Oxidases and oxygenases in regulation of vascular nitric oxide signaling and inflammatory responses

Immunologic Research

Volumn 26, Issue 1-3, 2002, Pages 107-118

  Aslan, Mutay ^a   Freeman, Bruce A ^b  

^a UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

^b UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

Author keywords

Endothelial nitric oxide synthase; Hydrogen peroxide; Lipoxygenase; Myeloperoxidase; Nitric oxide; Peroxynitrite; Prostaglandin endoperoxide synthase; Superoxide; Xanthine oxidase

Indexed keywords

CYCLIC GMP; GUANYLATE CYCLASE; HEME; HYDROGEN PEROXIDE; LIPOXYGENASE; METALLOPROTEIN; MYELOPEROXIDASE; NITRIC OXIDE; OXIDOREDUCTASE; OXYGENASE; PEROXYNITRITE; PROSTAGLANDIN SYNTHASE; REACTIVE OXYGEN METABOLITE; XANTHINE OXIDASE;

ARTICLE; CELL ADHESION; INFLAMMATION; LUNG ALVEOLUS EPITHELIUM; MACROPHAGE; NERVE CELL; NEUTROPHIL; NONHUMAN; PRIORITY JOURNAL; PROTEIN DOMAIN; SIGNAL TRANSDUCTION; SMOOTH MUSCLE FIBER; STEADY STATE; THROMBOCYTE; THROMBOCYTE AGGREGATION; VASCULAR ENDOTHELIUM;

ANIMALS; BLOOD VESSELS; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; INFLAMMATION; LIPOXYGENASE; MODELS, MOLECULAR; NITRIC OXIDE; OXIDOREDUCTASES; OXYGENASES; PEROXIDASE; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; REACTIVE OXYGEN SPECIES; SIGNAL TRANSDUCTION; XANTHINE OXIDASE;

EID: 0036394423     PISSN: 0257277X     EISSN: None     Source Type: Journal    
DOI: 10.1385/IR:26:1-3:107     Document Type: Article

References (96)

