Phenolic antioxidants: A rationale for design and evaluation of novel antioxidant drug for atherosclerosis

Free Radical Biology and Medicine

Volumn 28, Issue 10, 2000, Pages 1538-1546

  Noguchi, Noriko ^a   Niki, Etsuo ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Tocopherol; Antioxidant; Free radical; LDL oxidation; Lipid peroxidation; Probucol

Indexed keywords

2,3 DIHYDROXY 5 HYDROXY 2,2 DIPENTYL 4,6 DI TERT BUTYLBENZOFURAN; 4,6 DI TERT BUTYL 2,3 DIHYDRO 5 HYDROXY 2,2 DIPENTYLBENZOFURAN; ALPHA TOCOPHEROL; ANTIOXIDANT; FREE RADICAL; LOW DENSITY LIPOPROTEIN; UNCLASSIFIED DRUG;

AGING; ANTIOXIDANT ACTIVITY; ATHEROSCLEROSIS; CANCER; CONFERENCE PAPER; HUMAN; LIPID PEROXIDATION; OXIDATIVE STRESS; PRIORITY JOURNAL;

ANIMALS; ANTIOXIDANTS; ARTERIOSCLEROSIS; BENZOFURANS; DRUG DESIGN; DRUG STABILITY; FREE RADICAL SCAVENGERS; HUMANS; VITAMIN E;

EID: 0034656850     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(00)00256-2     Document Type: Conference Paper

References (72)

