U-101033E (2,4-diaminopyrrolopyrimidine), a potent inhibitor of membrane lipid peroxidation as assessed by the production of 4-hydroxynonenal, malondialdehyde, and 4-hydroxynonenal- protein adducts

Biochemical Pharmacology

Volumn 56, Issue 10, 1998, Pages 1371-1379

  Rohn, Troy T ^a   Nelson, Laura K ^a   Waeg, Georg ^b   Quinn, Mark T ^a  

^a MONTANA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF GRAZ   (Austria)

Author keywords

4 hydroxy 2 nonenal; antioxidant; free radicals; lipid peroxidation; oxidant stress; protein cross linking

Indexed keywords

2,4 DIAMINOPYRROLOPYRIMIDINE; 4 HYDROXYNONENAL; EDETIC ACID; MALONALDEHYDE; MEMBRANE LIPID; MEMBRANE PROTEIN; MONOCLONAL ANTIBODY; PYRROLOPYRIMIDINE DERIVATIVE; SUPEROXIDE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; ERYTHROCYTE MEMBRANE; HUMAN; HUMAN CELL; LIPID PEROXIDATION; PRIORITY JOURNAL; PROTEIN CROSS LINKING;

EID: 0031772147     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(98)00266-4     Document Type: Article

References (61)

