Protective effect of ebselen on cytotoxicity induced by cholestane-3 beta, 5 alpha, 6 beta-triol in ECV-304 cells

Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids

Volumn 1761, Issue 3, 2006, Pages 350-359

  Wu, Qingzhi ^a   Huang, Kaixun ^a  

^a HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Antiatherosclerotic; Ebselen; Oxidative stress; Oxysterol; Reactive oxygen species

Indexed keywords

CHOLESTANE 3BETA,5ALPHA,6BETA TRIOL (3 TRIOL); CHOLESTANE DERIVATIVE; EBSELEN; GLUTATHIONE PEROXIDASE; NITRIC OXIDE SYNTHASE; OXYGEN; OXYSTEROL; UNCLASSIFIED DRUG;

ARTICLE; CELL VIABILITY; CYTOTOXICITY; DOSE RESPONSE; DRUG EFFECT; ENZYME ACTIVITY; HUMAN; HUMAN CELL; MITOCHONDRION; PRIORITY JOURNAL; STATISTICAL SIGNIFICANCE;

ANTILIPEMIC AGENTS; ANTIOXIDANTS; AZOLES; CELL LINE; CELL SURVIVAL; CHOLESTANOLS; GLUTATHIONE; HUMANS; LIPID PEROXIDATION; MALONDIALDEHYDE; ORGANOSELENIUM COMPOUNDS; REACTIVE OXYGEN SPECIES; SULFHYDRYL COMPOUNDS;

EID: 33646128718     PISSN: 13881981     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbalip.2006.02.017     Document Type: Article

References (74)

