Free radical intermediates of phenytoin and related teratogens: Prostaglandin H synthase-catalyzed bioactivation, electron paramagnetic resonance spectrometry, and photochemical product analysis

Journal of Biological Chemistry

Volumn 273, Issue 39, 1998, Pages 25079-25088

  Parman, Toufan ^a   Chen, Guoman ^c   Wells, Peter G ^a,b  

^a UNIVERSITY OF TORONTO   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

^c UNIVERSITY OF GUELPH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

MEPHENYTOIN; PHENOBARBITAL; PHENYTOIN; TRIMETHADIONE;

ARTICLE; CHEMICAL TERATOGENESIS; ELECTRON SPIN RESONANCE; ENZYME ACTIVATION; MASS SPECTROMETRY; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; PHOTOLYSIS; PRIORITY JOURNAL;

BIOTRANSFORMATION; CATALYSIS; DEOXYGUANOSINE; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; OXIDATION-REDUCTION; PHENYTOIN; PHOTOCHEMISTRY; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; TERATOGENS;

EID: 0032566524     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.273.39.25079     Document Type: Article

References (60)

1. Hansen, D. K. (1991) Proc. Soc. Exp. Biol. Med. 197, 361-368
2. Hansen, D. K., Branham, W. S., Sheehan, D. M., and Holson, R. R. (1992) Proc. Soc. Exp. Biol. Med. 199, 501-508
3. Winn, L. M., and Wells, P. G. (1995) Eur. J. Neurol. 2, Suppl. 4, 5-29
4. Wells, P. G., and Winn, L. M. (1996) Crit. Rev. Biochem. Mol. Biol. 31, 1-40
5. Wells, P. G., and Winn, L. M. (1997) Comprehensive Toxicology (Sipes, I. G., McQueen, C. A., and Gandolfi, A. J., eds) Vol. 10, pp. 489-507, Pergamon Elsevier Science Ltd., Oxford, UK
6. Wells, P. G., Kim, P. M., Nicol, C. J., Parman, T., and Winn, L. M. (1997) Handbook of Experimental Pharmacology (Kavlock, R. J., and Daston, G. P., eds) Vol. 124, pp. 453-518, Springer-Verlag, Heidelberg
7. Wells, P. G., Küpfer, A., Lawson, J. A., and Harbison, R. D. (1982) J. Pharmacol. Exp. Ther. 221, 228-234
8. Wells, P. G., Nagai, M. K., and Spano Greco, G. (1989) Toxicol. Appl. Pharmacol. 97, 406-414
9. Wells, P. G., Kim, P. M., Laposa, R. R., Nicol, C. J., Parman, T., and Winn, L. M. (1997) Mutat. Res. 396, 65-78
10. Birkett, D. J., Mackenzie, P. I., Veronese, M. E., and Miners, J. O. (1993) Trends Pharmacol. Sci. 14, 292-294
11. Ozolins, T. R. S., Siksay, D. L. A., and Wells, P. G. (1996) J. Pharmacol. Exp. Ther. 277, 945-953
12. Kim, P. M., and Wells, P. G. (1996) Mol. Pharmacol. 49, 172-181
13. Winn, L. M., and Wells, P. G. (1997) Free Radical Biol. Med. 22, 607-621
14. Luning, U., and Skell, P. S. (1985) Tetrahedron 41, 4289-4302
15. Lind, J., Jonsson, M., Eriksen, T. E., Merenyi, G., and Eberson, L. (1993) J. Phys. Chem. 97, 1610-1614
16. Zhang, Y. H., Dong, M. H , Jiang, X. K., and Chow, Y. L. (1990) Can. J. Chem. 68, 1668-1675
17. Chow, Y. L., and Zhao, D. A. (1989) J. Org. Chem. 54, 530-534
18. Chow, Y. L., and Zhao, D. A. (1987) J. Org. Chem. 52, 1931-1939
19. Chow, Y. L., and Naguib, Y. M. A. (1984) Rev. Chem. Intermed. 5, 325-345
20. Skell, P. S., and Day, J. C. (1978) Acc. Chem. Res. 11, 381-387
21. Shriner, R. L., Fuson, R. C., and Curtin, D. Y. (eds) (1964) The Systematic Identification of Organic Compounds: A Laboratory Manual, 5th Ed., p. 289, John Wiley and Sons, Inc., New York
22. Hammarstrom, S. (1977) Biochim. Biophys. Acta 487, 517-519
23. Klein, K. L., Clark, K. E., and Scott, W. J., Jr. (1984) Prostaglandins 27, 659-672
24. Miranda, A. F., Wiley, M. J., and Wells, P. G. (1994) Toxicol. Appl. Pharmacol. 124, 230-241
