Proatherogenic effects of the cholesterol ozonolysis products, atheronal-A and atheronal-B

Biochemistry

Volumn 45, Issue 23, 2006, Pages 7162-7170

  Takeuchi, Cindy ^a   Galvé, Roger ^a   Nieva, Jorgé ^a   Witter, Daniel P ^b   Wentworth, Anita D ^a   Troseth, Ryan P ^a   Lerner, Richard A ^a   Wentworth Jr , Paul ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BLOOD VESSELS; CELL CULTURE; CELLS; DEGRADATION; OZONE; PROTEINS;

CELL-SURFACE ADHESION; LOW-DENSITY LIPOPROTEIN (LDL); MACROPHAGES; PROATHEROGENIC PROPERTIES;

CHOLESTEROL;

ATHERONAL A; ATHERONAL B; CD36 ANTIGEN; CHOLESTEROL; CHOLESTEROL DERIVATIVE; LOW DENSITY LIPOPROTEIN; OXIDIZED LOW DENSITY LIPOPROTEIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; ATHEROGENESIS; CELL DIFFERENTIATION; CHOLESTEROL METABOLISM; CYTOTOXICITY; ENDOTHELIUM CELL; FOAM CELL; HUMAN; HUMAN CELL; LIPID OXIDATION; MACROPHAGE ACTIVATION; MONOCYTE; MOUSE; NONHUMAN; OZONOLYSIS; PRIORITY JOURNAL; VASCULAR ENDOTHELIUM;

ANIMALS; ATHEROSCLEROSIS; CELL LINE; CHOLESTEROL; ENDOTHELIUM, VASCULAR; HUMANS; MACROPHAGES; MAGNETIC RESONANCE SPECTROSCOPY; MICE; OZONE; RECEPTORS, SCAVENGER; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 33745051110     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi0604330     Document Type: Article

References (44)

