HNE-derived 2-pentylpyrroles are generated during oxidation of LDL, are more prevalent in blood plasma from patients with renal disease or atherosclerosis, and are present in atherosclerotic plaques

Chemical Research in Toxicology

Volumn 13, Issue 7, 2000, Pages 557-564

  Salomon, Robert G ^a   Kaur, Kamaljit ^a   Podrez, Eugene ^b   Hoff, Henry F ^b   Krushinsky, Anatoly V ^b   Sayre, Lawrence M ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

^b LERNER RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYNONENAL; APOLIPOPROTEIN B; EPITOPE; FREE RADICAL; HEMOCYANIN; LOW DENSITY LIPOPROTEIN; PYRROLE DERIVATIVE;

ARTICLE; ATHEROSCLEROSIS; ATHEROSCLEROTIC PLAQUE; CARDIOVASCULAR DISEASE; CONNECTIVE TISSUE; ENZYME LINKED IMMUNOSORBENT ASSAY; HUMAN; HUMAN TISSUE; IMMUNOPRECIPITATION; KIDNEY DISEASE; KIDNEY FAILURE; LIPID OXIDATION; OXIDATION; OXIDATIVE STRESS;

ALDEHYDES; ARTERIOSCLEROSIS; CAROTID ARTERIES; HUMANS; IMMUNOHISTOCHEMISTRY; KIDNEY FAILURE, CHRONIC; LIPOPROTEINS, LDL; OXIDATION-REDUCTION; PYRROLES;

EID: 0033929845     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx000007u     Document Type: Article

References (57)

