and Ford-Hutchinson, A.W. 1993. Purification to homogeneity and the N-terminal sequence of human leukotriene C4 synthase: a homodimeric glutathione S-transferase composed of 18-kDa subunits. Proc. Natl. Acad. Sci. U.S.A. 90: 2015-2019.
31. Piper, P.J. 1984. Formation and actions of leukotrienes. Physiol. Rev. 64: 744-761.
32. Prasit, P., Belley, M., Evans, J.F., Gauthier, J.Y., Leveille, C., McFarlane, C.S., MacIntyre, E., Peterson, L., Piechuta, H., Therien, M., Young, R.N., and Zamboni, R. 1991. A new class of leukotriene biosynthesis inhibitors: the development of ((4-(4-chlorophenyl)-1-(4-(2-quinolinylmethoxy)phenyl)butyl)thio)-acetic acid, L-674,636. Bioorg. Med. Chem. Lett. 1: 645-648.
33. Prasit, P., Belley, M., Brideau, C., Chan, C., Charleson, S., Evans, J.F., Fortin, R., Ford-Hutchinson, A.W., Gillard, J.W., Guay, J., Hutchinson, J.H., Leger, S., Riendeau, D., Young, R.N., and Zamboni, R. 1992. A new class of leukotriene biosynthesis inhibitors: the discovery of MK0591. Bioorg. Med. Chem. Lett. 2: 1395-1398.
34. Rouzer, C.A., Ford-Hutchinson, A.W., Morton, H.E., and Gillard, J.W. 1990. MK886, a potent and specific leukotriene biosynthesis inhibitor blocks and reverses the membrane association of 5-lipoxygenase in ionophore-challenged leukocytes. J. Biol. Chem. 265: 1436-1442.
35. Samuelsson, B. 1983. Leukotrienes: mediators of immediate hypersensitivity reactions and inflammation. Science (Washington, D.C.), 220: 568-575.
36. Samuelsson, B. 1985. Leukotrienes and related compounds. Adv. Prostaglandin Thromboxane Leukot. Res. 15: 1-9.
37. Samuelsson, B., Dahlen, S.E., Lindgren, J.A., Rouzer, C.A., and Serhan, C.N. 1987. Leukotrienes and lipoxins: structures, biosynthesis, and biological effects. Science (Washington, D.C.), 237: 1171-1176.
38. Sharp, J.D., White, D.L., Chiou, X.G., Goodson, T., Gamboa, G.C., McClure, D., Burgett, S., Hoskins, J., Skatrud, P.L., Sportsman, J.R., Becker, G.W., Kang, L.H., Roberts, E.F., and Kramer, R.M. 1991. Molecular cloning and expression of human Ca(2+)-sensitive cytosolic phospholipase A2. J. Biol. Chem. 266: 14 850-14 853.
39. Shimuzu, T. 1988. Enzymes functional in the syntheses of leukotrienes and related compounds. Int. J. Biochem. 20: 661-666.
40. Taniguchi, Y., Tamura, G., Honma, M., Aizawa, T., Maruyama, N., Shirato, K., and Takishima, T. 1993. The effect of an oral leukotriene antagonist, ONO-1078, on allergen-induced immediate bronchoconstriction in asthmatic subjects. J. Allergy Clin. Immunol. 92: 507-512.
41. Tate, S.S., and Meister, A. 1978. Serine-borate complex as a transition-state inhibitor of gamma-glutamyl transpeptidase. Proc. Natl. Acad. Sci. U.S.A. 75: 4806-4809.
42. Vane, J.R. 1974. Mode of action of aspirin and similar compounds. Prostaglandin synthetase inhibitors. Their effects on physiological functions and states. Edited by H.J. Robinson and J.R. Vane. Raven Press, New York. pp. 219-222.
43. Vickers, P.J., Adam, M., Charleson, S., Coppolino, M.G., Evans, J.F., and Mancini, J.A. 1992. Identification of amino acid residues of 5-lipoxygenase-activating protein essential for the binding of leukotriene biosynthesis inhibitors. Mol. Pharmacol. 42: 94-102.
44. Vickers, P.J., Adam, M., Charleson, S., Abramovitz, M., O'Neill, G., and Mancini, J. A. 1993. Amino acid residues of 5-lipoxygenase-activating protein critical for the binding of leukotriene biosynthesis inhibitors. J. Lipid Mediat. 6: 31-42.
45. Welsch, D.J., Creely, D.P., Hauser, S.D., Mathis, K.J., Krivi, G.G., and Isakson, P.C. 1994. Molecular cloning and expression of human leukotriene-C4 synthase. Proc. Natl. Acad. Sci. U.S.A. 91: 9745-9749.
46. Young, R.N. 1989. Structural analysis of sulfido-peptide leukotrienes: application to the design of potent and specific antagonists of leukotriene D4. Adv. Prostaglandin Thromboxane Leukot. Res. 19: 643-646.
47. Zhao, D., Hughes, D.L., Bender, D.R., DeMarco, A.M., and Reider, P.J. 1991. Regioselective Fischer indole route to 3-unsubstituted indoles. J. Org. Chem. 56: 3001-3006.