Biological effects of oxysterols: Current status

Food and Chemical Toxicology

Volumn 34, Issue 2, 1996, Pages 193-211

  Guardiola, F ^a,b   Codony, R ^a   Addis, P B ^b   Rafecas, M ^a   Boatella, J ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLESTEROL DERIVATIVE;

ATHEROGENESIS; ATHEROSCLEROSIS; CARCINOGENICITY; CYTOTOXICITY; ETIOLOGY; HUMAN; HYPERCHOLESTEROLEMIA; MUTAGENICITY; NONHUMAN; OXIDATION; REVIEW; THROMBOSIS;

EID: 0029921575     PISSN: 02786915     EISSN: None     Source Type: Journal    
DOI: 10.1016/0278-6915(95)00094-1     Document Type: Review

References (219)

1. Addis P. B., Emanuel H. A., Bergmann S. D. and Zavoral J. H. (1989) Capillary GC quantification of cholesterol oxidation products in plasma lipoproteins of fasted humans. Free Radical Biology and Medicine 7, 179-182.
2. Addis P. B. and Park S. W. (1989) Role of lipid oxidation products in atherosclerosis. In Food Toxicology, a Perspective on the Relative Risks. Edited by S. L. Taylor and R. A. Scanlan. pp. 297-330. Marcel Dekker, New York.
3. Addis P. B. and Warner G. J. (1991) The potential health aspects of lipid oxidation products in food. In Free Radicals and Food Additives. Edited by O. I. Aruoma and B. Halliwell. pp. 77-119. Taylor and Francis, London.
4. Allemand I., Christ M., Pannecoucke X., Molina T., Luu B. and Briand P. (1993) Effect of oxysterol derivatives on the time course development of hepatocarcinoma in transgenic mice. Anticancer Research 13, 1097-1101.
5. Ansari G. A. S., Walker R. D., Smart V. B. and Smith L. L. (1982) Further investigations of mutagenic cholesterol preparations. Food and Chemical Toxicology 20, 35-41.
6. Astruc M. E., Beseme F., Defay R. and Crastes de Paulet A. (1985) Evidence for a hydroxysterol binding protein (OSBP) in different cell lines: characterization and biological implications. Journal of the American Oil Chemists' Society 62, 623a.
7. Ayala-Torres S., Johnson B. H. and Thompson E. B. (1994) Oxysterol sensitive and resistant lymphoid cells: correlation with regulation of cellular nucleic acid binding protein mRNA. Journal of Steroid Biochemistry and Molecular Biology 48, 307-315.
8. Bakos J. T., Johnson B. H. and Thompson E. B. (1993) Oxysterol-induced cell death in human leukemic T-cells correlates with oxysterol binding protein occupancy and is independent of glucocorticoid-induced apoptosis. Journal of Steroid Biochemistry and Molecular Biology 46, 415-426.
9. Baranowski A., Adams C. W. M., Bayliss High O. B. and Bowyer D. B. (1982) Connective tissue responses to oxysterols. Atherosclerosis 41, 255-266.
10. Bascoul J., Domergue N. and Crastes de Paulet A. (1985) Intestinal absorption of cholesterol autoxidation products in dietary fats. Journal of the American Oil Chemists' Society 62, 623a.
11. Bascoul J., Domergue N., Mourot J., Debry G. and Crastes de Paulet A. (1986) Intestinal absorption and fecal excretion of 5,6α-epoxy-5α-cholesta-3β-ol by the male Wistar rat. Lipids 21, 744-747.
12. Bates S. R., Jett C. M. and Miller J. E. (1983) Prevention of the hyperlipidemic serum or LDL-induced cellular cholesterol ester accumulation by 22-hydroxycholesterol and its analogue. Biochimica et Biophysica Acta 753, 281-293.
13. Beirne O. R., Heller R. and Watson J. A. (1977) Regulation of 3-hydroxy-3-methylglutaryl coenzyme A reductase in minimal deviation hepatoma 7288C. Immunological measurements in hepatoma tissue culture cell. Journal of Biological Chemistry 252, 950-954.
14. Bell J. J., Sargeant T. E. and Watson J. A. (1976) Inhibition of 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in hepatoma tissue culture cells by pure cholesterol and several cholesterol derivatives. Evidence supporting two distinct mechanisms. Journal of Biological Chemistry 251, 1745-1758.
15. Benga G., Hodârnau A., Ionescu M., Pop V. I., Frangopol P. T., Strujan V., Holmes R. P. and Kummerow F. A. (1983) A comparison of the effects of cholesterol and 25-hydroxycholesterol on egg yolk lecithin liposomes: spin label studies. Annals of the New York Academy of Sciences 414, 140-152.
16. Bernheimer A. W., Robinson W. G., Linder R., Mullins D., Yip Y. K., Cooper N. S., Seidman I. and Uwajima T. (1987) Toxicity of enzymically-oxidized low-density lipoprotein. Biochemical and Biophysical Research Communications 148, 260-266.
17. Bischoff F. (1969) Carcinogenic effect of steroids. Advances in Lipid Research 7, 165-244.
18. Björkhem I., Reihnér E., Angelin B., Ewerth S., Åkerlund J. E. and Einarsson K. (1987) On the possible use of the serum level of 7-hydroxycholesterol as a marker for increased activity of the cholesterol 7α-hydroxylase in humans. Journal of Lipid Research 28, 889-894.
19. Black H. S. and Chan J. T. (1976) Etiologic related studies of ultraviolet light-mediated carcinogenesis. Oncology 33, 119-122.
20. Black H. S. and Douglas D. R. (1972) Model system for the evaluation of the role of cholesterol α-oxide in ultraviolet carcinogenesis. Cancer Research 32, 2630-2632.
21. Black H. S. and Lo W. B. (1971) Formation of a carcinogen in human skin irradiated with ultraviolet light. Nature 234, 306-308.
22. Blackburn G. M., Rashid A. and Thompson M. H. (1979) Interaction of 5α,6α-cholesterol oxide with DNA and other nucleophiles. Journal of the Chemical Society, Chemical Communications 420-421.
23. Blankenship J. W., Van Gent C. M., Sandberg L. B., Roos P. J. and Scharffenberg J. A. (1991) Oxysterol incorporation into rat aorta resulting in elastin compositional changes. Lipids 26, 381-383.