1. Steinberg, D., Parthasarathy, S., Carew, T. E., Khoo, J. C., and Witztum, J. L. (1989) Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity. N. Engl. J. Med. 320, 915-924.
2. Clausen, J. (1984) Demential syndromes and the lipid metabolism. Acta Neurol. Scand. 70, 345-355.
3. Davies, K. J. A. (1995) Oxidative stress; the paradox of aerobic life. Biochem. Soc. Symp. 61, 1-31.
4. Parthasarathy, S., Steinberg, D., and Witztum, J. L. (1992) The role of oxidized low-density lipoproteins in the pathogenesis of atherosclerosis. Annu. Rev. Med. 43, 219-225.
5. Ylä-Herttuala, S., Palinski, W., Rosenfeld, M. E., Parthasarathy, S., Carew, T. E., Butler, S., Witztum, J. L., and Steinberg, D. (1989) Evidence for the presence of oxidatively modified low-density lipoprotein in atherosclerotic lesions of rabbit and man. J. Clin. Invest. 84, 1086-1095.
6. Hoff, H. F., and O'Neil, J. (1991) Lesion-derived low-density lipoprotein and oxidized low-density lipoprotein share a lability for aggregation, leading to enhanced macrophage degradation. Arterioscler. Thromb. 3, 1209-1222.
7. Witztum, J. L., and Steinberg, D. (1991) Role of oxidized low-density lipoprotein in atherogenesis. J. Clin. Invest. 88, 1785-1792.
8. Esterbauer, H., Jürgens, G., Quehenberger, O., and Koller, E. (1987) Autoxidation of human low-density lipoprotein: loss of polyunsaturated fatty acids and vitamin E and generation of aldehydes. J. Lipid Res. 28, 495.
9. Esterbauer, H., Schaur, R. J., and Zollner, H. (1991) Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radical Biol. Med. 11, 81-128.
10. Bellazzi, R., Maggi, E., Bellomo, G., Finardi, G., Gazo, A., Nai, M., Romanini, D., Falashi, F., Frattoni, A., and Perani, G. (1993) Low-density lipoprotein oxidation and antioxidized LDL antibodies in peritoneal dialysis patients. Adv. Peritoneal Dial. 9, 312-317.
11. Salonen, J. T., Ylä-Herttuala, S., Yamamoto, R., Butler, S., Korpela, H., Salonen, R., Nyyssönen, K., Palinski, W., and Witztum, J. L. (1992) Autoantibody against oxidised LDL and progression of carotid atherosclerosis. Lancet 339, 883-887.
12. Holvoet, P., Perez, G., Zhao, Z., Brouwers, E., Bernar, H., and Collen, D. (1995) Malondialdehyde-modified low-density lipoproteins in patients with atherosclerotic disease. J. Clin. Invest. 95, 2611-2619.
13. Kotani, K., Maekawa, M., Kanno, T., Kondo, A., Toda, N., and Manabe, M. (1994) Distribution of immunoreactive malondialdehyde-modified low-density lipoprotein in human serum. Biochim. Biophys. Acta 1215, 121-125.
14. Salmon, S., Maziere, C., Theron, L., Beucler, I., Jarrier-Ayrault, M., Goldstein, S., and Polonovski, J. (1987) Immunological detection of low-density lipoproteins modified by malondialdehyde in vitro or in vivo. Biochim. Biophys. Acta 920, 215-220.
15. Itabe, H., Yamamoto, H., Imanaka, T., Shimamura, K., Uchiyama, H., Kimura, J., Sanaka, T., Hata, Y., and Takano, T. (1996) Sensitive detection of oxidatively modified low-density lipoprotein using a monoclonal antibody. J. Lipid Res. 37, 45-53.
16. Maggi, E., Bellazzi, R., Gazo, A., Seccia, M., and Bellomo, G. (1994) Autoantibodies against oxidatively-modified LDL in uremic patients undergoing dialysis. Kidney Int. 46, 869-876.
17. 2-protein adducts. Kidney Int. 54, 637-645.
18. Lindner, A., Charra, B., Sherrard, D. J., and Scribner, B. H. (1974) Accelerated atherosclerosis in prolonged maintenance hemodialysis. N. Engl. J. Med. 290, 697-701.
19. Schauenstein, E., and Esterbauer, H. (1978) Formation and properties of reactive aldehydes. Ciba Found. Symp. 67, 225-244.
20. Benedetti, A., Comporti, M., and Esterbauer, H. (1980) Biochim. Biophys. Acta 620, 281-296.