1. Alberts B, Bray D, Lewis J, Raff M, Roberts K, Watson JD: Molecular Biology of the Cell, 3rd ed. New York, Garland, 1994.
2. Stamler JS, Singel DJ, Loscalzo J: Biochemistry of nitric oxide and its redox-activated forms. Science 1992;258:1898-1902.
3. Moncada S, Higgs EA: Endogenous nitric oxide: physiology, pathology and clinical relevance. Eur J Clin Invest 1991;21:3 61-374.
4. Beckman JS, Beckman TW, Chen J, Marshall PA, Freeman BA: Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide. Proc Natl Acad Sci USA 1990;87:1620-1624.
5. Lepoivre M, Flaman JM, Henry Y: Early loss of the tyrosyl radical in ribonucleotide reductase of adenocarcinoma cells producing nitric oxide. J Biol Chem 1992;267:22,994-30,000.
6. Buettner GR, Jurkiewicz BA: Ascorbate free radical as a marker of oxidative stress: an EPR study. Free Radic Biol Med 1993;14:49-55.
7. Radi R, Beckman JS, Bush KM, Freeman BA: Peroxynitrite-induced membrane lipid peroxidation: the cytotoxic potential of superoxide and nitric oxide. Arch Biochem Biophys 1991;288:481-487.
8. Rubbo H, Radi R, Trujillo M, Telleri R, Kalyanaraman B, Barnes S, Kirk M, Freeman BA: Nitric oxide regulation of superoxide and peroxynitrite-dependent lipid peroxidation: formation of novel nitrogen-containing oxidized lipid derivatives. J Biol Chem 1994;269:26,066-26,075.
9. O'Donnell VB, Eisefich JP, Chumley PH, Jablonsky MJ, Krishna NR, Kirk M, Barnes S, Darley-Usmar VM, Freeman BA: Nitration of unsaturated fatty acids by nitric oxide-derived reactive nitrogen species peroxynitrite, nitrous acid, nitrogen dioxide, and nitronium ion. Chem Res Toxicol 1999;12:83-92.
10. Radi R, Denicola A, Freeman BA: Peroxynitrite reactions with carbon dioxide-bicarbonate. Methods Enzymol 1999;301:353-367.
11. Placer ZA, Cushman LL, Johnson BC: Estimation of product of lipid peroxidation (malonyl dialdehyde) in biochemical systems. Anal Biochem 1966;16:359-364.
12. O'Donnell VB, Chumley PH, Hogg N, Bloodsworth A, Darley-Usmar VM, Freeman BA: Nitric oxide inhibition of lipid peroxidation: kinetics of reaction with lipid peroxyl radicals and comparison with alpha-tocopherol. Biochemistry 1997;36:15,216-15,223.
13. Tan S, McAdams M, Royall J, Freeman BA, Parks DA: Endothelial injury from a circulating mediator following rat liver ischemia. Free Radic Biol Med 1998;24:427-434.
14. Enroth C, Eger BT, Okamoto K, Nishino T, Nishino T, Pai EF: Crystal structures of bovine milk xanthine dehydrogenase and xanthine oxidase: structure-based mechanism of conversion. Proc Natl Acad Sci USA 2000;97:10,723-10,728.
15. Nagano T, Fridovich I: Superoxide radical from xanthine oxidase acting upon lumazine. J Free Radic Biol Med 1985;1:39-42.
16. Fridovich I: Quantitative aspects of the production of superoxide anion radical by milk xanthine oxidase. J Biol Chem 1970;245:4053-4057.
17. McCord JM, Fridovich I: The reduction of cytochrome c by milk xanthine oxidase. J Biol Chem 1968;243:5753-5760.
18. Tan S, Gelman S, Wheat JK, Parks DA: Circulating xanthine oxidase in human ischemia reperfusion. South Med J 1995;88:479-482.
19. Amaya Y, Yamazaki K, Sato M, Noda K, Nishino T, Nishino T. Proteolytic conversion of xanthine dehydrogenase from the NAD-dependent type to the O2-dependent type: amino acid sequence of rat liver xanthine dehydrogenase and identification of the cleavage sites of the enzyme protein during irreversible conversion by trypsin. J Biol Chem 1990;265:14,170-14,175.
20. Engerson TD, McKelvey TG, Rhyne DB, Boggio EB, Snyder SJ, Jones HP: Conversion of xanthine dehydrogenase to oxidase in ischemic rat tissues. J Clin Invest 1987;79:1564-1570.