1. Sohal RS and Weindruch R, Oxidative stress, caloric restriction, and aging. Science 273: 59-63, 1996.
2. Beckman KB and Ames BN, The free radical theory of aging matures. Physiol Rev 78: 547-581, 1998.
3. Gutteridge JM, Free radicals in disease processes: A compilation of cause and consequence. Free Radic Res Commun 19: 141-158, 1993.
4. Davies KJA, Oxidative stress: The paradox of aerobic life. Biochem Soc Symp 61: 1-31, 1995.
5. Epling CL, Stites DP, McHugh TM, Chong HO, Blackwood LL and Wara DW, Neutrophil function screening in-patients with chronic granulomatous disease by a flow cytometric method. Cytometry 13: 615-620, 1992.
6. Rikans LE and Hornbrook KR, Lipid peroxidation, antioxidant protection and aging. Biochim Biophys Acta 1362: 116-127, 1997.
7. Kehrer JP, Free radicals as mediators of tissue injury and disease. Crit Rev Toxicol 23: 21-48, 1993.
8. Esterbauer H, Zollner H and Schaur RJ, Hydroxyalkenals: Cytotoxic products of lipid peroxidation. ISI Atlas Sci Biochem 1: 311-317, 1988.
9. Esterbauer H, Schaur RJ and Zollner H, Chemistry and biochemistry of 4-hydroxynonenal, malondialdehyde and related aldehydes. Free Radic Biol Med 11: 81-128, 1991.
10. Nadkarni DV and Sayre LM, Structural definition of early lysine and histidine adduction chemistry of 4-hydroxynonenal. Chem Res Toxicol 8: 284-291, 1995.
11. Steinbrecher UP, Oxidation of human low density lipoprotein results in derivatization of lysine residues of apolipoprotein B by lipid peroxide decomposition products. J Biol Chem 262: 3603-3608, 1987.
12. Palinski W, Rosenfeld ME, Yla-Herttuala S, Gurtner G, Socher SS, Butler SW, Parthasarathy S, Carew TE, Steinberg D and Witztum JL, Low density lipoprotein undergoes oxidative modification in vivo. Proc Natl Acad Sci USA 86: 1372-1376, 1989.
13. Hoff HF, O'Neil J, Chisolm GM, Cole TB, Quehenberger O, Esterbauer H and Jurgens G, Modification of low density lipoprotein with 4-hydroxynonenal induces uptake by macrophages. Arteriosclerosis 9: 538-549, 1989.
14. Yoritaka A, Hattori N, Uchida K, Tanaka M, Stadtman ER and Mizuno Y, Immunohistochemical detection of 4-hydroxynonenal protein adducts in Parkinson disease. Proc Natl Acad Sci USA 93: 2696-2701, 1996.
15. Sayre LM, Zelasko DA, Harris PLR, Perry G, Salomon RG and Smith MA, 4-Hydroxynonenal-derived advanced lipid peroxidation end products are increased in Alzheimer's disease. J Neurochem 68: 2092-2097, 1997.
16. Quinn MT, Linner JG, Siemsen D, Dratz EA, Buescher ES and Jesaitis AJ, Immunocytochemical detection of lipid peroxidation in phagosomes of human neutrophils: Correlation with expression of flavocytochrome b. J Leukoc Biol 57: 415-421, 1995.
17. Sanderson KJ, van Rij AM, Wade CR and Sutherland WH, Lipid peroxidation of circulating low density lipoproteins with age, smoking and in peripheral vascular disease. Atherosclerosis 118:45-51, 1995.
18. Michel P, Eggert W, Albrecht-Nebe H and Grune T, Increased lipid peroxidation in children with autoimmune diseases. Acta Paediatr 86: 609-612, 1997.
19. Mooradian AD, Lung CC, Shah G, Mahmoud S and Pinnas JL, Age-related changes in tissue content of malondialdehyde-modified proteins. Life Sci 55: 1561-1566, 1994.
20. Rodríguez-Martínez MA, Alonso MJ, Redondo J, Salaíces M and Marin J, Role of lipid peroxidation and the glutathione-dependent antioxidant system in the impairment of endothelium-dependent relaxations with age. Br J Pharmacol 123: 113-121, 1998.
21. Aruoma OI, Characterization of drugs as antioxidant prophylactics. Free Radic Biol Med 20: 675-705, 1996.
22. Hall ED, Neuroprotective actions of glucocorticoid and non-glucocortcoid steroids in acute neuronal injury. Cell Mol Neurobiol 13: 415-432, 1993.
23. Hall ED and McCall JM, Antioxidant action of lazaroids. Methods Enzymol 234: 548-555, 1994.
