Cellular toxicity of oxycholesterols

BioEssays

Volumn 28, Issue 4, 2006, Pages 387-398

  Wielkoszyński, Tomasz ^a   Gawron, Katarzyna ^a   Strzelczyk, Joanna ^a   Bodzek, Piotr ^a   Zalewska Ziob, Marzena ^a   Trapp, Gizela ^a   Srebniak, Małgorzata ^a   Wiczkowski, Andrzej ^a  

^a MEDICAL UNIVERSITY OF SILESIA   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLESTEROL DERIVATIVE; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE; OXYCHOLESTEROL; UNCLASSIFIED DRUG;

APOPTOSIS; CELL ACTIVITY; CELL MEMBRANE; CYTOTOXICITY; GENE CONTROL; HOMEOSTASIS; IMMUNE SYSTEM; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; REVIEW; SIGNAL TRANSDUCTION;

ANIMALS; APOPTOSIS; CHOLESTEROL; HUMANS; HYDROXYMETHYLGLUTARYL COA REDUCTASES; OXIDATION-REDUCTION;

EID: 33645826543     PISSN: 02659247     EISSN: None     Source Type: Journal    
DOI: 10.1002/bies.20383     Document Type: Review

References (97)

1. Guardiola F, Codony R, Addis PB, Rafecas M, Boatella J. 1996. Biological effects of oxysterols: current status. Fd ChemToxic 34:193-211.
2. Ishii K, Adachi J, Tomita M, Kurosaka M, Ueno Y. 2002. Oxysterols as indices of oxidative stress in man after paraquat ingestion. Free Radic Res 36:163-168.
3. Dushkin M, Schwartz Y, Volsky N, Musatov M, Vereschagin E, et al. 1998. Effects of oxysterols upon macrophage and lymphocyte functions in vitro. Prostaglandins & other Lipid Mediators 55:219-236.
4. Lizard G, Monier S, Cordelet C, Gesquière L, Deckert V, et al. 1999. Characterization and comparison of the mode of cell death, apoptosis versus necrosis, induced by 7β-hydroxycholesterol and 7-ketocholesterol in the cells of the vascular wall. Arterioscler Thromb Vasc Biol 19: 1190-1200.
5. Ryan L, O'callaghan YC, O'Brien N. 2005. The role of the mitochondria in apoptosis induced by 7β-hydroxycholesterol and cholesterol-5β,6β- epoxide. Br J Nutr 94:519-525.
6. Hwang PL. 1991. Biological activities of oxygenated sterols: physiological and pathological implications. BioEssays 13:583-589.
7. Adcox C, Boyd L, Oehrl L, Allen J, Fenner G. 2001. Comparative effects of phytosterol oxides and cholesterol oxides in cultured macrophage-derived cell lines. J Agric Food Chem 49:2090-2095.
8. Po Chen Hu, Bing Huei Chen. 2002. Effects of riboflavin and fatty acid methyl esters on cholesterol oxidation during illumination. J Agric Food Chem 50:3572-3578.
9. Osada K, Sasaki E, Sugano M. 1994. Lymphatic absorption of oxidized cholesterol in rats. Lipids 29:555-559.
10. Cheng YW, Kang JJ, Shih YL, Lo YL, Wang CF. 2005. Cholesterol-3-beta, 5-alfa, 6-beta-triol induced genotoxicity through reactive oxygen species formation. Fd Chem Toxic 43:617-622.
11. Bodzek D, Janoszka B, Wielkoszynski T. 2000. Oxygenated derivatives of cholesterol. Occurence, biological activities, methods of analysis. (Utlenione pochodne cholesterolu. Wystȩpowanie, rola biologiczna, melody analizy. Wiadomości chemiczne 54:1089-1108.
12. Valenzuela A, Sanhueza J, Nieto S. 2003. Cholesterol oxidation: health hazard and the role of antioxidants in prevention. Biol Res 36:291-302.
13. Brown AJ, Jessup W. 1999. Oxysterols and atherosclerosis. Atherosclerosis 142:1-28.
14. Gelissen IC, Brown AJ, Mander EL, Kritharides L, Dean RT, et al. 1996. Sterol efflux is impaired from macrophage foam cells selectively enriched with 7-ketocholesterol. J Biol Chem 271:17852-17860.
