Levuglandins and isolevuglandins: Stealthy toxins of oxidative injury

Antioxidants and Redox Signaling

Volumn 7, Issue 1-2, 2005, Pages 185-201

  Salomon, Robert G ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; APOLIPOPROTEIN B; ARACHIDONIC ACID; DNA; ENDOPEROXIDE; FREE RADICAL; ISOLEVUGLANDIN; ISOPROSTANOID; LEVUGLANDIN; LEVULINALDEHYDE; LIPOPROTEIN A; MYELOPEROXIDASE; NEUROTOXIN; NUCLEIC ACID; OXIDIZED LOW DENSITY LIPOPROTEIN; PEROXIDE; PHOSPHOLIPID; PHOSPHOLIPID ESTER; PROSTAGLANDIN DERIVATIVE; PROSTAGLANDIN H2; PROSTAGLANDIN SYNTHASE; PROSTANOID; PROTEIN; SCHIFF BASE; UNCLASSIFIED DRUG;

AEROBIC METABOLISM; ALZHEIMER DISEASE; AUTOIMMUNITY; BLOOD BRAIN BARRIER; CANDIDA ALBICANS; COVALENT BOND; ENDOCYTOSIS; HUMAN; HYDROLYSIS; IMMUNOASSAY; ISCHEMIC HEART DISEASE; KIDNEY DISEASE; LIPID OXIDATION; LIPID PEROXIDATION; MACROPHAGE; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; PROTEIN CROSS LINKING; PROTEIN DNA INTERACTION; PROTEIN LIPID INTERACTION; REVIEW; RHEUMATOID ARTHRITIS; SCLERODERMA; SEPSIS; SYSTEMIC LUPUS ERYTHEMATOSUS;

ADULT; AGED; ANIMALS; AUTOIMMUNITY; BRAIN; CHOLESTEROL; COHORT STUDIES; CROSS-LINKING REAGENTS; HUMANS; HYDROLYSIS; ISOPROSTANES; LIPID PEROXIDATION; MACROPHAGES; MIDDLE AGED; MODELS, CHEMICAL; OXIDATIVE STRESS; PEROXIDES; PHOSPHOLIPIDS; PROSTAGLANDIN H2; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; PROSTAGLANDINS E; REACTIVE OXYGEN SPECIES;

CANDIDA; CANDIDA ALBICANS; SCLERODERMA;

EID: 13244281555     PISSN: 15230864     EISSN: None     Source Type: Journal    
DOI: 10.1089/ars.2005.7.185     Document Type: Review

References (109)

1. Amara A, Constans J, Chaugier C, Sebban A, Dubourg L, Peuchant E, Pellegrin JL, Leng B, Conri C, and Geffard M. Autoantibodies to malondialdehyde-modified epitope in connective tissue diseases and vasculitides. Clin Exp Immunol 101: 233-238, 1995.
2. Anderson MW, Crutchley DJ, Chaudhari A, Wilson AG, and Eling TE. Studies on the covalent binding of an inter-mediate(s) in prostaglandin biosynthesis to tissue macromolecules. Biochim Biophys Acta 573: 40-50, 1979.
3. Anthony DC, Boekelheide K, Anderson CW, and Graham DG. The effect of 3,4-dimethyl substitution on the neurotoxicity of 2,5-hexanedione. 11. Dimethyl substitution accelerates pyrrole formation and protein crosslinking. Toxicol Appl Pharmacol 71: 372-382, 1983.
4. 2+ channels activated by chlorpromazine and free radicals in membrane of human atrial myocytes. J Mol Cell Cardiol 30: 2623-2636, 1998.
5. Aratani Y, Koyama H, Nyui S, Suzuki K, Kura F, and Maeda N. Severe impairment in early host defense against Candida albicans in mice deficient in myeloperoxidase. Infect Immun 67: 1828-1836, 1999.
6. Arsenault GP, Althaus JR, and Divekar PV. Structure of the antibiotic botryodiplodin - use of chemical ionization mass spectrometry in organic structure determination. J Chem Soc Chem Commun 1414-1415, 1969.
7. Basu S. Radioimmunoassay of 8-iso-prostaglandin F2alpha: an index for oxidative injury via free radical catalysed lipid peroxidation. Prostaglandins Leukot Essent Fatty Acids 58: 319-325, 1998.
