Two modes of binding of N-hydroxyguanidines to no synthases: First evidence for the formation of iron - N-hydroxyguanidine complexes and key role of tetrahydrobiopterin in determining the binding mode

Biochemistry

Volumn 42, Issue 13, 2003, Pages 3858-3867

  Lefèvre Groboillot, David ^a   Frapart, Yves ^a   Desbois, Alain ^b   Zimmermann, Jean Luc ^b   Boucher, Jean Luc ^a   Gorren, Antonius C F ^d   Mayer, Bernd ^d   Stuehr, Dennis J ^c   Mansuy, Daniel ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b CEA SACLAY   (France)

^c LERNER RESEARCH INSTITUTE   (United States)

^d UNIVERSITY OF GRAZ   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; ELECTRON SPIN RESONANCE SPECTROSCOPY; OXIDATION; RAMAN SPECTROSCOPY; SYNTHESIS (CHEMICAL);

LIGANDS;

NITROGEN COMPOUNDS;

ARGININE; GUANIDINE DERIVATIVE; HEMOPROTEIN; HYDROGEN; IRON; IRON COMPLEX; LIGAND; N HYDROXYGUANIDINE; NITRIC OXIDE SYNTHASE; OXYGEN; OXYGENASE; PEROXIDASE; PROTEIN; RECOMBINANT ENZYME; TETRAHYDROBIOPTERIN; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ANALYTICAL PARAMETERS; ARTICLE; ATOMIC PARTICLE; BINDING AFFINITY; CALCULATION; CATALYSIS; CHEMICAL BOND; COMPLEX FORMATION; ELECTRON SPIN RESONANCE; ENZYME BINDING; NONHUMAN; OXIDATION; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN INTERACTION; PROTON TRANSPORT; RAMAN SPECTROMETRY; SPECTROSCOPY;

ARGININE; BINDING SITES; BIOPTERIN; CATALYSIS; ELECTRON SPIN RESONANCE SPECTROSCOPY; GUANIDINES; HEME; IRON; KINETICS; LIGANDS; NITRIC OXIDE SYNTHASE; NITRIC OXIDE SYNTHASE TYPE I; NITRIC OXIDE SYNTHASE TYPE II; NITRIC OXIDE SYNTHASE TYPE III; OXIDATION-REDUCTION; OXYGEN; PROTEIN BINDING; SPECTRUM ANALYSIS, RAMAN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0345701203     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi0272407     Document Type: Article

References (42)

