A rapid and simple screening test for potential inhibitors of tocopherol-mediated peroxidation of LDL lipids

Journal of Lipid Research

Volumn 37, Issue 4, 1996, Pages 853-867

  Witting, Paul K ^a   Westerlund, Christer ^b   Stocker, Roland ^a  

^a HEART RESEARCH INSTITUTE   (Australia)

^b ASTRAZENECA R AND D   (Sweden)

Author keywords

Antioxidant; Atherosclerosis; Electron spin resonance spectroscopy (ESR); tocopheroxyl radical

Indexed keywords

ALPHA TOCOPHEROL; ANTIOXIDANT; LOW DENSITY LIPOPROTEIN;

ADULT; ARTICLE; ATHEROSCLEROSIS; DRUG EFFECT; ELECTRON SPIN RESONANCE; HUMAN; LIPID ANALYSIS; LIPID PEROXIDATION; MALE; MICELLE; NORMAL HUMAN; PRIORITY JOURNAL;

ADULT; ANTIOXIDANTS; CETRIMONIUM COMPOUNDS; DRUG EVALUATION, PRECLINICAL; EVALUATION STUDIES; FREE RADICALS; HUMANS; LIPID PEROXIDATION; LIPOPROTEINS, LDL; MALE; MICELLES; MOLECULAR STRUCTURE; SODIUM DODECYL SULFATE; STRUCTURE-ACTIVITY RELATIONSHIP; VITAMIN E;

EID: 0029985683     PISSN: 00222275     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (46)