8. Bazan NG. The metabolism of omega-3 polyunsaturated fatty acids in the eye: the possible role of docosahexaenoic acid and docosanoids in retinal physiology and ocular pathology. Prog Clin Biol Res 312: 95-112, 1989.
9. Bernoud-Hubac N, Davies SS, Boutaud O, Montine TJ, and Roberts LJ 2nd. Formation of highly reactive gamma-ketoaldehydes (neuroketals) as products of the neuroprostane pathway. J Biol Chem 276: 30964-30970, 2001.
10. 2 via the levuglandin pathway. Biochemistry 38: 9389-9396, 1999.
11. Boutaud O, Brame CJ, Chaurand P, Li J, Rowlinson SW, Crews BC, Ji C, Marnett LJ, Caprioli RM, Roberts LJ 2nd, and Oates JA. Characterization of the lysyl adducts of prostaglandin H-synthases that are derived from oxygenation of arachidonic acid. Biochemistry 40: 6948-6955, 2001.
12. Boutaud O, Ou JJ, Chaurand P, Caprioli RM, Montine TJ, and Oates JA. Prostaglandin H2 (PGH2) accelerates formation of amyloid beta 1-42 oligomers. J Neurochem 82: 1003-1006, 2002.
13. Boutaud O, Li J, Zagol I, Shipp EA, Davies SS, Roberts LJ 2nd, and Oates JA. Levuglandinyl adducts of proteins are formed via a prostaglandin H2 synthase-dependent pathway after platelet activation. J Biol Chem 278: 16926-16928, 2003.
14. Brame CJ, Salomon RG, Morrow JD, and Roberts LJ 2nd. Identification of extremely reactive γ- ketoaldehydes (isolevuglandins) as products of the isoprostane pathway and characterization of their lysyl protein adducts. J Biol Chem 274: 13139-13146, 1999.
15. Brame CJ, Boutaud O, Davies SS, Yang T, Oates JA, Roden D, and Roberts LJ 2nd. Modification of proteins by isoketal-containing oxidized phospholipids. J Biol Chem 279: 13447-13451, 2004.
16. Breitner JC, and Zandi PP. Do nonsteroidal antiinflammatory drugs reduce the risk of Alzheimer's disease? N Engl J Med 345: 1567-1568, 2001.
17. Corey EJ, Shih C, and Cashman JR. Docosahexaenoic acid is a strong inhibitor of prostaglandin but not leukotriene biosynthesis. Proc Natl Acad Sci USA 80: 3581-3584, 1983.
18. Crutchley DJ, Hawkins HJ, Eling TE, and Anderson MW. Covalent binding of prostaglandins G2 and H2 to components of ram seminal vesicle microsomal fraction. Biochem Pharmacol 28: 1519-1523, 1979.
19. Cvetkovic JT, Wallberg-Jonsson S, Ahmed E, Rantapaa-Dahlqvist S, and Lefvert AK. Increased levels of autoantibodies against copper-oxidized low density lipoprotein, malondialdehyde-modified low density lipoprotein and cardiolipin in patients with rheumatoid arthritis. Rheumatology (Oxford) 41: 988-995, 2002.
20. Dabbagh AJ, and Frei B. Human suction blister interstitial fluid prevents metal ion-dependent oxidation of low density lipoprotein by macrophages and in cell-free systems. J Clin Invest 96: 1958-1966, 1995.
21. Davies SS, Amarnath V, Montine KS, Bernoud-Hubac N, Boutaud O, Montine TJ, and Roberts LJ 2nd. Effects of reactive γ-ketoaldehydes formed by the isoprostane pathway (isoketals) and cyclooxygenase pathway (levuglandins) on proteasome function. FASEB J 16: 715-717, 2002.
22. DeCaprio AP, Olajos EJ, and Weber P. Covalent binding of a neurotoxic n-hexane metabolite: conversion of primary amines to substituted pyrrole adducts by 2,5- hexanedione. Toxicol Appl Pharmacol 65: 440-450, 1982.
23. Delanty N, Reilly MP, Pratico D, Lawson JA, McCarthy JF, Wood AE, Ohnishi ST, Fitzgerald DJ, and FitzGerald GA. 8-epi PGF2 alpha generation during coronary reperfusion. A potential quantitative marker of oxidant stress in vivo. Circulation 95: 2492-2499, 1997.
24. Diczfalusy U, Falardeau P, and Hammarstrom S. Conversion of prostaglandin endoperoxides to C17-hydroxy acids catalyzed by human platelet thromboxane synthase. FEBS Lett 84: 271-274, 1977.
