Oxidative aldehyde deformylation catalyzed by NADPH-cytochrome P450 reductase and the flavoprotein domain of neuronal nitric oxide synthase

Biochemical and Biophysical Research Communications

Volumn 337, Issue 4, 2005, Pages 1107-1111

  Vatsis, Kostas P ^a   Coon, Minor J ^a  

^a UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

Aldehyde deformylation; Hydrogen peroxide; nNOS reductase domain; P450 reductase

Indexed keywords

1 PHENYLETHANOL; 2 PHENYLPROPIONALDEHYDE; ALCOHOL; ALDEHYDE; AZIDE; CARBOXYLIC ACID; CATALASE; CHELATING AGENT; CYTOCHROME P450; CYTOCHROME P450 REDUCTASE; ENZYME; FLAVOPROTEIN; FLAVOPROTEIN REDUCTASE; HYDROGEN PEROXIDE; METAL ION; NITRIC OXIDE SYNTHASE; OXYGEN RADICAL; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; SCAVENGER; UNCLASSIFIED DRUG; XENOBIOTIC AGENT;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CONCENTRATION (PARAMETERS); OXIDATIVE DEFORMYLATION; PRIORITY JOURNAL;

ANIMALS; BENZYL ALCOHOLS; CATALASE; CATALYSIS; FLAVOPROTEINS; FORMALDEHYDE; HYDROGEN PEROXIDE; NADPH-FERRIHEMOPROTEIN REDUCTASE; NITRIC OXIDE SYNTHASE TYPE I; OXIDATION-REDUCTION; RABBITS; RATS;

EID: 27144465756     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2005.09.167     Document Type: Article

References (23)