21. Kooij A: A re-evaluation of the tissue distribution and physiology of xanthine oxidoreductase. Histochem J 1994;26:889-915.
22. Giler S, Sperling O, Brosh S, Urca I, De Vries A: Proceedings: serum xanthine oxidase in hepatocellular damage. Isr J Med Sci 1975;11:1225.
23. Giler S, Sperling O, Brosh S, Urca I, De Vries A: Serum xanthine oxidase in jaundice. Clin Chim Acta 1975;63:37-40.
24. Parks DA, Granger DN: Ischemia-induced vascular changes: role of xanthine oxidase and hydroxyl radicals. Am J Physiol 1983;245: G285-G289.
25. Mohacsi A, Kozlovszky B, Kiss I, Seres I, Fulop T Jr: Neutrophils obtained from obliterative atherosclerotic patients exhibit enhanced resting respiratory burst and increased degranulation in response to various stimuli. Biochim Biophys Acta 1996;1316:210-216.
26. Quinlan GJ, Lamb NJ, Tilley R, Evans TW, Gutteridge JM: Plasma hypoxanthine levels in ARDS: implications for oxidative stress, morbidity, and mortality. Am J Respir Crit Care Med 1997;155:479-484.
27. Aslan M, Ryan TM, Adler B, Townes TM, Parks DA, Thompson JA, Tousson A, Gladwin MT, Patel RP, Tarpey MM, Batinic-Haberle I, White CR, Freeman BA: Oxygen radical inhibition of nitric oxide-dependent vascular function in sickle cell disease. Proc Natl Acad Sci USA 2001;98:15,215-15,220.
28. Houston M, Estevez A, Chumley P, Aslan M, Marklund S, Parks DA, Freeman BA: Binding of xanthine oxidase to vascular endothelium: kinetic characterization and oxidative impairment of nitric oxide-dependent signaling. J Biol Chem 1999;274:4985-4994.
29. Radi R, Rubbo H, Bush K, Freeman BA: Xanthine oxidase binding to glycosaminoglycans: kinetics and superoxide dismutase interactions of immobilized xanthine oxidase-heparin complexes. Arch Biochem Biophys 1997;339:125-135.
30. Paler-Martinez A, Panus PC, Chumley PH, Ryan U, Hardy MM, Freeman BA: Endogenous xanthine oxidase does not significantly contribute to vascular endothelial production of reactive oxygen species. Arch Biochem Biophys 1994;311:79-85.
31. Villa LM, Salas E, Darley-Usmar VM, Radomski MW, Moncada S: Peroxynitrite induces both vasodilatation and impaired vascular relaxation in the isolated perfused rat heart. Proc Natl Acad Sci USA 1994;91:12,383-12,387.
32. Cardillo C, Kilcoyne CM, Cannon RO 3rd, Quyyumi AA, Panza JA: Xanthine oxidase inhibition with oxypurinol improves endothelial vasodilator function in hypercholesterolemic but not in hypertensive patients. Hypertension 1997;30:57-63.
33. White CR, Darley-Usmar V, Berrington WR, McAdams M, Gore JZ, Thompson JA, Parks DA, Tarpey MM, Freeman BA: Circulating plasma xanthine oxidase contributes to vascular dysfunction in hypercholesterolemic rabbits. Proc Natl Acad Sci USA 1996;93:8745-8749.
34. White CR, Brock TA, Chang LY, Crapo J, Briscoe P, Ku D, Bradley WA, Gianturco SH, Gore J, Freeman BA, Tarpey MM: Superoxide and peroxynitrite in atherosclerosis. Proc Natl Acad Sci USA 1994;91:1044-1048.
35. Butler R, Morris AD, Belch JJ, Hill A, Struthers AD: Allopurinol normalizes endothelial dysfunction in type 2 diabetics with mild hypertension. Hypertension 2000;35:746-751.
36. Fiedler TJ, Davey CA, Fenna RE: X-ray crystal structure and characterization of halide-binding sites of human myeloperoxidase at 1.8 A resolution. J Biol Chem 2000;275:11,964-11,971.
37. Harrison JE, Schultz J: Studies on the chlorinating activity of myeloperoxidase. J Biol Chem 1976;251:1371-1374.
38. Abu-Soud HM, Hazen SL: Nitric oxide modulates the catalytic activity of myeloperoxidase. J Biol Chem 2000;275:5425-5430.