25. DiFranco E, Subbanagounder G, Kim S, Murthi K, Taneda S, Monnier VM, and Salomon RG. Formation and stability of pyrrole adducts in the reaction of levuglandin E2 with proteins. Chem Res Toxicol 8: 61-67, 1995.
26. Dustin LB, Shea CM, Soberman RJ, and Lu CY. Docosahexaenoic acid, a constituent of rodent fetal serum and fish oil diets, inhibits acquisition of macrophage tumoricidal function. J Immunol 144: 4888-4897, 1990.
27. Fling TE, Wilson AG, Chaudhari A, and Anderson MW. Covalent binding of an intermediate(s) in prostaglandin biosynthesis to guinea pig lung microsomal protein. Life Sci 21: 245-251, 1977.
28. Fitzpatrick FA, and Gorman RR. Platelet rich plasma transforms exogenous prostaglandin endoperoxide H2 into thromboxane A2. Prostaglandins 14: 881-889, 1977.
29. Flower RJ, Cheung HS, and Cushman DW. Quantitative determination of prostaglandins and malondialdehyde formed by the arachidonate oxygenase (prostaglandin synthetase) system of bovine seminal vesicle. Prostaglandins 4: 325-341, 1973.
30. Floyd RA. Antioxidants, oxidative stress, and degenerative neurological disorders. Proc Soc Exp Biol Med 222: 236-245, 1999.
31. Fogelman AM, Schechter I, Hokom M, Child JS, and Edwards PA. Malondialdehyde alteration of low-density lipoprotein leads to cholesterol accumulation in human monocyte-macrophages. Proc Natl Acad Sci USA 77: 2214-2218, 1980.
32. Foreman D, and Solomon RG. Evidence that the prostaglandin E2 receptor and the anhydrolevuglandin E2 receptor in the rat uterus are the same receptor. Prostaglandins 43: 263-270, 1992.
33. Foreman D, Zuk L, Miller DB, and Salomon RG. Effects of E2 levuglandins on the contractile activity of the rat uterus. Prostaglandins 34: 91-98, 1987.
34. Foreman D, Levison BS, Miller DB, and Salomon RG. Anhydrolevuglandin D2 inhibits the uterotonic activity of prostaglandins F2 alpha and D2. Prostaglandins 35: 115-122, 1988.
35. Foreman D, Parker C 3rd, Alonzo I, and Salomon RG. Physiological evidence for the possible existence of anhydrolevuglandin E2-like activity in extracts and media from uteri of rats. Prostaglandins 43: 573-582, 1992.
36. 2+ currents in isolated guinea-pig ventricular myocytes. Eur J Pharmacol 292: 337-340, 1995.
37. Graham DG, Szakal-Quin G, Priest JW, and Anthony DC. In vitro evidence that covalent crosslinking of neurofilaments occurs in gamma-diketone neuropathy. Proc Natl Acad Sci USA 81: 4979-4982, 1984.
38. Graham DG, Amarnath V, Valentine WM, Pyle SJ, and Anthony DC. Pathogenetic studies of hexane and carbon disulfide neurotoxicity. Crit Rev Toxicol 25: 91-112, 1995.
39. Gu X, Meer SG, Miyagi M, Rayborn ME, Hollyfield JG, Crabb JW, and Salomon RG. Carboxyethylpyrrole protein adducts and autoantibodies, biomarkers for age-related macular degeneration. J Biol Chem 278: 42027-42035, 2003.
40. Hajjar KA, and Nachman RL. The role of lipoprotein(a) in atherogenesis and thrombosis. Annu Rev Med 47: 423-442, 1996.
41. Hamberg M, and Fredholm BB. Isomerization of prostaglandin H2 into prostaglandin D2 in the presence of serum albumin. Biochim BiophysActa 431: 189-183, 1976.
42. Holvoet P, Perez G, Zhao Z, Brouwers E, Bernar H, and Collen D. Malondialdehyde-modified low density lipoproteins in patients with atherosclerotic disease. J Clin Invest 95: 2611-2619, 1995.
43. 2, an oxidation product of arachidonic acid. Biochim Biophys Acta 1344: 1-5, 1997.
44. in t'Veld BA, Ruitenberg A, Hofman A, Launer LJ, van Duijn CM, Stijnen T, Breteler MM, and Stricker BH. Nonsteroidal antiinflammatory drugs and the risk of Alzheimer's disease. N Engl J Med 345: 1515-1521, 2001.
