Antioxidant properties of 2,3-dimethoxy-5-methyl-6-(10-hydroxydecyl)- 1,4-benzoquinone (idebenone)

Chemical Research in Toxicology

Volumn 11, Issue 1, 1998, Pages 54-63

  Mordente, Alvaro ^a   Martorana, Giuseppe E ^a   Minotti, Giorgio ^a   Giardina, Bruno ^a  

^a CATHOLIC UNIVERSITY   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; ADENOSINE DIPHOSPHATE; ANTIOXIDANT; CYTOCHROME P450; HEMOGLOBIN; HYDROPEROXIDE; IDEBENONE; IRON COMPLEX; PEROXYNITRITE; SCAVENGER; TROLOX C;

ANIMAL CELL; ARTICLE; CELL PROTECTION; LIPID PEROXIDATION; LIVER MICROSOME; MALE; NONHUMAN; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; RAT;

ANTIOXIDANTS; ARACHIDONIC ACID; BENZOQUINONES; FREE RADICALS; LIPID PEROXIDATION; PEROXIDES;

ANIMALIA;

EID: 0031885039     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx970136j     Document Type: Article

References (58)

1. Halliwell, B. (1992) Reactive oxygen species and the central nervous system. J. Neurochem. 59, 1609-1623.
2. Olanow, C. W. (1993) A radical hypothesis for neurodegeneration. Trends Neurosci. 16, 439-444.
3. Bergamasco, B., Scarzella, L., and La Commare, P. (1994) Idebenone, a new drug in the treatment of cognitive impairment in patients with dementia of the Alzheimer type. Funct. Neurol. 9, 161-168.
4. Gillis, J. C., Benefield, P., and McTavish, D. (1994) Idebenone. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in age-related cognitive disorders. Drugs Aging 5, 133-152.
5. Curti, D., Izzo, E., Brambilla, L., Facchetti, G., Sangiovanni, G., and Brambilla, G. (1995) Effect of a ubiquinone-like molecule on oxidative energy metabolism in rat cortical synaptosomes at different ages. Neurochem. Res. 20, 1001-1006.
6. Nitta, A., Hasegawa, T., and Nabeshima, T. (1993) Oral administration of idebenone, a stimulator of NGF synthesis, recovers reduced NGF content in aged rat brain. Neurosci. Lett. 163, 219-222.
7. Suno, M., and Nagaoka, A. (1984) Inhibition of lipid peroxidation by a novel compound, idebenone (CV-2619). Jpn. J. Pharmacol. 35, 196-198.
8. Suno, M., and Nagaoka, A. (1984) Inhibition of lipid peroxidation by a novel compound (CV-2619) in brain mitochondria and mode of action of the inhibition. Biochem. Biophys. Res. Commun. 125, 1046-1052.
9. Miyamoto, M., Murphy, T. H., Schnaar, R. L., and Coyle, J. T. (1989) Antioxidants protect against glutamate-induced cytotoxicity in a neuronal cell line. J. Pharmacol. Exp. Ther. 250, 1132-1140.
10. Suno, M., Terashita, Z., and Nagaoka, A. (1989) Inhibition of platelet aggregation by idebenone and the mechanism of the inhibition. Arch. Gerontol. Geriatr. 8, 313-321.
11. Naito, M., Hayashi, T., Yamada, K., Asai, K., Yoshimine, N., and Iguchi, A. (1993) Protective effects of idebenone on vascular endothelial cells against toxicity induced by oxidatively modified low-density lipoprotein. Artery 20, 314-323.
12. Wieland, E., Schutz, E., Armstrong, V. W., Kuthe, F., Heller, C., and Oellerich, M. (1995) Idebenone protects hepatic microsomes against oxygen radical-mediated damage in organ preservation solutions. Transplantation 60, 444-451.
13. Rieske, J. S. (1967) Preparation and properties of reduced coenzyme Q-cytochrome c reductase (complex III of the respiratory chain). Methods Enzymol. 10, 239-245.
14. Tubaro, F., Micossi, E., and Ursini, F. (1996) The antioxidant capacity of complex mixtures by kinetic analysis of crocin bleaching inhibition. J. Am. Oil Chem. Soc. 73, 173-179.
15. Blois, M. S. (1958) Antioxidant determinations by the use of stable free radical. Nature 181, 1199-1200.
16. Rice Evans, C., and Miller, N. J. (1994) Total antioxidant status in plasma and body fluids. Methods Enzymol. 234, 279-293.
17. Barr, D. P., and Aust, S. D. (1993) On the mechanism of peroxidase-catalyzed oxygen production. Arch. Biochem. Biophys. 303, 377-382.