39. Marquez LA, Dunford HB: Kinetics of oxidation of tyrosine and dityrosine by myeloperoxidase compounds I and II: implications for lipoprotein peroxidation studies. J Biol Chem 1995;270:30,434-30,440.
40. Hsuanyu Y, Dunford HB: Oxidation of clozapine and ascorbate by myeloperoxidase. Arch Biochem Biophys 1999;368:413-420.
41. Eiserich JP, Butler J, van der Vliet A, Cross CE, Halliwell B: Nitric oxide rapidly scavenges tyrosine and tryptophan radicals. Biochem J 1995;310:745-749.
42. Shen K, DeLano FA, Zweifach BW, Schmid-Schonbein GW: Circulating leukocyte counts, activation, and degranulation in Dahl hypertensive rats. Circ Res 1995;76:276-283.
43. Biasucci LM, D'Onofrio G, Liuzzo G, Zini G, Monaco C, Caligiuri G, Tommasi M, Rebuzzi AG, Maseri A: Intracellular neutrophil myeloperoxidase is reduced in unstable angina and acute myocardial infarction, but its reduction is not related to ischemia. J Am Coll Cardiol 1996;27:611-616.
44. Baldus S, Eiserich JP, Mani A, Castro L, Figueroa M, Chumley P, Ma W, Tousson A, White CR, Bullard DC, Brennan ML, Lusis AJ, Moore KP, Freeman BA: Endothelial transcytosis of myeloperoxidase confers specificity to vascular ECM proteins as targets of tyrosine nitration. J Clin Invest 2001;108:1759-1770.
45. Peng HB, Rajavashisth TB, Libby P, Liao JK: Nitric oxide inhibits macrophage-colony stimulating factor gene transcription in vascular endothelial cells. J Biol Chem 1995;270:17,050-17,055.
46. Khan BV, Harrison DG, Olbrych MT, Alexander RW, Medford RM: Nitric oxide regulates vascular cell adhesion molecule I gene expression and redox-sensitive transcriptional events in human vascular endothelial cells. Proc Natl Acad Sci USA 1996;93:9114-9119.
47. De Caterina R, Libby P, Peng HB, Thannickal VJ. Rajavashisth TB, Gimbrone MA Jr, Shin WS, Liao JK: Nitric oxide decreases cytokine-induced endothelial activation: nitric oxide selectively reduces endothelial expression of adhesion molecules and proinflammatory cytokines. J Clin Invest 1995;96:60-68.
48. Shin WS, Hong YH, Peng HB, De Caterina R, Libby P, Liao JK: Nitric oxide attenuates vascular smooth muscle cell activation by interferon-gamma: the role of constitutive NF-kappa B activity. J Biol Chem 1996;271:11,317-11,324.
49. Vane JR: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol 1971;231:232-235.
50. Hirabayashi T, Shimizu T: Localization and regulation of cytosolic phospholipaseA(2). Biochim Biophys Acta 2000;1488:124-138.
51. Funk CD: Prostaglandins and leukotrienes: advances in eicosanoid biology. Science 2001;294:1871-1875.
52. Malkowski MG, Ginell SL, Smith WL, Garavito RM: The productive conformation of arachidonic acid bound to prostaglandin synthase. Science 2000;289:1933-1937.
53. Picot D, Loll PJ, Garavito RM: The X-ray crystal structure of the membrane protein prostaglandin H2 synthase-1. Nature 1994;367:243-249.
54. Smith WL, DeWitt DL, Garavito RM: Cyclooxygenases: structural, cellular, and molecular biology. Annu Rev Biochem 2000;69:145-182.
55. Mayes PA: Metabolism of unsaturated fatty acids and eicosanoids; in Harper's Biochemistry, 24th ed. Stamford, CT, Appleton & Lange, 1996, pp 236-244.
56. Marnett LJ, Rowlinson SW, Goodwin DC, Kalgutkar AS, Lanzo CA: Arachidonic acid oxygenation by COX-1 and COX-2: mechanisms of catalysis and inhibition. J Biol Chem 1999;274:22,903-22,906.
57. Shimokawa T, Kulmacz RJ, DeWitt DL, Smith WL: Tyrosine 385 of prostaglandin endoperoxide synthase is required for cyclooxygenase catalysis. J Biol Chem 1990;265:20,073-20,076.
58. Thuresson ED, Lakkides KM, Smith WL: Different catalytically competent arrangements of arachidonic acid within the cyclooxygenase active site of prostaglandin endoperoxide H synthase-1 lead to the formation of different oxygenated products. J Biol Chem 2000;275:8501-8507.
