OXIDATION OF N-HYDROXYGUANIDINES BY CYTOCHROMES P450 AND NO-SYNTHASES AND FORMATION OF NITRIC OXIDE

REFERENCES

• Pfeiffer S., Mayer B., Hemmens B. Nitric Oxide. Chemical Puzzles Posed by a Biological Messenger. Angew. Chem., Int. Ed. 1999; 38: 1714–1731
   PubMed Web of Science ®Google Scholar
• Stuehr D.J., Kwon N.S., Nathan C.F., Griffith O.W., Feldman P.L., Wiseman J. Nω-Hydroxy-l-arginine Is an Intermediate in the Biosynthesis of Nitric Oxide from l-Arginine. J. Biol. Chem. 1991; 266: 6259–6263
   PubMed Web of Science ®Google Scholar
• Knowles R.G., Moncada S. Nitric Oxide Synthases in Mammals. Biochem. J. 1994; 298: 249–258
   PubMed Web of Science ®Google Scholar
• Mansuy D., Renaud J.P. Heme-Thiolate Proteins Different from Cytochromes P450 Catalyzing Monooxygenation. Cytochrome P450, Structure, Mechanism and Biochemistry, P. Ortiz de Montellano. Plenum Press, New York 1995; 537–574
   Google Scholar
• Boucher J.L., Genet A., Vadon S., Delaforge M., Henry Y., Mansuy D. Cytochrome P450 Catalyzes the Oxidation of Nω-Hydroxy-l-arginine by NADPH and O2 to Nitric Oxide and Citrulline. Biochem. Biophys. Res. Commun. 1992; 187: 880–886
   PubMed Web of Science ®Google Scholar
• Renaud J.P., Boucher J.L., Vadon S., Delaforge M., Mansuy D. Particular Ability of Liver P450s3A to Catalyze the Oxidation of Nω-Hydroxyarginine to Citrulline and Nitrogen Oxides and Occurrence in NO Synthases of a Sequence Very Similar to the Heme-Binding Sequence in P450s. Biochem. Biophys. Res. Commun. 1993; 192: 53–60
   PubMed Web of Science ®Google Scholar
• Andronik-Lion V., Boucher J.L., Delaforge M., Henry Y., Mansuy D. Formation of Nitric Oxide by Cytochrome P450-Catalyzed Oxidation of Aromatic Amidoximes. Biochem. Biophys. Res. Commun. 1992; 185: 452–458
   PubMed Web of Science ®Google Scholar
• Clement B., Jung F. N-Hydroxylation of the Antiprotozoal Drug Pentamidine Catalyzed by Rabbit Liver Cytochrome P450 2C3 or Human Liver Microsomes, Microsomal Retroreduction, and Further Oxidative Transformation of the Formed Amidoximes. Drug Metab. Dispos. 1994; 22: 486–495
   PubMed Web of Science ®Google Scholar
• Jousserandot A., Boucher J.L., Desseaux C., Delaforge M., Mansuy D. Formation of Nitrogen Oxides Including NO from Oxidative Cleavage of C=N(OH) Bonds: A General Cytochrome P450-Dependent Reaction. Bioorg. Med. Chem. Lett. 1995; 5: 423–426
   Web of Science ®Google Scholar
• Jousserandot A., Boucher J.L., Henry Y., Niklaus B., Clement B., Mansuy D. Microsomal Cytochrome P450-Dependent Oxidation of N-Hydroxyguanidines, Amidoximes and Ketoximes: Mechanism of the Oxidative Cleavage of Their C=N(OH) Bond with Formation of Nitrogen Oxides. Biochemistry 1998; 37: 17179–17191
   PubMed Web of Science ®Google Scholar
• Clement B., Boucher J.L., Mansuy D., Harsdorf A. Microsomal Formation of Nitric Oxide and Cyanamides from Non-physiological N-Hydroxyguanidines: N-Hydroxydebrisoquine as a Model Substrate. Biochem. Pharmacol. 1999; 58: 439–445
   PubMed Web of Science ®Google Scholar