15. Björkhem I. 2002. Do oxysterols control cholesterol homeostasis? J Clin Invest 110:725-730.
16. Mattsson LH, Lindmark H, Diczfalusy U, Bjorkhem J, Ottossan M, et al. 1996. Oxysterols present in atherosclerotic tissue decrease the expression of lipoprotein lipase messenger RNA in human monocyte-derived macrophages. J Clin Invest 97:461-468.
17. Lim HK, Kang HK, Yoo ES, Kim BJ, Kim YW, et al. 2003. Oxysterols induce apoptosis and accumulation of cell cycle at G2/M phase in the human monocytic THP-1 cell line. Life Sciences 72:1389-1399.
18. Kandutsch AA, Chen HW. 1973. Inhibition of sterol synthesis in cultured mouse cells by 7α-hydroxycholesterol, 7β-hydroxycholesterol, and 7-ketocholesterol. J Biol Chem 248:8408-8417.
19. Kandutsch AA, Chen HW. 1974. Inhibition of sterol synthesis in cultured mouse cells by cholesterol derivatives oxygenated in the side chain. J Biol Chem 249:6057-6061.
20. Lyons MA, Brown AJ. 1999. Molecules in focus 7-Ketocholesterol. Int J Biochem Cell Biol 31:369-375.
21. Kandutsch AA, Chen HW. 1978. Inhibition of cholesterol synthesis by oxygenated sterols. Lipids 13:704-707.
22. Schroepfer GJ Jr, Parish EJ, Tsuda M, Raulston DL, Kandutsch AA. 1979. Inhibition of sterol biosynthesis in animal cells by 14α-alkyl substituted 15-oxygenated sterols. J Lipid Res 20:994-998.
23. Schroepfer GJ Jr, Parish EJ, Chen HW, Kandutsch AA. 1977. Inhibition of sterol biosynthesis in L cells and mouse liver cells by 15-oxygenated sterols. J Biol Chem 252:8975-8980.
24. Brown MS, Goldstein JL. 1974. Suppression of 3-hydroxy-3-methylglutaryl coenzyme A reductase activity and inhibition of growth of human fibroblasts by 7-ketocholesterol. J Biol Chem 249:7306-7314.
25. Brown MS, Dana SE, Goldstein JL. 1975. Cholesterol ester formation in cultured human fibroblasts. Stimulation by oxygenated sterols. J Biol Chem 250:4025-4027.
26. Spady DK, Cuthbert JA, Willard MN, Meidell RS. 1995. Adenovirus-mediated transfer of a gene encoding cholesterol 7α-hydroxylase into hamsters increases hepatic enzyme activity and reduces plasma total and low density lipoprotein cholesterol. J Clin Invest 96:700-709.
27. Mambetisaeva ET, Kosykh VA, Misharin AY, Malyugin AV, Kosenkov EI, et al. 1993. Effect of 5H-α-cholest-8(14)-en-3β-ol-15-one on cholesterol metabolism in cultured rabbit hepatocytes. Biochemistry 58:144-148.
28. Taylor FR, Saucier SE, Shown EP, Parish EJ, Kandutsch AA. 1984. Correlation between oxysterol binding to a cytosolic binding protein and potency in the repression of hydroxymethylglutaryl coenzyme A reductase. J Biol Chem 259:12382-12387.
29. Cavenee WK, Gibbons GF, Chen HW, Kandutsch AA. 1979. Effects of various oxygenated sterols on cellular sterol biosynthesis in Chinese hamster lung cells resistant to 25-hydroxycholesterol. Biochim Biophys Acta 575:255-265.
30. Axelson M, Larsson O. 1996. 27-Hydroxylated low density lipoprotein (LDL) cholesterol can be converted to 7α,27-dihydroxy-4-cholesten-3-one (cytosterone) before suppressing cholesterol production in normal human fibroblasts. Evidence that an altered metabolism of LDL cholesterol can underlie a defective feedback control in malignant cells. J Biol Chem 271:12724-12736.