1. Berliner J., and Heinecke J. The role of oxidized lipoproteins in atherogenesis. Free Radical Biol. Med. 20 (1996) 707-727
2. Hodis H.N., Crawford D.W., and Sevanian A. Cholesterol feeding increases plasma and aortic tissue cholesterol oxide levels in parallel: further evidence for the role of cholesterol oxidation in atherosclerosis. Atherosclerosis 89 (1991) 117-126
3. Yla-Herttuala S., Palinski W., Rosenfeld M., Parthasarathy S., Carew T., Butler S., Witztum J., and Steinberg D. Evidence for the presence of oxidatively modified low density lipoprotein in atherosclerotic lesions. J. Clin. Invest. 84 (1989) 1086-1095
4. Hodis H.N., Kramsch D.M., Avogaro P., Bittolo-Bon G., Cazzolato G., Hwang J., Peterson H., and Sevanian A. Biochemical and cytotoxic characteristics of an in vivo circulating oxidized low-density lipoprotein (LDL-). J. Lipid Res. 35 (1994) 669-677
5. Tuomainen T.P., Diczfalusy U., Kaikkonen J., Nyyssönen K., and Salonen J.T. Serum ferritin concentration is associated with plasma levels of cholesterol oxidation products in man. Free Radical Biol. Med. 35 (2003) 922-928
6. Rimner A., Al Makdessi S., Sweidan H., Wischhusen J., Rabenstein B., Shatat K., Mayer P., and Spyridopoulos I. Relevance and mechanism of oxysterol stereospecifity in coronary artery disease. Free Radical Biol. Med. 38 (2005) 535-544
7. Brown A.J., and Jessup W. Oxysterols and atherosclerosis. Atherosclerosis 142 (1999) 1-28
8. Bhadra S., Arshad M., Rymaszewski Z., Norman E., Wherley R., and Subbiah M. Oxidation of cholesterol moiety of low density lipoprotein in the presence of human endothelial cells or Cu2/ions: identification of major products and their effects. Biochem. Biophys. Res. Commun. 176 (1991) 431-440
9. Hughes H., Mathews B., Lenz M., and Guyton J. Cytotoxicity of oxidized LDL to porcine aortic smooth muscle cells is associate with the oxysterols 7-ketocholesterol and 7-hydroxycholesterol. Atherosclerosis 14 (1994) 1177-1185
10. Fong L., Parthasarathy S., Witztum J., and Steinberg D. Nonenzymatic oxidative cleavage of peptide bonds in apoprotein B-100. J. Lipid Res. 28 (1987) 1466-1477
11. Sevanian A., Berliner J., and Peterson H. Uptake, metabolism, and cytotoxicity of isomeric cholesterol-5,6-epoxides in rabbit aortic endothelial cells. J. Lipid Res. 32 (1991) 147-156
12. Morin R., and Peng S. Effects of cholesterol oxidation derivatives on cholesterol esterifying and cholesteryl ester hydrolytic enzyme activity of cultured rabbit aortic smooth muscle cells. Lipids 24 (1989) 217-220
13. Peng S., Taylor C., Hill J., and Morin R. Cholesterol oxidation derivatives and arterial endothelial damage. Atherosclerosis 54 (1985) 121-133
14. Heinecke J.W. Oxidants and antioxidants in the pathogenesis of atherosclerosis: implications for the oxidized low density lipoprotein hypothesis. Atherosclerosis 141 (1998) 1-15
15. Choy K.J., Deng Y.M., Hou J.Y., Wu B., Lau A., Witting P.K., and Stocker R. Coenzyme Q10 supplementation inhibits aortic lipid oxidation but fails to attenuate intimal thickening in balloon injured New Zealand white rabbits. Free Radical Biol. Med. 35 (2003) 300-309
16. Iuliano L., Pedersen J.Z., Camastra C., Bello V., Ceccarelli S., and Violi F. Protection of low density lipoprotein oxidation by the antioxidant agent IRFI005, a new synthetic hydrophilic vitamin E analogue. Free Radical Biol. Med. 26 (1999) 858-868
17. Schewe T. Molecular actions of ebselen-An anti-inflammatory antioxidant. Gen. Pharmacol. 26 (1995) 1153-1169
18. Sies H. Ebselen: a glutathione peroxidase mimic. Method Enzymol. 234 (1994) 476-482
19. Yang C.F., Shen H.M., and Ong C.N. Protective effect of ebselen against hydrogen peroxide-induced cytotoxicity and DNA damage in HepG2 cells. Biochem. Pharmacol. 57 (1999) 273-279
20. Ross R. Atherosclerosis-An inflammatory disease. N. Engl. J. Med. 340 (1999) 115-126
21. Takahashi K., Sawasaki Y., Hat J.I., Mukai K., and Goto T. Spontaneous transformation and immortalization of human endothelial cells. In vitro Cell. Dev. Biol. 25 (1990) 265-274
22. Brown J., Reading S.J., Jones S., Fitchett C.J., Howl J., Martin A., Longland C.L., Michelangeli F., Dubrova Y.E., and Brown C.A. Critical evaluation of ECV304 as a human endothelial cell model defined by genetic analysis and functional responses: a comparison with the human bladder cancer derived epithelial cell line T24/83. Lab. Invest. 80 (2000) 37-45
23. Kwon K.B., Yang J.Y., Ryu D.G., Rho H.W., Kim J.S., Park J.W., Kim H.R., and Park B.H. Vibrio vulnificus cytolysin induces superoxide anion-initiated apoptotic signaling pathway in human ECV 304 cells. J. Biol. Chem. 276 (2001) 47518-47523
