Macrophage-enhanced formation of cholesteryl ester-core aldehydes during oxidation of low density lipoprotein

Journal of Lipid Research

Volumn 40, Issue 7, 1999, Pages 1240-1253

  Karten, Barbara ^a   Boechzelt, Herbert ^a   Abuja, Peter M ^a   Mittelbach, Martin ^a   Sattler, Wolfgang ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

J774 cells; Lipopolysaccharide; Phorbol 12 myristate 13 acetate; Transition metals

Indexed keywords

5 OXOVALEROYL CHOLESTEROL; 9 OXONONANOYL CHOLESTEROL; ALDEHYDE; AMINO ACID; CHOLESTEROL DERIVATIVE; CHOLESTEROL ESTER; CHOLESTERYL ARACHIDONIC ACID; COPPER; IRON; LIPOPOLYSACCHARIDE; LOW DENSITY LIPOPROTEIN; LOW DENSITY LIPOPROTEIN CHOLESTERYL LINOLEIC ACID; METAL; PHORBOL 13 ACETATE 12 MYRISTATE; UNCLASSIFIED DRUG; VITAMIN;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; ATHEROGENESIS; CELL STIMULATION; CONTROLLED STUDY; CULTURE MEDIUM; LIPID OXIDATION; MACROPHAGE; MOUSE; NONHUMAN; PRIORITY JOURNAL;

ALDEHYDES; ANIMALS; CELLS, CULTURED; CHOLESTEROL; CULTURE MEDIA; LIPOPOLYSACCHARIDES; LIPOPROTEINS, LDL; MACROPHAGE ACTIVATION; MACROPHAGES; MICE; OXIDATION-REDUCTION; TETRADECANOYLPHORBOL ACETATE;

EID: 0032800214     PISSN: 00222275     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (67)