31. Axelson M, Larsson O, Zhang J, Shoda J, Sjövall J. 1995. Structural specificity in the suppression of HMG-CoA reductase in human fibroblasts by intermediates in bile and biosynthesis. J Lipid Res 36: 290-298.
32. Pinkerton FD, Spilman CH, Via DP, Schroepfer GJ Jr. 1993. Differing effects of three oxysterols on low density lipoprotein metabolism in Hep G2 cells. Biochem Biophys Res Commun 193:1091-1097.
33. Swaminathan S, Pinkerton FD, Numazawa S, Wilson WK, Schroepfer GJ Jr. 1992. Inhibitors of sterol synthesis. Chemical syntheses and spectral properties of 3β-hydroxy-5α-cholesta-8(14),24-dien-15-one, 3β,25- dihydroxy-5α-cholest-8(14)-en-15-one, and 3β,24-dihydroxy-5α- cholest-8(14)-en-15-one and their effects on 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in CHO-K1 cells. J Lipid Res 33:1503-1515
34. Swaminathan S, Pinkerton FD, Schroepfer GJ Jr. 1992. Inhibitors of sterol synthesis. 3β,25-Dihydroxy-5α-cholest-8(14)-en-15-one, an active metabolite of 37β-hydroxy-5α-cholest-8(14)-en-15-one. J Med Chem 35:793-795.
35. Kim HS, Wilson WK, Needleman DH, Pinkerton FD, Wilson DK, et al. 1989. Inhibitors of sterol synthesis. Chemical synthesis, structure, and biological activities of (25R)-3β,26-dihydroxy-5α-cholest-8(14)-en-15-one, a metabolite of 3β-hydroxy-5α-cholest-8(14)-en-15-one. J Lipid Res 30:247-261.
36. Schroepfer GJ Jr, Kim HS, Vermilion JL, Stephens TW, Pinkerton FD, et al. 1988. Enzymatic formation and chemical synthesis of an active metabolite of 3β-hydroxy-5α-cholest-8(14)-en-15-one, a potent regulator of cholesterol metabolism. Biochem Biophys Res Commun 151:130-136.
37. Zhang J, Dricu A, Sjövall J. 1997. Studies on the relationships between 7α-hydroxylation and the ability of 25- and 27-hydroxycholesterol to suppress the activity of HMG-CoA reductase. Biochim Biophys Acta 1344:241-249.
38. Martin KO, Reiss AB, Lathe R. Javitt NB. 1997. 7α-Hydroxylation of 27-hydroxycholesterol: biological role in the regulation of cholesterol synthesis. J Lipid Res 37:1053-1058.
39. Zhang J, Larsson O, Sjövall J. 1995. 7α-Hydroxylation of 25-hydroxycholesterol and 27-hydroxycholesterol in human fibroblasts. Biochim Biophys Acta 1256:353-359.
40. Taylor FR, Kandutsch AA, Gayen AK, Nelson JA, Steckbeck Nelson S, et al. 1986. 24,25-Epoxysterol metabolism in cultured mammalian cells and repression of 3-hydroxy-3-methylglutaryl-CoA reductase. J Biol Chem 261:15039-15044.
41. Gupta A, Sexton RC, Rudney H. 1986. Modulation of regulatory oxysterol formation and low density lipoprotein suppression of 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase activity by ketoconazole. A role for cytochrome P-450 in the regulation of HMG-CoA reductase in rat intestinal epithelial cells. J Biol Chem 261:8348-8356.
42. Panini S, Sexton RC, Gupta AK, Parish EJ, Chitrakorn S, et al. 1986. Regulation of 3-hydroxy-3-methylglutaryl coenzyme A reductase activity and cholesterol biosynthesis by oxylanosterols. J Lipid Res 27:1190-1204.
43. Panini S, Delate TA, Sinensky M. 1992. Post-translational regulation of 3-hydroxy-3-methylglutaryl coenzyme A reductase by (24S)-24,25-oxido-lanosterol. J Biol Chem 267:12647-12654.
