The enzymology and pharmacology of 5-lipoxygenase and 5-lipoxygenase activating protein

Clinical Reviews in Allergy and Immunology

Volumn 17, Issue 1-2, 1999, Pages 91-109

  Bell, Randy L ^a   Harris, Richard R ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4,5,6 TETRAHYDRO 1 PHENYL 3(2H) PYRIDAZINONE; 2 (3 PYRIDYLMETHYL)INDAZOLINONE; 2 CYCLOPENTYL 2 [4 (2 QUINOLINYLMETHOXY)PHENYL]ACETIC ACID; 3 AMINO 1 (3 TRIFLUOROMETHYLPHENYL) 2 PYRAZOLINE; 3 [3 TERT BUTYLTHIO 1 (4 CHLOROBENZYL) 5 (2 QUINOLINYLMETHOXY) 2 INDOLYL] 2,2 DIMETHYLPROPIONIC ACID; 3 [3 TERT BUTYLTHIO 1 (4 CHLOROBENZYL) 5 ISOPROPYL 2 INDOLYL] 2,2 DIMETHYLPROPIONIC ACID; 6 [[3 FLUORO 5 (3,4,5,6 TETRAHYDRO 4 METHOXY 2H PYRAN 4 YL)]PHENOXYMETHYL] 1 METHYL 2 QUINOLONE; A 93178; ALPHA PENTYL 3 (2 QUINOLYLMETHOXY)BENZYL ALCOHOL; ARACHIDONATE 5 LIPOXYGENASE; ARACHIDONATE 5 LIPOXYGENASE ACTIVATING PROTEIN; ATRELEUTON; DOCEBENONE; L 697198; LEUKOTRIENE; LIPOXYGENASE INHIBITOR; N [3 (3 PHENOXYPHENYL)ALLYL]ACETOHYDROXAMIC ACID; NORDIHYDROGUAIARETIC ACID; PROTEIN; PROTEIN INHIBITOR; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; ZILEUTON;

ADULT RESPIRATORY DISTRESS SYNDROME; BIOSYNTHESIS; ENCEPHALITIS; ENTERITIS; ENZYME STRUCTURE; ENZYMOLOGY; FATTY ACID OXIDATION; INFLAMMATION; NEPHRITIS; PATHOPHYSIOLOGY; PNEUMONIA; PROTEIN EXPRESSION; PROTEIN STRUCTURE; REVIEW; RHEUMATOID ARTHRITIS; SKIN INFLAMMATION; STRUCTURE ANALYSIS;

EID: 0032776388     PISSN: 10800549     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02737599     Document Type: Review

References (111)

1. Kellaway C, Trethewie E. The liberation of a slow reacting growth muscle-stimulating substance in anaphylaxis. Q J Exp Physiol 1940;30:121-145.
2. Borgeat P, Samuelsson B. Transformation of arachidonic acid by rabbit polymorphonuclear leukocytes. J Biol Chem 1979;254(8):2643-2646.
3. Parker C. Lipid mediators produced through the lipoxygenase pathway. Ann Rev Immunol 1987;5:65-84.
4. Ford-Hutchinson A, Gresser M, Young R. 5-Lipoxygenase. Annu Rev Biochem 1994;63:383-417.
5. Samuelsson B, Funk C. Enzymes involved in the biosynthesis of leukotriene B4. J Biol Chem 1989;264 (33):19,469-19,472.
6. Fonteh A, Bass D, Marshall L, Seeds M, Samet J, Chilton F. Evidence that secretory phospholipase A2 plays a role in arachidonic acid release and eicosanoid biosynthesis by mast cells. J Immnol 1994;152:5438-5446.
7. Leslie C, Voelker D, JY C, Wall M, Zeliarney P. Properties and purification of an arachidonoyl-hydrolyzing phospholipose A2 from a macrophage cell line, RAW 264.7. Biochem Biophys Acta 1988;963:476-492.
8. 2. J Biol Chem 1994;269(4):2365-2368.
9. Neufeld E, Majerus P. Arachidonate release and phosphatidic acid turnover in stimulated human platelets. J Biol Chem 1983;258(4):2461-2467.