24. Bundy GL, Ayer DE, Banitt LS, Belonga KL, Mizsak SA, Palmer JR, Tustin JM, Chin JE, Hall ED, Linseman KL, Richards IM, Scherch HM, Sun FF, Yonkers PA, Larson PG, Lin JM, Padbury GE, Aaron CS and Mayo JK, Synthesis of novel 2,4-diaminopyrrolo-[2,3-d]pyrimidines with antioxidant, neuroprotective, and antiasthma activity. J Med Chem 38: 4161-4163, 1995.
25. Smith SL, Scherch HM and Hall ED, Protective effects of tirilazad mesylate and metabolite U-89678 against blood-brain barrier damage after subarachnoid hemorrhage and lipid peroxidative neuronal injury. J Neurosur 84: 229-233, 1996.
26. Kim H, Koehler RC, Hum PD, Hall ED and Traystman RJ, Amelioration of impaired cerebral metabolism after severe acidotic ischemia by tirilazad posttreatment in dogs. Stroke 27: 114-121, 1997.
27. Hall ED, Andrus PK, Smith SL, Fleck TJ, Scherch HM, Lutzke BS, Sawada GA, Althaus JS, Vonvoigtlander PF, Padbury GE, Larson PG, Palmer JR and Bundy GL, Pyrrolopyrimidines: Novel brain-penetrating antioxidants with neuroprotective activity in brain injury and ischemia models. J Pharmacol Exp Ther 281: 895-904, 1997.
28. + pump ATPase of human red blood cell membranes. Biochem Pharmacol 46: 525-534, 1993.
29. +-pump ATPase by iron-generated free radicals. Protection by 6,7-dimethyl-2,4-di-1-pyrrolidinyl-7H-pyrrolo[2,3-d]pyrimidine sulfate (U-89843D), a potent, novel, antioxidant/free radical scavenger. Biochem Pharmacol 51: 471-476, 1996.
30. Waeg G, Dimsity G and Esterbauer H, Monoclonal antibodies for detection of 4-hydroxynonenal modified proteins. Free Radic Res 25: 149-159, 1996.
31. Smith PK, Krohn RI, Hermanson GT, Mallia AK, Gartner FH, Provenzano MD, Fujimoto EK, Goeke NM, Olson BJ and Klenk CD, Measurement of protein using bicinchoninic acid. Anal Biochem 150: 76-85, 1985.
32. Smith GS, Mercer DW, Cross JM, Barreto JC and Miller TA, Gastric injury induced by ethanol and ischemia-reperfusion in the rat. Dig Dis Sci 41: 1157-1164, 1997.
33. Laight DW, Andrews TJ, Haj-Yehia AI, Carrier MJ, and Ånggård EE, Microassay of superoxide anion scavenging activity in vitro. Environ Toxicol Pharmacol 3: 65-68, 1997.
34. Quinn MT, Parkos CA and Jesaitis AJ, The lateral organization of components of the membrane skeleton and superoxide generation in the plasma membrane of stimulated human neutrophils. Biochim Biophys Acta 987: 83-94, 1989.
35. Esterbauer H and Cheeseman KH, Determination of aldehydic lipid peroxidation products: Malonaldehyde and 4-hydroxynonenal. Methods Enzymol 186: 407-421, 1990.
36. Janero DR, Malondialdehyde and thiobarbituric acid-reactivity as diagnostic indices of lipid peroxidation and peroxidative tissue injury. Free Radic Biol Med 9: 515-540, 1990.
37. Esterbauer H, Aldehydic products of lipid peroxidation. In: Free Radicals, Lipid Peroxidation, and Cancer (Eds. McBrien DCH and Slater TF), pp. 101-128. Academic Press, London, 1982.
38. Halliwell B and Gutteridge JMC, Free Radicals in Biology and Medicine. Oxford University Press, New York, 1989.
39. Siems WG, Grune T and Esterbauer H, 4-Hydroxynonenal formation during ischemia and reperfusion of rat small intestine. Life Sci 57: 785-789, 1995.
40. Blasig IE, Grune T, Schönheit K, Rohde E, Jakstadt M, Haseloff RF and Siems WG, 4-Hydroxynonenal, a novel indicator of lipid peroxidation for reperfusion injury of the myocardium. Am J Physiol 269: H14-H22, 1995.
41. Li L, Hamilton RF Jr, Kirichenko A and Holian A, 4-Hydroxynonenal-induced cell death in murine alveolar macrophages. Toxicol Appl Pharmacol 139: 135-143, 1996.
42. Karlhuber GM, Bauer HC and Eckl PM, Cytotoxic and genotoxic effects of 4-hydroxynonenal in cerebral endothelial cells. Mutat Res 381: 209-216, 1997.
43. Bruce-Keller AJ, Li YJ, Lovell MA, Kraemer PJ, Gary DS, Brown RR, Markesbery WR and Mattson MP, 4-Hydroxynonenal, a product of lipid peroxidation, damages cholinergic neurons and impairs visuospatial memory in rats. J Neuropathol Exp Neurol 57: 257-267, 1998.
