Oxidation of N-4-chlorophenyl-N′-hydroxyguanidine to N-(4-chlorophenyl)urea and nitric oxide by photoexcited iron porphyrins

European Journal of Inorganic Chemistry

Volumn , Issue 15, 2004, Pages 3127-3135

  Maldotti, Andrea ^a   Molinari, Alessandra ^a   Vitali, Irene ^a   Ganzaroli, Elena ^a   Battioni, Pierrette ^b   Mathieu, Delphine ^b   Mansuy, Daniel ^b  

^a UNIVERSITY OF FERRARA   (Italy)

^b UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Nitric oxide; O O activation; Photooxidation; Porphyrins; Protein models

Indexed keywords

COORDINATION REACTIONS; ELECTRON SPIN RESONANCE SPECTROSCOPY; IRON COMPOUNDS; METABOLISM; MOLECULAR OXYGEN; NITRIC OXIDE; PHOTOOXIDATION; REACTION INTERMEDIATES; UREA;

END-PRODUCTS; IRON PORPHYRIN; IRON-PORPHYRIN; N -HYDROXYGUANIDINE; O-O ACTIVATION; PHOTOCHEMICALS; PHOTOPRODUCTS; PROTEIN MODELS; SECONDARY REACTIONS; TETRAKIS;

PORPHYRINS;

GUANIDINE DERIVATIVE; IMIDAZOLE DERIVATIVE; IRON DERIVATIVE; NITRIC OXIDE; OXYGEN; PORPHYRIN DERIVATIVE; SCAVENGER; UREA DERIVATIVE;

ARTICLE; ELECTRON SPIN RESONANCE; MOLECULAR DYNAMICS; OXIDATION; PHOTOCHEMISTRY;

EID: 4544266392     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200400056     Document Type: Article

References (50)