1. Steinberg, D., S. Parthasarathy, T. E. Carew, J. C. Khoo, and J. L. Witztum. 1989. Beyond cholesterol: modifications of low-density lipoprotein that increase its atherogenicity. N. Engl. J. Med. 320: 915-924.
2. Esterbauer, H., and P. Ramos. 1995. Chemistry and pathophysiology of oxidation of LDL. Rev. Physiol. Biochem. Pharmacol. 127: 31-64.
3. Goldstein, J. L., and M. S. Brown. 1977. Low-density lipoprotein pathway and its relation to atherosclerosis. Annu. Rev. Biochem. 46: 897-930.
4. Chait, A., and J. W. Heinecke. 1994. Lipoprotein modification: cellular mechanisms. Curr. Opin. Lipidol. 5: 365-370.
5. Crane, F. L., I. L. Sun, M. G. Clark, C. Grebing, and H. Löw. 1985. Transplasma-membrane redox systems in growth and development. Biochim. Biophys. Acta. 811: 233-264.
6. Garner, B., D. van Reyk, R. T. Dean, and W. Jessup. 1997. Direct copper reduction by macrophages. Its role in low density lipoprotein oxidation. J. Biol. Chem. 272: 6927-6935.
7. Witz, G. 1989. Biological interaction of of α,β-unsaturated aldehydes. Free Radical Biol Med. 7: 333-349.
8. Girotti, A. W. 1998. Lipid hydroperoxide generation, turnover, and effector action in biological systems. J. Lipid Res. 39: 1529-1542.
9. Terao, J. 1990. Reactions of lipid hydroperoxides. In Membrane Lipid Oxidation. C. Pelfrey, editor. CRC Press, Boca Raton. 219-238.
10. Itabe, H. 1998. Oxidized phospholipids as a new landmark in atherosclerosis. Prog. Lipid Res. 37: 181-207.
11. Watson, A. D., N. Leitinger, M. Navab, K. F. Faull, S. Hörkkö, J. L. Witztum, W. Palinski, D. Schwenke, R. G. Salomon, W. Sha, G. Sub-banagounder, A. M. Fogelman, and J. A. Berliner. 1997. Structural identification by mass spectrometry of oxidized phospholipids in minimally oxidized low density lipoprotein that induce monocyte/ endothelial interactions and evidence for their presence in vivo. J. Biol. Chem. 272: 13597-13607.
12. Kamido, H., A. Kuksis, L. Marai, and J. J. Myher. 1992. Identification of cholesterol-bound core aldehydes in copper-oxidized low density lipoprotein. FEBS Lett. 304: 269-272.
13. Kamido, H., A. Kuksis, L. Marai, and J. J. Myher. 1993. Identification of core aldehydes among in vitro peroxidation products of cholesteryl esters. Lipids. 28: 331-336.
14. Kamido, H., A. Kuksis, L. Marai, and J. J. Myher. 1995. Lipid ester-bound aldehydes among copper-catalyzed peroxidation products of human plasma lipoproteins. J. Lipid Res. 36: 1876-1886.
15. Hoppe, G., A. Ravandi, D. Herrera, A. Kuksis, and H. F. Hoff. 1997. Oxidation products of cholesteryl linoleate are resistant to hydrolysis in macrophages, form complexes with proteins, and are present in human atherosclerotic lesions. J. Lipid Res. 38: 1347-1360.
16. Karten, B., H. Boechzelt, P. M. Abuja, M. Mittelbach, K. Oettl, and W. Sattler. 1998. Femtomole analysis of 9-oxononanoyl cholesterol by high performance liquid chromatography. J. Lipid Res. 39: 1508-1519.
17. Boechzelt, H., B. Karten, P. M. Abuja, W. Sattler, and M. Mittelbach. 1998. Synthesis of 9-oxononanoyl cholesterol by ozonization. J. Lipid Res. 39: 1503-1507.
18. Sattler, W., G. M. Kostner, G. Waeg, and H. Esterbauer. 1991. Oxidation of lipoprotein Lp(a). A comparison with low-density lipoproteins. Biochim. Biophys. Acta. 1081: 65-74.
19. Goldstein, J. L., S. K. Basu, and M. S. Brown. 1983. Receptor-mediated endocytosis of low-density lipoprotein in cultured cells. Methods Enzymol. 98: 241-260.
20. Lowry, O. H., N. J. Rosebrough, A. L. Farr, and R. J. Randall. 1951. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193: 265-275.
21. Panzenboeck, U., S. Raitmayer, H. Reicher, H. Lindner, O. Glatter, E. Malle, and W. Sattler. 1997. Effects of reagent and enzymatically generated hypochlorite on physicochemical and metabolic properties of high density lipoproteins. J. Biol. Chem. 272: 29711-29720.
22. Sattler, W., D. Mohr, and R. Stocker. 1994. Rapid isolation of lipoproteins and assessment of their peroxidation by high-performance liquid chromatography postcolumn chemiluminescence. Methods Enzymol. 233: 469-489.
23. Esterbauer, H., and K. H. Cheeseman. 1990. Determination of aldehydic lipid peroxidation product: malondialdehyde and 4-hydroxynonenal. Methods Enzymol. 186:407-421.
24. Jessup, W., J. A. Simpson, and R. T. Dean. 1993. Does superoxide radical have a role in macrophage-mediated oxidative modification of LDL? Atherosclerosis. 99: 107-120.
