Redox behaviour of azulenyl nitrones: fully reversible one electron oxidation by cyclic voltammetry at potentials in the range of biological antioxidants

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David A. Becker, Reina Natero, Luis Echegoyen and Raphael C. Lawson


Abstract

The one electron oxidation chemistry of azulenyl nitrones 4 and 5 employing cyclic voltammetry reveals that, unlike conventional nitrone spin traps such as PBN and S-PBN, such oxidation is electrochemically and chemically reversible at potentials near or within those of important biological chain-breaking antioxidants.


References

  1. (a) Natural Antioxidants in Human Health and Disease, ed. B. Frei, Academic Press, San Diego, 1994 Search PubMed; (b) Free Radical Damage and Its Control, ed. C. A. Rice-Evans and R. H. Burdon, Elsevier, New York, 1994 Search PubMed; (c) E. D. Hall and J. M. McCall, in Methods in Enzymology, ed. L. Packer, Academic Press, San Diego, 1994, vol. 234, p. 548 Search PubMed.
  2. D. Steinberg, S. Parthasarathy, T. E. Carew, J. C. Khoo and J. L. Witztum, New Engl. J. Med., 1989, 320, 915 Search PubMed.
  3. B. N. Ames, Science, 1983, 221, 1256 CrossRef CAS.
  4. P. H. Chan, Stroke, 1996, 27, 1124 Search PubMed.
  5. M. B. Yin, J.-H. Kang, H.-S. Yim, H.-S. Kwak, P. B. Chock and E. R. Stadtman, Proc. Natl. Acad. Sci. USA, 1996, 93, 5709 CrossRef and references therein.
  6. M. E. Harris, Y. N. Wang, N. W. Pedigo, K. Hensley, D. A. Butterfield and J. M. Carney, J. Neurochem., 1996, 67, 277 CAS.
  7. (a) Y. Higuchi and S. Matsukawa, Free Radical Biol. Med., 1998, 24, 418 CrossRef CAS; (b) B. Ferger, C. Vanamsterdam, C. Seyfried and K. Kuschinsky, J. Neurochem., 1998, 70, 276 CAS; (c) A. Frederiksson, P. Eriksson and T. Archer, J. Neural Transmission, 1997, 104, 579 Search PubMed; (d) E. Lancelot, M.-L. Revand, R. G. Boulu, M. Plotkine and J. Callebert, Free Radical Biol. Med., 1997, 23, 1031 CrossRef CAS; (e) T. L. Fevig, S. M. Bowden, D. A. Janowick, B. K. Jones, H. R. Munson, D. F. Ohlweiler and C. E. Thomas, J. Med. Chem., 1996, 39, 4988 CrossRef CAS; (f) V. Castagne and P. G. H. Clarke, Proc. R. Soc. London, B, 1996, 263, 1193 Search PubMed; (g) C. A. Sack, D. J. Socci, B. M. Crandall and G. W. Arendash, Neurosci. Lett., 1996, 205, 181 CrossRef CAS; (h) J. A. Joseph, R. Villalobsmolina, N. Denisova, S. Erat, R. Cutler and J. Strain, Free Radical Biol. Med., 1996, 20, 821 CrossRef CAS; (i) N. Nakao, E. M. Grasbon-Frodl, H. Winder and P. Brundin, Neuroscience, 1996, 73, 185 CrossRef CAS; (j) J. B. Schultz, R. T. Matthews, B. G. Jenkins, P. Brar and M. F. Beal, J. Cereb. Blood Flow Metab., 1995, 15, 948 Search PubMed; (k) J. Folbergrova, Q. Zhao, K. Katsura and B. K. Siesjo, Proc. Natl. Acad. Sci. USA, 1995, 92, 5057 CAS; (l) R. Edamatsu, A. Mori and L. Packer, Biochem. Biophys. Res. Commun., 1995, 211, 847 CrossRef CAS; (m) Q. Chen, A. Fischer, J. D. Reagan, L.