59. Dietz R, Nastainczyk W, Ruf HH: Higher oxidation states of prostaglandin H synthase: rapid electronic spectroscopy detected two spectral intermediates during the peroxidase reaction with prostaglandin G2. Eur J Biochem 1988;171:321-328.
60. Salvemini D, Seibert K, Masferrer JL, Misko TP, Currie MG, Needleman P: Endogenous nitric oxide enhances prostaglandin production in a model of renal inflammation. J Clin Invest 1994;93:1940-1947.
61. Salvemini D, Currie MG, Mollace V: Nitric oxide-mediated cyclooxygenase activation: a key event in the antiplatelet effects of nitrovasodilators. J Clin Invest 1996;97:2562-2568.
62. Motta AB, Gonzalez ET, Rudolph I, Gimeno MF: Regulation of prostaglandin production by nitric oxide in rat smooth muscle myometrial cells. Prostaglandins Leukot Essent Fatty Acids 1999;60:73-76.
63. Landino LM, Crews BC, Timmons MD, Morrow JD, Marnett LJ: Peroxynitrite, the coupling product of nitric oxide and superoxide, activates prostaglandin biosynthesis. Proc Natl Acad Sci USA 1996;93:15,069-15,074.
64. O'Donnell VB, Coles B, Lewis MJ, Crews BC, Marnett LJ, Freeman BA: Catalytic consumption of nitric oxide by prostaglandin H synthase-1 regulates platelet function. J Biol Chem 2000;275:38,239-38,244.
65. Vane JR, Mitchell JA, Appleton I, Tomlinson A, Bishop-Bailey D, Croxtall J, Willoughby DA: Inducible isoforms of cyclooxygenase and nitric-oxide synthase in inflammation. Proc Natl Acad Sci USA 1994;91:2046-2050.
66. Draheim JE, Carroll RT, McNemar TB, Dunham WR, Sands RH, Funk MO Jr: Lipoxygenase isoenzymes: a spectroscopic and structural characterization of soybean seed enzymes. Arch Biochem Biophys 1989;269:208-218.
67. Ford-Hutchinson AW: Regulation of leukotriene biosynthesis. Cancer Metastasis Rev 1994;13:257-267.
68. Slappendel S, Veldink GA, Vliegenthart JF, Aasa R, Malmstrom BG: EPR spectroscopy of soybean lipoxygenase-1: description and quantification of the highspin fe(III) signals. Biochim Biophys Acta 1981;667:77-86.
69. Gan QF, Browner MF, Sloane DL, Sigal E: Defining the arachidonic acid binding site of human 15-lipoxygenase: molecular modeling and mutagenesis. J Biol Chem 1996;271:25,412-25,418.
70. Nakatsuka M, Osawa Y: Selective inhibition of the 12-lipoxygenase pathway of arachidonic acid metabolism by L-arginine or sodium nitroprusside in intact human platelets. Biochem Biophys Res Commun 1994;200:1630-1634.
71. Holzhutter HG, Wiesner R, Rathmann J, Stosser R, Kuhn H: A kinetic model for the interaction of nitric oxide with a mammalian lipoxygenase. Eur J Biochem 1997;245:608-616.
72. Wiesner R, Rathmann J, Holzhutter HG, Stosser R, Mader K, Nolting H, Kuhn H: Nitric oxide oxidises a ferrous mammalian lipoxygenase to a pre-activated ferric species. FEBS Lett 1996;389:229-232.
73. Radi R: Reactions of nitric oxide with metalloproteins. Chem Res Toxicol 1996;9:828-835.
74. O'Donnell VB, Taylor KB, Parthasarathy S, Kuhn H, Koesling D, Friebe A, Bloodsworth A, Darley-Usmar VM, Freeman BA: 15-Lipoxygenase catalytically consumes nitric oxide and impairs activation of guanylate cyclase. J Biol Chem 1999;274:20,083-20,091.
75. Bylund J, Kunz T, Valmsen K, Oliw EH: Cytochromes P450 with bisallylic hydroxylation activity on arachidonic and linoleic acids studied with human recombinant enzymes and with human and rat liver microsomes. J Pharmacol Exp Ther 1998;284:51-60.
76. van Leyen K, Duvoisin RM, Engelhardt H, Wiedmann M: A function for lipoxygenase in programmed organelle degradation. Nature 1998;395:392-395.
