PPN-type nitrones: preparation and use of a new series of β-phosphorylated spin-trapping agents[hair space]

(Note: The full text of this document is currently only available in the PDF Version )

Cécile Rizzi, Sylvain Marque, Florence Belin, Jean-Claude Bouteiller, Robert Lauricella, Béatrice Tuccio, Viviane Cerri and Paul Tordo


Abstract

The synthesis of six members of a new series of β-phosphorylated nitrones derived from α-phenyl-N-tert-butylnitrone (PBN)[hair space]‡ is described. A new method, based on HPLC, is used to evaluate their n-octanol–phosphate buffer partition coefficient. As is the case for other PBN-type traps, the lipophilicity of these nitrones is found to be greatly dependent on the structure of their aromatic moiety. The capacity of these compounds to act as spin trapping agents is surveyed by using them to trap various free radicals in organic or aqueous media, and the EPR parameters of the different spin adducts obtained are reported herein.


References

  1. H. Sies, Angew. Chem., Int. Ed. Engl., 1986, 25, 1058 CrossRef; E. Lai, C. Crossley, R. Sridhar, H. Misra, E. Janzen and P. McCay, Arch. Biochem. Biophys., 1986, 224, 156 CrossRef; B. Halliwell and J. M. Gutteridge, Free Radicals in Biology and Medicine, Clarendon Press, Oxford, 2nd edn., 1989 Search PubMed; D. Brackett, E. Lai, M. Lerner, M. Wilson and P. McCay, Free Radical Res. Commun., 1989, 7, 315 Search PubMed; I. Zini, A. Tomasi, R. Grimaldi, V. Vannini and L. Agnati, Neurosci. Lett., 1992, 138, 279 Search PubMed; V. Darley-Usmar, H. Wiseman and B. Halliwell, FEBS Lett., 1995, 369, 131 CrossRef CAS; M. Martinez-Cayela, Biochimie, 1995, 77, 147 CrossRef CAS; M. Kadiiska, M. Burkitt, Q.-H. Xiang and R. Mason, J. Clin. Invest., 1995, 96, 1653 CrossRef; P. Byvoet, J. Balis, S. Shelley, M. Montgomery and M. Barber, Arch. Biochem. Biophys., 1995, 319, 464 Search PubMed.
  2. E. Janzen, R. D. Hinton and Y. Kotake, Tetrahedron Lett., 1992, 33, 1257 CrossRef CAS; E. Janzen, Y. Kotake and R. D. Hinton, Free Radical Biol. Med., 1992, 12, 169 CrossRef CAS; S. Pou, C. L. Ramos, T. Gladwell, E. Renks, M. Centra, D. Young, M. Cohen and G. Rosen, Anal. Biochem., 1994, 217, 76 CrossRef CAS; B. Kalyanaraman, J. Joseph and S. Parthasarathy, Biochem. Soc. Trans., 1993, 21, 318 CAS; J. North, A. Spector and G. Buettner, Am. J. Physiol., 1994, 267, C177 Search PubMed; H. Connor, W. Gao, R. P. Mason and R. G. Thurman, Free Radical Biol. Med., 1994, 16, 871 CrossRef; D. R. Moore, L. A. Reinke and P. B. McCay, Mol. Pharmacol., 1995, 47, 1224 Search PubMed.
  3. R. Huie and W. R. Cherry, J. Org. Chem., 1985, 50, 1531 CrossRef CAS; W. E. Acree, W. Bacon and A. J. Leo, Int. J. Pharm., 1984, 20, 209 CrossRef CAS; E. A. Konorev, J. E. Baker, J. Joseph and B. Kalyanaraman, Free Radical Biol. Med., 1993, 14, 127 CrossRef CAS; E. G. Janzen, D. L. Haire, G. A. Coulter, H. J. Stronks, P. H. Krygsman, R. A. Towner and G. W. Hilborn, J. Org. Chem., 1989, 54, 2915 CrossRef CAS.
  4. G. R. Buettner, Free Radical Biol. Med., 1987, 3, 259 CrossRef CAS.
  5. J. W. Lown, S. K. Sim and H. H. Chen, Can. J. Biochem., 1978, 56, 1042 CAS; P. R. Marriot, M. J. Perkins and D. Griller, Can. J. Chem., 1979, 58, 803.
  6. A. Zeghdaoui, B. Tuccio, J. P. Finet, V. Cerri and P. Tordo, J. Chem. Soc., Perkin Trans. 2, 1995, 2087 RSC.
  7. V. Roubaud, R. Lauricella, B. Tuccio, J. C. Bouteiller and P. Tordo, Res. Chem. Intermed., 1996, 22, 405 CrossRef CAS.
  8. B. Tuccio, A. Zeghdaoui, J. P. Finet, V. Cerri and P. Tordo, Res. Chem. Intermed., 1996, 22, 393 CAS.
  9. K. A. Petrov, V. A. Chauzov, L. V. Pastukhova and N. N. Bogdanov, Zh. Obshch. Khim., 1976, 46, 1246 CAS.
  10. E. G. Janzen, M. S. West, Y. Kotake and C. DuBose, J. Biochem. Biophys. Methods, 1996, 32, 183 CrossRef CAS.
  11. D. R. Duling, J. Magn. Reson., 1994, 104, 105 CrossRef CAS.
  12. P. Tordo, M. Boyer, A. Friedmann, O. Santero and L. Pujol, J. Phys. Chem., 1978, 82, 1742 CrossRef CAS; A. Mercier, Y. Berchadsky, Badrudin, S. Pietri and P. Tordo, Tetrahedron Lett., 1991, 32, 2125 CrossRef CAS; F. Le Moigne, A. Mercier and P. Tordo, Tetrahedron Lett., 1991, 32, 3841 CrossRef CAS.
  13. K. Altenburg, Z. Chem., 1987, 27, 340; A. Alberti and A. Hudson, J. Chem. Soc., Faraday Trans., 1990, 86, 3207 RSC; A. Il'yasov, I. Morozova, A. Vafina, R. Zaripova and M. Balakina, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 5, 1024 Search PubMed.
  14. E. G. Janzen, C. DuBose and Y. Kotake, Tetrahedron Lett., 1990, 31, 7395 CrossRef CAS.
  15. C. Fréjaville, H. Karoui, B. Tuccio, F. LeMoigne, M. Culcasi, S. Pietri, R. Lauricella and P. Tordo, J. Med. Chem., 1995, 38, 258 CrossRef CAS.
  16. B. Tuccio, R. Lauricella, C. Fréjaville, J. C. Bouteiller and P. Tordo, J. Chem. Soc., Perkin Trans. 2, 1995, 295 RSC.
  17. E. Finkelstein, G. M. Rosen and E. J. Rauckman, Mol. Pharmacol., 1979, 16, 676 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.