1. W.L. Backes NADPH-cytochrome P450 reductase: function J.B. Schenkman H. Greim Handbook of Experimental Pharmacology, vol. 105: Cytochrome P450 1993 Springer-Verlag Berlin 15 34
2. A.L. Shen, and C.B. Kasper Protein and gene structure and regulation of NADPH-cytochrome P450 oxidoreductase J.B. Schenkman H. Greim Handbook of Experimental Pharmacology, vol. 105: Cytochrome P450 1993 Springer-Verlag Berlin 35 59
3. H.W. Strobel, A.V. Hodgson, and S. Shen NADPH-cytochrome P450 reductase and its structural and functional domains P.R. Ortiz de Montellano Cytochrome P450: Structure, Mechanism, and Biochemistry 2nd ed. 1995 Plenum Press New York 225 244
4. M. Wang, D.L. Roberts, R. Paschke, T.M. Shea, B.S.S. Masters, and J.-J.P. Kim Three-dimensional structure of NADPH-cytochrome P450 reductase: prototype for FMN- and FAD-containing enzymes Proc. Natl. Acad. Sci. USA 94 1997 8411 8416
5. C.J. Henderson, D.M.E. Otto, D. Carrie, M.A. Magnuson, A.W. McLaren, I. Rosewell, and C.R. Wolf Inactivation of the hepatic cytochrome P450 system by conditional deletion of hepatic cytochrome P450 reductase J. Biol. Chem. 278 2003 13480 13486
6. J. Gu, Y. Weng, Q.-Y. Zhang, H. Cui, M. Behr, L. Wu, W. Yang, L. Zhang, and X. Ding Liver-specific deletion of the NADPH-cytochrome P450 reductase gene: impact on plasma cholesterol homeostasis and the function and regulation of microsomal cytochrome P450 and heme oxygenase J. Biol. Chem. 278 2003 25895 25901
7. K. Watanabe, S. Narimatsu, I. Yamamoto, and H. Yoshimura Oxygenation mechanism in conversion of aldehyde to carboxylic acid catalyzed by a cytochrome P-450 isozyme J. Biol. Chem. 266 1991 2709 2711
8. C.-L. Kuo, A.D.N. Vaz, and M.J. Coon Metabolic activation of trans-4-hydroxy-2-nonenal, a toxic product of membrane lipid peroxidation and inhibitor of P450 cytochromes J. Biol. Chem. 272 1997 22611 22616
9. G.M. Raner, E.W. Chiang, A.D.N. Vaz, and M.J. Coon Mechanism-based inactivation of cytochrome P450 2B4 by aldehydes: relationship to aldehyde deformylation via a peroxyhemiacetal intermediate Biochemistry 36 1997 4895 4902
10. A.D.N. Vaz, E.S. Roberts, and M.J. Coon Olefin formation in the oxidative deformylation of aldehydes by cytochrome P-450. Mechanistic implications for catalysis by oxygen-derived peroxide J. Am. Chem. Soc. 113 1991 5886 5887
11. M. Akhtar, M.R. Calder, D.L. Corina, and J.N. Wright Mechanistic studies on C-19 demethylation in oestrogen biosynthesis Biochem. J. 201 1982 569 580
12. R.T. Fischer, J.M. Trzaskos, R.L. Magolda, S.S. Ko, C.S. Brosz, and B. Larsen Lanosterol 14α-methyl demethylase: isolation and characterization of the third metabolically generated oxidative demethylation intermediate J. Biol. Chem. 266 1991 6124 6132
13. D.C. Swinney, and A.Y. Mak Androgen formation by cytochrome P450 CYP17. Solvent isotope effect and pL studies suggest a role for protons in the regulation of oxene versus peroxide chemistry Biochemistry 33 1994 2185 2190
14. E.S. Roberts, A.D.N. Vaz, and M.J. Coon Catalysis by cytochrome P-450 of an oxidative reaction in xenobiotic aldehyde metabolism: deformylation with olefin formation Proc. Natl. Acad. Sci. USA 88 1991 8963 8966
15. A.D.N. Vaz, S.J. Pernecky, G.M. Raner, and M.J. Coon Peroxo-iron and oxenoid-iron species as alternative oxygenating agents in cytochrome P450-catalyzed reactions: switching by threonine-302 to alanine mutagenesis of cytochrome P450 2B4 Proc. Natl. Acad. Sci. USA 93 1996 4644 4648
16. A.D.N. Vaz, K.J. Kessell, and M.J. Coon Aromatization of a bicyclic steroid analog, 3-oxodecalin-4-ene-10-carboxaldehyde, by liver microsomal cytochrome P450 2B4 Biochemistry 33 1994 13651 13661
17. K.P. Vatsis, H.-M. Peng, and M.J. Coon Replacement of active-site cysteine-436 by serine converts cytochrome P450 2B4 into an NADPH oxidase with negligible monooxygenase activity J. Inorg. Biochem. 91 2002 542 553
18. K.P. Vatsis, H.-M. Peng, and M.J. Coon Abolition of oxygenase function, retention of NADPH oxidase activity, and emergence of peroxidase activity upon replacement of the axial cysteine-436 ligand by histidine in cytochrome P450 2B4 Arch. Biochem. Biophys. 434 2005 128 138
19. K.P. Vatsis, and M.J. Coon Ipso-substitution by cytochrome P450 with conversion of p-hydroxybenzene derivatives to hydroquinone: evidence for hydroperoxo-iron as the active oxygen species Arch. Biochem. Biophys. 397 2002 119 129
20. E.A Rozhkova, N. Fujimoto, I. Sagami, S.N. Daff, and T. Shimizu Interactions between the isolated oxygenase and reductase domains of neuronal nitric-oxide synthase: assessing the role of calmodulin J. Biol. Chem. 277 2002 16888 16894
21. J.L. Vermilion, and M.J. Coon Purified liver microsomal NADPH-cytochrome P-450 reductase: spectral characterization of oxidation-reduction states J. Biol. Chem. 253 1978 2694 2704
22. 5 and NADPH-cytochrome c reductase from rat liver microsomes J. Biochem. (Tokyo) 67 1970 249 257
23. N. Oshino, R. Oshino, and B. Chance The characteristics of the 'peroxidatic' reaction of catalase in ethanol oxidation Biochem. J. 131 1973 555 567