-Y. Yan and B. N. Ames, Proc. Natl. Acad. Sci. USA, 1995, 92, 4337 CAS; (n) C. E. Thomas, D. F. Ohlweiler and B. Kalyanaraman, J. Biol. Chem., 1994, 269, 28 055 CAS; (o) K. Hensley, J. M. Carney, M. P. Mattson, M. Aksenova, M. Harris, J. F. Wu, R. A. Floyd and D. A. Butterfield, Proc. Natl. Acad. Sci. USA, 1994, 91, 3270 CAS.
  8. D. A. Becker, in Organic Synthesis: Theory and Application, vol. 4, JAI Press Monograph Series, ed. T. Hudlicky, in the press Search PubMed.
  9. (a) G. R. Buettner, Arch. Biochem. Biophys., 1993, 300, 535 CrossRef CAS; (b) J. L. Grant, V. J. Kramer, R. Ding and L. D. Kispert, J. Am. Chem. Soc., 1988, 110, 2151 CrossRef CAS.
  10. G. L. McIntyre, H. N. Blount, H. J. Stronks, R. V. Shetty and E. G. Janzen, J. Phys. Chem., 1980, 84, 916 CrossRef CAS.
  11. D. A. Becker, J. Am. Chem. Soc., 1996, 118, 905 CrossRef CAS.
  12. J. S. Althaus, T. J. Fleck, D. A. Becker, E. D. Hall and P. F. Von VoigtlanderFree Radical Biol. Med., in the press Search PubMed.
  13. M. E. Gurney, R. Lui, J. S. Althaus, E. D. Hall and D. A. BeckerAge, in the press Search PubMed.
  14. R. Lui, J. S. Althuas, B. R. Ellerbrock, D. A. Becker and M. E. GurneyAnn. Neurol., submitted for publication Search PubMed.
  15. P. Klevenyi, R. T. Matthews, M. Wermer, L. Yang, U. MacGarvey, D. A. Becker, R. Natero and M. F. BealExp. Neurol., in the press Search PubMed.
  16. R. J. Waltman and J. Bargon, Can. J. Chem., 1986, 64, 76 CAS.
  17. J. Bargon, S. Mohmand and R. J. Waltman, Mol. Cryst. Liq. Cryst., 1983, 93, 279 CrossRef CAS.
  18. C. J. Cooksey, J. L. Courtneidge, A. G. Davies, P. S. Gregory, J. C. Evans and C. C. Rowlands, J. Chem. Soc., Perkin Trans. 2, 1988, 807 RSC.
  19. H. G. Aurich, K. Hahn and K. Stork, Angew. Chem., Int. Ed. Engl., 1975, 14, 551 CrossRef.
  20. M. G. Simic and E. P. L. Hunter, J. Free Radicals Biol. Med., 1986, 2, 227 Search PubMed.
  21. E. G. Janzen and D. L. Haire, in Advances in Free Radical Chemistry, ed. D. D. Tanner, JAI Press, Greenwich, 1990, vol. 1, p. 253 Search PubMed.
  22. A. Kaifer and L. Echegoyen, in Cation Binding by Macrocycles: Complexation of Cationic Species by Crown Ethers, ed. Y. Inoue and G. W. Gokel, Marcel Dekker, New York, 1990, ch. 8, p. 363 Search PubMed.
  23. E. F. Ullman, J. H. Osiecki, D. G. B. Boocock and R. Darey, J. Am. Chem. Soc., 1972, 94, 7049 CrossRef CAS.
  24. H. G. Aurich and K. D. Mobus, Tetrahedron, 1989, 45, 5805 CrossRef CAS.
  25. K. Hensley, M. Aksenova, J. M. Carney, M. Harris and D. A. Butterfield, NeuroReport, 1995, 6, 493 Search PubMed and references therein.
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