1. Thomas C.E. Approach and rationale for the design of synthetic antioxidants as therapeutic agents. Packer L., Cadenas E. Handbook of synthetic antioxidants. 1997;1-52 Marcel Dekker, New York.
2. Steinberg D., Parthasarathy S., Carew T.E., Khoo J.C., Witztum J.L. Beyond cholesterol Modification of low-density lipoprotein that increase its atherogenicity . N. Engl. J. Med. 320:1989;915-924.
3. Hazell L.J., Arnold L., Flowers D., Waeg G., Malle E., Stocker R. Presence of hypochlorite-modified proteins in human atherosclerotic lesions. J. Clin. Invest. 97:1996;1535-1544.
4. Itabe H., Takashima E., Iwasaki H., Kimura J., Yoshida Y., Imanaka T., Takano T. A monoclonal antibody against oxidized lipoprotein recognized foam cells in atherosclerotic lesions. Complex formation of oxidized phosphatidylcholines and polypeptides. J. Biol. Chem. 269:1994;15274-15279.
5. Jansen H., Ghanem H., Kuypers J.H., Birkenhager J.C. Autoantibodies against malondialdehyde-modified LDL are elevated in subjects with an LDL subclass pattern B. Atherosclerosis. 115:1995;255-262.
6. Bellomo G., Maggi E., Poli M., Agosta F.G., Bollati P., Finardi G. Autoantibodies against oxidatively modified low-density lipoproteins in NIDDM. Diabetes. 44:1995;60-66.
7. Stampfer M.J., Hennekens C.H., Manson J.E., Coditz G.A., Rosner B., Willett W.C. Vitamin E consumption and the risk of coronary disease in women. N. Engl. J. Med. 328:1993;1444-1449.
8. Rimm E.B., Stampfer M.J., Ascherio A., Giovannucci E., Goditz G.A., Willett W.C. Vitamin E consumption and the risk of coronary heart disease in men. N. Engl. J. Med. 328:1993;1450-1456.
9. Gey K.F. Vitamin E plus C and interacting conutrients required for optimal health. BioFactors. 7:1998;113-174.
10. Kita T., Nagano Y., Yokode M., Ishii K., Kume N., Ooshima A., Yoshida H., Kawai C. Probucol prevents the progression of atherosclerosis in Watanabe heritable hyperlipidemic rabbit, an animal model for familial hypercholesterolemia. Proc. Natl. Acad. Sci. USA. 84:1987;5928-5931.
11. Carew T.E., Schwenke D.C., Steinberg D. 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. 84:1987;7725-7729.
12. Steinberg D. Studies on the mechanism of action of probucol. Am. J. Cardiol. 57:1986;16H-21H.
13. Cynshi O., Kawabe Y., Suzuki T., Takashima Y., Kaise H., Nakamura M., Ohba Y., Kato Y., Tamura K., Hayasaka A., Higashida A., Sakaguchi H., Takeya M., Takahashi K., Inoue K., Noguchi N., Niki E., Kodama T. Antiatherogenic effects of the antioxidant BO-653 in three different animals models. Proc. Natl. Acad. Sci. USA. 95:1998;10123-10128.
14. Niki E., Noguchi N., Tsuchihashi H., Gotoh N. Interaction among vitamin C, vitamin E, and β-carotene. Am. J. Clin. Nutr. 62:1995;1322S-1326S.
15. Esterbauer H., Rotheneder M., Striegl G., Waeg G., Ashy A., Sattler W., Jürgens G. Vitamin E and other lipophilic antioxidants protect LDL against oxidation. Fat. Sci. Technol. 91:1989;316-324.
16. Burton G.W., Doba T., Gabe E.J., Hughes L., Lee F.L., Prasa L., Ingold K.U. Autoxidation of biological molecules. 4. Maximizing the antioxidant activity of phenols. J. Am. Chem. Soc. 107:1985;7053-7065.
17. Mukai K., Okabe K., Hosose H. Synthesis and stopped-flow investigation of antioxidant activity of tocopherols. Finding of new tocopherol derivatives having the highest antioxidant activity among phenolic antioxidants. J. Org. Chem. 54:1989;557-560.
18. Burton G.W., Ingold K.U. Vitamin E application of the principles of physical organic chemistry to the exploration of its structure and function . Acc. Chem. Res. 194:1986;194-201.
19. Gotoh N., Shimizu K., Komuro E., Tsuchiya J., Noguchi N., Niki E. Antioxidant activities of probucol against lipid peroxidation. Biochim. Biophys. Acta. 1128:1992;147-154.
