Reactivity of ubiquinone and ubiquinol with superoxide and the hydroperoxyl radical: implications for in vivo antioxidant activity

Free Radical Biology and Medicine

Volumn 46, Issue 1, 2009, Pages 105-109

  Maroz, Andrej ^a   Anderson, Robert F ^a   Smith, Robin A J ^b   Murphy, Michael P ^c  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b UNIVERSITY OF OTAGO   (New Zealand)

^c UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Free radicals; Pulse radiolysis; Superoxide; Ubiquinol; Ubiquinone

Indexed keywords

IDEBENONE; MITOQUINOL; MITOQUINONE; SUPEROXIDE; UBIQUINONE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; IN VIVO STUDY; MITOCHONDRIAL MEMBRANE; PRIORITY JOURNAL; PULSE RADIOLYSIS;

ANTIOXIDANTS; CYTOPROTECTION; ELECTRON TRANSPORT; HYDROGEN PEROXIDE; LIPID PEROXIDATION; MITOCHONDRIA; MITOCHONDRIAL MEMBRANES; MODELS, CHEMICAL; OXIDATIVE STRESS; PULSE RADIOLYSIS; SUPEROXIDES; UBIQUINONE; WATER;

EID: 57449103542     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2008.09.033     Document Type: Article

References (34)