24. Bochelen D., Eclancher F., Kupferberg A., Privat A. and Mersel M. (1992) 7β-hydroxycholesterol and 7β-hydroxycholesteryl-3-esters reduce the extent of reactive gliosis caused by an electrolytic lesion in rat brain. Neuroscience 51, 827-834.
25. Boissonneault G. A., Hennig B. and Ouyang C. M. (1991a) Oxysterols, cholesterol biosynthesis, and vascular endothelial cell monolayer barrier function. Proceedings of the Society for Experimental Biology and Medicine 196, 338-343.
26. Boissonneault G. A., Hennig B., Wang Y., Ouyang C. M., Krahulik K., Cunnup L. and Oeltgen P. R. (1991b) Effect of oxysterol-enriched low density lipoprotein on endothelial barrier function in culture. Annals of Nutrition and Metabolism 35, 226-232.
27. Brooks C. J. W., Cole J. W., MacLachlan J. and Lawrie T. D. V. (1985) Some aspects of the analysis of minor oxygenated sterols in serum and in serum lipoprotein fractions. Journal of the American Oil Chemists' Society 62, 622a.
28. Brooks C. J. W., McKenna R. M., Cole W. J., MacLachlan J. and Lawrie T. D. V. (1983) Profile analysis of oxygenated sterols in plasma and serum. Biochemical Society Transactions 11, 700-701.
29. Brown M. S., Dana S. E. and Goldstein J. L. (1974) Regulation of 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in cultured fibroblasts. Comparison of cells from a normal subject and from a patient with homozygous familial hypercholesterolaemia. Journal of Biological Chemistry 249, 789-796.
30. Brown M. S. and Goldstein J. L. (1974) Suppression of 3-hydroxy-3-methylglutaryl coenzyme A reductase activity and inhibition of growth of human fibroblast by 7-ketocholesterol. Journal of Biological Chemistry 249, 7306-7314.
31. Brown M. S. and Goldstein J. L. (1975) Regulation of the activity of the low density lipoprotein receptor in human fibroblast. Cell 6, 307-316.
32. Carr T. P., Parks J. S. and Rudel L. L. (1992) Hepatic ACAT activity in African green monkeys is highly correlated to plasma LDL cholesteryl ester enrichment and coronary artery atherosclerosis. Arteriosclerosis and Thrombosis 12, 1274-1283.
33. Cavenee W. K., Chen H. W. and Kandutsch A. A. (1981) Regulation of cholesterol biosynthesis in enucleated cells. Journal of Biological Chemistry 256, 2675-2681.
34. Chan J. T. and Black H. S. (1974) Skin carcinogenesis: cholesterol-5α,6α-epoxide hydrase activity in mouse skin irradiated with ultraviolet light. Science 186, 1216-1217.
35. Chang T. Y. and Limanek J. S. (1980) Regulation of cytosolic acetoacetyl coenzyme A thiolase. 3-hydroxy-3-methylglutaryl coenzyme A synthase. 3-hydroxy-3-methylglutaryl coenzyme A reductase and mevalonate kinase by low density lipoprotein and by 25-hydroxycholesterol in Chinese hamster ovary cell. Journal of Biological Chemistry 255, 7787-7795.
36. Chang T. Y., Limanek J. S. and Chang C. C. Y. (1981) Evidence indicating that inactivation of 3-hydroxy-3-methylglutaryl coenzyme A reductase by low density lipoprotein or by 25-hydroxycholesterol requires mediator protein(s) with rapid turnover rate. Journal of Biological Chemistry 256, 6174-6180.
37. Chen H. W., Cavenee W. K. and Kandutsch A. A. (1979) Sterol synthesis in variant Chinese hamster lung cells selected for resistance to 25-hydroxy-cholesterol. Cross resistance to 7-ketocholesterol. 20α-Hydroxycholesterol and serum. Journal of Biological Chemistry 254, 715-720.
38. Chen H. W., Kandutsch A. A. and Waymouth C. (1974) Inhibition of cell growth by oxygenated derivatives of cholesterol. Nature 251, 419-421.
39. Chen H. W., Richards B. A. and Kandutsch A. A. (1982) Inhibition of protein synthesis blocks the response to 25-hydroxycholesterol by inhibiting degradation of hydroxymethylglutaryl-CoA reductase. Biochimica et Biophysica Acta 712, 484-489.
40. Cheng D., Chang C. C., Qu X. and Chang T. Y. (1995) Activation of acyl-coenzyme A: cholesterol acyltransferase by cholesterol or by oxysterol in a cell-free system. Journal of Biological Chemistry 270, 685-695.
41. Choi J. W., Lundquist E. N. and Peffley D. M. (1993) Inhibition of protein synthesis in baby-hamster kidney cells blocks oxysterol-mediated suppression of 3-hydroxy-3-methylglutaryl CoA reductase mRNA at a post-transcriptional level. Biochemical Journal 296, 859-866.
42. Christ M., Ji Y. H., Moog C., Pannecoucke X., Schmitt G., Bischoff P. and Luu B. (1991) Antitumor activity of oxysterols. Effect of two water-soluble monophosphoric acid diesters of 7β-hydroxycholesterol on mastocytoma P815 in vivo. Anticancer Research 11, 359-364.
43. Christ M., Luu B., Mejia J. E., Moosbrugger I. and Bischoff P. (1993) Apoptosis induced by oxysterols in murine lymphoma cells and in normal thymocytes. Immunology 78, 455-60.
44. 1H NMR study. FEBS Letters 355, 81-90.
45. Crastes de Paulet A., Astruc M. E. and Bascoul J. (1988) Les oxystérols: Propriétés biologiques et problèmes nutritionnels. In Biologie des Lipides Chez L'homme. Edited by L. Dousty-Blazy and F. Mendy. pp. 154-174. Editions Médicales Internationales, Paris.
46. Danielson H. and Horning M. G. (1962) On the oxidation of cholesterol by blood in vitro. Acta Chemica Scandinavica 16, 774-775.
47. De Flora S., Camoirano A., Zanacchi P. and Bennicelli C. (1984) Mutagenicity testing with TA97 and TA102 of 30 DNA-damaging compounds, negative with other Salmonella strains. Mutation Research 134, 159-165.
48. Dollis D. and Schuber F. (1994) Effects of a 2,3-oxidosqualene-lanosterol cyclase inhibitor 2,3:22,23-dioxidosqualene and 24,25-epoxycholesterol on the regulation of cholesterol biosynthesis in human hepatoma cell line HepG2. Biochemical Pharmacology 48, 49-57.