10. MacDonald J, Sprecher H. Phospholipid fatty acid remodeling in mammalian cells. Biochem Biophys Acta 1991;1084:105-121.
11. 4 synthase and 5-lipoxygenase activating protein. Proc NY Acad Sci 1994;744:78-83.
12. 4 hydrolase in human leukocytes. J Biol Chem 1984;259(20):12,339-12,345.
13. Serhan C. Lipoxin biosynthesis and its impact in inflammatory and vascular events. Biochim Biophys Acta 1994;1212:1-25.
14. Dixon R, Jones R, Diehl R, Bennett C, Kargman S, Rouzer C. Cloning of the cDNA for human 5-lipoxygenase. Proc Natl Acad Sci 1988;85:416-420.
15. Matsumoto T, Funk C, Radmark O, Houg J, Jornvall H, Samuelsson B. Molecular cloning and amino acid sequence of human 5-lipoxygenase. Proc Natl Acad Sci USA 1988;85:26-30.
16. Percival M. Human 5-lipoxygenase contains an essential iron. J Biol Chem 1991;266(16):10,058-10,061.
17. Riendeau D, Fakgucyret H, Guay J, Uedla N, Yamamoto S. Pseudoperoxidase activity of 5-lipoxygenase stimulated by potent benzofuranol and N-hydroxyurea inhibitors of the lipoxygenase reaction. Biochem J 1991;274:287-292.
18. 4. Biochem, 1994;269(4):2627-2631.
19. Gillmor S, Villasenor A, Fletterick R, Sigal E, Browner M. The structure of mammalian 15-lipoxygenase reveals similarity to the lipases and the determinants of substrate specificity. Nature Struct Biol 1997;4(12):1003-1009.
20. Solomon E, Zhou J, Neese F, Pavel E. New insights from spectroscopy into the structure/function relationships of lipoxygenases. J Chem Biol 1997;4:795-808.
21. Miller A, Allen B, Ziboh V. Lipoxygenase metabolism is required for interleukin-3 dependent proliferation and cell cycle progression of thre human M-07e cell line. J Cell Physiol 1997;170:309-315.
22. Mancini J, Abramovitz M, Cox M, Wong E, Charleson S, Perrier H, Wang Z, Prasit P, Vickers P. 5-lipoxygenase activating protein is an arachidonate binding protein. FEBS Letts 1993;318(3):277-281.
23. Vickers P, Adam M, Charleson S, Coppolino M, Evans J, Mancini J. Identification of amino acid residues of 5-lipoxygenase-activating protein essential for the binding of leukotriene biosynthesis inhibitors. Mol Pharmacol 1992;42:94-102.
24. Penrose JF, Baldasaro MH, Webster M, Xu K, Austen KF, Lam BK. Molecular cloning of the gene for mouse leukotriene-C4 synthase. Eur J Biochem 1997; 248(3):807-813.
25. Ponton A, Thirion J, Sirois P. Repression of the 5-lipoxygenase gene by c-myb overexpression in differentiated HL-60 cells. Prostaglandins 1997;53:49-58.
26. Kennedy B, Diehl R, Bole Y, Adam M, Dixon R. Gene characterization and promoter analysis of the human 5-lipoxygenase activation" protein (FLAP). J Biol Chem 1990;266(13):8511-8516.
27. Coffey M, Wllcoxen S, Peters-Golden. Increases in 5-Lipoxygenase activating protein expression account for enhanced capacity for 5-Lipoxygenase metabolism that accompanies differentiation of peripheral blood monocytes into alveolar macrophages. Am J Resp Cell Mol. Biol 1994;11:153-158.
28. 2 and 5-lipoxygenase. J Exp Med 1995;182:197-206.
29. Lepley R, Fitzpatrick F. 5-lipoxygenase contains a functional Src homology 3-binding motif that interacts with the Src homology 3 domain of Grb2 and cytoskeletal proteins. J Biol Chem 1994;269(39):24,163-24,168.
30. Lepley R, Fitzpatrick F. Inhibition of mitogen-activated protein kinase kinase blocks activation and redistribution of 5-Lipoxygenase in HL-60 cells. Arch Biochem Biophys 1996;331(1):141-144.