18. Terao, K., and Niki, E. (1986) Damage to biological tissues induced by radical initiator 2,2
19. Glazer, A. N. (1990) Phycoerythrin fluorescence-based assay for reactive oxygen species. Methods Enzymol. 186, 161-168.
20. Kuypers, F. A., van den Berg, J. J., Schalkwijk, C., Roelofsen, B., and Op den Kamp, J. A. (1987) Parinaric acid as a sensitive fluorescent probe for the determination of lipid peroxidation. Biochim. Biophys. Acta 921, 266-274.
21. van den Berg, J. J., Op den Kamp, J. A., Lubin, B. H., Roelofsen, B., and Kuypers, F. A. (1992) Kinetics and site specificity of hydroperoxide-induced oxidative damage in red blood cells. Free Radical Biol. Med. 12, 487-498.
22. Schultz, J. R., Ellerby, L. M., Gralla, E. B., Valentine, J. S., and Clarke, C. F. (1996) Autoxidation of ubiquinol-6 is independent of Superoxide dismutase. Biochemistry 35, 6595-6603.
23. Holler, T. P., and Hopkins, P. B. (1989) A qualitative fluorescence-based assay for tyrosyl radical scavenging activity: ovothiol A is an efficient scavenger. Anal. Biochem. 180, 326-330.
24. Mordente, A., Santini, S. A., Miggiano, A. G., Martorana, G. E., Petitti, T., Minotti, G., and Giardina, B. (1994) The interaction of short chain coenzyme Q analogues with different redox states of myoglobin. J. Biol. Chem. 269, 27394-27400.
25. Giulivi, C., Romero, F. J., and Cadenas, E. (1992) The interaction of Trolox C, a water-soluble vitamin E analogue, with ferrylmyoglobin: Reduction of the oxoferryl moiety. Arch. Biochem. Biophys. 299, 302-312.
26. Buege, J. A., and Aust, S. D. (1978) Microsomal lipid peroxidation. Methods Enzymol. 52, 302-310.
27. Ryan, T. P., Samokyszyn, V. M., Dellis, S., and Aust, S. D. (1990) Effects of (+)-1,2-bis(3,5-dioxopiperazin-l-yl)propane (ADR-529) on iron-catalyzed lipid peroxidation. Chem. Res. Toxicol. 3, 384-390.
28. Crow, J. P., Beckman, J. S., and McCord, J. M. (1995) Sensitivity of the essential zinc-thiolate moiety of yeast alcohol dehydrogenase to hypochlorite and peroxynitrite. Biochemistry 34, 3544-3552.
29. Minotti, G. (1992) The role of an endogenous nonheme iron in microsomal redox reactions. Arch. Biochem. Biophys. 297, 189-198.
30. Laudicina, D. C., and Marnett, L. J. (1990) Enhancement of hydroperoxide-dependent lipid peroxidation in rat liver microsomes by ascorbic acid. Arch. Biochem. Biophys. 278, 73-80.
31. Minotti, G. (1989) Adriamycin-dependent release of iron from microsomal membranes. Arch. Biochem. Biophys. 268, 398-403.
32. Stoschek, C. (1990) Quantitation of protein. Methods Enzymol. 182, 58-60.
33. Omura, T., and Sato, R. (1964) The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J. Biol. Chem. 239, 2379-2385.
34. Teng, C., Hsiao, G., Inoue, T., and Satoh, M. (1996) N-Allylseco-boldine as a novel antioxidant against peroxidative damage. Eur. J. Pharmacol 303, 129-139.
35. Tsuchiya, M., Scita, G., Freisieben, H. J., Kagan, V. E., and Packer, L. (1992) Antioxidant radical-scavenging activity of carotenoids and retinoids compared to alpha-tocopherol. Methods Enzymol. 213, 460-472.
36. Maiorino, M., Roveri, A., and Ursini, F. (1992) Antioxidant effect of Ebselen (PZ 51): Peroxidase mimetic activity on phospholipid and cholesterol hydroperoxides vs free radical scavenger activity. Arch. Biochem. Biophys. 295, 404-409.
37. Giulivi, C., and Cadenas, E. (1994) Ferrylmyoglobin: Formation and chemical reactivity toward electron-donating compounds. Methods Enzymol. 233, 189-202.
38. Pryor, W. A., and Squadrito, G. L. (1995) The chemistry of peroxynitrite: A product from the reaction of nitric oxide with Superoxide. Am. J. Physiol. 268, L699-L722.
39. Beckman, J. S., Chen, J., Crow, J. P., and Ye, Y. Z. (1994) Reactions of nitric oxide, Superoxide and peroxynitrite with Superoxide dismutase in neurodegeneration. Prog. Brain Res. 103, 371-380.
40. Minotti, G. (1993) Sources and role of iron in lipid peroxidation. Chem. Res. Toxicol. 6, 134-146.
