P450 reductase and cytochrome b5 interactions with cytochrome P450: Effects on house fly CYP6A1 catalysis

Insect Biochemistry and Molecular Biology

Volumn 38, Issue 11, 2008, Pages 1008-1015

  Murataliev, Marat B ^a,b   Guzov, Victor M ^a   Walker, F Ann ^b   Feyereisen, René ^a,c  

^a UNIVERSITY OF ARIZONA   (United States)

^b University of Arizona   (United States)

^c CNRS   (France)

Author keywords

Cytochrome b5; P450 reductase; Reactive oxygen species; Stoichiometry; Uncoupling; Xenobiotic metabolism

Indexed keywords

CYTOCHROME B5; CYTOCHROME P450; HEPTACHLOR; INSECT PROTEIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; TESTOSTERONE;

ANIMAL; ARTICLE; CATALYSIS; ENZYMOLOGY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HOUSE FLY; HYDROXYLATION; METABOLISM;

ANIMALS; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; CYTOCHROMES B5; HEPTACHLOR; HOUSEFLIES; HYDROXYLATION; INSECT PROTEINS; NADPH-FERRIHEMOPROTEIN REDUCTASE; TESTOSTERONE;

MUSCA DOMESTICA;

EID: 55749090372     PISSN: 09651748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ibmb.2008.08.007     Document Type: Article

References (44)

