PPN-type nitrones: Preparation and use of a new series of β-phosphorylated spin-trapping agents

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 12, 1997, Pages 2513-2518

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

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001299577     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a702469j     Document Type: Article

References (39)

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