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. Kita, T., Y. Nagano, M. Yokode, K. Ishii, N. Kume, A. Ooshima, H. Yoshida, and C. Kawai. 1987. Probucol prevents the progression of atherosclerosis in Watanabe heritable hyperlipidemic rabbit, an animal model for familial hypercholesterolemia. Proc. Natl. Acad. Sci. USA. 84: 5928-5931.
3. Carew, T. E., D. C. Schwenke, and D. Steinberg. 1987. Antiatherogenic effect of probucol unrelated to its hypocholesterolemic effect: evidence that antioxidants in vivo can selectively inhibit low density lipoprotein degradation in macrophage-rich fatty streaks and slow the progression of atherosclerosis in the Watanabe heritable hyperlipidemic rabbit. Proc. Natl. Acad. Sci. USA. 84: 7725-7729.
4. Mao, S. J., M. T. Yates, A. E. Rechtin, R. L. Jackson, and W. A. Van-Sickle. 1991. Antioxidant activity of probucol and its analogues in hypercholesterolemic Watanabe rabbits. J. Med. Chem. 34: 298-302.
5. Sparrow, C. P., T. W. Doebber, J. Olszewski, M. S. Wu, J. Ventre, K. A. Stevens, and Y. S. Chao. 1992. Low density lipoprotein is protected from oxidation and the progression of atherosclerosis is slowed in cholesterol-fed rabbits by the antioxidant N,N′-diphenyl-phenylenediamine. J. Clin. Invest. 89: 1885-1891.
6. Fruebis, J., D. Steinberg, H. A. Dresel, and T. A. Carew. 1994. A comparison of the antiatherogenic effects of probucol and a structural analogue of probucol in low density lipoprotein receptor-deficient rabbits. J. Clin. Invest. 94: 392-398.
7. Esterbauer, H., G. Jürgens, O. Quehenberger, and E. Koller. 1987. Autoxidation of human low density lipoprotein: loss of polyunsaturated fatty acids and vitamin E and generation of aldehydes. J. Lipid Res. 28: 495-509.
8. Sasahara, M., E. W. Raines, A. Chait, T. E. Carew, D. Steinberg, P. W. Wahl, and R. Ross. 1994. Inhibition of hypercholesterolemia-induced atherosclerosis in the non-human primate by probucol. 1. Is the extent of atherosclerosis related to resistance of LDL to oxidation? J. Clin. Invest. 94: 155-164.
9. Bowry, V. W., and R. Stocker. 1993. Tocopherol-mediated peroxidation. The pro-oxidant effect of vitamin E on the radical-initiated oxidation of human low-density lipoprotein. J. Am. Chem. Soc. 115: 6029-6040.
10. Witting, P.K., V.W. Bowry, and R. Stocker. 1995. Inverse deuterium kinetic isotope effect for peroxidation in human low density lipoprotein (LDL): a simple test for tocopherol-mediated peroxidation of LDL lipids. FEBS Lett. 375: 45-49.
11. Bowry, V. W., K. U. Ingold, and R. Stocker. 1992. Vitamin E in human low-density lipoprotein. When and how this antioxidant becomes a pro-oxidant. Biochem. J. 288: 341-344.
12. Stocker, R. 1994. Lipoprotein oxidation: mechanistic aspects, methodological approaches and clinical relevance. Curr. Opin. Lipidol. 5: 422-433.
13. Ingold, K. U., V. W. Bowry, R. Stocker, and C. Walling. 1993. Autoxidation of lipids and antioxidation by α-tocopherol and ubiquinol in homogeneous solution and in aqueous dispersions of lipids. The unrecognized consequences of lipid particle size as exemplified by the oxidation of human low density lipoprotein. Proc. Natl. Acad. Sci. USA. 90: 45-49.
14. Bowry, V. W., D. Mohr, J. Cleary, and R. Stocker. 1995. Prevention of tocopherol-mediated peroxidation of ubiquinol-10-free human low density lipoprotein. J. Biol. Chem. 270: 5756-5763.
15. Buettner, G. R. 1990. Use of ascorbate as test for catalytic metals in simple buffers. Methods Enzymol. 186: 125-127.
16. Lang, J. K., K. Gohil, and L. Packer. 1986. Simultaneous determination of tocopherols, ubiquinols, and ubiquinones in blood, plasma, tissue homogenates, and subcellular fractions. Anal. Biochem. 157: 106-116.
17. Bisby, R. H., and A. W. Parker. 1991. Reactions of the alpha-tocopheroxyl radical in micellar solutions studied by nanosecond laser flash photolysis. FEBS Lett. 290: 205-208.
18. Sattler, W., D. Mohr, and R. Stocker. 1994. Rapid isolation of lipoproteins and assessment of their peroxidation by HPLC postcolumn chemiluminescence. Methods Enzymol. 233: 469-489.
19. Lowry, O. H., N. J. Rosebrough, A. L. Farr, and R. J. Randall. 1951. Protein measurement with Folin phenol reagent. J. Biol. Chem. 193: 265-275.
20. Mehlhorn, R. J., S. Sumida, and L. Packer. 1989. Tocopheroxyl radical persistence and tocopherol consumption in liposomes and in vitamin E-enriched rat liver mitochondria and microsomes. J. Biol. Chem. 264: 13448-13452.
21. Sharma, M. K., and G. R. Buettner. 1993. Interaction of vitamin C and vitamin E during free radical stress in plasma: an ESR study. Free Radical Biol. & Med. 14: 649-653.
22. Kalyanaraman, B., V. M. Darley-Usmar, J. Wood, J. Joseph, and S. Parthasarathy. 1992. Synergistic interaction between the probucol phenoxyl radical and ascorbic acid in inhibiting the oxidation of low density lipoprotein. J. Biol. Chem. 267: 6789-6795.
23. Esterbauer, H., G. Striegl, H. Puhl, and M. Rotheneder. 1989. Continuous monitoring of in vitro oxidation of human low density lipoprotein. Free Radical Res. Commun. 6: 67-75.