44. Jurgens G, Lang J and Esterbauer H, Modification of human low-density lipoprotein by the lipid peroxidation product 4-hydroxynonenal. Biochim Biophys Acta 875: 103-114, 1986.
45. Curzio M, Esterbauer H, DiMauro C, Cecchini G and Dianzani MU, Chemotactic activity of the lipid peroxidation product 4-hydroxynonenal and homologous hydroxyalkenals. Biol Chem Hoppe Seyler 367: 321-329, 1986.
46. Curzio M, Esterbauer H, Poli G, Biasi F, Cecchini G, DiMauro C, Cappello N and Dianzani MU, Possible role of aldehydic lipid peroxidation products as chemoattractants. Int J Tissue React 9: 295-306, 1987.
47. Uchida K and Stadtman ER, Covalent attachment of 4-hydroxynonenal to glyceraldehyde-3-phosphate dehydrogenase. A possible involvement of intra- and intermolecular cross-linking reaction. J Biol Chem 268: 6388-6393, 1993.
48. +-ATPaSe. Free Radic Biol Med 20: 215-223, 1996.
49. Schmidt H, Grune T, Müller R, Siems WG and Wauer RR, Increased levels of lipid peroxidation products malondialdehyde and 4-hydroxynonenal after perinatal hypoxia. Pediatr Res 40: 15-20, 1996.
50. Requena JR, Fu MX, Ahmed MU, Jenkins AJ, Lyons TJ, Baynes JW and Thorpe SR, Quantification of malondialdehyde and 4-hydroxynonenal adducts to lysine residues in native and oxidized human low-density lipoprotein. Biochem J 322: 317-325, 1997.
51. Hartley DP and Petersen DR, Profiles of hepatic cellular protein adduction by malondialdehyde and 4-hydroxynonenal - Studies with isolated hepatocytes. Adv Exp Med Biol 414: 123-131, 1997.
52. Hartley DP, Kroll DJ and Petersen DR, Prooxidant-initiated lipid peroxidation in isolated rat hepatocytes: Detection of 4-hydroxynonenal- and malondialdehyde-protein adducts. Chem Res Toxicol 10: 895-905, 1997.
53. Friguet B, Stadtman ER and Szweda LI, Modification of glucose-6-phosphate dehydrogenase by 4-hydroxy-2-nonenal. Formation of cross-linked protein that inhibits the multicatalytic protease. J Biol Chem 269: 21639-21643, 1994.
54. Friguet B and Szweda LI, Inhibition of the multicatalytic proteinase (proteasome) by 4-hydroxy-2-nonenal cross-linked protein. FEBS Lett 405: 21-25, 1997.
55. Blanc EM, Keller JN, Fernandez S and Mattson MP, 4-Hydroxynonenal, a lipid peroxidation product, impairs glutamate transport in cortical astrocytes. Glia 22: 149-160, 1998.
56. Greilberger J and Jurgens G, Oxidation of high-density lipoprotein HDL3 leads to exposure of apo-AI and apo-AII epitopes and to formation of aldehyde protein adducts, and influences binding of oxidized low-density lipoprotein to type I and type III collagen in vitro. Biochem J 331: 185-191, 1998.
57. Horie K, Miyata T, Maeda K, Miyata S, Sugiyama S, Sakai H, Strihou CY, Monnier VM, Witztum JL and Kurokawa K, Immunohistochemical colocalization of glycoxidation products and lipid peroxidation products in diabetic renal glomerular lesions. Implication for glycoxidative stress in the pathogenesis of diabetic nephropathy. J Clin Invest 100: 2995-3004, 1997.
58. Traverso N, Menini S, Cosso L, Odetti P, Albano E, Pronzato MA and Marinari UM, Immunological evidence for increased oxidative stress in diabetic rats. Diabetologia 41: 265-270, 1998.
59. Paradis V, Kollinger M, Fabre M, Holstege A, Poynard T and Bedossa P, In situ detection of lipid peroxidation by-products in chronic liver diseases. Hepatology 26: 135-142, 1997.
60. Hall ED, McCall JM and Means ED, Therapeutic potential of the lazaroids (21-aminosteroids) in central nervous system trauma, ischemia and subarachnoid hemmorrhage. Adv Pharmacol 28: 221-268, 1994.
61. Kassel NF, Haley EC, Apperson-Hansen C and Alves WM, A randomized, double-blind, vehicle-controlled trial of tirilazad mesylate in patients with aneuroysmal subarachnoid hemorrhage. J Neurosurg 84: 221-228, 1996.