31. Brock T, McNish R, Peters-Golden M. Translocation and leukotriene synthetic capacity of nuclear 5-lipoxygenase in rat basophilic leukemia cells and alveolar macrophages. J Biol Chem 1996;270(37):21,652-21,658.
32. 2 to the nuclear fraction upon macrophage activation. BBRC 1993;196(1):147-153.
33. Woods J, Evans J, Ethier D, Scott S, Vickers P, Hearn L, Heibein J, Charleson S, Singer I. 5-lipoxygenase & 5-lipoxygenase-activating protein are localized in the nuclear envelope of activated human leukocytes. J Exp Med 1993;178:1935-1946.
34. 2 5-lipoxygenase, & 5-lipoxygenase-activating protein at the nuclear membrane of A23187-stimulated human neutrophils. Eur J Biochem 1996;238:250-258.
35. 4 secretion from normal murine mast cells by a probenecid-sensitive and multidrug resistance-associated protein-independent mechanism. J Immunol 1997;158:4916-4920.
36. 4 export pump in murine mastocytoma cells as a homolog of the multidrug-resistance protein. Eur J Biochem 1996;242:201-205.
37. Peters-Golden M, Feyssa A. Transcellular eicosanoid synthesis in cocultures of alveolar epithelial cells and macrophages. Am J Physiol 1993;264:L438-L447.
38. 4. Proc Natl Acad Sci USA 1985;82:6632-6636.
39. Bigby T, Meslier N. Transcellular lipoxygenase metabolism between monocytes and platelets. J Immunol 1989;143:1948-1954.
40. Bell R, Summers J, Harris R. Leukotriene modulators as therapeutic agents in asthma and other inflammatory diseases. Ann Rep Med Chem 1997;32:91-100.
41. DuBuske L, Grossman J, Dube L, Swanson L, Lancaster J. Randomized trial of zileuton in patients with moderate asthma: Effect of reduced dosing frequency and amounts on pulmonary function and asthma symptoms. Am J Man Care 1997;3:633-640.
42. Rosenberg MA, Torres MJ, Valencia A, Garcia JJ, Miranda A, Drajesk JF, Brandwein S, Lanni C, Blanca M. The effect of a 5-lipoxygenase (5 LO) inhibitor ABT-761 on inhaled house dust mite early asthmatic response. J Allergy Clin Immunol 1995;352.
43. Shuaib Nasser SM, Bell GS, Hawksworth RJ, Spruce KE, MacMillan R, Williams AJ, Lee TH, Arm JP. Effect of the 5-lipoxygenase inhibitor ZD2138 on allergen-induced early and late asthmatic responses. Thorax 1994;49:743-748.
44. Carter GW, Young PR, Albert DH, Elouska J, Dyer R, Bell RL, Summers JB, Brooks DW. 5-Lipoxygenase inhibitory activity of zileuton. J Pharmacol Exp Ther 1991;256:929-937.
45. Young PR, Bell RL, Lanni C, Summers JB, Brooks DW, Carter GW. Inhibition of leukotriene biosynthesis in the rat peritoneal cavity. Eur J Pharmacol 1991; 205:259-266.
46. Malo PE, Bell RL, Shaughnessy TK, Summers JB, Brooks DW, Carter GW. The 5-lipoxygenase inhibitory activity of zileuton in in vitro and in vivo models of antigen-induced airway anaphylaxis. Pulm Pharmacol 1994;7:73-79.
47. Goetzl EJ, Goldman DW, Naccache PH, Sha'afi RI, Pickett WC. Mediation of leukocyte components of inflammatory reactions by lipoxygenase products of arachidonic acid. Adv Prostaglandin Thromboxane Leukotriene Res, 1982; 9:273-282.
48. Namovic M, Walsh R, Goodfellow C, Harris R, Carter G, Bell R. Pharmacological modulation of eosinophil influx into the lungs of brown norway rats. Eur J Pharmacol 1996;315:81-88.
49. 4 production. J Cell Phys 1992;153:187-195.
50. Grimminger F, Kreusler B, Schneider IJ, Becker G, Seeger W. Influence of microvascular adherence on neutrophil leukotriene generation. J Immunol 1990;144(5):1866-1872.