1. [1a] A. Maldotti, A. Molinari, R. Amadelli, Chem. Rev. 2002, 102, 3811-3836.
2. [1b] B. Meunier, A. Robert, G. Pratviel, J. Bernadou, in The Porphyrin Handbook (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 2000, vol. 4, 119-174.
3. [1c] A. Maldotti, L. Andreotti, A. Molinari, V. Carassiti, J. Biol. Inorg. Chem. 1999, 4, 154-161.
4. [1d] L. Weber, R. Hommel, J. Behling, G. Haufe, H. Hennig, J. Am. Chem. Soc. 1994, 116, 2400-2408.
5. [1e] K. S. Suslick, R. A. Watson, New J. Chem. 1992, 16, 633-642.
6. [2a] A. Maldotti, C. Bartocci, G. Varani, A. Molinari, P. Battioni, D. Mansuy, Inorg. Chem. 1996, 35, 1126-1131.
7. [2b] A. Maldotti, A. Molinari, L. Andreotti, M. Fogagnolo, R. Amadelli, Chem. Commun. 1998, 507-508.
8. [2c] A. Maldotti, L. Andreotti, A. Molinari, G. Varani, G. Cerichelli, M. Chiarini, Green Chem. 2001, 3, 42-46.
9. [2d] R. D. Arasasingham, A. L. Balch, C. R. Cornman, L. Latos-Grazynski, J. Am. Chem. Soc. 1989, 111, 4357-4363.
10. [2e] A. L. Balch, R. L. Hart, L. Latos-Grazynski, T. G. Traylor, J. Am. Chem. Soc. 1990, 112, 7382-7388.
11. R. L. Cheng, L. Latos-Grazynsky, A. L. Balch, Inorg. Chem. 1982, 21, 2412-2418.
12. C. Bartocci, A. Maldotti, G. Varani, V. Carassiti, P. Battioni, D. Mansuy, Inorg. Chem. 1991, 30, 1255-1259.
13. W. K. Alderton, C. E. Cooper, R. G. Knowles, Biochem. J. 2001, 357, 593-615.
14. [5b] B. S. S. Masters, K. McMillian, E. A. Sheta, J. S. Nishimura, L. J. Roman, P. Martasek, FASEB J. 1996,10, 552-558.
15. [5c] D. Mansuy, J. P. Renaud, in Cytochrome P450: Structure, Mechanism, and Biochemistry (Ed.: P. R. Ortiz de Montellano), Plenum Press, New York and London, 1995, p. 537-574.
16. [5d] J. T. Groves, C. C. Y. Wang, Curr. Opin. Chem. 2000, 4, 687-695.
17. [5e] G. M. Rosen. P. Tsai, S. Pou, Chem. Rev. 2002, 102, 1191-1199.
18. [6a] B. R. Crane, A. S. Arvai, D. K. Ghosh, C. Wu, E. D. Getzoff, D. J. Stuehr, J. A. Tainer, Science 1998. 279, 2121-2126.
19. [6b] C. S. Raman, H. Li, P. Martasek, V. Krai, B. S. S. Masters, T. L. Poulos, Cell 1998, 95, 939-950.
20. [7a] Groves, Y.-Z. Han in Cytochrome P450: Structure, Mechanism, and Biochemistry (Ed.: P. R. Ortiz de Montellano), Plenum Press, New York and London, 1995, p. 3-48.
21. [7b] M. Sono, M. P. Roach, E. D. Coulter, J. H. Dawson, Chem. Rev. 1996, 96, 2841-2888.
22. [7c] M. Couture, D. J. Stuehr, D. L. Rousseau, N. Bee, A. C. Gorren, C. Voelker, J. Biol Chem. 2000, 275, 3201-3205,
23. [7d] B. Mayer, R. Lange, J. Biol. Chem. 1998, 273, 13502-13508,
24. [7e] K. M. Ruske, M. M. Spiering, M. A. Marietta, Biochemistry 1998, 37, 15503-15512.
25. [8a] D. J, Stuehr, N. S. Kwon, C. F. Nathan, O. W. Griffith, P. L. Feldman, J. Wiseman, J. Biol. Chem. 1991, 266, 6259-6263.
26. [8b] P. Klatt, K. Schmidt, G. Uray, B. Mayer, J. Biol. Chem. 1993, 268, 14781-14787.
27. [9a] C. Wei; Z. Wang, A. Meade, J. McDonald, D. Stuehr, J. Inorg. Biochem. 2002, 91, 618-624.
28. [9b] C.-C. Wei, B. R. Crane, D. J. Stuehr, Chem. Rev. 2003, 103, 2365-2375.
29. [9c] D. Mathieu, Y. M. Frapart, J. F. Bartoli, J. L. Boucher, P. Battioni, D. Mansuy, Chem. Commun. 2004. 54-55.
30. C. C. Y. Wang, D. M. Ho, J. T. Groves, J. Am. Chem. Soc. 1999, 121, 12094-12103.
31. [11a] A. Renodon-Corniere, J.-L. Boucher, S. Dijol, D. J. Stuehr, D. Mansuy, Biochemistry 1999, 38, 4663-4668.
32. [11b] A. Renodon-Corniere, S. Dijol, C. Perollier, D. Lefèvre-Groboillot, J.-L. Boucher, R. Attias, M.-A. Sari, D. J. Stuehr, D. Mansuy, J. Med. Chem. 2002, 45, 944-954.
33. [12a] J. P. Collman, R. R. Gagne, T. R. Halbert, J. C. Marchon, C. A. Reed, J. Am. Chem. Soc. 1973, 95, 7668-7870.
34. [12b] J. P. Collman, R. R. Gagne, C. A. Reed, T. R. Halbert, G. Lang, W. T. Robinson, J. Am. Chem. Soc. 1975, 97, 1427-1439.
35. [13a] D. Lefevre-Groboillot, S. Dijols, J. L. Boucher, J. P. Mahy, R. Ricoux, A. Desbois, J. L. Zimmermann, D. Mansuy, Biochemistry 2001, 40, 9909-9917.
36. [13b] D. Lefevre-Groboillot, Y. Frapart, A. Desbois, J. L. Zimmermann, J. L. Boucher, A. C. F. Gorren, B. Mayer, D. J. Stuehr, D. Mansuy, Biochemistry 2003, 42, 3858-3867.
37. [14a] M. J. Ciague, J. S. Wishnok, M. A. Marietta, Biochemistry 1997, 36, 14465-14473.
38. [14b] J. Fukuto, G. C. Wallace, R. Hszieh, G. Chaudhrui, Biochem. Pharmacol. 1992, 43, 607-613.
39. Z. Wei, M. D. Ryan, Inorg. Chim. Acta 2001, 314, 49-53.
40. E. G. Janzen, Acc. Chem. Res. 1971, 4, 31-39.
41. [17a] T. Akaike, M. Yoshida, Y. Miyamoto, K. Sato, M. Kohno, K. Sasamoto. K. Miyazaki, S. Ueda, H. Maeda, Biochemistry 1993, 32, 827-832.
42. [17b] R. Ricoux, J.-L. Boucher, D. Mandon, Y.-M. Frapart, Y. Henry, D. Mansuy, J.-P. Mahy, Ew. J. Biochem. 2003, 270, 47-55.
43. N. Sennequier, J. L. Boucher, P. Battioni, D. Mansuy, Tetrahedron Lett. 1995, 36, 6059-6062.
44. [19a] M. A._ Marletta, J. Biol. Chem. 1993, 268, 12231-12234.
45. [19b] H. G. Korth, R. Sustmann, C. Thater, A. R. Butler, K. U. Ingold, J. Biol. Chem. 1994, 269, 17776-17779.
46. [19c] H. Huang, J. M. Hah, R. B. Silverman, J. Am. Chem. Soc. 2001, 123, 2674-2676.
47. [19d] A. R. Hurshman, C. Krebs, D. E. Edmondson. B. M. Huynh, M. A. Marletta, Biochemistry 1999, 38, 15689-15696.
48. Z.-Q. Wang, C. Wei, S. Ghosh, A. L. Meade, C. Hemann. R. Hille, D. J. Stuehr, Biochemistry 2001, 40, 12819-12825,
49. D. L. Wertz, J. S. Valentine, in Structure and Bonding: Metaloxo and Metal-peroxo Species in Catalytic Oxidations (Ed.: B. Meunier), Springer-Verlag, Berlin. Heidelberg, New York, 2000, 97, 37-60.
50. P. Battioni, J. P. Renaud, J. F. Bartoli, J. F. Reina-Artiles, M. Fort, D. Mansuy, J. Am. Chem. Soc. 1988, 110, 8462-8470.