49. Drevon C. A. and Evensen S. A. (1984) Demonstration of intact intracellular cholesterol esterification and normal low-density lipoprotein pathway in fibroblasts from a patient with lecithin: cholesterol acyltransferase deficiency. Biochimica el Biophysica Acta 794, 479-483.
50. Duthie G. G. (1991) Antioxidant hypothesis of cardiovascular disease. Trends in Food Science and Technology August, 205-207.
51. Emanuel H. A., Hassel C. A., Addis P. B., Bergmann S. D. and Zavoral J. H. (1991) Plasma cholesterol oxidation products (oxysterols) in human subjects fed a meal rich in oxysterols. Journal of Food Science 56, 843-847.
52. Fitch B. (1994) Antioxidants: health implications. INFORM 5, 242-252.
53. Fornas E., Martinez-Sales V., Camañas A. and Baguena J. (1984) Intestinal absorption of cholesterol autoxidation products in the rat. Archivos de Farmacologia y Toxicologia 10, 175-182.
54. Gey K. F. (1986) On the antioxidant hypothesis with regard to arteriosclerosis. Bibliotheca Nutritio et Dieta 37, 53-91.
55. Gibbons G. F. (1983) Molecular control of 3-hydroxy-3-methylglutaryl coenzyme A reductase: the role of oxygenated sterols. In 3-Hydroxy-3-methylglutaryl Coenzyme A Reductase. Edited by J. R. Sabine, pp. 153-168. CRC Press, Boca Ratón, FL.
56. Gilbert J. D., Brooks C. J. W. and Harland W. A. (1972) Lipids of human atheroma. VII. Isolation of diesters of cholest-5-ene-3β,26-diol from extracts of advanced atherosclerotic lesions of human aorta. Biochimica et Biophysica Acta 270, 149-155.
57. Glatt H., Jung R. and Oesch F. (1983) Bacterial mutagenicity investigation of epoxides: drugs, drug metabolites, steroids and pesticides. Mutation Research 111, 99-118.
58. Glomset J. A., Geld M. H. and Farnsworth C. C. (1990) Prenyl proteins in eukaryotic cells: a new type of membrane anchor. Trends in Biochemical Sciences 15, 139-142.
59. Goldstein J. L. and Brown M. S. (1977) The low density lipoprotein pathway and its relation to atherosclerosis. Annual Review of Biochemistry 46, 897-930.
60. Goldstein J. L., Kita T. and Brown M. S. (1983) Defective lipoprotein receptor and atherosclerosis. New England Journal of Medicine 309, 288-296.
61. Gray M. F., Lawrie T. D. V. and Brooks C. J. W. (1971) Isolation and identification of cholesterol α-oxide and other minor sterols in human serum. Lipids 6, 836-843.
62. Griminger P. and Fisher H. (1986) The effect of dried and fresh eggs on plasma cholesterol and atherosclerosis in chickens. Poultry Science 65, 979-982.
63. Grinstead G. F., Trzaskos J. M., Billheimer J. T. and Gaylor J. L. (1983) Cytosolic modulators of activities of microsomal enzymes of cholesterol biosynthesis. Effects of acil-CoA inhibition and cytosolic Z-protein. Biochimica et Biophysica Acta 751, 41-51.
64. Gruenke L. D., Graig J. C., Petrakis N. L. and Lyon M. B. (1987) Analysis of cholesterol, cholesterol-5,6-epoxides and cholestane-3β,5α,6β-triol in nipple aspirates of human breast fluid by gas chromatography/mass spectrometry. Biomedical and Environmental Mass Spectrometry 14, 335-338.
65. Guardiola F., Codony R., Rafecas M. and Boatella J. (1995) Formación de derivados oxidados del colesterol en alimentos. Grasas y Aceites 46, 202-212.
66. Guo X., Ohno Y., Miyajima A., Sunouchi M. and Takanaka A. (1993) Oxysterols inhibit gap junctional communications between rat hepatocytes in primary culture. Pharmacology and Toxicology 73, 10-13.
67. Guyton J. R., Black B. L. and Seidel C. L. (1990) Focal toxicity of oxysterols in vascular smooth muscle cell culture. American Journal of Pathology 137, 425-434.
68. Hagiwara H., Nagasaki T., Inada Y., Saito Y., Yasuda T., Kojima H., Morisaki M. and Ikekawa N. (1982) The interaction of cholesterol analogues with phospholipid -the effect of length of side-chain and configuration of a hydroxyl group introduced in the side-chain. Biochemistry International 5, 329-336.
69. Harland W. A., Smith A. G. and Gilbert J. D. (1973) Tissue reaction to atheroma lipids. Journal of Pathology 111, 247-253.
70. Herian A. M., Kuehl N. M. and Lee K. (1985) Growth inhibition of Mycoplasma gallisepticum following membrane insertion of cholesterol autoxidation products. Journal of Food Protection 48, 1050-1053.
71. scc-substrate interactions. Role of the 3β- and side chain hydroxyls in binding to oxidized and reduced forms of the enzyme. Journal of Biological Chemistry 261, 2743-2749.
72. Hietter H., Bischoff P., Beck J. P., Ourisson G. and Luu B. (1986) Comparative effects of 7β-hydroxycholesterol towards murine lymphomas, lymphoblasts and lymphocytes: selective cytotoxicity and blastogenesis inhibition. Cancer Biochemistry Biophysics 9, 75-83.
73. Higley N. A., Beery J. T., Taylor S. L., Porter J. W., Dziuba J. A. and Lalich J. J. (1986) Comparative atherogenic effects of cholesterol and cholesterol oxides. Atherosclerosis 62, 91-104.
74. Hill J. C. (1984) Effects of cytotoxic cholesterol autoxidation derivatives on membrane function. Dissertation Abstracts International B 45, 1158a.
75. Hill J. C., Peng S. K., Morin R. J. and Taylor C. B. (1984) Effects of cholesterol autoxidation derivatives on hexose transport in cultured aortic smooth muscle cells. Experimental and Molecular Pathology 41, 249-257.
76. Hill J. C., Peng S. K., Safarik J. and Taylor C. B. (1983) Effects on hexose transport and cholesterol uptake by cholesterol oxidation products in cultured aortic smooth muscle cells. Federation Proceedings 42, 787a.