44. Leonard DA, Kotarski MA, Tessiatore JE, Favata MF, Trzaskos JM. 1994. Post-transcriptional regulation of 3-hydroxy-3-methylglutaryl coenzyme A reductase by 3β-hydroxy-lanost-8-en-32-al, an intermediate in the conversion of lanosterol to cholesterol. Arch Biochem Biophys 310: 152-157.
45. Schroepfer GJ Jr, Parish EJ, Kisic A, Frome DM, Kandutsch AA. 1981. Inhibitors of sterol synthesis. Syntheses and activities of new derivatives of 15-oxygenated sterols. Chem Phys Lipids 29:201-211.
46. Frye LL, Cusack KP, Leonard DA, Anderson JA. 1994. Oxolanosterol oximes: dual-action inhibitors of cholesterol biosynthesis. J Lipid Res 35:1333-1344.
47. Chisolm GM, Ma G, Irwin KC, Martin LL, Gunderson KG, et al. 1994. 7β-Hydroperoxycholest-5-en-3β-ol, a component of human atherosclerotic lesions, is the primary cytotoxin of oxidized human low density lipoprotein. Proc Natl Acad Sci USA 91:11452-11456.
48. Colles SM, Irwin KC, Chisolm GM. 1996. Roles of multiple oxidized LDL lipids in cellular injury: dominance of 7β-hydroperoxycholesterol. J Lipid Res 37:2018-2028.
49. Clare K, Hardwick SJ, Carpenter KLH, Weeratunge N, Mitchinson MJ. 1995. Toxicity of oxysterols to human monocytes-macrophages. Atherosclerosis 118:67-75.
50. Christ M, Luu B, Mejia JE, Moosbrugger I, Bischoff P. 1993. Apoptosis induced by oxysterols in murine lymphoma cells and in normal thymocytes. Immunology 78:455-460.
51. Liu Y, Mattsson L, Wiklund O. 1997. Macrophages isolated from human atherosclerotic plaques produce IL-8, and oxysterols may have a regulatory funtion for IL-8 production. Arterioscler Thromb Vasc Biol 17:317-323.
52. Guyton JR, Lenz ML, Matthews B, Hughes H, Karsan D, et al. 1995. Toxicity of oxidized low density lipoproteins for vascular smooth muscle cells and partial protection by antioxidants. Atherosclerosis 118:237-249.
53. Marinovich M, Guizzetti M, Ghilardi F, Paoletti R, Galli CL. 1995. Effect of 25-hydroxycholesterol, 26-hydroxycholesterol and its analogue, 26-aminocholesterol on protein content, protein synthesis and LDH leakage in mouse epidermal cells. Toxicology 99:125-134.
54. Chang JY, Liu L-Z. 1997. 25-Hydroxycholesterol causes death but does not prevent nerve growth factor-induced neunte outgrowth in PC12 cells. Neurochem Int 31:517-523.
55. Chang JY, Liu L-Z. 1998. Neurotoxicity of cholesterol oxides on cultured cerebellar granule cells. Neurochem Int 32:317-323.
56. Chang JY, Liu L-Z. 1998. Toxicity of cholesterol oxides on cultured neuroretinal cells. Curr Eye Res 17:95-103.
57. Kölsch H, Lütjohann D, Tulke A, Björkhem I, Rao ML. 1999. The neurotoxic effect of 24-hydroxycholesterol on SH-SY5Y human neuroblastoma cells. Brain Res 818:171-175.
58. Aupeix K, Weltin D, Mejia JE, Christ M, Marchial J, et al. 1995. Oxysterol-induced apoptosis in human monocytic cell lines. Immunobiology 194:415-428.
59. Hayden JM, Brachova L, Higgins K, Obermiller L, Sevanian A, et al. 2002. Induction of monocyte differentiation and foam cell formation in vitro by 7-ketocholesterol. J Lipid Res 43:26-35.
60. Nishio E, Watanabe Y. 1996. Oxysterols induced apoptosis in cultured smooth muscle cells through CPP32 protease activation and bcl-2 protein downregulation. Biochem Biophys Res Commun 226:928-934.
61. Lizard G, Gueldry S, Deckert V, Gambert P, Lagrost L. 1997. Evaluation of the cytotoxic effects of some oxysterols and of cholesterol on endothelial cell growth: methodological aspects. Pathol Biol 45:281-290.