51. Brady H, Serhan C. Adhesion promotes transcellular leukotriene biosynthesis during neutrophil-glomerular endothelial cell interactions: Inhibition by antibodies against CD18 and L selectin. BBRC 1992;186(3):1307-1314.
52. 4 activated human endothelial cells promote transendothelial neutrophil migration. J Leuko Biol 1997;62:203-209.
53. 4 induced hyperadhesiveness of endothelial cells for neutrophils. BBRC 1990;166(2):848-851.
54. Boot J, Kitchen E, Walker J, Harvey J, Dawson W. Directional movement of cells in vivo and in vitro under the influence of 5-lipoxygenase inhibitors. Br J Dermatol 1985;113(28):168-176.
55. Harris R, Komater V, Marett R, Wilcox D, Bell R. Effect of mast cell deficiency and leukotriene inhibition on the influx of eosinophils induced by eotaxin. J Leuko Biol 1997;62:688-691.
56. Nathan RA. Anti-leukotriene agents: A new direction in asthma therapy. J Asthma 1996;33(6):353-366.
57. Drazen JM, Austen FK. Leukotrienes and airway responses. Am Rev Resp Dis 1987;(136):985-998.
58. 4 synthase. Int Arch Allergy Immun 1995;107:19-24.
59. Dahlen S-E, Dahlen B, Ihre E, Kumlin M, Franzen L, Stensvad F, Larsson C, Bloomqvist H, Bjorck T, Zetterstrom O. The leukotriene biosynthesis inhibitor BAY x1005 is a potent inhibitor of allergen-induced airway obstruction and leukotriene formation in man. Am Rev Resp Dis 1993;147:A837.
60. Bisgaard H. Sulphidoleukotrienes in human allergic diseases. Dan Med Bull 1989;36(2):142-159.
61. Funayama T, Sekizawa K, Yamaya M, Yamauchi K, Ohno I, Ohrui T, Terajima M, Okinaga S, Sasaki H. Role of leukotriene-degrading enzymes in pulmonary response to antigen infusion in sensitized guinea pigs in vivo. Am J Respir Cell Mol Biol 1996;15(2):260-267.
62. Marom Z, Shelhamer J, Berger M, Frank M, Kaliner M. Anaphylatoxin C3a enhances mucous glycoprotein release from human airways in vitro. J Exp Med 1985;161(4):657-668.
63. 4 on mucociliary and respiratory function in allergic and nonallergic sheep. J Appl Physiol 1985;59(5):1416-1422.
64. Drazen JM, Austen KF, Lewis RA, Clark DA, Goto G, Marfat A, Corey EJ. Comparative airway and vascular activities of leukotrienes C and D in vivo and in vitro. Proc Natl Acad Sci USA 1980;77(7):4354-4358.
65. Ford Hutchinson A, Bray MA, Doig MV, Shipley ME, Smith MJ. Leukotriene B, a potent chemokinetic and aggregating substance released from polymorphonuclear leukocytes. Nature 1980;286(5770):264,265.
66. Bell RL, Harris RR, Malo PE, Bouska JB, Shaughnessy TK, Hulkower KI, Brooks CDW, Carter GW. ABT-761 Attenuates bronchoconstriction and pulmonary inflammation in rodents. J Pharmacol Exp Ther 1997;280:1366-1373.
67. Kusner E, Buckner C, Dea D, DeHaas IC, Marks R, Krell R. The 5-lipoxygenase inhibitors ZD2138 and ZM230487 are potent and selective inhibitors of several antigen-induced guinea-pig pulmonary responses. Eur J Pharmacol 1994;25; 7(3):285-292.
68. Tagari P, Becker A, Brideau C, Frenette R, Sadl V, Thomas E, Vickers P, Ford HA. Leukotriene generation and metabolism in dogs: Inhibition of biosynthesis by MK-0591. J Pharmacol Exp Ther 1993;265:416-425.
69. Nagai H, Takeda H, Uno T, Tanaka H, Matsuo A. Effect of a novel leukotoriene synthesis inhibitor, BAY x1005, on the antigen-and LPS-induced airway hyperresponsiveness in guinea pigs. Prostaglandins 1996;51(2):139-148.