45. 2 crosslinks proteins. Prostaglandins 37: 471-480, 1989.
46. Iyer RS, Miller DB, and Salomon RG. Prostaglandin endoperoxides. 26. Decomposition of levuglandin E2. Dehydration and allylic rearrangement products. J Org Chem 55: 3175-3180, 1990.
47. 2 with proteins. J. Org. Chem. 59: 6038-6043, 1994.
48. 2-protein adducts bind glycine: a model for protein crosslinking. Prostaglandins 40: 187-203, 1990.
49. 2+ channel. Mol Pharmacol 53: 497-503, 1998.
50. Khair-el-Din TA, Sicher SC, Vazquez MA, Wright WJ, and Lu CY. Docosahexaenoic acid, a major constituent of fetal serum and fish oil diets, inhibits IFN gamma-induced Ia-expression by murine macrophages in vitro. J Immunol 154: 1296-1306, 1995.
51. Knight BL, Perombelon YF, Soutar AK, Wade DP, and Seed M. Catabolism of lipoprotein(a) in familial hypercholesterolaemic subjects. Atherosclerosis 87: 227-237, 1991.
52. 2. J Org Chem 59: 6044-6050, 1994.
53. Kwon KH, Kwon HM, Hong BK, Kim DS, Lee JY, Ryu SK, Park BE, Park HY, Kim JH, Yoon YW, Cho SY, and Kim HS. Autoantibody against, malondialdehyde-modified low density lipoprotein in patients with non-diabetic unstable angina: a potential role in immunologic reaction of plaque instability. Yonsei Med J 43: 203-210, 2002.
54. Lehning EJ, Jortner BS, Fox JH, Arezzo JC, Kitano T, and LoPachin RM. γ-Diketone peripheral neuropathy. I. Quality morphometric analyses of axonal atrophy and swelling. Toxicol Appl Pharmacol 165: 127-140, 2000.
55. Levison BS, Miller DB, and Salomon RG. Total synthesis of anhydrolevuglandin D2. Tetrahedron Lett. 25: 4633-4636, 1984.
56. Maggi E, Bellazzi R, Gazo A, Seccia M, and Bellomo G. Autoantibodies against oxidatively-modified LDL in uremic patients undergoing dialysis. Kidney Int 46: 869-876, 1994.
57. Maggi E, Chiesa R, Melissano G, Castellano R, Astore D, Grossi A, Finardi G, and Bellomo G. LDL oxidation in patients with severe carotid atherosclerosis. A study of in vitro and in vivo oxidation markers. Arterioscler Thromb 14: 1892-1899, 1994.
58. Mai J, Goswami SK, Bruckner G, and Kinsella JE. A new prostaglandin, C22-PGF4 alpha, synthesized from docosahexaenoic acid (C22:6n3) by trout gill. Prostaglandins 21: 691-698, 1981.
59. Markesbery WR. Oxidative stress hypothesis in Alzheimer's disease. Free Radic Biol Med 23: 134-147, 1997.
60. Masters CL, Simms G, Weinman NA, Multhaup G, McDonald BL, and Beyreuther K. Amyloid plaque core protein in Alzheimer disease and Down syndrome. Proc Natl Acad Sci USA 82: 4245-4249, 1985.
61. Miguel J, Oro J, Bensch KG, and Johnson JE. Lipofuscin: Fine-Structural and Biochemical Studies. In: Free Radicals in Biology, edited by Pryor WA. New York: Academic Press, 1977, pp. 133-182.
62. 2. J Org Chem 55: 3164-3175, 1990.
63. Moreau S, Lablache-Combier A, Biguet J, Foulon C, and Delfosse M. Botryodiplodin, a mycotoxin synthesized by a strain of P. roqueforti. J Org Chem 47: 2358-2359, 1982.
64. Morrow JD, Hill KE, Burk RF, Nammour TM, Badr KF, and Roberts LJ 2nd. A series of prostaglandin F2-like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanism. Proc Natl Acad Sci USA 87: 9383-9387, 1990.
65. Morrow JD, Awad JA, Kato T, Takahashi K, Badr KF, Roberts LJ 2nd, and Burk RF. Formation of novel non-cyclooxygenase-derived prostanoids (F2-isoprostanes) in carbon tetrachloride hepatotoxicity. An animal model of lipid peroxidation. J Clin Invest 90: 2502-2507, 1992.