21. Hoff, H. F., O'Neil, J., Chisholm, G. M., Cole, T. B., Quehenberger, O., Esterbauer, H., and Jürgens, G. (1989) Modification of LDL with 4-hydroxynonenal induces uptake of LDL by macrophages. Arteriosclerosis 9, 538-549.
22. Nadkarni, D. V., and Sayre, L. M. (1995) Structural definition of early lysine and histidine adduction chemistry of 4-hydroxynonenal. Chem. Res. Toxicol. 8, 284.
23. Uchida, K., and Stadtman, E. R. (1992) Modifications of histidine residues in proteins by reaction with 4-hydroxynonenal. Proc. Natl. Acad. Sci. U.S.A. 89, 4544-4588.
24. Uchida, K., and Stadtman, E. R. (1993) Covalent attachment of 4-hydroxynonenal to glyceraldehyde-3-phosphate dehydrogenase. A possible involvement of intra- and intermolecular cross-linking reaction. J. Biol. Chem. 268, 6388-6693.
25. Uchida, K., Toyokuni, S., Nishikawa, K., Kawakishi, S., Oda, H., Hiai, H., and Stadtman, E. R. (1994) Michael addition-type 4-hydroxy-2-nonenal adducts in modified low-density lipoproteins: Markers for atherosclerosis. Biochemistry 33, 12487-12494.
26. Requena, J. R., Fu, M. X., Ahmed, M. U., Jenkins, A. J., Lyons, T. J., Baynes, J. W., and Thorpe, S. R. (1997) Quantification of malondialdehyde and 4-hydroxynonenal adducts to lysine residues in native and oxidized human low-density lipoprotein. Biochem. J. 322, 317-325.
27. Bruenner, B. A., Jones, A. D., and German, J. B. (1995) Direct characterization of protein adducts of the lipid peroxidation product 4-hydroxy-2-nonenal using electrospray mass spectrometry. Chem. Res. Toxicol. 8, 552-559.
28. Sayre, L. M., Sha, W., Xu, G., Kaur, K., Nadkarni, D., Subbanagounder, G., and Salomon, R. G. (1996) Immunochemical Evidence Supporting 2-Pentylpyrrole Formation on Proteins Exposed to 4-Hydroxy-2-nonenal. Chem. Res. Toxicol. 9, 1194-1201.
29. 2-protein adducts in human plasma and vasaculature. Chem. Res. Toxicol. 10, 536-545.
30. Salomon, R. G., Subbanagounder, G., Singh, U., O'Neil, J., and Hoff, H. F. (1997) Oxidation of Low-Density Lipoproteins Produces Levuglandin-Protein Adducts. Chem. Res. Toxicol. 10, 750-759.
31. Smith, P. K., Krohn, R. I., Hermanson, G. T., Mallia, A. K., Gartner, F. H., Provenzano, M. D., Fujimoto, E. K., Goeke, N. M., Olson, B. J., and Klenk, D. C. (1985) Measurement of protein using bicinchoninic acid. Anal. Biochem. 150, 76-85 [published erratum, (1987) Anal. Biochem. 163 (1), 279].
32. Hatch, F. T., and Lees, R. S. (1968) Practical methods for plasma lipoprotein analysis. Adv. Lipid Res. 6, 1-68.
33. Hoff, H. F., Jackson, R. L., Mao, J. T., and Gotto, A. M. (1974) Localization of low-density lipoproteins in arterial lesions from normolipidemics employing a purified fluorescent labeled antibody. Biochim. Biophys. Acta 351, 407-415.
34. Uchida, K., Osawa, T., Hiroshi, H., and Toyokuni, S. (1995) 4-Hydroxy-2-nonenal-trapping ELISA: direct evidence for the release of a cytotoxic aldehyde from oxidized low-density lipoproteins. Biochem. Biophys. Res. Commun. 212, 1068-1073.
35. Choi, S. Y., Pang, L., Kern, P. A., Kayden, H. J., Curtiss, L. K., Vanni-Reyes, T. M., and Goldberg, I. J. (1997) Dissociation of LPL and LDL: effects of lipoproteins and anti-apoB antibodies. J. Lipid Res. 38, 77-85.
36. Lynch, S. M., Morrow, J. D., Roberts, L. J., and Frei, B. (1994) J. Clin. Invest. 93, 998-1004.
37. Esterbauer, H., Gebicki, J., Puhl, H., and Jürgens, G. (1992) The role of lipid peroxidation and antioxidants in oxidative modification of LDL. Free Radical Biol. Med. 13, 341-390.
38. Wardlaw, A. C. (1985) in Practical Statistics for Experimental Biologists, pp 42-153, John Wiley, New York.
39. Lewis, A. E. (1966) in Biostatistics, pp 52-61, Reinhold, New York.
40. Cooper, B. E. (1969) in Statistics for Experimentalists, pp 206-252, Pergamon Press, Elmsford, NY.
41. Rabinowitz, S. S., and Gordon, S. (1991) J. Exp. Med. 174, 827-836.