70. Stenson WF. Role of eicosanoids as mediators of inflammation in inflammatory bowel disease. Scand J Gastroenterol Suppl 1990;172:3018.
71. 4 from activated neutrophils. Gut 1987;28(2):181-185.
72. Rask MJ, Bukhave K, Laursen LS, Lauritsen K. 5-Lipoxygenase inhibitors for the treatment of inflammatory bowel disease. Agents Actions 1992;C37.
73. 4 receptor antagonist, SC-41930, on acetic acid-induced colonic inflammation. Agents Actions 1989;27(3-4):395-397.
74. Zarif A, Eiznhamer D, Callaghan C, Doria M, Broutman L, Keshavarzian A. The effect of a selective 5-lipoxygenase inhibitor, zileuton, on tissue damage in acute colonic inflammations in rats. Inflammation 1996;20(3):217-227.
75. 4 receptor antagonist, SC 53228. Inflammation 1995;19(2):193-205.
76. Zingarelli B, Squadrito F, Graziani P, Camerini R, Caputi A. Effects of zileuton, a new 5-Lipoxygenase inhibitor, in experimentally induced colitis in rats. Agents Actions 1993;39(3-4):150-156.
77. Ikehata A, Hiwatashi N, Kinouchi Y, Yamazaki H, Ito K, Toyota T. Altered Leukotriene B4 metabolism in colonic mucosa with inflamrnratory bowel disease. Scand J Gastroenterol 1995;30(1):44-49.
78. Greaves MW, Camp RD. Prostaglandins, leukotrienes, phospholipase, platelet activating factor, and cytokines: An integrated approach to inflammation of human skin. Arch Dermatol Res 1988;280(Suppl):S33-S41.
79. Kragballe K, Voorhees JJ. Modulation of epidermal cell division and growth by oxygenation products of arachidonic acid. J Allergy Clin Immunol, 1984;74:426-429.
80. 4) in human skin. J Invest Dermatol 1983;80(2):115-119.
81. 4 and platelet activating factor in guinea pig passive cutaneous anaphylaxis. Eur J Pharmacol 1991;204(2):157-163.
82. Teixeria MM HPG. Effect of a 5-lipoxygnease inhibitor, ZM 230487, on cutaneous allergic inflammation in the skin. Br J Pharmacol 1994;111(4):1205-1211.
83. 4 production by peripheral blood neutrophils in rheumatoid arthritis. Scand J Rheumatol 1989;18(4):213-219.
84. Belch JJ. Eicosanoids and rheumatology: Inflammatory and vascular aspects. Prostaglandins Leukot Essent Fatty Acids 1989;36(4):219-234.
85. 4 plays a critical role in the progression of collagen-induced arthritis. Proc Natl Acad Sci USA 1995;92(2):517-521.
86. Griffiths R, Smith M, Roach M, Stock J, Stam E, Milici A, Scampoli D, Eskra J, Byrum R, Koller B, McNeish J. Collagen-induced arlhritis is reduced in 5-lipoxygenase-activating protein deficient mice. J Exp Med 1997;185(6):1123-1129.
87. Weinblatt ME, Kremer JM, Coblyn JS, Helfgott S, Maier AL, Petrillo G, Henson B, Rubin P, Sperling R. Zileuton, a 5-lipoxygenase inhibitor in rheumatoid arthritis. J Rheumatol 1992;19:1537-1541.
88. Lammers CHSP, Facchinetti P, ASrrang JM, Madamba SG, Siggins GR, Piomelli D. Arachidonic 5-lipoxygenase and its activating protein: Prominent hippocampal expression and role in somatostatin signaling. J Neurochem 1996; 66(1):147-152.
89. 4 alterations in rat forebrain ischemia and reperfusion and effects of AA-861, CV-3988. Acta Neurochir Suppl (Wien) 1994;60:296-299.
90. Leiflke E, Seregi A, Heldt R, Hertting G. In vivo comparative study of the seizure- and ischemia-induced synthesis of eicosanoids in the brain of gerbils. Arch Int Pharmacodyn Ther 1994;328(2):145-154.