20. Niki, E.; Takahashi, M.; Komuro, E. Antioxidant activity of vitamin E in liposomal membranes. Chem. Lett. 1573-1576; 1986.
21. Niki E., Komuro E. Inhibition of peroxidation of membranes. Simic M.G., Taylor K.A., Ward J.F., von Sonntag C. Oxygen radicals in biology and medicine. 1989;561-566 Plenum Publishing Corp, New York.
22. Barclay L.R.C. Model biomembranes quantitative studies of peroxidation, antioxidant action, partitioning, and oxidative stress . Can. J. Chem. 71:1993;1-16.
23. Barclay L.R.C., Baskin K.A., Dakin K.A., Locke S.J., Vinqvist M.R. The antioxidant activities of phenolic antioxidants in free radical peroxidation of phospholipid membranes. Can. J. Chem. 68:1990;2258-2269.
24. Gotoh N., Noguchi N., Tsuchiya J., Morita K., Sakai H., Shimasaki H., Niki E. Inhibition of oxidation of low density lipoprotein by vitamin E and related compounds. Free Radic. Res. 24:1996;123-134.
25. Niki E., Noguchi N., Gotoh N. Dynamics of peroxidation and its inhibition by antioxidants. Biochem. Soc. Trans. 21:1993;313-317.
26. Cillard J., Cillard P., Cormier M. α-Tocopherol prooxidant effect in aqueous media increased autoxidation rate of linoleic acid . J. Am. Oil Chem. Soc. 57:1980;252-255.
27. Terao J., Matsushita S. The peroxidizing effect of α-tocopherol autoxidation of methyl linoleate in bulk phase. Lipids. 21:1986;2555-2560.
28. Takahashi M., Yoshikawa Y., Niki E. Oxidation of lipids. XVII. Crossover effect of tocopherols in the spontaneous oxidation of methyl linoleate. Bull. Chem. Soc. Jpn. 62:1989;1885-1890.
29. Mukai K. Synthesis and kinetic study of antioxidant and prooxidant actions of vitamin E derivatives. Packer L., Fuchs J. Vitamin E in health and disease. 1993;97-119 Marcel Dekker, New York.
30. Upston J.M., Terentis A.C., Stocker R. Tocopherol-mediated peroxidation of lipoproteins implications for vitamin E as a potential antiatherogenic supplement . FASEB J. 13:1999;977-994.
31. Matsuo M., Matsumoto S., Iitaka Y., Niki E. Radical scavenging reactions of vitamin E and its model compound, 2,2,5,7,8-pentamethyl-6-chromanol, in a tert-butylperoxyl radical-generating system. J. Am. Chem. Soc. 111:1989;7179-7189.
32. Niki E., Kawakami A., Saito M., Yamamoto Y., Tsuchiya J., Kamiya Y. Effect of phytyl side chain of vitamin E on its antioxidant activity. J. Biol. Chem. 260:1985;2191-2196.
33. Niki E., Komuro E., Takahashi M., Urano S., Ito E., Terao K. Oxidative hemolysis of erythrocytes and its inhibition by free radical scavengers. J. Biol. Chem. 263:1988;19809-19814.
34. Noguchi N., Iwaki Y., Takahashi M., Komuro E., Kato Y., Tamura K., Cynshi O., Kodama T., Niki E. 2,3-Dihydroxy-2,2-dipentyl-4,6-di-tert-butyl-benzofuran; design and evaluation as a novel radical-scavenging antioxidant against lipid peroxidation. Arch. Biochem. Biophys. 342:1997;236-243.
35. Barclay L.R.C., Vinqvist M.R., Mukai K., Itoh S., Morimoto H. Chain-breaking phenolic antioxidants; steric and electronic effects in polyalkylchromanols, tocopherol analogs, hydroquinone, and superior antioxidants of the polyalkylbenzochromanol and naphthofuran class. J. Org. Chem. 58:1993;7416-7420.
36. Watanabe, A.; Noguchi, N.; Fujisawa, A.; Kodama, T.; Niki, E.; Tamura, K.; Cynshi, O. Stability and reactivity of aryloxyl radicals derived from a novel antioxidant BO-653 and related compounds. Effects of substituent and side chain in solution and membranes. J. Am. Chem. Soc. In press; 2000.
37. Takahashi M., Tsuchiya J., Niki E. Scavenging of radicals by vitamin E in the membranes as studied by spin labeling. J. Am. Chem. Soc. 111:1989;6350-6353.