24. Cao S., Yao J., McCabe T.J., Yao Q., Katusic Z.S., Sessa W.C., and Shah V. Direct interaction between endothelial nitricoxide synthase and Dynamin-2. J. Biol. Chem. 276 (2001) 14249-14256
25. Bessede G., Miguet C., Gambert P., Neel D., and Lizard G. Efficiency of homocysteine plus copper in inducing apoptosis is inversely proportional to γ-glutamyl transpeptidase activity. FASEB J. 15 (2001) 1927-1940
26. Osanai T., Saitoh M., Sasaki S., Tomita H., Matsunaga T., and Okumura K. Effect of shear stress on asymmetric dimethylarginine release from vascular endothelial cells. Hypertension 42 (2003) 985-990
27. Dunk C., and Ahmed A. Vascular endothelial growth factor receptor-2-mediated mitogenesis is negatively regulated by vascular endothelial growth factor receptor-1 in tumor epithelial cells. Am. J. Pathol. 158 (2001) 265-273
28. Volk R., Schwartz J.J., Li J., Rosenberg R.D., and Simons M. The role of syndecan cytoplasmic domain in basic fibroblast growth factor-dependent signal transduction. J. Biol. Chem. 274 (1999) 24417-24424
29. Dhanabal M., Ramchandran R., Volk R., Stillman I.E., Lombardo M., Iruela-Arispe M.L., Simons M., and Sukhatme V.P. Endostatin: yeast production, mutants, and antitumor effect in renal cell carcinoma. Cancer Res. 59 (1999) 189-197
30. Mossman T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65 (1983) 55-63
31. Spitz D.R., and Oberley L.W. An assay for superoxide dismutase activity in mammalian tissue homogenates. Anal. Biochem. 179 (1989) 8-18
32. Ellman G.L. Tissue sulfhydryl groups. Arch. Biochem. Biophys. 82 (1959) 70-77
33. Uchiyama M., and Mihara M. Determination of malonaldehyde precursor in tissues by thiobarbituric acid test. Anal. Biochem. 86 (1978) 271-278
34. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein. J. Biochem. 72 (1976) 248-254
35. Ronot X., Benel L., Adolphe M., and Mounolou J.C. Mitochondrial analysis in living cells: the use of rhodamine 123 and flow cytometry. Biol. Cell 57 (1986) 1-7
36. Zoccarato F., Caallini L., and Deana R. Pathway of hydrogen peroxide generation in guinea pig cerebral cortex mitochondria. Biochem. Biophys. Res. Commun. 1549 (1988) 727-734
37. Shen H.M., Yang C.F., and Ong C.N. Sodium selenite-induced oxidative stress and apoptosis in human hepatoma HepG2 cells. Int. J. Cancer 81 (1999) 820-828
38. Sauer H., Wefer K., Vetrugno V., Pocchiari M., Gissel C., Sachinidis A., Hescheler K., and Wartenberg M. Regulation of intrinsic prion protein by growth factors and TNF-α: the role of intracellular reactive oxygen species. Free Radical Biol. Med. 35 (2003) 586-594
39. Noguchi N., Watanabe A., and Shi H.L. Diverse functions of antioxidants. Free Radical Res. 33 (2000) 809-817
40. Juan G., Cavazzoni M., Saez G.T., and O'Connor J.E. A fast kinetic method for assessing mitochondrial membrane potential in isolated hepatocytes with rhodamine 123 and flow cytometry. Cytometry 15 (1994) 335-342
41. Cormier M.J., and Prichard P.M. An investigation of the mechanism of the luminescent peroxidation of luminol by stopped flow techniques. J. Biol. Chem. 243 (1968) 4706-4714
42. Jones O.T.G., and Hancock J.T. Assays of plasma membrane NADPH oxidase. Methods Enzymol. 233 (1994) 222-229
43. Seitz W.R. Chemiluminescence detection of enzymically generated peroxide. Methods Enzymol. 57 (1978) 445-462
44. Galutzov B., and Ganeva V. Lucigenin-derived chemiluminescence in Saccharomyces cerevisiae. Bioelectrochem. Bioenerg. 44 (1997) 77-82
45. Rembish S.J., and Trush M.A. Further evidence that lucigenin-derived chemiluminescence monitors mitochondrial superoxide generation in rat alveolar macrophages. Free Radical Biol. Med. 17 (1994) 117-126
46. Colles S.M., Maxson J.M., Carlson S.G., and Chisolm G.M. Oxidized LDL-induced injury and apoptosis in atherosclerosis. Potential roles for oxysterols. Trends Cardiovasc. Med. 11 (2001) 131-138
47. Sevanian A., Hodis H.N., Hwang J., McLeod L.L., and Peterson H. Characterization of endothelial cell injury by cholesterol oxidation products found in oxidized LDL. J. Lipid Res. 36 (1995) 1971-1986
48. Ramasamy S., Boissonneault G.A., and Hennig B. Oxysterol-induced endothelial cell dysfunction in culture. J. Am. Coll. Nutr. 11 (1992) 532-538
49. Qing Y., Yang J., Zhu L.Q., Niu F.L., Cui W., Wang S.R., and Jiang L.D. Proliferation and apoptosis of human umbilical vein endothelial cells induced by oxidized low density lipoprotein. Chin. J. Pathophysiol. 19 (2003) 334-339
50. Mahfouz M.M., and Kummerow F.A. Cholesterol-rich diets have different effects on lipid peroxidation, cholesterol oxides, and antioxidant enzymes in rats and rabbits. J. Nutr. Biochem. 11 (2000) 293-302
51. Minor R.L., Myers P.R., Guerra R., Bates J.N., and Harrison D.G. Diet-induced atherosclerosis increases the release of nitrogen oxide from rabbit aorta. J. Clin. Invest. 86 (1990) 2109-2116