1. Andersen J.F., Utermohlen J.G., and Feyereisen R. Expression of house fly CYP6A1 and NADPH-cytochrome P450 reductase in Escherichia coli and reconstitution of an insecticide-metabolizing P450 system. Biochemistry 33 (1994) 2171-2177
2. Andersen J.F., Walding J.K., Evans P.H., Bowers W.S., and Feyereisen R. Substrate specificity for the epoxidation of terpenoids and active site topology of house fly cytochrome P450 6A1. Chem. Res. Toxicol. 10 (1997) 156-164
3. 5 augments the 17,20-lyase activity of hyman P450c17 without direct electron transfer. J. Biol. Chem. 273 (1998) 3158-3165
4. Bast A. Is formation of reactive oxygen by cytochrome P-450 perilous and predictable?. Trends Pharmacol. Sci. 7 (1986) 266-270
5. Bernhardt R. Cytochromes P450 as versatile biocatalysts. J. Biotechnol. 124 (2006) 128-145
6. 5 and cytochrome P-450 reductase with cytochrome P-450 in the membrane of reconstituted vesicles. J. Biol. Chem. 257 (1982) 4783-4787
7. 5 in mixed function oxidations: effect of microsomal binding of the hemoprotein on hepatic N-demethylations. Adv. Exp. Med. Biol. 58 (1975) 467-483
8. Dunkov B.C., Guzov V.M., Mocelin G., Shotkoski F., Brun A., Amichot M., ffrench-Constant R.H., and Feyereisen R. The Drosophila cytochrome P450 gene Cyp6a2: structure, localization, heterologous expression, and induction by phenobarbital. DNA Cell Biol. 16 (1997) 1345-1356
9. Estabrook R.W., Franklin M.R., Cohen B., Shigamatzu A., and Hildebrandt A.G. Biochemical and genetic factors influencing drug metabolism. Influence of hepatic microsomal mixed function oxidation reactions on cellular metabolic control. Metabolism 20 (1971) 187-199
10. 5. Biochemistry 40 (2001) 4879-4891
11. Feyereisen R. Insect cytochrome P450. In: Gilbert L.I., Iatrou K., and Gill S.S. (Eds). Comprehensive Molecular Insect Science (2005), Elsevier, Amsterdam vol. 4, pp. 1-77
12. Feyereisen R. Evolution of insect P450. Biochem. Soc. Trans. 34 (2006) 1252-1255
13. Feyereisen R., Koener J.F., Cariño F.A., and Daggett A.S. Biochemistry and molecular biology of insect cytochrome P450. In: Hagedorn H.H., et al. (Ed). Molecular Insect Science (1990), Plenum Press, New York 263-272
14. French J.S., Guengerich F.P., and Coon M.J. Interactions of cytochrome P-450, NADPH-cytochrome P-450 reductase, phospholipid, and substrate in the reconstituted liver microsomal enzyme system. J. Biol. Chem. 255 (1980) 4112-4119
15. Guengerich F.P., Ballou D.P., and Coon M.J. Spectral intermediates in the reaction of oxygen with purified liver microsomal cytochrome P-450. Biochem. Biophys. Res. Commun. 70 (1976) 951-956
16. 5. J. Biol. Chem. 271 (1996) 26637-26645
17. Hildebrandt A.G., Roots I., Tjoe M., and Heinemeyer G. Hydrogen peroxide in hepatic microsomes. Meth. Enzymol. 52 (1978) 342-350
18. Jacobsen N.E., Kövér K.E., Murataliev M.B., Feyereisen R., and Walker F.A. Structure and stereochemistry of products of hydroxylation of human steroid hormones by a housefly cytochrome P450 (CYP6A1). Magn. Reson. Chem. 44 (2006) 467-474
19. Kominami S., Owaki A., Iwanaga T., Tagashira-Ikushiro H., and Yamazaki T. The rate-determining step in P450 C21-catalyzing reactions in a membrane-reconstituted system. J. Biol. Chem. 276 (2001) 10753-10758
20. Li X., Schuler M.A., and Berenbaum M.R. Molecular mechanisms of metabolic resistance to synthetic and natural xenobiotics. Annu. Rev. Entomol. 52 (2007) 231-253
21. 5 effects vary with substrate. Arch. Biochem. Biophys. 385 (2001) 311-321
22. Lowry O.H., Rosebrough N.J., Farr A.L., and Randall R.J. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 195 (1951) 265-275
23. Miwa G.T., and Lu A.Y.H. The association of cytochrome P-450 and NADPH-cytochrome P-450 reductase in phospholipid membranes. Arch. Biochem. Biophys. 234 (1984) 161-166
24. Miwa G.T., West S.B., Huang M.-T., and Lu A.Y.H. Studies on the association of cytochrome P-450 and NADPH-cytochrome c reductase during catalysis in a reconstituted hydroxylating system. J. Biol. Chem. 254 (1979) 5695-5700
25. Murataliev M.B., and Feyereisen R. Functional interactions in cytochrome P450BM3. Fatty acid substrate binding alters electron-transfer properties of the flavoprotein domain. Biochemistry 35 (1996) 15029-15037
26. Murataliev M.B., Ariño A., Guzov V.M., and Feyereisen R. Kinetic mechanism of cytochrome P450 reductase from the house fly (Musca domestica). Insect Biochem. Mol. Biol. 29 (1999) 233-242
27. Murataliev M.B., Feyereisen R., and Walker F.A. Electron transfer in diflavin reductases. Biochim. Biophys. Acta 1698 (2004) 1-26
28. 5 with flavocytochrome P450 BM3 and its domains. Drug. Metab. Rev. 39 (2007) 599-617
29. Ortiz de Montellano P.R., and De Voss J.J. Substrate oxidation by cytochrome P450 enzymes. In: Ortiz de Montellano P.R. (Ed). Cytochrome P450: Structure, Mechanism and Biochemistry (2005), Kluwer Academic, New York 183-245
30. 5 rules uncoupling mechanisms. Biochemistry 37 (1998) 11412-11424
31. 5 in cytochrome P450 reactions. J. Biochem. Mol. Toxicol. 16 (2002) 311-316
32. Sabourault C., Guzov V.M., Koener J.F., Claudianos C., Plapp Jr. F.W., and Feyereisen R. Overproduction of a P450 that metabolizes diazinon is linked to a loss-of-function in the chromosome 2 ali-esterase (MdalphaE7) gene in resistant house flies. Insect Mol. Biol. 10 (2001) 609-618
33. 5. Pharmacol. Ther. 97 (2003) 139-152
34. Shephard E.A., Phillips I.R., Bayney R.M., Pike S.F., and Rabin B.R. Quantification of NADPH:cytochrome P-450 reductase in liver microsomes by a specific radioimmunoassay technique. Biochem. J. 211 (1983) 333-340
35. 5 binding to the terminal hemoprotein. J. Biol. Chem. 258 (1983) 13444-13452
36. Tindberg N., and Ingelmann-Sundberg M. Cytochrome P-450 and oxygen toxicity. Oxygen-dependent induction of ethanol-inducible cytochrome P-450 (IIEI) in rat liver and lung. Biochemistry 28 (1989) 4499-4504
37. 5 on CYP3A4 activity and stability in vivo. Arch. Biochem. Biophys. 366 (1999) 116-124
38. Wen Z., Pan L., Berenbaum M.B., and Schuler M.A. Metabolism of linear and angular furanocoumarins by Papilio polyxenes CYP6B1 co-expressed with NADPH cytochrome P450 reductase. Insect Biochem. Mol. Biol. 33 (2003) 937-947
39. Werck-Reichhart D., and Feyereisen R. Cytochromes P450: a success story. Genome Biol. 1 (2000) 3003.1-3003.9
40. 5 in the oxidation of 7-ethoxycoumarin, chlorzoxazone, aniline, and N-nitrosodimethylamine by recombinant cytochrome P450 2E1 and by human liver microsomes. Biochem. Pharmacol. 52 (1996) 301-309
41. 5 in the oxidation of testosterone and nifedipine by recombinant cytochrome P450 3A4 and by human liver microsomes. Arch. Biochem. Biophys. 325 (1996) 174-182
42. 5 or heme oxygenase. J. Biol. Chem. 276 (2001) 30885-30891
43. 5 on xenobiotic oxidations catalyzed by 12 recombinant human cytochrome P450s expressed in membranes of Escherichia coli. Protein Expr. Purif. 24 3 (2002) 329-337
44. 5 inhibits electron transfer from NADPH-cytochrome P450 reductase to ferric cytochrome P450 2B4. J. Biol. Chem. 283 (2008) 5217-5225