Research on Chemical Intermediates

, Volume 26, Issue 3, pp 269–282 | Cite as

A study on the interactions between coenzyme Q 0 and superoxide anion. Could ubiquinones mimic superoxide dismutase (SOD)?

  • Rita Petrucci
  • Elisabetta Giorgini
  • Elisabetta Damiani
  • Patricia Carloni
  • Giancarlo Marrosu
  • Antonio Trazza
  • Gian Paolo Littarru
  • Lucedio Greci


An electrochemical study was carried out on 1,4-benzoquinone, duroquinone, coenzymes Q 0 and Q 10 in the absence and in the presence of molecular oxygen in aprotic (DMF) and protic (DMF/H2O 95:5 (v/v)) media. Water was added because the investigated reactions are deeply influenced by the presence of protons. Q 0 and Q 10 exhibited a similar electrochemical behaviour. Since Q 0 is more soluble in protic medium than the biologically more important analogue Q 10 , it was chosen as a model for a more detailed investigation. Voltammetric studies of Q 0 carried out in aprotic and protic media in the presence of oxygen showed that, besides simple O2 ·− dismutation, the Q 0 promoted dismutation of O2 ·− should also be considered. Spectroelectrochemical experiments with the same experimental conditions support the electrochemical results, showing that in the presence of superoxide and in aprotic medium semiquinone Q 0 ·− gives rise to a disproportionation equilibrium, while in the presence of water it tends to be reoxidized to the starting Q 0 by OOH·. EPR measurements are also in agreement with these results.