77. Hodis H. N., Chauhan A., Hashimoto S., Crawford D. W. and Sevanian A. (1992) Probucol reduces plasma and aortic wall oxysterol levels in cholesterol fed rabbits independently of its plasma cholesterol lowering effect. Atherosclerosis 96, 125-134.
78. Hodis H. N., Kramsch D. M., Avogaro P., Bittolo-Bon G., Cazzolato G., Hwang J., Peterson H. and Sevanian A. (1994) Biochemical and cytotoxic characteristics of an in vivo circulating oxidized low density lipoprotein (LDL). Journal of Lipid Research 35, 669-677.
79. 2+. Federation Proceedings 45, 310a.
80. Hrelia S., Bordoni A., Caboni M. F., Lercker G., Capella P., Turchetto E. and Biagi P. (1994) Effect of cholesterol-5α,6α-epoxide supplementation to cultured cardiomyocytes. Biochemistry and Molecular Biology International 32, 565-573.
81. Hu B., Peng S. K., Brubaker D. and Morin R. J. (1990) Influence of cholesterol oxides and antioxidants on prostacyclin production by cultured endothelial cells. FASEB Journal 4, 910a.
82. Hubbard R. W., Ono Y. and Sanchez A. (1989) Atherogenic effect of oxidized products of cholesterol. Progress in Food Nutrition Sciences 13, 17-44.
83. Hughes H., Mathews B., Lenz M. L. and Guyton J. R. (1994) Cytotoxicity of oxidized LDL to porcine aortic smooth muscle cells is associated with the oxysterols 7-ketocholesterol and 7-hydroxycholesterol. Arteriosclerosis and Thrombosis 14, 1177-1185.
84. Hwang P. L. H. (1992) Inhibitors of protein and RNAQ synthesis block the cytotoxic effects of oxygenated sterols. Biochimica et Biophysica Acta 1136, 5-11.
85. Imai H. and Lee K. T. (1983) Mosaicism in female hybrid hares heterozygous for glucose-6-phosphate dehydrogenase. IV. Aortic atherosclerosis in hybrid hares fed alternating cholesterol-supplemented and nonsupplemented diets. Experimental and Molecular Pathology 39, 11-23.
86. Imai H. and Nakamura H. (1980) Short-term responses to cholesterol and oxygenated derivatives. Federation Proceedings 39, 772a.
87. Imai H., Werthessen N. T., Subramanyam V., LeQuesne P. W., Soloway A. H. and Kanisawa M. (1980) Angiotoxicity of oxygenated sterols and possible precursors. Science 207, 651-653.
88. Imai H., Werthessen N. T., Taylor C. B. and Lee K. T. (1976) Angiotoxicity and arteriosclerosis due to contaminants of USP-grade cholesterol. Archives of Pathology and Laboratory Medicine 100, 565-572.
89. Jacobson M. S. (1987) Cholesterol oxides in Indian ghee: possible cause of unexplained high risk of atherosclerosis in Indian immigrant populations. Lancet September 19, 656-658.
90. Jacobson M. S., Nair P. P., Naseem S. M., Smith T. D. and Heald F. P. (1981) Oxygenated cholesterols: new risk factors for atherosclerosis? Pediatric Research 15, 535a.
91. Jacobson M. S., Price M. G., Shamoo A. E. and Heald F. P. (1985) Atherogenesis in white carneau pigeons: effects of low-level cholestane-triol feeding. Atherosclerosis 57, 209-217.
92. Johnson B. H. and Smith L. L. (1983) Mutagens in human aortal lipids. Federation Proceedings 42, 2089a.
93. Johnson B. H. and Smith L. L. (1984) A search for mutagens in human aortal lipid extracts. Atherosclerosis 53, 331-336.
94. Kadis B. (1978) Steroid epoxides in biological systems: a review. Journal of Steroid Biochemistry 9, 75-81.
95. Kandutsch A. A. and Chen H. W. (1973) Inhibition of sterol synthesis in cultured mouse cells by 7α-hydroxycholesterol, 7β-hydroxycholesterol and 7-ketocholesterol. Journal of Biological Chemistry 248, 8408-8417.
96. Kandutsch A. A. and Chen H. W. (1974) Inhibition of sterol synthesis in cultured mouse cells by cholesterol derivatives oxygenated in the side chain. Journal of Biological Chemistry 249, 6057-6061.
97. Kandutsch A. A. and Chen H. W. (1978) Inhibition of cholesterol synthesis by oxygenated sterols. Lipids 13, 704-707.
98. Kandutsch A. A., Chen H. W. and Heieniger H. J. (1978) Biological activity of some oxygenated sterols. Science 201, 498-501.
99. Kandutsch A. A. and Shown E. P. (1981) Assay of oxysterol-binding protein in a mouse fibroblast, cell-free system. Journal of Biological Chemistry 256, 13068-13073.
100. Kandutsch A. A. and Thompson E. B. (1980) Cytosolic proteins that bind oxygenated sterols. Cellular distribution, specificity, and some properties. Journal of Biological Chemistry 255, 10813-10826.
101. Kelsey M. I. and Pienta R. J. (1979) Transformation of hamster embryo cells by cholesterol α-epoxide and lithocholic acid. Cancer Letters 6, 143-149.
102. Kelsey M. I. and Pienta R. J. (1981) Transformation of hamster embryo cells by neutral sterols and bile acids. Toxicology Letters 9, 177-182.
103. scc. Biochimica et Biophysica Acta 666, 370-381.
104. Kosykh V. A., Lankin V., Podrez E. A., Dmitry K. N., Volgushev S. A., Victorov A. V., Repin V. S. and Smirnov V. N. (1989) Very low density lipoprotein secretion by cultured hepatocytes of rabbits receiving old commercial and purified cholesterol. Lipids 24, 109-115.
105. Kraemer R., Pomerantz K. B., Joseph-Silverstein J. and Hajjar D. P. (1993) Induction of basic fibroblast growth factor mRNA and protein synthesis in smooth muscle cells by cholesteryl ester enrichment and 25-hydroxycholesterol. Journal of Biological Chemistry 268, 8040-8045.
106. Krull U. J., Thompson M., Vandenberg E. T. and Wong H. E. (1985) Langmuir-Blodgett film characteristics and phospholipid membrane ion conduction. Part I. Modification by cholesterol and oxidized derivatives. Analytica Chimica Acta 174, 83-94.