77. Kuhn H, Chan L: The role of 15-lipoxygenasein atherogenesis: pro- and antiatherogenic actions. Curr Opin Lipidol 1997;8:111-117.
78. Sendobry SM, Cornicelli JA, Welch K, Bocan T, Tait B, Trivedi BK, Colbry N, Dyer RD, Feinmark SJ, Daugherty A: Attenuation of diet-induced atherosclerosis in rabbits with a highly selective 15-lipoxygenase inhibitor lacking significant antioxidant properties. Br J Pharmacol 1997;120:1199-1206.
79. Oliw EH: Oxygenation of polyunsaturated fatty acids by cytochrome P450 monooxygenases. Prog Lipid Res 1994;33:329-354.
80. Judd AM, Spangelo BL, Ehreth JT, MacLeod RM: A possible role for lipoxygenase and epoxygenase arachidonate metabolites in prolactin release from pituitary cells. Neuroendocrinology 1988;48:407-416.
81. Oyekan AO, McGiff JC, Quilley J: Cytochrome P-450-dependent vasodilation of rat kidney by arachidonic acid. Am J Physiol 1991;261:H714-H719.
82. Fitzpatrick FA, Murphy RC. Cytochrome P-450 metabolism of arachidonic acid: formation and biological actions of "epoxygenase"-derived eicosanoids. Pharmacol Rev 1988;40:229-241.
83. Harder DR, Campbell WB, Roman RJ: Role of cytochrome P-450 enzymes and metabolites of arachidonic acid in the control of vasculartone. J Vasc Res 1995;32:79-92.
84. Negro-Vilar A, Snyder GD, Falck JR, Manna S, Chacos N, Capdevila J: Involvement of eicosanoids in release of oxytocin and vasopressin from the neural lobe of the rat pituitary. Endocrinology 1985;116:2663-2668.
85. Hildebrandt E, Albanesi JP, Falck JR, Campbell WB: Regulation of calcium influx and catecholamine secretion in chromaffin cells by a cytochrome P450 metabolite of arachidonic acid. J Lipid Res 1995;36:2599-2608.
86. Falck JR, Manna S, Moltz J, Chacos N, Capdevila J: Epoxyeicosatrienoic acids stimulate glucagon and insulin release from isolated rat pancreatic islets. Biochem Biophys Res Commun 1983;114:743-749.
87. Hu S, Kim HS: Activation of K+ channel in vascular smooth muscles by cytochrome P450 metabolites of arachidonic acid. Eur J Pharmacol 1993;230:215-221.
88. 2+ entry in human and bovine endothelial cells. J Physiol 1995;482:259-274.
89. Alonso-Galicia M, Sun CW, Falck JR, Harder DR, Roman RJ: Contribution of 20-HETE to the vasodilator actions of nitric oxide in renal arteries. Am J Physiol 1998;275:F370-F378.
90. Alonso-Galicia M, Hudetz AG, Shen H, Harder DR, Roman RJ: Contribution of 20-HETE to vasodilator actions of nitric oxide in the cerebral microcirculation. Stroke 1999;30:2727-2734.
91. Radi R: Reactions of nitric oxide with metalloproteins. Chem Res Toxicol 1996;9:828-835.
92. Cleeter MW, Cooper JM, Darley-Usmar VM, Moncada S, Schapira AH: Reversible inhibition of cytochrome c oxidase, the terminal enzyme of the mitochondrial respiratory chain, by nitric oxide: implications for neurodegenerative diseases. FEBS Lett 1994;345:50-54.
93. Abu-Soud HM, Wang J, Rousseau DL, Fukuto JM, Ignarro LJ, Stuehr DJ: Neuronal nitric oxide synthase self-inactivates by forming a ferrous-nitrosyl complex during aerobic catalysis. J Biol Chem 1995;270:22,997-23,006.
94. Drapier JC, Hibbs JB Jr: Differentiation of murine macrophages to express nonspecific cytotoxicity for tumor cells results in L-arginine-dependent inhibition of mitochondrial iron-sulfur enzymes in the macrophage effector cells. J Immunol 1988;140:2829-2838.
95. Wink DA, Osawa Y, Darbyshire JF, Jones CR, Eshenaur SC, Nims RW: Inhibition of cytochromes P450 by nitric oxide and a nitric oxide-releasing agent. Arch Biochem Biophys 1993;300:115-123.
96. Fenna R, Zeng J, Davey C: Structure of the green heme in myeloperoxidase. Arch Biochem Biophys 1995;316:653-656.