38. Noguchi N., Okimoto Y., Tsuchiya J., Cynshi O., Kodama T., Niki E. Inhibition of oxidation of low-density lipoprotein by a novel antioxidant BO-653 prepared by theoretical design. Arch. Biochem. Biophys. 347:1997;141-147.
39. Müller K., Carpenter K.L.H., Freeman M.A., Mitchinson M.J. Antioxidant BO-653 and human macrophage-mediated LDL oxidation. Free Rad. Res. 30:1999;59-71.
40. Zhang S.H., Reddick R.L., Avdievich E., Surles L.K., Jones R.G., Reynolds J.B., Quarfordt S.H., Maeda N. Paradoxical enhancement of atherosclerosis by probucol treatment in apolipoprotein E-deficient mice. J. Clin. Invest. 99:1997;2858-2866.
41. Bahnhart R.L., Busch S.J., Jackson R.L. Concentration-dependent antioxidant activity of probucol in low density lipoproteins in vitro probucol degradation precedes lipoprotein oxidation . J. Lipid Res. 30:1989;1703-1710.
42. Mao S.J., Yates M.T., Jackson R.L. Antioxidant activity and serum level of probucol and probucol metabolites. Methods Enzymol. 234:1994;505-513.
43. O'Leary V.J., Tilling L., Fleetwood G., Stone D., Darley-Usmar V.M. The resistance of low density lipoprotein to oxidation promoted by copper and its use as an index of antioxidant therapy. Atherosclerosis. 119:1996;169-179.
44. Witting P.K., Pettersson K., Ostlund-Lindqvist A.-M., Westerlund C., Eriksson A.W., Stocker R. Inhibition of a coantioxidant of aortic lipoprotein lipid peroxidation and atherosclerosis in apolipoprotein E and low density lipoprotein receptor gene double knockout mice. FASEB J. 13:1999;667-675.
45. Witting P., Pettersson K., Ostlund-Lindqvist A.-M., Westerlund C., Wagberg M., Stocker R. Discussions of atherogenesis from aortic accumulation of lipid hydroperoxides in Watanabe herritable hyperlipidemic rabbits. J. Clin. Invest. 104:1999;213-220.
46. Keaney J.F. Jr, Simon D.I., Freedman J.E. Vitamin E and vascular homeostasis implications for atherosclerosis . FASEB J. 13:1999;965-976.
47. Kugiyama K., Kerns S.A., Morrisett J.D., Roberts R., Henry P.D. Impairment of endothelium-dependent arterial relaxation by lysolecithin in modified low-density lipoproteins. Nature (Lond.). 344:1990;160-162.
48. Keaney J.F. Jr, Gaziano J.M., Xu A., Frei B., Curran-Celantano J., Shwaery G.T., Loscalzo J., Vita J.A. Dietary antioxidants preserve endothelium-dependent vessel relaxation in cholesterol-fed rabbits. Proc. Natl. Acad. Sci. USA. 90:1993;11880-11884.
49. Stewart-Lee A.L., Forster L.A., Nourooz-Zadeh J., Ferns G.A.A., Anggard E.E. Vitamin E protects against impairment of endothelium-mediated relaxations in cholesterol-fed rabbits. Arterioscler. Thromb. 14:1994;494-499.
50. Keaney J.F. Jr, Guo Y., Cunningham D., Shwaery G.T., Xu A., Vita J.A. Vascular incorporation of α-tocopherol prevents endothelial dysfunction due to oxidized LDL by inhibiting protein kinase C stimulation. J. Clin. Invest. 98:1996;386-394.
51. Koh K.K., Blum A., Schenke W.H., Hathaway L., Mincemoyer R., Panza J.A., Cannon R.O. III. Vitamin E improves endothelium-dependent vasodilator responsiveness comparable to estrogen in postmenopausal women. Circulation. 99:1999;354-360.
52. Kugiyama K., Doi H., Motoyama T., Soejima H., Misumi K., Kawano H., Nakagawa O., Yoshimura M., Ogawa H., Matsumura T., Sugiyama S., Nakano T., Nakajima K., Yasue H. Association of remnant lipoprotein levels with impairment of endothelium-dependent vasomotor function in human coronary arteries. Circulation. 97:1998;2519-2526.
53. Kugiyama K., Motoyama T., Doi H., Kawano H., Hirai N., Soejima H., Miyao Y., Takazoe K., Moriyama Y., Mizuno Y., Tsunoda R., Ogawa H., Sakamoto T., Sugiyama S., Yasue H. Improvement of endothelial vasomotor dysfunction by treatment with alpha-tocopherol in patients with high remnant lipoproteins levels. J. Am. Coll. Cardiol. 33:1999;1512-1518.