66. Moule Y and Darracq N. Absence of DNA breaks during repair of DNA-protein cross-links induced by the mycotoxin botryodiplodin in mammalian cells. Carcinogenesis 5: 1375-1377, 1984.
67. Moule Y, Decloitre F, and Hamon G. Mutagenicity of the mycotoxin botryodiplodin in the Salmonella typhimurium/microsomal activation test. Environ Mutagen 3: 287-291, 1981.
68. Moule Y, Douce C, Moreau S, and Darracq N. Effects of the mycotoxin botryodiplodin on mammalian cells in culture. Chem Biol Interact 31: 155-164, 1981.
69. Moule Y, Renauld F, Darracq N, and Douce C. DNA-protein cross-linking by the mycotoxin, botryodiplodin, in mammalian cells. Carcinogenesis 3: 211-214, 1982.
70. 2 inhibits mitosis and microtubule assembly. Prostaglandins 39: 611-622, 1990.
71. 2. Biochemistry 32: 4090-4097, 1993.
72. Nugteren DH, and Christ-Hazelhof E. Chemical and enzymic conversions of the prostaglandin endoperoxide PGH2. Adv Prostaglandin Thromboxane Res 6: 129-137, 1980.
73. Nugteren DH and Hazelhof E. Isolation and properties of intermediates in prostaglandin biosynthesis. Biochim Biophys Acta 326: 448-461, 1973.
74. 1. Recl Trav Chim Pays Bas 86: 1237-1245, 1967.
75. Podrez EA, O'Neil J, Salomon RG, Schreiber MJ, and Hoff HF. Measurement of oxidation in plasma Lp(a) in CAPD patients using a novel ELISA. Kidney Int 54: 637-645, 1998.
76. Poliakov E, Brennan ML, Macpherson J, Zhang R, Sha W, Narine L, Salomon RG, and Hazen SL. Isolevuglandins, a novel class of isoprostenoid derivatives, function as integrated sensors of oxidant stress and are generated by myeloperoxidase in vivo. FASEB J 17: 2209-2220, 2003.
77. Pratico D, Lawson JA, and Fitzgerald GA. Cyclooxygenase-dependent formation of the isoprostane 8-epi prostaglandin F2 alpha. Ann N Y Acad Sci 744: 139-145, 1994.
78. Ramakrishnan N, Clay ME, Xue LY, Evans HH, Rodriguez-Antunez A, and Oleinick NL. Induction of DNA-protein cross-links in Chinese hamster cells by the photodynamic action of chloroaluminum phthalocyanine and visible light. Photochem Photobiol 48: 297-303, 1988.
79. Rao GH, Radha E, and White JG. Effect of docosahexaenoic acid (DHA) on arachidonic acid metabolism and platelet function. Biochem Biophys Res Commun 117:549-555, 1983.
80. Raz A, Kenig-Wakshal R, and Schwartzman M. Effect of organic sulfur compounds on the chemical and enzymatic transformations of prostaglandin endoperoxide H2. Biochim Biophys Acta 488: 322-329, 1977.
81. Roberts LJ 2nd and Morrow JD. Isoprostanes. Novel markers of endogenous lipid peroxidation and potential mediators of oxidant injury. Ann N Y Acad Sci 744: 237-242, 1994.
82. Roberts LJ 2nd, Salomon RG, Morrow JD, and Brame CJ. New developments in the isoprostane pathway: identification of novel highly reactive γ-ketoaldehydes (isolevuglandins) and characterization of their protein adducts. FASEB J 13: 1157-1168, 1999.
83. Rogers J, Kirby LC, Hempelman SR, Berry DL, McGeer PL, Kaszniak AW, Zalinski J, Cofield M, Mansukhani L, Willson P, et al. Clinical trial of indomethacin in Alzheimer's disease. Neurology 43: 1609-1611, 1993.
84. Roher AE, Chaney MO, Kuo YM, Webster SD, Stine WB, Haverkamp LJ, Woods AS, Cotter RJ, Tuohy JM, Krafft GA, Bonnell BS, and Emmerling MR. Morphology and toxicity of Aβ-(1-42) dimer derived from neuritic and vascular amyloid deposits of Alzheimer's disease. J Biol Chem 271: 20631-20635, 1996.
85. Salomon RG, and Miller DB. Levuglandins: isolation, characterization, and total synthesis of new secoprostanoid products from prostaglandin endoperoxides. Adv Prostaglandin Thromboxane Leukot Res 15: 323-326, 1985.