1. Libby, P., Ridker, P. M., and Maseri, A. (2002) Inflammation and atherosclerosis, Circulation 105, 1135-1143.
2. Brennan, M. L., and Hazen, S. L. (2003) Emerging role of myeloperoxidase and oxidant stress markers in cardiovascular risk assessment, Curr. Opin. Lipidol. 14, 353-359.
3. Brennan, M. L., Penn, M. S., van Lente, F., Nambi, V., Shishehbor, M. H., Aviles, R. J., Goormastic, M., Pepoy, M. L., McErlean, E. S., Topol, E. J., Nissen, S. E., and Hazen, S. L. (2003) Prognostic value of myeloperoxidase in patients with chest pain, N. Engl. J. Med. 349, 1595-1604.
4. Wentworth, P., Jr., Nieva, J., Takeuchi, C., Galve, R., Wentworth, A. D., Dilley, R. B., DeLaria, G. A., Saven, A., Babior, B. M., Janda, K. D., Eschenmoser, A., and Lerner, R. A. (2003) Evidence for ozone formation in human atherosclerotic arteries, Science 302, 1053-1056.
5. Smith, L. L. (1981) Cholesterol Autoxidation, Plenum Press, New York.
6. Wang, K., Bermúdez, E., and Pryor, W. A. (1993) The ozonation of cholesterol: Separation and identification of 2,4-dinitrophenylhydrazine derivatization products of 3β-hydroxy-5-oxo-5,6-secocholestan-6-al, Steroids 58, 225-229.
7. Deleted during publication.
8. Zhang, Q. H., Powers, E. T., Nieva, J., Huff, M. E., Dendle, M. A., Bieschke, J., Glabe, C. G., Eschenmoser, A., Wentworth, P., Lerner, R. A., and Kelly, J. W. (2004) Metabolite-initiated protein misfolding may trigger Alzheimer's disease, Proc. Natl. Acad. Sci. U.S.A. 101, 4752-4757.
9. Wachtel, E., Bach, D., Epand, R. F., Tishbee, A., and Epand, R. M. (2006) A product of ozonolysis of cholesterol alters the biophysical properties of phosphatidylethanolamine membranes, Biochemistry 45, 1345-1351.
10. Rydberg, E. K., Salomonsson, L., Hulten, L. M., Noren, K., Bondjers, G., Wiklund, O., Bjornheden, T., and Ohlsson, B. G. (2003) Hypoxia increases 25-hydroxycholesterol-induced interleukin-8 protein secretion in human macrophages, Atherosclerosis 170, 245-252.
11. Liao, H. S., Kodama, T., and Geng, Y. J. (2000) Expression of class A scavenger receptor inhibits apoptosis of macrophages triggered by oxidized low-density lipoprotein and oxysterol, Arterioscler., Thromb., Vasc. Biol. 20, 1968-1975.
12. Cader, A. A., Steinberg, F. M., Mazzone, T., and Chait, A. (1997) Mechanisms of enhanced macrophage apoE secretion by oxidized LDL, J. Lipid Res. 38, 981-991.
13. Landis, M. S., Patel, H. V., and Capone, J. P. (2002) Oxysterol activators of liver X receptor and 9-cis-retinoic acid promote sequential steps in the synthesis and secretion of tumor necrosis factor-α from human monocytes, J. Biol. Chem. 277, 4713-4721.
14. Reaven, P. D., Grasse, B. J., and Tribble, J. D. (1994) Effects of linoleate-enriched and oleate-enriched diets in combination with α-tocopherol on the susceptibility of LDL and LDL subfractions to oxidative modification in humans, Arterioscler., Thromb., Vasc. Biol. 14, 557-566.
15. Ohkawa, H., Ohishi, N., and Yagi, K. (1979) Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction, Anal. Biochem. 95, 351-358.
16. Nichols, W. W., Buynak, E. B., Bradt, C., Hill, R., Aronson, M., Jarrell, B. E., Mueller, S. N., and Levine, E. M. (1987) Cytogenetic evaluation of human endothelial cell cultures, J. Cell. Physiol. 132, 453-462.
17. Ralph, P., Moore, M. A., and Nilsson, K. (1976) Lysozyme synthesis by established human and murine histiocytic lymphoma cell lines, J. Exp. Med. 143, 1528-1533.
18. Tsuchiya, S., Kobayashi, Y., Goto, Y., Okumura, H., Nakae, S., Konno, T., and Tada, K. (1982) Induction of maturation in cultured human monocytic leukemia cells by a phorbol diester, Cancer Res. 42, 1530-1536.
19. Sundstrom, C., and Nilsson, K. (1976) Establishment and characterization of a human histiocytic lymphoma cell line (U-937), Int. J. Cancer 17, 565-577.
20. Huh, H. Y., Pearce, S. F., Yesner, L. M., Schindler, J. L., and Silverstein, R. L. (1996) Regulated expression of CD36 during monocyte-to-macrophage differentiation: Potential role of CD36 in foam cell formation, Blood 87, 2020-2028.
21. Zwirner, J., Werfel, T., Wilken, H. C., Theile, E., and Gotze, O. (1998) Anaphylatoxin C3a but not C3a(desArg) is a chemotaxin for the mouse macrophage cell line J774, Eur. J. Immunol. 28, 1570-1577.
22. Wilkinson, P. C. (1988) Micropore filter methods for leukocyte chemotaxis, Methods Enzymol. 162, 38-50.
23. Ng, M. K., Nakhla, S., Baoutina, A., Jessup, W., Handelsman, D. J., and Celermajer, D. S. (2003) Dehydroepiandrosterone, an adrenal androgen, increases human foam cell formation: A potentially pro-atherogenic effect, J. Am. Coll. Cardiol. 42, 1967-1974.
24. Khan, B. V., Parthasarathy, S. S., Alexander, R. W., and Medford, R. M. (1995) Modified low-density lipoprotein and its constituents augment cytokine-activated vascular cell adhesion molecule-1 gene expression in human vascular endothelial cells, J. Clin. Invest. 95, 1262-1270.