25. Sattler, W., H. Reicher, P. Ramos, U. Panzenboeck, M. Hayn, H. Esterbauer, E. Malle, and G. M. Kostner. 1996. Preparation of fatty acid methyl esters from lipoprotein and macrophage lipid sub-classes in thin-layer plates. Lipids. 31: 1303-1310.
26. McNally, A. K., G. M. Chisolm, D. W. Morel, and M. K. Cathcart. 1990. Activated human monocytes oxidize low-density lipoprotein by a lipoxygenase-dependent pathway. J. Immunol. 145: 254-259.
27. Kontush, A., S. Meyer, B. Finckh, A. Kohlschütter, and U. Beisiegel. 1996. α-Tocopherol as a reductant for Cu(II) in human lipoproteins. Triggering role in the initiation of lipid peroxidation. J. Biol. Chem. 271: 11106-11112.
28. Proudfoot, J. M., K. D. Croft, I. B. Puddey, and L. J. Beilin. 1997. The role of copper reduction by α-tocopherol in low-density lipoprotein oxidation. Free Radical Biol. Med. 23: 720-728.
29. Patel, R. P., D. Svistunenko, M. T. Wilson, and V. M. Darley-Usmar. 1997. Reduction of Cu(II) by lipid hydroperoxides: implications for the copper-dependent oxidation of low density lipoprotein. Biochem. J. 322: 425-433.
30. Thomas, C. E., and R. L. Jackson. 1991. Lipid hydroperoxide involvement in copper-dependent and independent oxidation of low density lipoproteins. J. Pharmacol. Exp. Ther. 256: 1182-1188.
31. Hamilton, T. A., and D. O. Adams. 1987. Molecular mechanisms of signal transduction in macrophages. Immunol. Today. 8: 151-158.
32. Esterbauer, H., H. Zollner, and R. J. Schaur. 1990. Aldehydes formed by lipid peroxidation: mechanisms of formation, occurrence and determination. In Membrane Lipid Oxidation. C. Pelfrey, editor. CRC Press, Boca Raton. 239-268.
33. Smith, C., M. J. Mitchinson, O. I. Aruoma, and B. Halliwell. 1992. Stimulation of lipid peroxidation and hydroxyl-radical generation by the contents of human atherosclerotic lesions. Biochem. J. 286: 901-905.
34. Kritharides, L., W. Jessup, and R. T. Dean. 1995. Macrophages both iron and copper to oxidize low-density lipoprotein in Hanks' balanced salt solution. Arch. Biochem. Biophys. 323: 127-136.
35. Lamb, D. J., M. J. Mitchinson, and D. S. Leake. 1995. Transition metal ions within human atherosclerotic lesions can catalyse the oxidation of low density lipoprotein by macrophages. FEBS Lett. 374: 12-16.
36. Santanam, N., and S. Parthasarathy. 1995. Cellular cysteine generation does not contribute to the initiation of LDL oxidation. J. Lipid Res. 36: 2203-2211.
37. Hu, M-L., Y-K. Chen, and Y-F. Lin. 1995. The antioxidant and prooxidant activity of some B vitamins and vitamin-like compounds. Chem. Biol. Interact. 97: 63-73.
38. Tandon, S. K., S. J. Flora, and S. Singh. 1987. Chelation in metal intoxication. XXIV: Influence of various components of vitamin B complex on the therapeutic efficacy of disodium calcium versenate in lead intoxication. Pharmacol. Toxicol. 60: 62-65.
39. Lucius, R., R. Mentlein, and J. Sievers. 1998. Riboflavin-mediated axonal degeneration of postnatal retinal ganglion cells in vitro is related to the formation of free radicals. Free Radical Biol. Med. 24: 798-808.
40. Rivera, C. A., M. D. Wheeler, N. Enomoto, and R.G. Thurman. 1998. A choline-rich diet improves survival in a rat model of endotoxin shock. Am. J. Physiol. 275: G862-G867.
41. Zingarelli, B., M. O'Connor, H. Wong, A. L. Salzman, and C. Szabo. 1996. Peroxynitrite-mediated DNA strand breakage activates polyadenosine diphosphate ribosyl synthetase and causes cellular energy depletion in macrophages stimulated with bacterial lipopolysaccharide. J. Immunol. 156: 350-358.
42. Pellat-Deceunynck, C., J. Wietzerbin, and J. C. Drapier. 1994. Nicotinamide inhibits nitric oxide synthase mRNA induction in activated macrophages. Biochem. J. 297: 53-58.
43. Gilad, E., B. Zingarelli, A. L. Salzman, and C. Szabo. 1997. Protection by inhibition of poly (ADP-ribose) synthetase against oxidant injury in cardiac myoblasts in vitro. J. Mol. Cell. Cardiol. 29: 2585-2597.
44. Verhoef, P., M. J. Stampfer, E. B. Rimm. 1998. Folate and coronary heart disease. Curr. Opin. Lipidol. 9: 17-22.
45. Calingasan, N. Y., L. C. H. Park, L. L. Calo, R. R. Trifiletti, S. E. Gandy, and G. E. Gibson. 1998. Induction of nitric oxide synthase and microglial responses precede selective cell death induced by chronic impairment of oxidative metabolism. Am. J. Pathol. 153: 599-610.