52. Rubanyi G.M., and Vanhoutte P.M. Oxygen-derived free radicals, endothelium, and responsiveness of vascular smooth muscle. Am. J. Physiol. 250 (1986) 815-821
53. Aliev G., Bodin P., and Burnstock G. Free radical generators cause changes in endothelial and inducible nitric oxide synthases and endothelin-1 immunoreactivity in endothelial cells from hyperlipidemic rabbits. Mol. Gen. Metab. 63 (1998) 191-197
54. Koppenol W.H. The basic chemistry of nitrogen monoxide and peroxynitrite. Free Radical Biol. Med. 25 (1998) 385-391
55. Manning P., Cookson M.R., McNeil C.J., Figlewicz D., and Shaw P.J. Superoxide-induced nitric oxide release from cultured glial cells. Brain Res. 911 (2001) 203-210
56. McPherson D.B., Kilker R.P., and Foley T.D. Superoxide activates constitutive nitric oxide synthase in a brain particulate fraction. Biochem. Biophys. Res. Commun. 296 (2002) 413-418
57. Suzuki Y.J., Forman H.J., and Sevanian A. Oxidants as stimulators of signal transduction. Free Radical Biol. Med. 22 (1997) 269-285
58. Ohara Y., Peterson T.E., and Harrison D.G. Hypercholesterolemia increases endothelial superoxide anion production. J. Clin. Invest. 91 (1993) 2546-2551
59. Alexander R.W. Theodore Cooper Memorial Lecture. Hypertension and the pathogenesis of atherosclerosis. Oxidative stress and the mediation of arterial inflammatory response: a new perspective. Hypertension 25 (1995) 155-161
60. Ǧoffeŷ M.D., Cole R.A., Ćolles S.M., and Chisolrn G.M. In vitro cell injury by oxidized low density lipoprotein involves lipid hydroperoxide-induced formation of alkoxyl, lipid, and peroxyl radicals. J. Clin. Invest. 96 (1995) 1866-1873
61. Lizard G., Monier S., Cordelet C., Gesquiere L., Deckert V., Gueldry S., Lagrost L., and Gambert P. Characterization and comparison of mode of cell death, apoptosis versus necrosis, induced by 7beta-hydroxycholesterol and 7-ketocholesteril in the cells of the vascular wall. Arterioscler. Thromb. Vasc. Biol. 19 (1999) 1190-1200
62. Lizard G., Gueldry S., Sordet O., Monier S., Athias A., Miguet C., Bessede G., Lemaire S., Solary E., and Gambert P. Glutathione is implicated in the control of 7-ketocholesterol-induced apoptosis, which is associated with radical oxygen species production. FASEB J. 12 (1998) 1651-1663
63. Myhre O., Andersen J.M., Aarnes H., and Fonnum F. Evaluation of the probes 2′, 7′-dichlorofluorescin diacetate, luminol, and lucigenin as indicators of reactive species formation. Biochem. Pharmacol. 65 (2003) 1575-1582
64. Li Y.B., Zhu H., and Trush M.A. Detection of mitochondria-derived reactive oxygen species production by the chemilumigenic probes lucigenin and luminol. Biochim. Biophys. Acta 1428 (1999) 1-12
65. Harada-Shiba M., Kinoshita M., Kamido H., and Shimokado K. Oxidized low density lipoprotein induces apoptosis in cultured human umbilical vein endothelial cells by common and unique mechanisms. J. Biol. Chem. 273 (1998) 9681-9687
66. Gracia-Ruiz C., Colell A., Mari M., Morales A., and Fernandez-Checa J.C. Direct effect of ceramide on the mitochondrial electron transport chain leads to generation of reactive oxygen species. J. Biol. Chem. 272 (1997) 11369-11377
67. Cai H., and Harrison D.G. Endothelial dysfunction in cardiovascular diseases: the role of oxidant stress. Circ. Res. 87 (2000) 840-844
68. Guzik T.J., West N.E.J., Black E., McDonald D., Ratnatunga C., Pillai R., and Channon K.M. Vascular superoxide production by NAD(P)H oxidase: association with endothelial dysfunction and clinical risk factors. Circ. Res. 86 (2000) 85-90
69. Warnholtz A., Nickenig G., Schulz E., Macharzina R., Brasen J.H., Skatchkov M., Heitzer T., Stasch J.P., Griendling K.K., Harrison D.G., Bohm M., Meinertz T., and Münzel T. Increased NADH-oxidase-mediated superoxide production in the early stages of atherosclerosis: evidence for involvement of the renin-angiotensin system. Circulation 99 (1999) 2027-2033
70. Dimmeler S., Rippmann V., Weiland U., Haendeler J., and Zeiher A.M. Angiotensin II induces apoptosis of human endothelial cells. Protective effect of nitric oxide. Circ. Res. 81 (1997) 970-976
71. Masumoto H., and Sies H. The reaction of ebselen with peroxynitrite. Chem. Res. Toxicol. 9 (1996) 262-267
72. Masumoto K., Kissner R., Koppenol W.H., and Sies H. Kinetic study of the reaction of ebselen with peroxytrite. FEBS Lett. 398 (1996) 179-182
73. Daiber A., Zou M.H., Bachschmid M., and Ullrich V. Ebselen as a peroxynitrite scavenger in vitro and ex vivo. Biochem. Pharmacol. 59 (2000) 153-160
74. Wagner G., Schuch G., Akerboom T.P.M., and Sies H. Transport of ebselen in plasma and its transfer to binding sites in the hepatocyte. Biochem. Pharmacol. 48 (1994) 1137-1144