• Sennequier N., Boucher J.L., Battioni P., Mansuy D. Superoxide Anion Efficiently Performs the Oxidative Cleavage of C=NOH Bonds of Amidoximes and N-Hydroxyguanidines with Formation of Nitrogen Oxides. Tetrahedron Lett. 1995; 36: 6059–6062
   Web of Science ®Google Scholar
• Everett S.A., Dennis M.F., Patel K.B., Statford M.R.L., Wardman P. Oxidative Denitrification of Nω-Hydroxy-l-arginine by the Superoxide Radical Anion. Biochem. J. 1996; 317: 17–21
   PubMed Web of Science ®Google Scholar
• Caro A.A., Cederbaum A.I., Stoyanorvsky D.A. Oxidation of the Ketoxime Acetoxime to Nitric Oxide by Oxygen Radical-Generating System. Nitric Oxide: Biol. Chem. 2001; 5: 413–424
   PubMed Web of Science ®Google Scholar
• Moali C., Boucher J.L., Renodon-Cornière A., Stuehr D.J., Mansuy D. Oxidations of Nω-Hydroxyarginine Analogues and Various N-Hydroxyguanidines by NO Synthase II: Key Role of Tetrahydrobiopterin in the Reaction Mechanism and Substrate Selectivity. Chem. Res. Toxicol. 2001; 14: 202–210
   PubMed Web of Science ®Google Scholar
• Rusche K.M., Spiering M.M., Marletta M.A. Reactions Catalyzed by Tetrahydrobiopterin-Free Nitric Oxide Synthase. Biochemistry 1998; 37: 15503–15512
   PubMed Web of Science ®Google Scholar
• Moali C., Boucher J.L., Sari M.A., Stuehr D.J., Mansuy D. Substrate Specificity of NO Synthases: Detailed Comparison of l-Arginine, Homo-l-Arginine, Their N-Omega-Hydroxy Derivatives, and N-Omega-Hydroxy-Nor-l-arginine. Biochemistry 1998; 37: 10453–10460
   PubMed Web of Science ®Google Scholar
• Mansuy D., Boucher J.L., Clement B. On the Mechanism of Nitric Oxide Formation upon Oxidative Cleavage of C=N(OH) Bonds by NO-Synthases and Cytochromes P450. Biochimie 1995; 77: 661–667
   PubMed Web of Science ®Google Scholar
• Adak S., Wang Q., Stuehr D.J. Arginine Conversion to Nitroxide by Tetrahydrobiopterin-Free Neuronal Nitric-Oxide Synthase. Implications for Mechanism. J. Biol. Chem. 2000; 275: 33554–33561
   PubMed Web of Science ®Google Scholar
• Dijols S., Perollier C., Lefevre-Groboillot D., Pethe S., Attias R., Boucher J.L., Stuehr D.J., Mansuy D. Oxidation of Nω-Hydroxyarginine Analogues by NO-Synthase: The Simple, Non-amino Acid N-Butyl N′-Hydroxyguanidine Is Almost as Efficient an NO Precursor as Nω-Hydroxyarginine. J. Med. Chem. 2001; 44: 3199–3202
   PubMed Web of Science ®Google Scholar
• Renodon-Cornière A., Boucher J.L., Dijols S., Stuehr D.J., Mansuy D. Efficient Formation of Nitric Oxide from Selective Oxidation of N-Aryl N′-Hydroxyguanidines by Inducible Nitric Oxide Synthase. Biochemistry 1999; 38: 4663–4668
   PubMed Web of Science ®Google Scholar
• Renodon-Cornière A., Dijols S., Perollier C., Lefevre-Groboillot D., Boucher J.L., Attias R., Sari M.A., Stuehr D.J., Mansuy D. N-Aryl N′-Hydroxyguanidines, a New Class of NO-Donors After Selective Oxidation by Nitric Oxide Synthases: Structure–Activity Relationship. J. Med. Chem. 2002; 45: 944–954
   PubMed Web of Science ®Google Scholar
• Abu-Soud H.M., Presta A., Mayer B., Stuehr D.J. Analysis of Neuronal NO Synthase Under Single-Turnover Conditions: Conversion of Nω-Hydroxyarginine to Nitric Oxide and Citrulline. Biochemistry 1997; 36: 10811–10816
   PubMed Web of Science ®Google Scholar