Radical Anion Anodic Peak Ubiquinone Voltammetric Study Semiquinone Radical 
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  1. 1.
    S. Al-Malaika, in C. Booth and C. Price (Eds.), Comprehensive Polymer Science, Pergamon Press, Oxford, New York, 1989, 2, 539; J. Pospisil and P.P. Klemchuk, Oxidation Inhibition in Organic Materials, CRC Press Inc., Boca Raton, Florida, 1989, 1 and 2; B. Halliwell and J.M.C. Gutteridge in Lund (Ed.), Free Radicals in Biology and Medicine,, Clarendon Press, Oxford, 1993; C.E. Eriksson, and A. Na in F. Corongiu, S. Banni, M.A. Dessi and C. Rice-Evans (Eds.), Free Radicals and Antioxidants in Nutrition, Richelieu Press, 1993, 205–224.Google Scholar
  2. 2.
    S.A. Mortensen, Clin. Invest.,, 71, 116 (1993); S.R. Thomas, J. Neuzil and R. Stocker, Arterioscler. Thromb. Vasc. Biol., 16, 687 (1996).CrossRefGoogle Scholar
  3. 3.
    G. Lenaz, M. Battino, C. Castelluccio, R. Fato, M. Cavozzoni, H. Ranchova, C. Bovina, G. Formiggini and G.P. Castelli, Free. Rad. Res. Comm., 8, 317 (1990).CrossRefGoogle Scholar
  4. 4.
    E. Cadenas, A. Boveris, C.I. Ragan and A.O.M. Stoppani, Arch. Biochem. Biophys., 180, 248 (1977).CrossRefGoogle Scholar
  5. 5.
    R.C. Prince, P.L. Dutton and J.M. Bruce, FEBS Lett., 160, 273 (1983).CrossRefGoogle Scholar
  6. 6.
    K. Sugioka, M. Nakano, H. Totsune-Nakano, H. Minakami, S. Tero-Kubota and Y. Ikegami, Biochim. Biophis. Acta., 936, 377 (1988).CrossRefGoogle Scholar
  7. 7.
    H. Nohl and W. Jordan, Biochem. Biophys. Res. Commun., 138, 533 (1986).CrossRefGoogle Scholar
  8. 8.
    P. Carloni, E. Damiani, L. Greci, P. Stipa, G. Marrosu, R. Petrucci and A. Trazza, Tetrahedron, 52, 11257 (1996).Google Scholar
  9. 9.
    A. Brunmark and E. Cadenas, Free Rad. Biol. Med., 7, 435 91989).CrossRefGoogle Scholar
  10. 10.
    Y.A. Ilan, G. Czapski and D. Meisel, Biochim. Bhiophys. Acta, 430(2), 209 91976); G.R. Buettner, Arch. Biochem. Biophys., 300, 535 (1993).CrossRefGoogle Scholar
  11. 11.
    T. Ozawa and A. Hanaki, Chem. Pharm. Bull., 31, 2535 (1983).Google Scholar
  12. 12.
    C.C. Winterbourn, Arch. Biochem. Biophys., 209, 159 (1981).CrossRefGoogle Scholar
  13. 13.
    D.A. Stoyanovsky, A.N. Osipov, P.J. Quinn and V.E. Kagan, Arch. Biochem. Biophys., 323, 343 91995); H. Nohl, L. Gille and A. V. Kozlov, Free Rad. Biol. Med., 25, 666 (1988); K. Schnurr, M. Hellwing, B. Seidemann, P. Jungblut, H. Kuhn, S.M. Rapoport and T. Schewe, Free Rad. Biol. Med., 20, 11 (1996).CrossRefGoogle Scholar
  14. 14.
    H. Nohl, L. Gille, K. Schonheit and Y. Liu, Free Rad. Biol. Med., 20, 207 (1996).CrossRefGoogle Scholar
  15. 15.
    J. Wilshire and D.T. Sawyer, Acc. Chem. Res., 12, 105 (1979).CrossRefGoogle Scholar
  16. 16.
    D.T. Sawyer, M.J. Gibian, M.M. Morrison and T. Seo, J. Am. Chem. Soc., 100, 627 (1978).CrossRefGoogle Scholar
  17. 17.
    A.A. Frimer Organic Reactions Involving the Superoxide Anion, in S. Patai (Ed.), The Chemistry of Functional Groups. Peroxides, Wiley, New York, 1983, 429.Google Scholar
  18. 18.
    G. Merenyi, J. Lind and L. Engman, J. Chem. Soc. Perkin Trans. 2, 2551 (1994).Google Scholar
  19. 19.
    B. Kantilal, B. Patel and J.S. Willson, J. Chem. Soc. Faraday Trans. 1, 69, 814 (1973).CrossRefGoogle Scholar
  20. 20.
    J.M. McCord and I. Fridovich, J. Biol. Chem., 243, 5753 (1968).Google Scholar
  21. 21.
    R.S.K.A. Gamage, S. Umapathy and A.J. McQuillan, J. Electroanal. Chem., 284, 229 (1990); M. Degli Esposti, E. Ferri, G. Lenaz, Ital. J. Biochem., 30, 437 (1981).CrossRefGoogle Scholar
  22. 22.
    K.B. Ulmschneider and H.B. Stegmann, Semiquinones and Related Species in H. Fischer and K.-H. Hellwege (Eds.), Magnetic Properties of Free radicals. Part dl: Organic Anion Radicals, Landolt-Börnstein Ser. II/9,, Springer-Verlag, Berlin-Heidelberg, 1980.Google Scholar
  23. 23.
    R. Andruzzi, A. Trazza, L. Greci and L. Marchetti, Ann. Chim. (Rome), 69, 583 (1979).Google Scholar
  24. 24.
    D.T. Sawyer and J.J. Gibian, Tetrahedron, 35, 1471 (1979).CrossRefGoogle Scholar
  25. 25.
    D.T. Sawyer and J.L. Roberts Jr., J. Electroanal. Chem., 12, 90 (1969).CrossRefGoogle Scholar
  26. 26.
    L. Eberson, Electron Transfer Reactions in Organic Chemistry, Springer-Verlag, Heidelberg, 1987.Google Scholar
  27. 27.
    E. Pellizzetti, E. Mentasti and E. Pramauro, Inorg. Chem., 17, 1988 (1978).Google Scholar

Copyright information

© VSP 2000

Authors and Affiliations

  • Rita Petrucci
    • 1
  • Elisabetta Giorgini
    • 2
  • Elisabetta Damiani
    • 2
  • Patricia Carloni
    • 2
  • Giancarlo Marrosu
    • 1
  • Antonio Trazza
    • 1
  • Gian Paolo Littarru
    • 3
  • Lucedio Greci
    • 2
  1. 1.Dipartimento di Ingegneria Chimica, dei Materiali, delle Materie Prime e MetallurgiaUniversità “La Sapienza”RomaItaly
  2. 2.Dipartimento di Scienze dei Materiali e della Terra, UniversitàAnconaItaly
  3. 3.Istituto di Biochimica, UniversitàAnconaItaly

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