86. Salomon RG, and Salomon MF. 2,3-Dioxabicyclo[2.2.1]heptane. The strained bicyclic peroxide nucleus of prostaglandin endoperoxides. J Am Chem Soc 99: 3501-3503, 1977.
87. Salomon RG, Salomon MF, and Coughlin DJ. Prostaglandin endoperoxides. 6. A polar transition state in the thermal rearrangement of 2,3-dioxabicyclo[2.2.1] heptane. J Am Chem Soc 100: 660-662, 1978.
88. 2. J Am Chem Soc 106: 8296-8298, 1984.
89. 2 and a novel intramolecular 1,2-hydride shift during endoperoxide fragmentation in aqueous solution. J Am Chem Soc 106: 6049-6060, 1984.
90. 2 with proteins. Prostaglandins 34: 643-656, 1987.
91. 2-protein adducts in human plasma and vasculature. Chem Res Toxicol 10: 536-545, 1997.
92. Salomon RG, Subbanagounder G, Singh U, O'Neil J, and Hoff HF. Oxidation of low-density lipoproteins produces levuglandin-protein adducts. Chem Res Toxicol 10: 750-759, 1997.
93. 2, a product of the isoprostane pathway, in oxidized low density lipoprotein. J Biol Chem 274: 20271-20280, 1999.
94. Salomon RG, Batyreva E, Kaur K, Sprecher DL, Schreiber MJ, Crabb JW, Penn MS, DiCorletoe AM, Hazen SL, and Podrez EA. Isolevuglandin-protein adducts in humans: products of free radical-induced lipid oxidation through the isoprostane pathway. Biochim Biophys Acta 1485:225-235, 2000.
95. Salonen JT, Yla-Herttuala S, Yamamoto R, Butler S, Korpela H, Salonen R, Nyyssonen K, Palinski W, and Witztum JL. Autoantibody against oxidised LDL and progression of carotid atherosclerosis. Lancet 339: 883-887, 1992.
96. San Gupta R, Chandran RR, and Divekar PV. Botryo-diplodin - a new antibiotic from Botryodiplodia theobromae. II. Production, isolation and biological properties. Indian J Exp Biol 4: 152-153, 1966.
97. 2. Prostaglandins Leukot Essent Fatty Acids 47: 105-110, 1992.
98. Sha W and Salomon RG. Total Synthesis of 17-isolevuglandin E4 and the structure of C22-PGF4α. J Org Chem 65: 5315-5326, 2000.
99. + pump current in isolated rabbit ventricular myocytes using the whole-cell voltage-clamp technique. Inhibition of the pump by oxidant stress. Circ Res 72: 91-101, 1993.
100. Spector IM. Animal longevity and protein turnover rate. Nature 249: 66, 1974.
101. Stein JH and Rosenson RS. Lipoprotein Lp(a) excess and coronary heart disease. Arch Intern Med 157: 1170-1176, 1997.
102. Steinbrecher UP, Parthasarathy S, Leake DS, Witztum JL, and Steinberg D. Modification of low density lipoprotein by endothelial cells involves lipid peroxidation and degradation of low density lipoprotein phospholipids. Proc Natl Acad Sci USA 81: 3883-3887, 1984.
103. Tappel AL. Measurement of and protection from in vivo lipid peroxidation. In: Free Radicals in Biology, Vol. 4, edited by Pryor WA. New York: Academic Press, 1980, pp. 1-47.
104. Tokube K, Kiyosue T, and Arita M. Openings of cardiac KATP channel by oxygen free radicals produced by xanthine oxidase reaction. Am J Physiol 271: H478-H489, 1996.
105. 2+ channels: a possible involvement of free radicals. J Neurochem 68: 265-271, 1997.
106. Witztum JL. Susceptibility of low-density lipoprotein to oxidative modification. Am J Med 94: 347-349, 1993.
107. Witztum JL and Steinberg D. Role of oxidized low density lipoprotein in atherogenesis. J Clin Invest 88: 1785-1792, 1991.
108. + channel mRNA in cultured atrial cardiac myocytes (AT-1 cells). Circ Res 75: 870-878, 1994.
109. Zhang R, Brennan ML, Shen Z, MacPherson JC, Schmitt D, Molenda CE, and Hazen SL. Myeloperoxidase functions as a major enzymatic catalyst for initiation of lipid peroxidation at sites of inflammation. J Biol Chem 277: 46116-46122, 2002.