1. Kerwin, J. F., Jr., Lancaster, J. R., Jr., and Feldman, P. L. (1995) J. Med. Chem. 38, 4343-4362.
2. Alderton, W. K., Cooper, C. E., and Knowles, R. G. (2001) Biochem. J. 357, 593-615.
3. Masters, B. S. S., McMillan, K., Sheta, E. A., Nishimura, J. S., Roman, L. J., and Martasek, P. (1996) FASEB J. 10, 552-558.
4. Stuehr, D. J., Kwon, N. S., Nathan, C. F., Griffith, O. W., Feldman, P. L., and Wiseman, J. (1991) J. Biol. Chem. 266, 6259-6263.
5. Klatt, P., Schmidt, K., Uray, G., and Mayer, B. (1993) J. Biol. Chem. 268, 14781-14787.
6. Crane, B. R., Arvai, A. S., Ghosh, D. K., Wu, C., Getzoff, E. D., Stuehr, D. J., and Tainer, J. A. (1998) Science 279, 2121-2126.
7. Raman, C. S., Li, H., Martasek, P., Kral, V., Masters, B. S. S., and Poulos, T. L. (1998) Cell 95, 939-950.
8. Renodon-Corniere, A., Boucher, J.-L., Dijols, S., Stuehr, D. J., and Mansuy, D, (1999) Biochemistry 38, 4663-4668.
9. Dijols, S., Perollier, C., Lefèvre-Groboillot, D., Pethe, S., Attias, R., Boucher, J.-L., Stuehr, D. J., and Mansuy, D. (2001) J. Med. Chem. 44, 3199-3202.
10. Renodon-Corniere, A., Dijols, S., Perollier, C., Lefèvre-Groboillot, D., Boucher, J.-L., Attias, R., Sari, M.-A., Stuehr, D., and Mansuy, D. (2002) J. Med. Chem. 45, 944-954.
11. Crane, B. R., Arvai, A. S., Ghosh, S., Getzoff, E. D., Stuehr, D. J., and Tainer, J. A. (2000) Biochemistry 39, 4608-4621.
12. Raman, C. S., Li, H., Martasek, P., Southan, G., Masters, B. S. S., and Poulos, T. L. (2001) Biochemistry 40, 13448-13455.
13. Lefèvre-Groboillot, D., Dijols, S., Boucher, J.-L., Mahy, J.-P., Ricoux, R., Desbois, A., Zimmermann, J.-L., and Mansuy, D. (2001) Biochemistry 40, 9909-9917.
14. Ghosh, D. K., Wu, C., Pitters, E., Moloney, M., Werner, E. R., Mayer, B., and Stuehr, D. J. (1997) Biochemistry 36, 10609-10619.
15. Abu-Soud, H. M., Gachhui, R., Raushel, F. M., and Stuehr, D. J. (1997) J. Biol. Chem. 272. 17349-17353.
16. Gorren, A. C. F., Bec, N., Schrammel, A., Werner, E. R., Lange, R., and Mayer, B. (2000) Biochemistry 39, 11763-11770.
17. Wu, C., Zhang, J., Abu-Soud, H., Ghosh, D. K., and Stuehr, D. J. (1996) Biochem. Biophys. Res. Commun. 222, 439-444.
18. Bradford, M. M. (1976) Anal. Biochem. 72, 248-252.
19. Sono, M., Ledbetter, A. P., McMillan, K., Roman, L. J., Shea, T. M., Masters, B. S. S., and Dawson, J. H. (1999) Biochemistry 38, 15853-15862.
20. Rusche, K. M., and Marletta, M. A. (2001) J. Biol. Chem. 276, 421-427.
21. Taylor, C. P. (1977) Biochim. Biophys. Acta 491. 137-148.
22. McMillan, K., and Masters, B. S. S. (1993) Biochemistry 32, 9875-9880.
23. Tierney D. L., Huang, H., Martasek, P., Masters, B. S. S., Silverman, R. B., and Hoffman, B. M. (1999) Biochemistry 38, 3704-3710.
24. Chabin, R. M., McCauley, E., Calaycay, J. R., Kelly, T. M., MacNaul, K. L., Wolfe, G. C., Hutchinson, N. I., Madhusudanaraju, S., Schmidt, J. A., Kozarich, J. W., and Wong, K. K. (1996) Biochemistry 35, 9567-9575.
25. Salerno, J. C., Martasek, P., Roman, L. J., and Masters, B. S. S. (1996) Biochemistry 35, 7626-7630.
26. Spiro, T. G., and Li, X.-Y. (1988) in Biological Applications of Raman Spectroscopy (Spiro, T. G., Ed.) Vol. 3, pp 1-37, Wiley, New York.
27. Wang, J., Stuehr, D. J., Ikeda-Saito, M., and Rousseau, D. L. (1993) J. Biol. Chem. 268, 22255-22258.
28. Abu-Soud, H. M., Wang, J., Rousseau, D. L., and Stuehr, D. J. (1999) Biochemistry 38, 12446-12451.
29. Wang, J., Stuehr, D. J., and Rousseau, D. L. (1995) Biochemistry 34, 7080-7087.
30. Schelvis, J. P., Berka, V., Babcock, G. T., and Tsai, A. L. (2002) Biochemistry 41, 5695-5701.
31. Hu, S., Smith, K. M., and Spiro, T. G. (1996) J. Am. Chem. Soc. 118, 12638-12646.
32. Abu-Soud, H. M., Wu, C., Ghosh, D. K., and Stuehr, D. J. (1998) Biochemistry 37, 3777-3786.
33. Renodon, A., Boucher, J.-L., Wu, C., Gachhui, R., Sari, M.-A., Mansuy, D., and Stuehr, D. J. (1998) Biochemistry 37, 6367-6374.
34. Gerber, N. C., Rodriguez-Crespo, I., Nishida, C. R., and Ortiz de Montellano, P. R. (1997) J. Biol. Chem. 272, 6285-6290.
35. Gorren, A. C., Schrammel, A., Schmidt, K., and Mayer, B. (1997) Biochemistry 36, 4360-4366.
36. Boucher, J. L., Delaforge, M., and Mansuy, D. (1994) Biochemistry 33, 7811-7818.
37. Hart-Davis, J., Battioni, P., Boucher, J. L., and Mansuy, D. (1998) J. Am. Chem. Soc. 120, 12524-12530.
38. Wang, C., Ho, D., and Groves, J. T. (1999) J. Am. Chem. Soc. 121, 12094-12103.
39. Blumberg, W. E., and Peisach, J. (1971) in Probes of Sructure and Function of Macromolecules and Membranes (Chance, B., Yonetani, T., and Mildvan, A. S., Eds.) Vol. 2, pp 215-229, Academic Press, New York.
40. Dawson, J. H., Andersson, L. A., and Sono, M. (1982) J. Biol. Chem. 257, 3606-3617.
41. Sono, M., and Dawson, J. H. (1982) J. Biol. Chem. 257, 5496-5502.
42. Davydov, R., Ledbetter-Rogers, A., Martasek, P., Larukhin, M., Sono, M., Dawson, J. H., Masters, B. S. S., and Hoffman, B. M. (2002) Biochemistry 41, 10375-10381.