107. Krut L. H. (1982a) Solubility of cholesterol in vitro promoted by oxidation products of cholesterol. Atherosclerosis 43, 95-104.
108. Krut L. H. (1982b) Clearance of subcutaneous implants of cholesterol in the rat promoted by oxidation products of cholesterol. Atherosclerosis 43, 105-118.
109. Kucuk O., Stoner-Picking J., Yachnin S., Gordon L. I., Williams R. M., Lis J. and Westerman M. P. (1992) Inhibition of NK cell-mediated cytotoxicity by oxysterols. Cellular Immunology 139, 541-549.
110. scc-adrenodoxin interactions. Ionic effects on binding, and regulation of cytochrome reduction by bound steroid substrates. Journal of Biological Chemistry 260, 8810-8816.
111. scc. Evidence for an intramitochondrial cholesterol translocator. Journal of Biological Chemistry 262, 9181-9188.
112. Larsen S. D., Spilman C. H., Yagi Y., Dinh D. M., Hart K. L. and Hess G. F. (1994) Design and synthesis of seco-oxysterol analogs as potential inhibitors of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase gene transcription. Journal of Medicinal Chemistry 37, 2343-2351.
113. Levin D. E., Hollstein M., Christman M. F., Schwiers E. A. and Ames B. N. (1982) A new Salmonella tester strain (TA102) with A-T base pairs at the site of mutation detects oxidative mutagens. Proceedings of the National Academy of Sciences of the U.S.A. 79, 7445-7449.
114. Lo W. B. and Black H. S. (1972) Formation of cholesterolderived photoproducts in human skin. Journal of Investigative Dermatology 58, 278-283.
115. Lorenzo J. L., Allorio M., Bernini F., Corsini A. and Fumagalli R. (1987) Regulation of low density lipoprotein metabolism by 26-hydroxycholesterol in human fibroblasts. FEBS Letters 218, 77-80.
116. Luu B. (1986) Use of in vitro cell cultures to study cytotoxic properties of natural products. In Advances in Medical Phytochemistry. Edited by D. Barton and W. D. Ollis. pp. 97-101. John Libbey, London.
117. Luu B. and Moog C. (1991) Oxysterols: biological activities and physicochemical studies. Biochimie 73, 1371-1320.
118. Maerker G. and Bunick F. J. (1986) Cholesterol oxides II. Measurement of the 5,6-epoxides during cholesterol oxidation in aqueous dispersions. Journal of the American Oil Chemists' Society 63, 771-777.
119. Maerker G., Nungesser E. H. and Bunick F. J. (1988) Reaction of cholesterol 5,6-epoxides with simulated gastric juice. Lipids 23, 761-765.
120. Maltese W. A., Reitz B. A. and Volpe J. J. (1981) Selective decrease of the viability and the sterol content of proliferating versus quiescent glioma cells exposed to 25-hydroxycholesterol. Cancer Research 41, 3448-3452.
121. Maor I. and Aviram M. (1994) Oxidized low density lipoprotein leads to macrophage accumulation of unesterified cholesterol as a result of lysosomal trapping of the lipoprotein hydrolyzed cholesteryl ester. Journal of Lipid Research 35, 803-819.
122. Martínez-Sales V., Fornas E. and Camañas A. (1985) Prostacyclin production and lipid peroxidation in the aorta of rats fed with cholesterol oxidation products. Artery 12, 213-219.
123. Mason J. I. and Hemsell P. G. (1982) Cholesterol sulfate metabolism in human fetal adrenal mitochondria. Endocrinology 111, 208-213.
124. Matthias D., Becker C. H., Godicke W., Schmidt R. and Ponsold K. (1987) Action of cholestane-3β,5α,6β-triol on rats with particular reference to the aorta. Atherosclerosis 63, 115-124.
125. Miller L. R., Needleman D. H., Brabson J. S., Wang K. S. and Schroepfer G. J. (1987) 5α-cholest-8(14)-en-3β-ol-15-one. A competitive substrate for acyl coenzyme A: cholesterol acyl transferase. Biochemical and Biophysical Research Communications 148, 934-940.
126. Missler S. R., Wasilchuk B. A. and Merritt C. (1985) Separation and identification of cholesterol oxidation products in dried egg preparations. Journal of Food Science 50, 595-598, 646.
127. Mitchell I. G. (1980) Forward mutation in Escherichia coli and gene conversion in Saccharomyces cerevisiae compared quantitatively with reversion in Salmonella typhimurium. Agents and Actions 10, 287-295.
128. Moog C., Frank N., Luu B. and Bertram B. (1993) Metabolism of new anticancer oxysterol derivatives in rats. Anticancer Research 13, 953-958.
129. Moog C., Hergueux J., Italiano L., Luu B. and Bischoff P. (1986) Inhibition of lymphocyte activation by 7,25-dihydroxy-cholesterol: a preliminary report. IRCS Medical Science 14, 1207-1208.
130. Moog C., Ji Y. H., Walzinger C., Luu B. and Bischoff P. (1990) Studies on the immunological properties of oxysterols: in vivo actions of 7,25-dihydroxycholesterol upon peritoneal cells. Immunology 70, 344-350.
131. Morin R. J., Hu B., Peng S. K. and Sevanian A. (1992) Cholesterol oxidation and cancer. In Biological Effects of Cholesterol Oxides. Edited by S. K. Peng and R. J. Morin. pp. 191-202. CRC Press, Boca Raton, FL.
132. Morin R. J. and Peng S. K. (1989) Effects of cholesterol oxidation derivatives on cholesterol esterifying and cholesteryl ester hydrolytic enzyme activity of cultured rabbit aortic smooth muscle cells. Lipids 24, 217-220.
133. Naseem S. M. and Heald F. P. (1987) Cytotoxicity of cholesterol oxides and their effects on cholesterol metabolism in cultured human aortic smooth muscle cells. Biochemistry International 14, 71-84.
134. Needleman D. H., Strong K. A., Stemke K. A., Brabson J. S., Kisic A. and Schroepfer G. J. (1987) Inhibitors of sterol synthesis. Effect of dietary 5α-cholest-8(14)-en-3β-ol-15-one on ACAT activity of jejunal microsomes of the rat. Biochemical and Biophysical Research Communications 148, 920-925.