24. Tribble, D. L., J. J. M. van den Berg, P. A. Motchnik, B. N. Ames, D. M. Lewis, A. Chait, and R. M. Krauss. 1994. Oxidative susceptibility of low density lipoprotein subtractions is related to their ubiquinol-10 and alpha-tocopherol content. Proc. Natl. Acad. Sci. USA. 91: 1183-1187.
25. Puhl, H., G. Waeg, and H. Esterbauer. 1994. Methods to determine oxidation of low-density lipoproteins. Methods Enzymol. 233: 425-441.
26. Pryor, W. A., J. A. Cornicelli, L.J. Devall, B. Tait, B. K. Trivedi, D. T. Witiak, and M. Wu. 1993. A rapid screening test to determine the antioxidant potencies of natural and synthetic antioxidants. J. Org. Chem. 58: 3521-3532.
27. Foti, M., K. U. Ingold, and J. Lusztyk. 1994. The surprisingly high reactivity of phenoxyl radicals. J. Am. Chem. Soc. 116: 9440-9447.
28. Mukai, K., K. Daifuku, K. Okabe, T. Tanigaki, and K. Inoue. 1991. Structure-activity relationship in the quenching reaction of singlet oxygen by tocopherol (vitamin E) derivatives and related phenols. Finding of linear correlation between the rates of quenching of singlet oxygen and scavenging of peroxyl and phenoxyl radicals in solution. J. Org. Chem. 56: 4188-4192.
29. Kohar, I., M. Baca, C. Suarna, R. Stocker, and P. Southwell-Keely. 1995. Is α-tocopherol a reservoir for α-tocopheryl hydroquinone? Free Radical Biol. & Med. 19: 197-207.
30. Sato, K., E. Niki, and H. Shimasaki. 1990. Free radical-mediated chain oxidation of low density lipoprotein and its synergistic inhibition by vitamin E and vitamin C. Arch. Biochem. Biophys. 279: 402-405.
31. Stocker, R., V. W. Bowry, and B. Frei. 1991. Ubiquinol-10 protects human low density lipoprotein more efficiently against lipid peroxidation than docs α-tocopherol. Proc. Natl. Acad. Sci. USA. 88: 1646-1650.
32. Mohr, D., V. W. Bowry, and R. Stocker. 1992. Dietary supplementation with coenzyme Q10 results in increased levels of ubiquinol-10 within circulating lipoproteins and increased resistance of human low density lipoprotein to the initiation of lipid peroxidation. Biochim. Biophys. Acta. 1126: 247-254.
33. Stocker, R., and E. Peterhans. 1989. Synergistic interaction between vitamin E and the bile pigments bilirubin and biliverdin. Biochim. Biophys. Acta. 1002: 238-244.
34. Neuzil, J., and R. Stocker. 1994. Free and albumin-bound bilirubin is an efficient co-antioxidant for α-tocopherol, inhibiting plasma and low density lipoprotein lipid peroxidation. J. Biol. Chem. 269: 16712-16719.
35. Laranjinha, J. A., L. M. Almeida, and V. M. Madeira. 1994. Reactivity of dietary phenolic acids with peroxyl radicals: antioxidant activity upon low density lipoprotein peroxidation. Biochem. Pharmacol. 48: 487-494.
36. O'Brien, K., Y. Nagano, A. Gown, T. Kita, and A. Chait. 1991. Probucol treatment affects the cellular composition but not anti-oxidized low density lipoprotein immunoreactivity of plaques from Watanabe heritable hyperlipidemic rabbits. Arterioscler. Thromb. 11: 751-759.
37. Baumann, D. S., M. Doblas, G. Schonfeld, G. A. Sicard, and A. Daugherty. 1994. Probucol reduces the cellularity of aortic intimal thickening at anastomotic regions adjacent to prostetic grafts in cholesterol-fed rabbits. Arterioscler. Thromb. 14: 162-167.
38. Stein, Y., O. Stein, B. Delplanque, J. D. Fesmire, D. M. Lee, and P. Alaupovic. 1989. Lack of effect of probucol on atheroma formation in cholesterol-fed rabbits kept at comparable plasma cholesterol levels. Atherosclerosis. 75: 145-155.
39. Parthasarathy, S., S. G. Young, J. L. Witztum, R. C. Pittman, and D. Steinberg. 1986. Probucol inhibits oxidative modification of low density lipoprotein. J. Clin. Invest. 77: 641-644.
40. Barnhart, R. L., S. J. Busch, and R. L. Jackson. 1989. Concentration-dependent antioxidant activity of probucol in low density lipoproteins in vitro: probucol degradation precedes lipoprotein oxidation. J. Lipid Res. 30: 1703-1710.
41. Regnstrom, J., G. Walldius, L. A. Carlson, and J. Nilsson. 1990. Effect of probucol treatment on the susceptibility of low density lipoprotein isolated from hypercholesterolemic patients to become oxidatively modified in vitro. Atherosclerosis. 82: 43-51.
42. Cristol, L. S., I. Jialal, and S. M. Grundy. 1992. Effect of low-dose probucol therapy on LDL oxidation and the plasma lipoprotein profile in male volunteers. Atherosclerosis. 97: 11-20.
43. Gotoh, N., K. Shimizu, E. Komuro, J. Tsuchiya, N. Noguchi, and E. Niki. 1992. Antioxidant activities of probucol against lipid peroxidation. Biochim. Biophys. Acta. 1128: 147-154.
44. Barnhart, J. W., J. A. Sefranka, and D. D. McIntosh. 1970. Hypocholesterolemic effect of 4,4′-(isopropylidenedithio)-bis(2,6-di-t-butylphenol) (probucol). Am. J. Clin. Nutr. 23: 1229-1233.
45. Ku, G., N. S. Doherty, L. F. Schmidt, R. L. Jackson, and R. J. Dinerstein. 1990. Ex vivo lipopolysaccharide-induced interleukin-1 secretion from murine peritoneal macrophages inhibited by probucol, a hypocholesterolemic agent with antioxidant properties. FASEB J. 4: 1645-1653.
46. Pfeuffer, M. A., B. M. Richard, and R. C. Pittman. 1992. Probucol increases the selective uptake of HDL cholesterol esters by HepG2 human hepatoma cells. Arterioscler. Thromb. 12: 870-878.