25. March, J. (1992) Advanced Organic Chemistry: Reactions, Mechanisms, and Structures, 4th Ed., p. 897, John Wiley and Sons, Inc., New York
26. Downing, D. T., Barve, J. A., Gunstone, F. D., Jacobsberg, F. R., and Jie, M. L. (1972) Biochim. Biophys. Acta 280, 343-347
27. Sun, F. F., McGuire, J. C., Morton, D. R., Pike, J. E., Sprecher, H., and Kunau, W. H. (1981) Prostaglandins 21, 333-343
28. Coffey, J. W., Fiedler-Nagy, C., Nemzak, R., Batula-Bernardo, C., and Sullivan, A. C. (1982) Fed. Proc. 41, 1551
29. Van Wauwe, J., and Goossens, J. (1983) Prostaglandins 26, 725-730
30. Hageman, W. E., Rose, M. P., and Persico, F. J. (1986) Prostaglandins 32, 563-578
31. Yu, W. K., and Wells, P. G. (1995) Toxicol. Appl. Pharmacol. 131, 1-12
32. Liu, L., and Wells, P. G. (1995) Free Radical Biol. Med. 19, 639-648
33. Kim, P. M., Winn, L. M., Parman, T., and Wells, P. G. (1997) J. Pharmacol. Exp. Ther. 280, 200-209
34. Speidel, B. D., and Meadow, S. R. (1972) Lancet ii, 839-843
35. Seip, M. (1976) Acta Paediatr. Scand. 65, 617-621
36. Rudd, N. L., and Freedom, R. M. (1979) J. Pediatr. 94, 835-837
37. Ornoy, A., and Cohen, E. (1996) Arch. Dis. Child. 75, 517-520
38. Finnell, R. H., Shields, H. E., Taylor, S. M., and Chernoff, G. F. (1987) Teratology 35, 177-185
39. Finnell, R. H., Bennett, G. D., Slattery, J, T., Amore, B. M., Bajpai, M., and Levy, R. H. (1995) Teratology 52, 324-332
40. Küpfer, A., Roberts, R. K., Schenker, S., and Branch, R. A. (1981) J. Pharmacol. Exp. Ther. 218, 193-199
41. Küpfer, A., Desmond, P., Roberts, R., Shenker, S., and Branch, R. A. (1979) Clin. Res. 27, 235 (abstr.)
42. Clayson, D, B., Mehta, R., and Iverson, F. (1994) Mutat. Res. 317, 25-42
43. Shigenaga, M. K., Park, J. W., Cundy, K. C., Gimeno, C. J., and Ames, B. N. (1990) Methods Enzymol. 186, 521-530
44. Spitz, D. R., Dewey, W. D., and Li, G. C. (1987) J. Cell. Physiol. 131, 364-373
45. Ames, B. N. (1989) Free Radical Res. Commun. 7, 121-128
46. Spector, A., Kleiman, N. J., Huang, R. D., and Wang, R. R. (1989) Exp. Eye Res. 49, 685-698
47. Juchau, M. R., Lee, Q. P., and Fantel, A. G. (1992) Drug Metab. Rev. 24, 195-238
48. Fantel, A. G. (1996) Teratology 53, 196-217
49. Nicol, C. J., Harrison, M. L., Laposa, R. R., Gimelshtein, I. L., and Wells, P. G. (1995) Nat. Genet. 10, 181-187
50. Laposa, R. R., and Wells, P. G. (1995) Toxicologist 15, 161 (abstr.)
51. Laposa, R. R., Chan, K. L., Wiley, M. J., and Wells, P. G. (1996) Fundam. Appl. Toxicol. 30, Suppl. 2, 195 (abstr.)
52. Kasai, H., Crain, P. F., Kuchino, Y., Nishimura, S., Oostsuyama, A., and Tanooka, H. (1986) Carcinogenesis 7, 1849-1851
53. Arlen, R. R., and Wells, P. G. (1990) FASEB J. 4, 608 (abstr.)
54. Vaca, C. E., Wilhelm, J., and Harms-Ringdahl, M. (1988) Mutat. Res. 195, 137-149
55. Slatter, J. G., Rashed, M. S., Pearson, P. G., Han, D. H., and Baillie, T. A. (1990) Chem. Res. Toxicol. 4, 157-161
56. Pearson, P. G., Slatter, J. G., Rashed, M. S., Han, D. H., and Baillie, T. A. (1990) Chem. Res. Toxicol. 4, 436-444
57. Kukreja, R. C., Kontos, H. A., Hess, M. L., and Ellis, E. F. (1986) Circ. Res. 59, 612
58. Halliwell, B., and Gutteridge, J. M. C. (1989) Free Radicals in Biology and Medicine, 2nd Ed., p. 18, Clarendon Press, Oxford
59. Wells, P. G., Davidovich, O., and Mark, T. M. (1991) Toxicologist 11, 1131 (abstr.)
60. Parman, T., Chen, G., and Wells, P. G. (1996) Fundam. Appl. Toxicol. 30 (Suppl. 1, Part 2), 1260 (abstr.)