135. Neyses L., Locher R., Stimpel M., Streuli R. and Vetter W. (1985) Stereospecific modulation of the calcium channel in human erythrocytes by cholesterol and its oxidized derivatives. Biochemical Journal 227, 105-112.
136. Neyses L., Stimpel M., Locher R., Kueffer B. and Vetter W. (1984) Cholesterol and its oxidized derivatives modulate the calcium channel in human red blood cells. Journal of Hypertension 2 (Suppl. 3), 489-492.
137. Nordman P., Díez-Ibáñez M., Chessebeuf-Padieu M., Luu B., Mack G. and Mersel M. (1989) Toxic effects of 7β-hydroxycholesterol on rat liver primary cultures, epithelial lines and co-cultures. Cell Biology and Toxicology 5, 261-270.
138. Oram J. F., Brinton E. A. and Bierman E. L. (1981) Regulation of high density lipoprotein receptor activity in cultured human skin fibroblasts and human arterial smooth muscle cells. Journal of Clinical Investigation 72, 1611-1621.
139. Osada K., Sasaki E. and Sugano M. (1994) Lymphatic absorption of oxidized cholesterol in rats. Lipids 29, 555-559.
140. Parish E. J., Tsuda M. and Schroepfer G. J. (1979) Synthesis properties and reactions of 3β-benzoyloxy-7α-15β-dichloro-5α-cholest-8(14)-ene. Chemistry and Physics of Lipids 24, 167-182.
141. Parsons P. G. and Goss P. (1978) Chromosome damage and DNA repair induced in human fibroblasts by UV and cholesterol oxide. Australian Journal of Experimental Biology and Medical Science 56, 287-296.
142. Patel N. T. and Thompson E. B. (1990) Human oxysterol-binding protein. I. Identification and characterization in liver. Journal of Clinical Endocrinology and Metabolism 71, 1637-1644.
143. Peng S. K., Hu B., Brubaker D., Marcus C. and Morin R. J. (1990) Cholesterol oxides enhance platelet adhesion to endothelial cells in vitro. FASEB Journal 4, 910a.
144. Peng S. K., Hu B. and Morin R. J. (1991) Angiotoxicity and atherogenicity of cholesterol oxides. Journal of Clinical Laboratory Analysis 5, 144-152.
145. Peng S. K. and Morin R. J. (1987) Effects on membrane function by cholesterol oxidation derivatives in cultured aortic smooth muscle cells. Artery 14, 85-99.
146. Peng S. K., Morin R. J., Phillips G. A. and Xia G. Z. (1986) Absorption and transport of cholesterol autoxidation derivatives in rabbits. Federation Proceedings 45, 230a.
147. Peng S. K., Morin R. J. and Sentovich S. (1985a) The effect of cholesterol oxidation products on membrane function. Journal of the American Oil Chemists' Society 62, 634-635a.
148. Peng S. K., Phillips G. A., Xia G. Z. and Morin R. J. (1987) Transport of cholesterol autoxidation products in rabbit lipoproteins. Atherosclerosis 64, 1-6.
149. Peng S. K., Taylor C. B., Hill J. C. and Morin R. J. (1985b) Cholesterol oxidation derivatives and arterial endothelial damage. Atherosclerosis 54, 121-133.
150. Peng S. K., Taylor C. B., Hill J. C. and Safarik J. (1982a) Effect of oxidized cholesterol on the aorta of rabbits: scanning electron microscopic observations. Proceedings of the Electron Microscopy Society of America, 40th Annual Meeting. pp. 340-341. San Francisco Press, San Francisco, CA.
151. Peng S. K., Taylor C. B., Huang W. Y., Hill J. C. and Mikkelson B. (1980) The distribution of 25-hydroxycholesterol in lipoproteins of squirrel monkeys and its roles in atherogenesis. Federation Proceedings 39, 589a.
152. Peng S. K., Taylor C. B., Mosbach E. H., Huang W. Y., Hill J. and Mikkelson B. (1982b) Distribution of 25-hydroxycholesterol in plasma lipoprotein and its role in atherogenesis. A study in squirrel monkeys. Atherosclerosis 41, 395-402.
153. Peng S. K., Taylor C. B., Safarik J., Hill J. and Mikkelson B. (1982c) Arteriosclerosis induced by 25-hydroxycholesterol in squirrel monkeys. Federation Proceedings 41, 452a.
154. Peng S. K., Taylor C. B., Tham P. and Mikkelson B. (1977) Effect of oxidation derivatives of cholesterol on cultured aortic smooth muscle cells. American Journal of Pathology 86, 53-54a.
155. Peng S. K., Wu A. Y., Colacicco L. A., Mikkelson B. and Taylor C. B. (1983) Inhibition of prostaglandin synthesis by cholesterol oxidation products in cultured aortic smooth muscle cells. Federation Proceedings 42, 809a.
156. Peterson A. R., Peterson H., Spears C. P., Trosko J. E. and Sevanian A. (1988) Mutagenic characterization of cholesterol epoxides in Chinese hamster V79 cells. Mutation Research 203, 355-366.
157. Petrakis N. L., Gruenke L. D. and Craig J. C. (1981) Cholesterol and cholesterol epoxides in nipple aspirates of human breast fluid. Cancer Research 41, 2563-2565.
158. Pinkerton F. D., Pelley R. P. and Shroepfer G. J. Jr (1992) Synergistic action of two oxysterols in the lowering of HMG-CoA reductase activity in CHO-K1 cells. Biochemical and Biophysical Research Communications 186, 569-573.
159. Pinkerton F. D., Spilman C. H., Via D. P. and Schroepfer G. J. Jr (1993) Differing effects of three oxysterols on low density lipoprotein metabolism in HepG2 cells. Biochemical and Biophysical Research Communications 193, 1091-1097.
160. Prasad C. R. and Subramanian R. (1992) Qualitative and comparative
161. Raaphorst G. P., Azzam E. I., Langlois R. and Van Lier J. E. (1987) Effect of cholesterol α and β epoxides on cell killing and transformation. Biochemical Pharmacology 36, 2369-2372.
162. Ramasamy S., Boissonneault G. A. and Hennig B. (1992) Oxysterol-induced endothelial cell dysfunction in culture. Journal of the American College of Nutrition 11, 532-538.
163. Reddy B. S. and Wynder E. L. (1977) Metabolic epidemiology of colon cancer. Fecal bile acids and neutral sterols in colon cancer patients and patients with adenomatous polyps. Cancer 39, 2533-2539.