62. Zhang J, Xue Y, Jondal M, Sjövall J. 1997. 7α-Hydroxylation and 3-dehydrogenation abolish the ability of 25-hydroxycholesterol and 27-hydroxycholesterol to induce apoptosis in thymocytes. Eur J Biochem 247:129-135.
63. Lizard G, Deckert V, Dubrez L, Moisant M, Gambert P, et al. 1996. Induction of apoptosis in endothelial cells treated with cholesterol oxides. Am J Pathol 148:1625-1638.
64. Palladini G, Finardi G, Bellomo G. 1996. Disruption of actin microfilament organization by cholesterol oxides in 73/73 endothelial cells. Exp Cell Res 223:72-82.
65. Ryan L, O'Callaghan YC, O'Brien NM. 2004. Comparison of the apoptotic processes induced by the oxysterols 7β-hydroxycholesterol and cholesterol-5β,6β-epoxide. Cell Biol Toxicol 20:313-323.
66. O'callaghan YC, Woods JA, O'brien NM. 2002. Characteristics of 7β-hydroxycholesterol induced cell death in a human monocytic blood cell line, U937, and a human hepatoma cell line, Hep G2. Toxicol In Vitro 16:245-251.
67. O'sullivan AJ, O'callaghan YC, O'brien NM. 2005. Differential effects of mixtures of cholesterol oxidation products on bovine aortic endothelial cells and human monocytic U937 cells. Int J Toxicol 24:173-179.
68. Nishio E, Arimura S, Watanabe Y. 1996. Oxidized LDL induces apoptosis in cultured smooth muscle cells: a possible role for 7-ketocholesterol. Biochem Biophys Res Commun 223:413-418.
69. Berthier A, Lemaire-Ewing S, Prunet C, Montange T, Vejux A, et al. 2005. 7-ketocholesterol-induced apoptosis. Involvement of several pro-apoptotic but also anti-apoptotic calcium-dependent transduction pathways. FEBS J 272:3093-3104.
70. Sevanian A, Hodis HN, Hwang J, McLeod LL, Peterson H. 1995. Characterization of endothelial cell injury by cholesterol oxidation products found in oxidized LDL. J Lipid Res 36:1971-1986.
71. Zhou Q, Jimi S, Smith TL, Kummerow FA. 1991. The effect of 25-hydroxycholesterol on accumulation of intracellular calcium. Cell Calcium 12:467-476.
72. Neyes L, Locher R, Stimpel R, Vetter W. 1985. Stereospecific modulation of the calcium channel in human erythrocytes by cholesterol and its oxidized derivatives. Biochem J 227:105-112.
73. Liu H, Yuan L, Xu S, Zhang T, Wang K. 2004. Cholestane-3β,5α, 6β-triol promotes vascular smooth muscle cells calcyfication. Life Sci 76:533-543. A5
74. 2+ uptake and lipid content in cultured human arterial smooth muscle cells treated with 26-hydroxycholesterol. Artery 21:182-192.
75. Peng S-K, Hu B, Peng AY, Morin RJ. 1993. Effect of cholesterol oxides on prostacyclin production and platelet adhesion. Artery 20:122-134.
76. Deckert V, Perségol L, Viens L, Lizard G, Athias A, et al. 1997. Inhibitors of arterial relaxation amoung components of human oxidized low-density lipoproteins. Cholesterol derivatives oxidized in position 7 are potent inhibitors of endothelium-dependent relaxation. Circulation 95:723-731.
77. Johansson M, Bocher V, Lehto M, Chinetti G, Kuismanen E, et al. 2003. The two variants of oxysterol binding protein-related protein-1 display different tissue expression patterns, have different intracellular localization, and are functionally distinct. MBC 14:903-915.
78. Edwards PA, Ericsson J. 1998. Signaling molecules derived from the cholesterol biosynthetic pathway: mechanisms of action and possible roles in human disease. Curr Opin Lipidol 9:433-440.
79. Janowski BA, Willy PJ, Devi TR, Falck JR, Mangelsdorf DJ. 1996. An oxysterol signaling pathway mediated by the nuclear receptor LXR alpha. Nature 383:728-731.