25. Huang, W. C., Chan, S. T., Yang, T. L., Tzeng, C. C., and Chen, C. C. (2004) Inhibition of ICAM-1 gene expression, monocyte adhesion and cancer cell invasion by targeting IKK complex: Molecular and functional study of novel α-methylene-γ-butyrolactone derivatives, Carcinogenesis 25, 1925-1934.
26. Ridgway, N. D., Dawson, P. A., Ho, Y. K., Brown, M. S., and Goldstein, J. L. (1992) Translocation of oxysterol binding protein to Golgi apparatus triggered by ligand binding, J. Cell Biol. 116, 307-319.
27. Johansson, M., Bocher, V., Lehto, M., Chinetti, G., Kuismanen, E., Ehnholm, C., Staels, B., and Olkkonen, V. M. (2003) The two variants of oxysterol binding protein-related protein-1 display different tissue expression patterns, have different intracellular localization, and are functionally distinct, Mol. Biol. Cell 14, 903-915.
28. Nicholson, A. C., Han, J., Febbraio, M., Silversterin, R. L., and Hajjar, D. P. (2001) Role of CD36, the macrophage class B scavenger receptor, in atherosclerosis, Ann. N.Y. Acad. Sci. 947, 224-228.
29. Kunjathoor, V. V., Febbraio, M., Podrez, E. A., Moore, K. J., Andersson, L., Koehn, S., Rhee, J. S., Silverstein, R., Hoff, H. F., and Freeman, M. W. (2002) Scavenger receptors class A-I/II and CD36 are the principal receptors responsible for the uptake of modified low-density lipoprotein leading to lipid loading in macrophages, J. Biol. Chem. 277, 49982-49988.
30. Yoshida, H., Quehenberger, O., Kondratenko, N., Green, S., and Steinberg, D. (1998) Minimally oxidized low-density lipoprotein increases expression of scavenger receptor A, CD36, and macrosialin in resident mouse peritoneal macrophages, Arterioscler., Thromb., Vasc. Biol. 18, 794-802.
31. Han, J., Hajjar, D. P., Febbraio, M., and Nicholson, A. C. (1997) Native and modified low-density lipoproteins increase the functional expression of the macrophage class B scavenger receptor, CD36, J. Biol. Chem. 272, 21654-21659.
32. Nakagawa, T., Nozaki, S., Nishida, M., Yakub, J. M., Tomiyama, Y., Nakata, A., Matsumoto, K., Funahashi, T., Kameda-Takemura, K., Kurata, Y., Yamashita, S., and Matsuzawa, Y. (1998) Oxidized LDL increases and interferon-γ decreases expression of CD36 in human monocyte-derived macrophages, Arterioscler., Thromb., Vasc. Biol. 18, 1350-1357.
33. Parthasarathy, S., Quinn, M. T., and Steinberg, D. (1988) Is oxidized low-density lipoprotein involved in the recruitment and retention of monocyte/macrophages in the artery wall during the initiation of atherosclerosis? Basic Life Sci. 49, 375-380.
34. Quinn, M. T., Parthasarathy, S., Fong, L. G., and Steinberg, D. (1987) Oxidatively modified low-density lipoproteins: A potential role in recruitment and retention of monocyte/macrophages during atherogenesis, Proc. Natl. Acad. Sci. U.S.A. 84, 2995-2998.
35. Pataki, M., Lusztig, G., and Robenek, H. (1992) Endocytosis of oxidized LDL and reversibility of migration inhibition in macrophage-derived foam cells in vitro. A mechanism for atherosclerosis regression? Arterioscler., Thromb., Vasc. Biol. 12, 936-944.
36. Zerbinatti, C. V., and Gore, R. W. (2003) Uptake of modified low-density lipoproteins alters actin distribution and locomotor forces in macrophages, Am. J. Physiol. Cell Physiol. 284, C555-C561.
37. Vielma, S. A., Mironova, M., Ku, J. R., and Lopes-Virella, M. F. (2004) Oxidized LDL further enhances expression of adhesion molecules in Chlamydophila pneumoniae-infected endothelial cells, J. Lipid Res. 45, 873-880.
38. Charo, I. F., Bekeart, L. S., and Phillips, D. R. (1987) Platelet glycoprotein IIb-IIIa-like proteins mediate endothelial cell attachment to adhesive proteins and the extracellular matrix, J. Biol. Chem. 262, 9935-9938.
39. Hayden, J. M., Brachova, L., Higgins, K., Obermiller, L., Sevanian, A., Khandrika, S., and Reaven, P. D. (2002) Induction of monocyte differentiation and foam cell formation in vitro by 7-ketocholesterol, J. Lipid Res. 43, 26-35.
40. Hayden, J. M., Brachova, L., Higgins, K., Obermiller, L., Sevanian, A., Khandrika, S., and Reaven, P. D. (2002) Induction of monocyte differentiation and foam cell formation in vitro by 7-ketocholesterol, J. Lipid Res. 43, 26-35.
41. Brown, A. J., and Jessup, W. (1999) Oxysterols and atherosclerosis, Atherosclerosis 142, 1-28.
42. Brown, A. J., Leong, S. L., Dean, R. T., and Jessup, W. (1997) 7-Hydroperoxycholesterol and its products in oxidized low-density lipoprotein and human atherosclerotic plaque, J. Lipid Res. 38, 1730-1745.
43. Pulfer, M. K., Taube, C., Gelfand, E., and Murphy, R. C. (2005) Ozone exposure in vivo and formation of biologically active oxysterols in the lung, J. Phamacol. Exp. Ther. 312, 256-264.
44. Pulfer, M. K., and Murphy, R. C. (2004) Formation of biologically active oxysterols during ozonolysis of cholesterol present in lung surfactant, J. Biol. Chem. 279, 26331-26338.