164. Rodríguez R. J., Arunachalam T. A., Parks L. W. and Caspi E. (1983) Growth of a sterol auxotroph derived from Saccharomyces cerivisiae on chemically synthetized derivatives of cholesterol possessing side-chain modifications. Lipids 18, 772-775.
165. Rong S., Bergmann C., Luu B., Beck J. P. and Ourisson G. (1985) Activité antitumorale in vivo de dérivés hydrosolubles de 7-hydroxycholestérols. Comptes Rendus de l'Academie des Sciences de Paris 300 (ser. III), 89-94.
166. Rooney M., Tamura-Lis W., Lis L., Yachnin S., Kucuk O. and Kauffman J. W. (1986) The influence of oxygenated sterol compounds on dipalmitoylphosphatidylcholine bi-layer structure and packing. Chemistry and Physics of Lipids 41, 81-92.
167. Ross R. (1986) The pathogenesis of atherosclerosis - an update. New England Journal of Medicine 314, 488-500.
168. Ross R. (1987) Platelet-derived growth factor. Annual Review of Medicine 38, 71-79.
169. Rueff J. and Halpern M. (1985) Testing human lipoproteins for mutagenic activity in the Salmonella/microsome assay. In Lipid Metabolism and its Pathology. Edited by M. Halpern. pp. 161-167. Plenum Press, New York.
170. Ruiz-Rubio M., Alejandre-Duran E. and Pueyo C. (1985) Oxidative mutagens specific for A-T base pairs induce forward mutations to L-arabinose resistance in Salmonella typhimurium. Mutation Research 147, 153-163.
171. Saito Y., Shimada H., Imada T., Kikuchi T., Ikekawa N. and Inada Y. (1985) Lysis of platelets and erythrocytes by the incorporation of a unique oxygenated sterol: 22R-hydroxycholesterol. Journal of Membrane Biology 83, 187-191.
172. Sato Y. and Somoda Y. (1981) Effects of lanosterol analogs on cholesterol biosynthesis from lanosterol. Chemical and Pharmaceutical Bulletin 29, 2604-2609.
173. Sato Y., Somoda Y., Morisaki M. and Ikekawa N. (1984) Oxygenated sterols as inhibitors of enzymatic conversion of dihydrolanosterol into cholesterol. Chemical and Pharmaceutical Bulletin 32, 3305-3308.
174. Saucier S. E., Kandutsch A. A., Clark D. S. and Spencer T. A. (1993) Hepatic uptake and metabolism of ingested 24-hydroxycholesterol and 24(S),25-epoxycholesterol. Biochimica et Biophysica Acta 1166, 115-123.
175. Schafer W. R., Kim R., Sterne R., Thorner J., Kim S. H. and Rine J. (1989) Genetic and pharmacological suppression of oncogenic mutations in RAS genes of yeast and humans. Science 245, 379-385.
176. Sentovich S., Morin R. J. and Peng S. K. (1985) Effects of cholesterol oxidation derivatives on endocytosis of rabbit vascular endothelium. Federation Proceedings 44, 1263a.
177. Sevanian A. and McLeod L. L. (1986) Catalytic properties and inhibition of hepatic cholesterol-epoxide hydrolase. Journal of Biological Chemistry 261, 54-59.
178. Sevanian A. and Peterson A. R. (1984) Cholesterol epoxide is a direct acting mutagen. Proceedings of the National Academy of Sciences of the U.S.A. 81, 4198-4202.
179. Sevanian A. and Peterson A. R. (1986) The cytotoxic and mutagenic properties of cholesterol oxidation products. Food and Chemical Toxicology 24, 1103-1110.
180. Sevanian A., Stein R. A. and Mead J. F. (1980) Lipid epoxide hydrolase in rat lung preparations. Biochimica et Biophysica Acta 614, 489-500.
181. Sinensky M., Duwe G. and Pinkerton F. (1979) Defective regulation of 3-hydroxy-3-methylglutaryl coenzyme A reductase in a somatic cell mutant. Journal of Biological Chemistry 254, 4482.
182. Sinensky M. and Mueller G. (1981) Cytosolic 25-hydroxycholesterol binding activity of Chinese hamster ovary cells. Archives of Biochemistry and Biophysics 209, 314-320.
183. Smith L. L. (1990) Mechanisms of formation of oxysterols: a general survey. In Free Radicals, Lipoproteins, and Membrane Lipids. Edited by A. Crastes de Paulet, L. Douste-Blazy and R. Paoletti. pp. 115-132. Plenum Press, New York.
184. Smith L. L. (1991) Another cholesterol hypothesis: cholesterol as antioxidant. Free Radical Biology and Medicine 11, 47-61.
185. Smith L. L. and Johnson B. H. (1989) Biological activities of oxysterols. Free Radical Biology and Medicine 7, 285-332.
186. Smith L. L., Made Gowda N. M. and Teng J. I. (1987) Sterol hydroperoxide metabolism by Salmonella typhimurium. Journal of Steroid Biochemistry 26, 259-264.
187. Smith L. L., Smart V. B. and Ansari G. A. S. (1979) Mutagenic cholesterol preparations. Mutation Research 68, 23-30.
188. Smith L. L., Smart V. B. and Made Gowda N. M. (1986) Mutagenic sterol hydroperoxides. Mutation Research 161, 39-48.
189. Smith L. L. and Van Lier J. E. (1970) Sterol metabolism IX. 26-hydroxycholesterol levels in the human aorta. Atherosclerosis 12, 1-14.
190. Sporer A., Brill D. R. and Schaffner C. P. (1982) Epoxycholesterols in secretions and tissue of normal, benign, and cancerous human prostate glands. Urology 20, 244-250.
191. Srinivasan G., Patel N. T. and Thompson E. B. (1993) Characterization of the human oxysterol receptor overexpressed in the baculovirus system. Receptor 3, 99-111.
192. Stimpel M., Neyses L., Locher R., Streuli R. and Vetter W. (1985) Variations of the membraneous cholesterol content alter the calcium influx through the calcium-specific entry channel in human erythrocytes. Journal of the American Oil Chemists' Society 62, 634a.
193. Streuli R. A., Chung J., Scanu A. M. and Yachnin S. (1981) Serum lipoproteins modulate oxygenated sterol insertion into human red cell membranes. Science 212, 1294-1296.