42. Rosenfeld, E. R., Palinski, W., Ylä-Herttuala, S., Butler, S., and Witztum, J. L. (1990) Distribution of oxidation specific lipid-protein adducts and apolipoprotein B in atherosclerotic lesions of varying severity from WHHL rabbits. Arteriosclerosis 10, 336-349.
43. Palinski, W., Yla-Herttuala, S., Rosenfeld, M. E., Butler, S. W., Socher, S. A., Parthasarathy, S., Curtiss, L. K., and Witztum, J. L. (1990) Antisera and monoclonal antibodies specific for epitopes generated during oxidative modification of low-density lipoprotein. Arteriosclerosis 10, 325-335.
44. Hörkkö, S., Miller, E., Dudl, E., Reaven, P., Curtiss, L. K., Zvaifler, N. J., Terkeltaub, R., Branch, D. W., Palinski, W., and Witzum, J. L. (1996) Antiphospholipid antibodies are directed against epitopes of oxidized phospholipids. Recognition of cardiolipin by monoclonal antibodies to epitopes of oxidized low-density lipoprotein. J. Clin. Invest. 98, 815-825.
45. Winyard, P. G., Tatzber, F., Esterbauer, H., Kus, M. L., Blake, D. R., and Morris, C. J. (1993) Presence of foam cells containing oxidised low-density lipoprotein in the synovial membrane from patients with rheumatoid arthritis. Ann. Rheum. Dis. 52, 677-680.
46. Mapp, P. I., Grootveld, M. C., and Blake, D. R. (1995) Hypoxia, oxidative stress and rheumatoid arthritis. Med. Bull. 51, 419-436.
47. Grisham, M. B. (1994) Oxidants and free radicals in inflammatory bowel disease. Lancet 344, 859-861.
48. Toshniwal, P. K., and Zarling, E. J. (1992) Evidence for increased lipid peroxidation in multiple sclerosis. Neurochem. Res. 17, 205-207.
49. Newcombe, J., Li, H., and Cuzner, M. L. (1994) Low-density lipoprotein uptake by macrophages in multiple sclerosis plaques: implications for pathogenesis. Neuropathol. Appl. Neurobiol. 20, 152-162.
50. Sayre, L. M., Zelasko, D. A., Harris, P. L. R., Perry, G., Salomon, R. G., and Smith, M. A. (1997) 4-Hydroxynonenal-derived advanced lipid peroxidation end products are increased in Alzheimer's disease. J. Neurochem. 68, 2092-2097.
51. Castellani, R. J., Perry, G., Harris, P. L., Cohen, M. L., Sayre, L. M., Salomon, R. G., and Smith, M. A. (1998) Advanced lipid peroxidation end-products in Alexander's disease. Brain Res. 787, 15-18.
52. Amarnath, V., Valentine, W. M., Montaine, T. J., Patterson, W. H., Amarnath, K., Bassett, C. N., and Grahm, D. G. (1998) Reactions of 4-Hydroxy-2(E)-nonenal and Related Aldehydes with Proteins Studied by Carbon-13 Nuclear Magnetic Resonance Spectroscopy. Chem. Res. Toxicol. 11, 317-328.
53. Selley, M. L., Bartlett, M. R., McGuiness, J. A., Hapel, A. J., and Ardlie, N. G. (1989) Determination of the lipid peroxidation product trans-4-hydroxy-2-nonenal in biological samples by high-performance liquid chromatography and combined capillary gas chromatography-negative-ion chemical ionisation mass spectrometry. J. Chromatogr. 488, 329-340.
54. Selley, M. L., Bourne, M. R., Tymms, K. E., Brook, A. S., Duffield, A. M., and Ardlie, N. G. (1992) Occurrence of (E)-4-hydroxy-2-nonenal in plasma and synovial fluid of patients with rheumatoid arthritis and osteoarthritis. Ann. Rheum. Dis. 51, 481-484.
55. Stromaier, H., Hinghofer-Szalkay, H., and Schaur, R. J. (1995) Detection of 4-hydroxynonenal (HNE) as a physiological component in human plasma. J. Lipid Mediators Cell Signalling 11, 51-61.
56. O'Brien, K. D., Alpers, C. E., Hokanson, J. E., Wang, S., and Chait, A. (1996) Oxidation-specific epitopes in human coronary atherosclerosis are not limited to oxidized low-density lipoprotein. Circulation 94, 1216-1225.
57. Page, R. C., and Benditt, E. P. (1969) Collagen has a discrete family of reactive hydroxylysyl and lysyl side-chain amino groups. Science 163, 578-580.