41. 2+-dependent lipid peroxidation. Free Radical Biol. Med. 3, 379-387.
42. Svingen, B. A., Buege, J. A., O'Neal, F. O., and Aust, S. D. (1979) The mechanism of NADPH-dependent lipid peroxidation. The propagation of lipid peroxidation. J. Biol. Chem. 254, 5892-5899.
43. Weiss, R. H., Arnold, J. L., and Estabrook, R. W. (1987) Transformation of an arachidonic acid hydroperoxide into epoxyhydroxy and trihydroxy fatty acids by liver microsomal cytochrome P-450. Arch. Biochem. Biophys. 252, 334-338.
44. Heinecke, J. W., Li, W., Francis, G. A., and Goldstein, J. A. (1993) Tyrosyl radical generated by myeloperoxidase catalyzes the oxidative cross-linking of proteins. J. Clin. Invest. 91, 2866-2872.
45. Thomas, C. E., Morehouse, L. A., and Aust, S. D. (1985) Ferritin and superoxide-dependent lipid peroxidation. J. Biol. Chem. 260, 3275-3280.
46. Keyer, K., and Imlay, J. A. (1996) Superoxide accelerates DNA damage by elevating free-iron levels. Proc. Natl. Acad. Sci. U.S.A. 93, 13635-13640.
47. Puppo, A., and Halliwell, B. (1988) Formation of hydroxyl radicals from hydrogen peroxide in the presence of iron. Is haemoglobin a biological Fenton reagent? Biochem. J. 249, 185-190.
48. Bucher, J. R., Tien, M., and Aust, S. D. (1983) The requirement for ferric in the initiation of lipid peroxidation by chelated ferrous iron. Biochem. Biophys. Res. Commun. 111, 777-784.
49. Minotti, G., Mancuso, C., Frustaci, A., Mordente, A., Santini, S. A., Calafiore, A. M., Liberi, G., and Gentiloni, N. (1996) Paradoxical inhibition of cardiac lipid peroxidation in cancer patients treated with doxorubicin. Pharmacologic and molecular reappraisal of anthracycline cardiotoxicity. J. Clin. Invest. 98, 650-661.
50. Stocker, R., and Suarna, C. (1993) Extracellular reduction of ubiquinone-1 and -10 by human Hep G2 and blood cells. Biochim. Biophys. Acta 1158, 15-22.
51. Vaillant, F., Larm, J. A., McMullen, G. L., Wolvetang, E. J., and Lawen, A. (1996) Effectors of the mammalian plasma membrane NADH-oxidoreductase system. Short-chain ubiquinone analogues as potent stimulators. J. Bioenerg. Biomembr. 28, 531-540.
52. Beyer, R. E., Segura Aguilar, J., Di Bernardo, S., Cavazzoni, M., Fato, R., Fiorentini, D., Galli, M. C., Setti, M., Landi, L., and Lenaz, G. (1996) The role of DT-diaphorase in the maintenance of the reduced antioxidant form of coenzyme Q in membrane systems. Proc. Natl. Acad. Sci. U.S.A. 93, 2528-2532.
53. Zhang, Y., Aberg, F., Appelkvist, E. L., Dallner, G., and Ernster, L. (1995) Uptake of dietary coenzyme Q supplement is limited in rats. J. Nutr. 125, 446-453.
54. Lonnrot, K., Metsa Ketela, T., Molnar, G., Ahonen, J., Latvala, M., Peltola, J., Pietila, T., and Alho, H. (1996) The effect of ascorbate and ubiquinone supplementation on plasma and CSF total antioxidant capacity. Free Radical Biol. Med. 21, 211-217.
55. Pappert, E. J., Tangney, C. C., Goetz, C. G., Ling, Z. D., Lipton, J. W., Stebbins, G. T., and Carvey, P. M. (1996) Alpha-tocopherol in the ventricular cerebrospinal fluid of Parkinson's disease patients: Dose-response study and correlations with plasma levels. Neurology 47, 1037-1042.
56. Sano, M., Ernesto, C., Thomas, R., Klauber, M. R., Schafer, K., Grundman, M., Woodbury, P., Growdon, J., Cotman, C. W., Pfeiffer, E., and Schneider, L. S. (1997) A controlled trial of selegiline, alpha-tocopherol, or both as treatment for Alzheimer disease. N. Engl. J. Med. 336, 1216-1222.
57. Torii, H., Yoshida, K., Kobayashi, T., Tsukamoto, T., and Tanayama, S. (1985) Disposition of idebenone (CV-2619), a new cerebral metabolism improving agent, in rats and dogs. J. Pharmacobiodyn. 8, 457-467.
58. Nagai, Y., Yoshida, K., Narumi, S., Tanayama, S., and Nagaoka, A. (1989) Brain distribution of idebenone and its effect on local cerebral glucose utilization in rats. Arch. Gerontol. Geriatr. 8, 257-272.