80. Lala DS, Syka PM, Lazarchik SB, Mangelsdorf DJ, Parker KL, et al. 1997. Activation of the orphan nuclear receptor steroidogenic factor 1 by oxysterols. Proc Natl Acad Sci USA 94:4895-4900.
81. Lehmann JM, Kliewer SA, Moore LB, Smith-Oliver TA, Oliver BB, et al. 1997. Activation of the nuclear receptor LXR by oxysterols defines a new hormone response pathway. J Biol Chem 272:3137-3140.
82. Fu X, Menke JG, Chen Y, Zhou G, MacNaul KL, et al. 2001. 27-hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells. J Biol Chem 276:38378-38387.
83. Yoshikawa T, Shimano H, Amemiya-Kudo M, Yahagi N, Hasty AH, et al. 2001. Identification of liver X receptor-retinoid X receptor as an activator of the sterol regulatory element-binding protein 1c gene promoter. Mol Cell Biol 21:2991-3000.
84. Olkkonen VM, Lehto M. 2004. Oxysterols and oxysterol binding proteins: role in lipid metabolism and atherosclerosis. Ann Med 36:562-572.
85. Olkkonen V. 2004. Oxysterol binding protein and its homologues: new regulatory factors involved in lipid metabolism. Curr Opin Lipidol 15:321-327.
86. Thompson EB, Ayala-Torres S. 1999. Oxysterols and apoptosis: evidence for gene regulation outside the cholesterol pathway. Crit Rev Biochem Mol Biol 34:25-32.
87. Schmuth M, Bikle DD, Willson PM, Mangelsdorf DJ, Elias PM, et al. 2005. Pro-differentiating effects of oxysterols in keratinocytes. Exp Dermatol 14:154-155.
88. Kha HT, Basseri B, Shouhed D, Richardson J, Tetradis S, et al. 2004. Oxysterols regulate differentiation of mesenchymal stem cells: pro-bone and anti-fat. J Bone Miner Res 19:830-840.
89. Girao H, Shang F, Pereira P. 2003. 7-ketocholesterol stimulates differentiation of lens epithelial cells. Mol Vis 9:497-501.
90. Kucuk O, Stoner-Picking J, Yachnin S, Gordon LI, Williams RM, et al. 1992. Inhibition of NK-cell-mediated cytotoxicity by oxysterols. Cellular Immunology 139:541-549.
91. Leonarduzzi G, Gamba P, Sottero B, Kadi A, Robbesyn F, et al. 2005. Oxysterol induced up-regulation of MCP-1 expression and synthesis and macrophage cells. Free Radic BiOl Med 39:1152-1161.
92. Martinet W, De-Bie M, Schrijvers DM, De-Meyer GR, Herman AG, et al. 2004. 7-ketocholesterol induces protein ubiquitination, myelin figure formation, and light chain 3 processing in vascular smooth muscle cells. Arterioscler Thromb Vasc Biol 24:2296-2301.
93. Kucuk O, Stoner-Picking S, Yachnin S, Gordon LJ, Williams RM, et al. 1994. Inhibition of cytolytic T-lymphocyte activity by oxysterols. Lipids 29:657-660.
94. Yoon JH, Canbay AE, Werneburg NW, Lee SP, Gores GJ. 2004. Oxysterols induce cyclooxygenase-2 expression in cholangiocytes: implications for biliary tract carcinogenesis. Hepatology 39:732-738.
95. Seo DW, Choi HS, Lee SP, Kuver R. 2004. Oxysterols from human bile induce apoptosis of canine gallbladder epithelial cells in monolayer culture. Am. J. Physiol. Gastrointest. Liver Physiol 287:61247-1256.
96. Wolfreys AM, Hepburn PA. 2002. Safety evaluation of phytosterol esters. Part 7. Assessment of mutagenic activity of phytosterols, phytosterol esters and the cholesterol derivative, 4-cholesten-3-one. Fd Chem Toxic 40:461-470.
97. Spiteller G. 1998. Linoleic acid peroxidation-the dominant lipid peroxidation process in low density lipoprotein-and its relationship to chronic diseases. Chem Phys Lipids 95:105-162.