194. Tabacik C., Aliau S. and Sainte-Marie J. (1987) Regulation of cholesterol biosynthesis at a stage after the 3-hydroxy-3-methylglutaryl-CoA reductase step in normal and leukemic (L2C) guinea pig lymphocytes. Biochimica et Biophysica Acta 921, 405-410.
195. Tamasawa N., Tamasawa A., Takebe K. and Hayakari M. (1994) The effect of dietary 7-ketocholesterol, inhibitor of sterol synthesis, on hepatic microsomal cholesterol 7α-hydroxylase activity in rat. Biochimica el Biophysica Acta 1214, 20-26.
196. Tanaka R. D., Edwards P. A., Lan S. F. and Fogelman A. M. (1983) Regulation of 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in avian myeloblasts. Journal of Biological Chemistry 258, 13331-13339.
197. Tanaka M. and Kanamaru S. (1993) Capillary gas chromatography quantification of cholesterol in copper-oxidized low-density lipoprotein. Biological and Pharmaceutical Bulletin 16, 538-543.
198. Taylor F. R. (1992) Correlation among oxysterol potencies in the regulation of the degradation of 3-hydroxy-3-methylglutaryl CoA reductase, the repression of 3-hydroxy-3-methylglutaryl CoA synthase and affinities for the oxysterol receptor. Biochemical and Biophysical Research Communications 186, 182-189.
199. Taylor C. B. and Peng S. K. (1985) Cytotoxicity and atherogenicity of oxidized cholesterol. Journal of the American Oil Chemists' Society 62, 633a.
200. Taylor C. B., Peng S. K., Werthessen N. T., Tham P. and Lee K. T. (1979) Spontaneously occurring angiotoxic derivatives of cholesterol. American Journal of Clinical Nutrition 32, 40-57.
201. Taylor F. R., Saucier S. E., Shown E. P., Parish E. J. and Kandutsch A. A. (1984) Correlation between oxysterol binding to a cytosolic binding protein and potency in the repression of hydroxymethylglutaryl coenzyme A reductase. Journal of Biological Chemistry 259, 12382-12387.
202. Tertov V. V., Sobenin I. A., Gabbasov Z. A., Popov E. G., Jaakkola O., Solakivi T., Nikkari T., Smirnov V. N. and Orekhov A. N. (1992a) Multiple-modified desialylated low density lipoproteins that cause intracellular lipid accumulation. Isolation, fractionation and characterization. Laboratory Investigation 67, 665-675.
203. Tertov V. V., Sobenin I. A. and Orekhov A. N. (1992b) Characterization of desialylated low-density lipoproteins which cause intracellular lipid accumulation. International Journal of Tissue Reactions 14, 155-162.
204. Tipton C. L., Leung P. C., Johnson J. S., Brooks R. J. and Beitz D. C. (1987) Cholesterol hydroperoxides inhibit calmodulin and suppress atherogenesis in rabbits. Biochemical and Biophysical Research Communications 146, 1166-1172.
205. Toda T., Leszczynski D. and Kummerow F. (1981) Angiotoxic effects of dietary 7-ketocholesterol in chick aorta. Paroi Arterielle 7, 167-176.
206. Trzaskos J. M., Magolda R. L., Favata M. F., Fischer R. T., Johnson P. R., Chen H. W., Ko S. S., Leonard D. A. and Gaylor J. L. (1993) Modulation of 3-hydroxy-3-methylglutaryl CoA reductase by 15α-fluorolanost-7-en-3β-ol. A mechanism-based inhibitor of cholesterol biosynthesis. Journal of Biological Chemistry 268, 22591-22599.
207. Tuckey R. C. and Kamin H. (1982) The oxyferro complex of purified adrenal cytochrome P-450. Federation Proceedings 41, 1405a.
208. Van Lier J. E. and Smith L. L. (1967) Sterol metabolism I. 26-hydroxycholesterol in the human aorta. Biochemistry 6, 3269-3278.
209. Warner G. J. (1994) Effect of dietary oxysterols on cellular cholesterol metabolism in the human hepatoma cell line, HepG2 [PhD thesis]. St Paul, MN: University of Minnesota.
210. Watabe T., Kanai M., Isobe M. and Ozawa N. (1980) Cholesterol α- and β-epoxides as obligatory intermediates in the hepatic microsomal metabolism of cholesterol to cholestanetriol. Biochimica et Biophysica Acta 619, 414-419.
211. 1, and 25-hydroxycholesterol stimulate osteoblast-like vascular cells to calcify. Journal of Clinical Investigation 93, 2106-2113.
212. 2 (prostacyclin) by cultured human and bovine endothelial cells. Proceedings of the National Academy of Sciences of the U.S.A. 74, 3922-3926.
213. Werthle M., Bochelen D., Adamczyk M., Kupferberg A., Poulet P., Chambron J., Lutz P., Privat A. and Mersel M. (1994) Local administration of 7β-hydroxycholesterol-3-oleate inhibits growth of experimental rat C6 glioblastoma. Cancer Research 54, 998-1003.
214. Wrensch M. R., Petrakis N. L., Gruenke L. D., Miike R., Ernster V. L., King E. B., Hauck W. W., Craig J. C. and Goodson W. H. (1989) III. Breast fluid cholesterol and cholesterol β-epoxide concentrations in women with benign breast disease. Cancer Research 49, 2168-2174.
215. 2 by catalase induction in Salmonella typhimurium. Mutation Research 141, 145-147.
216. Xu X., Glover M. and Lambeth J. D. (1987) Cholesterol sulfate inhibition of intramitochondrial cholesterol translocation in rat adrenal. Federation Proceedings 46, 2051a.
217. Yachnin S., Chung J. and Scanu A. M. (1982) Inhibition of oxygenated sterol entry into human red cells and lymphocytes by isolated serum lipoproteins. Biochimica et Biophysica Acta 713, 538-546.
218. Zhou Q., Smith T. L. and Kummerow F. A. (1993) Cytotoxicity of oxysterols on cultured smooth muscle cells from human umbilical arteries. Proceedings of the Society for Experimental Biology and Medicine 202, 75-80.
219. Zwijsen R. M., Oudenhoven I. M. and de Haan L. H. (1992) Effects of cholesterol and oxysterols on gap junctional communications between human smooth muscle cells. European Journal of Pharmacology 228, 115-120.