46. Langlais, P. J., G. Anderson, S. X. Guo, S. C. Bondy. 1997. Increased cerebral free radical production during thiamine deficiency. Metab. Brain Dis. 12: 137-143.
47. Heinecke, J. W., L. Baker, H. Rosen, and A. Chait. 1986. Superoxide-mediated modification of low density lipoproteins by arterial smooth muscle cells. J. Clin. Invest. 262: 10098-10103.
48. Steinbrecher, U. P. 1988. Role of superoxide in endothelial-cell modification of low-density lipoproteins. Biochim. Biophys. Acta. 959: 20-30.
49. Fang, X., N. L. Weintraub, C. D. Rios, D. A. Chappell, R. M. Zwacka, J. F. Engelhardt, L. W. Oberley, T. Yan, D. D. Heistad, and A. A. Spector. 1998. Overexpression of human superoxide dismutase inhibits oxidation of low-density lipoprotein by endothelial cells. Circ. Res. 82: 1289-1297.
50. mutase. Arterioscler. Thromb. Vasc. Biol. 17:1734-1740.
51. Heinecke, J. W., H. Rosen, and L. A. Suzuki. 1987. The role of sulfur-containing amino acids in superoxide production and modification of low density lipoprotein by arterial smooth muscle cells. J. Biol. Chem. 262: 10098-10103.
52. Heinecke, J. W., M. Kawamura, L. Suzuki, and A. Chait. 1993. Oxidation of low density lipoprotein by thiols: superoxide-dependent and -independent mechanisms. J. Lipid Res. 34: 2051-2061.
53. Sparrow, C. P., and J. Olszewski. 1993. Cellular oxidation of low density lipoprotein is caused by thiol production in media containing transition metal ions. J. Lipid Res. 34: 1219-1228.
54. Heinecke, J. W. 1994. Cellular mechanisms for the oxidative modification of lipoproteins: implications for atherogenesis. Coronary Artery Dis. 5: 205-210.
55. Rodriguez-Aguilera, J. C., K. Nakayama, A. Arroyo, J. M. Viallalba, and P. Navas. 1993. Transplasma membrane redox system of HL-60 is controlled by cAMP. J. Biol. Chem. 268: 26346-26349.
56. Jian, Z. J., Z. Yang, G. L. Mason, D. O. Slauson, and P. N. Bochsler. 1995. Regulation of superoxide anion generation in bovine alveolar macrophages by bacterial lipopolysaccharide, serum proteins, and modulators of signal transduction. Inflammation. 19: 637-650.
57. Fujiwara, K., H. Sato, and S. Bannai. 1998. Involvement of endotoxins or tumor necrosis factor-α in macrophage-mediated oxidation of low density lipoprotein. FEBS Lett. 431: 116-120.
58. Funk, J. L., K. R. Feingold, A. H. Moser, and C. Grunfeld. 1993. Lipopolysaccharide stimulation of RAW 264.7 macrophages induces lipid accumulation and foam cell formation. Atherosclerosis. 98: 67-82.
59. Yancey, P. G., and W. G. Jerome. 1998. Lysosomal sequestration of free and esterified cholesterol from oxidized low density lipoprotein in macrophages of different species. J. Lipid Res. 39: 1349-1361.
60. Li, W., X. Yuan, A. G. Olsson, and U. T. Brunk. 1998. Uptake of oxidized LDL by macrophages results in partial lysosomal enzyme inactivation and relocation. Arterioscler. Thromb. Vase. Bid. 18:177-184.
61. Rosenfeld, M. E., W. Palinski, S. Yla-Herttuala, S. Butler, and J. L. Witztum. 1990. Distribution of oxidation specific lipid-protein adducts and apolipoprotein B in atherosclerotic lesions of varying severity from WHHL rabbits. Arteriosclerosis. 10: 336-349.
62. Ball, R. Y., K. L. Carpenter, J. H. Enright, S. L. Hartley, and M. J. Mitchinson. 1987. Ceroid accumulation by murine peritoneal macrophages exposed to artificial lipoproteins. Br. J. Exp. Pathol. 68: 427-438.
63. Mander, E. L., R. T. Dean, K. K. Stanley, and W. Jessup. 1994. Apolipoprotein B of oxidized LDL accumulates in the lysosomes of macrophages. Biochim. Biophys. Acta. 1212: 80-92.
64. Shichiri, G., M. Kinoshita, and Y. Saeki. 1993. Polyunsaturated fatty acid metabolism and acetylated low density lipoprotein uptake in J774A.1 cells. Arch. Biochem. Biaphys. 303: 231-237.
65. Rinninger, F., M. Brundert, S. Jäckle, T. Kaiser, and H. Greten. 1995. Selective uptake of low-density lipoprolein-associated cholesteryl esters by human fibroblasts, human HepG2 hepatoma cells and J774 macrophages in culture. Biochim. Biophys. Acta. 1255: 141-153.
66. Green, S. R., and R. C. Pittman. 1991. Selective uptake of cholesteryl esters from low density lipoproteins in vitro and in vivo. J. Lipid Res. 32: 667-678.
67. Tabas, I. 1997. Phospholipid metabolism in cholesterol-loaded macrophages. Curr. Opin. Lipidol. 8: 263-267.