1. Crane F.L. Hydroquinone dehydrogenases. Annu. Rev. Biochem. 46 (1977) 439-469
2. Ernster L., and Dallner G. Biochemical, physiological and medical aspects of ubiquinone function. Biochim. Biophys. Acta 1271 (1995) 195-204
3. James A.M., Smith R.A.J., and Murphy M.P. Antioxidant and prooxidant properties of mitochondrial coenzyme Q. Arch. Biochem. Biophys. 423 (2004) 47-56
4. Frei B., Kim M.C., and Ames B.N. Ubiquinol-10 is an effective lipid-soluble antioxidant at physiological concentrations. Proc. Natl. Acad. Sci. USA 87 (1990) 4879-4883
5. Beckman K.B., and Ames B.N. The free radical theory of aging matures. Physiol. Rev. 78 (1998) 547-581
6. Finkel T. Radical medicine: treating ageing to cure disease. Nat. Rev. Mol. Cell Biol. 6 (2005) 971-976
7. Murphy M.P., and Smith R.A.J. Targeting antioxidants to mitochondria by conjugation to lipophilic cations. Annu. Rev. Pharmacol. Toxicol. 47 (2007) 629-656
8. Hausse A.O., Aggoun Y., Bonnet D., Sidi D., Munnich A., Rotig A., and Rustin P. Idebenone and reduced cardiac hypertrophy in Friedreich's ataxia. Heart 87 (2002) 346-349
9. Shults C.W., Oakes D., Kieburtz K., Beal M.F., Haas R., Plumb S., Juncos J.L., Nutt J., Shoulson I., Carter J., Kompoliti K., Perlmutter J.S., Reich S., Stern M., Watts R.L., Kurlan R., Molho E., Harrison M., and Lew M. Effects of coenzyme Q10 in early Parkinson disease: evidence of slowing of the functional decline. Arch. Neurol. 59 (2002) 1541-1550
10. Kelso G.F., Porteous C.M., Coulter C.V., Hughes G., Porteous W.K., Ledgerwood E.C., Smith R.A.J., and Murphy M.P. Selective targeting of a redox-active ubiquinone to mitochondria within cells. J. Biol. Chem. 276 (2001) 4588-4596
11. Balaban R.S., Nemoto S., and Finkel T. Mitochondria, oxidants, and aging. Cell 120 (2005) 483-495
12. Bobrowski M., Liwo A., and Hirao K. Theoretical study of the energetics of the reactions of triplet dioxygen with hydroquinone, semiquinone, and their protonated forms: relation to the mechanism of superoxide generation in the respiratory chain. J. Phys. Chem. 111 (2007) 3543-3549
13. Patel K.B., and Willson R.L. Semiquinone free radicals and oxygen. Pulse radiolysis study of one electron transfer equilibria. J. Chem. Soc. Faraday Trans. I 69 (1973) 814-821
14. Sawyer D.T., and Valentine J.S. How super is superoxide?. Acc. Chem. Res. 14 (1981) 393-400
15. -) radicals. Biochim. Biophys. Acta 778 (1984) 579-585
16. James A.M., Sharpley M.S., Manas A.R., Frerman F.E., Hirst J., Smith R.A.J., and Murphy M.P. Interaction of the mitochondria-targeted antioxidant MitoQ with phospholipid bilayers and ubiquinone oxidoreductases. J. Biol. Chem. 282 (2007) 14708-14718
17. Taylor, K. M.; Smith, R.A.J. Mitoquinone derivatives used as mitochondrially targeted antioxidants, and preparation thereof. Patent application: WO 2005019232 (Antipodean Biotechnology Ltd, N.Z.). 2005.
18. Taylor, K. M.; Smith, R.A.J. Preparation of mitoquinone derivatives as mitochondrially targeted antioxidants. U.S. patent application 2005019232 (Antipodean Pharmaceuticals, Inc., USA). 2006: Cont-in-part of U.S. Ser. No. 172,916.
19. Morimoto H. Ubiquinone and related compounds. XL. Synthesis and biochemical behavior of idebenone and related compounds. Naturwissenschaften 76 (1989) 200-205
20. Anderson R.F., Denny W.A., Li W., Packer J.E., Tercel M., and Wilson W.R. Pulse radiolysis studies on the fragmentation of arylmethyl quaternary nitrogen mustards by one-electron reduction in aqueous solution. J. Phys. Chem. A 101 (1997) 9704-9709
21. Battino, E. R. IUPAC Solubility Data Series, Vol. 7, Oxygen and Ozone. Pergamon Press, Oxford, 1981.
22. Dias A.M.A., Bonifacio R.P., Marrucho I.M., Padua A.A., and Costa Gomes M.F. Solubility of oxygen in n-hexane and in n-perfluorohexane: experimental determination and prediction by molecular simulation. Phys. Chem. Chem. Phys. 5 (2003) 543-549
23. Meisel D., and Czapski G. One-electron transfer equilibria and redox potentials of radicals studied by pulse radiolysis. J. Phys. Chem. 79 (1975) 1503-1509
24. Afanas'ev I.B. Superoxide Ion: Chemistry and Biological Implications Vol. I (1989), CRC Press, Boca Raton, FL
25. Prince R.C., Dutton P.L., and Bruce J.M. Electrochemistry of ubiquinones, menaquinones and plastoquinones in aprotic solvents. FEBS Lett. 160 (1983) 273-276
26. •. J. Phys. Chem. 79 (1975) 397-402
27. •OOH radical by coenzyme Q. J. Am. Chem. Soc. 126 (2004) 920-927
28. •- radicals in aqueous solution. J. Phys. Chem. Ref. Data 14 (1985) 1041-1100
29. Muller F.L., Liu Y., and Van Remmen H. Complex III releases superoxide to both sides of the inner mitochondrial membrane. J. Biol. Chem. 279 (2004) 49064-49073
30. Ross M.F., Prime T.A., Abakumova I., James A.M., Porteous C.M., Smith R.A.J., and Murphy M.P. Rapid and extensive uptake and activation of hydrophobic triphenylphosphonium cations within cells. Biochem. J. 411 (2008) 633-645
31. - with unsaturated fatty acids. J. Biol. Chem. 258 (1983) 4759-4761
32. Kagan V., Serbinova E., and Packer L. Antioxidant effects of ubiquinones in microsomes and mitochondria are mediated by tocopherol recycling. Biochem. Biophys. Res. Commun. 169 (1990) 851-857
33. Rich P.R. Electron and proton transfers through quinones and cytochrome bc complexes. Biochim. Biophys. Acta 768 (1984) 53-79
34. Land E.J., and Swallow A.J. One-electron reactions in biochemical systems as studied by pulse radiolysis. 3. Ubiquinone. J. Biol. Chem. 245 (1970) 1890-1894