91. Shohami E, Glantz L, Nates J, Feuerstein G. The mixed lipoxygenase/cyclooxygenase inhibitor SK&F 105809 reduces cerebral edema after closed head injury in rat. J Basic Clin Physiol Pharmacol 1992;3(2):99-107.
92. Petric R, Ford-Hutchinson A. Elevated cysteinyl leukotriene excretion in experimental glomerulonephritis. Kidney Int 1994;46(5):1322-1329.
93. 4 synthase: Characterization, partial purification and alterations in experimental glomerulonephritis. Biochem Biophys Acta 1995;1254(2):207-215.
94. Petric R, Ford-Hutchinson A. Inhibition of leukotriene biosynthesis improves renal function in experimental glomerulonephritis. J Lipid Mediat Cell Signal 1995;11(3):231-240.
95. Tanaka T, Kita T, Liu R, Tanaka N. Protective effect of peptide leukotriene antagonist on renal failure induced by a tourniquet in rabbits. Forensic Sci Int 1995;71(1):57-64.
96. Albrightson C, Short B, Dytko G, Zabko-Potapovich B, Brickson B, Adams J, Griswold D. Selective inhibition of 5-lipoxygenase attenuates glomerulonephritis in the rat. Kidney Int 1994;45(5):1301-1310.
97. Nassar G, Badr K. Role of leukotrienes and lipoxygenases in glomerular injury. Miner Electrolyte Metab 1995;21(4-5):262-270.
98. 4 and peptidoleukotrienes in the pathogenesis of allograft injury. J Immunol 1994;152(2):867-876.
99. Goldstein RE, Ezra D, Laurindo FR, Feuerstein GZ. Coronary and pulmonary vascular effects of leukotrienes and PAF-acether. Pharmacol Res Commun 1986;18(Suppl):151-162.
100. Bradley LM, Goldstein RE, Feuerstein G, Czaja JF. Circulatory effects of PAF-acether in newborn piglets. Am J Physiol 1989;256:H205-H212.
101. Bessin P. PAF-acether and leukotriene participation in acute circulatory shock. Pharmacol Res Commun 1986;18:51-59.
102. 4 in human neutrophils. Pharmacol Res Commun 1986;18:51-59.
103. 4-receptor antagonist in endotoxin shock: A prospective, controlled trial in a porcine model. Crit Care Med 1993;21(12):1825-1837.
104. Schutzer K, Larsson A, Risberg B, Falk A. Leukotriene receptor antagonism prevents lung protein leakage and hypoxaemia in a septic cat model. Eur Respir J 1994;7(6):1131-1137.
105. Ishizaka AHN, Sakamaki F, Tasaka S, Nakamura H, Kishikwas K, Yamada A, Obata T, Sayama K, Urano, T. Effects of ONO-1078, a peptide leukotriene antagonist, on endotoxin induced acute lung injury. Am J Repir Crit Care Med 1994;150:1325-1331.
106. Chen X, Sheller JR, Johnson EN, Funk CD. Role of leukotrienes revealed by targeted disruption of the 5-lipoxygenase gene. Nature 1994;372:179-182.
107. Goulet J, Snouwaert J, Latour A, Coffman T, Koller B. Altered inflammatory responses in leukotriene-deficient mice. Proc Natl Acad Sci USA 1994; 91(26):12,852-12,856.
108. Byrum R, Goulet J, Griffiths R, Koller B. Role of the 5-lipoxygenase-activation protein (FLAP) in murine acute inflammatory responses. J Exp Med 1997;185(6): 1065-1075.
109. Funk C, Chen X, Kurre U, Griffis G. Leukotriene-deficient mice generated by targeted disruption of the 5-lipoxygenase gene. Adv Prostaglandin Thromboxane Leukotriene Res 1995;23:145-150.
110. Irvin C, Tu Y, Sheller J, Funk C. 5-Lipoxygenase products are necessary for ovalbumin induced airway responsiveness in mice. Am J Physiol 1997;272(6 pt 1):L1053-L1058.
111. Bailie M, Standiford T, Laiachalk L, Coffey M, Stricter R, Peters-Golden M. Leukotriene deficient mice manifest enhanced lethality firom Klebsiella pneumonia in association with decreased alveolar macrophage phagocytic and bactericidal activities. J Immunol 1996;157:5221-5224.