54. Motoyama T., Kawano H., Kugiyama K., Hirashima O., Ohgushi M., Tsunoda R., Moriyama Y., Miyao Y., Yoshimura M., Ogawa H., Yasue H. Vitamin E administration improves impairment of endothelium-dependent vasodilation in patients with coronary spastic angina. J. Am. College Cardiol. 32:1998;1672-1679.
55. Anderson T.J., Meredith I.T., Yeung A.C., Frei B., Selwyn A.P., Ganz P. The effect of cholesterol-lowering and antioxidant therapy on endothelium-dependent coronary vasomotion. N. Engl. J. Med. 332:1995;488-493.
56. Boscoboinik D., Szewczyk A., Azzi A. Alpha-tocopherol (vitamin E) regulates vascular smooth muscle cell proliferation and protein kinase C activity. Arch. Biochem. Biophys. 286:1991;264-269.
57. Boscoboinik D., Szewczyk A., Hensey C., Azzi A. Inhibition of cell proliferation by α-tocopherol. J. Biol. Chem. 266:1991;6188-6194.
58. Ozer N.K., Palozza P., Boscoboinik D., Azzi A. d-Alpha-tocopherol inhibits low density lipoprotein induced proliferation and protein kinase C activity in vascular smooth muscle cell. FEBS Lett. 322:1993;307-310.
59. Tasinato A., Boscoboinik D., Bartoli G.M., Maroni P., Azzi A. d-Alpha-tocopherol inhibition of vascular smooth muscle cell proliferation occurs at physiological concentrations, correlates with protein kinase C inhibition, and independent of its antioxidant properties. Proc. Natl. Acad. Sci. USA. 92:1995;12190-12194.
60. Faruqi R., de la Motta C., DiCorleto P. Alpha-tocopherol inhibits agonist-induced monocytic cell adhesion to cultured human endothelial cells. J. Clin. Invest. 94:1994;592-600.
61. Devaraj S., Li D., Jialal I. The effects of alpha-tocopherol supplementation on monocyte function decreased lipid oxidation interleukin 1 secretion, and monocyte adhesion to endothelium . J. Clin. Invest. 98:1996;756-763.
62. Rao, N. K.; Simon, D. I.; Xu, H.; Keaney, J. F. Jr. α-Tocopherol inhibits Mac-1 (CD11b/CD18)-dependent monocyte adhesion. Circulation 96:I-489; 1997.
63. Yoshida N., Yoshikawa T., Manabe H., Terasawa Y., Nondo M., Noguchi N., Niki E. Vitamin E protects against polymorphonuclear leukocyte-dependent adhesion to endothelial cells. J. Leukocyte Biol. 65:1999;757-763.
64. Heinecke J.W. Is lipid peroxidation relevant to atherogenesis? J. Clin. Invest. 104:1999;135-136.
65. Noguchi N., Numano R., Kaneda H., Niki E. Oxidation of lipids in low density lipoprotein particles. Free Rad. Res. 29:1998;43-52.
66. Karten B., Boechzelt H., Mittelbach M., Sattler W. Core aldehydes Formation occurrence and biological significance . Recent Res. Devel. Lipids Res. 3:1999;23-41.
67. Esterbauer H., Schaur R.J., Zollner H. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radic. Biol. Med. 11:1991;81-128.
68. Uchida K., Kanematsu M., Sakai K., Matsuda T., Hattori N., Mizuno Y., Suzuki D., Miyata T., Noguchi N., Niki E. Protein-bound acrolein potential markers for oxidative stress . Proc. Natl. Acad. Sci. USA. 95:1998;4882-4887.
69. Uchida K., Kanematsu M., Morimitsu Y., Osawa T., Noguchi N., Niki E. Acrolein is a product of lipid peroxidation reaction. J. Biol. Chem. 273:1998;16058-16066.
70. Sakai M., Miyazaki A., Hakamata H., Sasaki T., Yui S., Yamazaki M., Shichiri M., Horiuchi S. Lysophosphatidylcholine plays an essential role in the mitogenic effect of oxidized low density lipoprotein on murine macrophages. J. Biol. Chem. 269:1994;31430-31435.
71. Itabe H. Oxidized phospholipids as a new landmark in atherosclerosis. Prog. Lipid Res. 37:1998;181-207.
72. Brown A.J., Jessup W. Oxysterols and atherosclerosis. Atherosclerosis. 142:1999;1-28.