P450-containing systems

Last modified: Fri Dec 5 16:38:10 GMT 2003

• Andersen, J.F., Utermohlen, J.G. and Feyereisen, R. (1994) Expression of house fly CYP6A1 and NADPH-cytochrome P450 reductase in Escherichia coli and reconstitution of an insecticide-metabolizing P450 system. Biochemistry 33, 2171-2177.
• Aramaki, H., Fujita, M., Sagara, Y., Amemura, A. and Horiuchi, T. (1994) Heterologous expression of the cytochrome P450cam hydroxylase operon and the repressor gene of Pseudomonas putida in Escherichia coli. FEMS Microbiol. Lett. 123, 49-54.
• Ayalogu, E.O., Snelling, J., Lewis, D.F.V., Talwar, S., Clifford, M.N. and Ioannides, C. (1995) Induction of hepatic CYP1A2 by the oral administration of caffeine to rats: Lack of association with the Ah locus. Biochim. Biophys. Acta 1272, 89-94.
• Bernhardt, R. and Gunsalus, I.C. (1992) Reconstitution of cytochrome P4502B4 (LM2) activity with camphor and linalool monooxygenase electron donors. Biochem. Biophys. Res. Commun. 187, 310-317.
• Blake, J.A.R., Pritchard, M., Ding, S., Smith, G.C.M., Burchell, B., Wolf, C.R. and Friedberg, T. (1996) Coexpression of a human P450 (CYP3A4) and P450 reductase generates a highly functional monooxygenase system in Escherichia coli. FEBS Lett. 387, 210-214.
• Bredt, D.S. and Snyder, S.H. (1994) Nitric oxide: a physiologic messenger molecule. Annu. Rev. Biochem. 63, 175-195.
• Buters, J.T., Shou, M., Hardwick, J.P., Korzekwa, K.R. and Gonzalez, F.J. (1995) DNA-directed expression of human cytochrome P450 CYP1A1 using baculovirus. Purification, dependency on NADPH-P450 oxidoreductase, and reconstitution of catalytic properties without purification. Drug. Metab. Dispos. 23, 696-701.
• Centeno, F. and Gutierrez-Merino, C. (1992) Location of functional centers in the microsomal cytochrome P450 system. Biochemistry 31, 8473-8481.
• Cherradi, N., Chambaz, E.M. and Defaye, G. (1995) Organization of 3ß-hydroxysteroid dehydrogenase/isomerase and cytochrome P450_scc into a catalytically active molecular complex in bovine adrenocortical mitochondria. J. Steroid Biochem. Mol. Biol. 55, 507-514.
• Damon, M., Fautrel, A., Marc, N., Guillouzo, A. and Corcos, L. (1996) Isolation of a new mouse cDNA clone: hybrid form of cytochrome P450 2b10 and NADPH-cytochrome P450 oxidoreductase. Biochem. Biophys. Res. Commun. 226, 900-905.
• Degtyarenko, K.N. (1995) Structural domains of P450-containing monooxygenase systems. Protein Engineering 8, 737-747.
• Degtyarenko, K.N. and Archakov, A.I. (1993) Molecular evolution of P450 superfamily and P450-containing monooxygenase systems. FEBS Lett. 332, 1-8.
• De Mot, R. and Parret, A.H.A. (2002) A novel class of self-sufficient cytochrome P450 monooxygenases in prokaryotes. Trends Microbiol. 10, 502-508.
• Dong, J. and Porter, T.D. (1996) Coexpression of mammalian cytochrome P450 and reductase in Escherichia coli. Arch. Biochem. Biophys. 327, 254-259.
• Duport, C., Spagnoli, R., Degryse, E. and Pompon, D. (1998) Self-sufficient biosynthesis of pregnenolone and progesterone in engineered yeast. Nature Biotechnol. 16, 186-189.
• Durst, F., Benveniste, I., Salaun, J.-P. and Werck-Reichhart, D. (1992) Function, mechanism and regulation of cytochrome P-450 enzymes in plants. Biochem. Soc. Trans. 20, 353-357.
• Dus, K.M. (1984) Camphor hydroxylase of Pseudomonas putida: vestiges of sequence homology in cytochrome P-450CAM, putidaredoxin, and related proteins. Proc. Natl. Acad. Sci. USA 81, 1664-1668.
• Feyereisen, R. (1995) Molecular biology of insecticide resistance. Toxicol. Lett. 82-83, 83-90.
• Fulco, A.J. (1991) P450_BM-3 and other inducible bacterial P450 cytochromes: biochemistry and regulation. Annu. Rev. Pharmacol. Toxicol. 31, 177-203.
• Gautier, J.C., Urban, P., Beaune, P. and Pompon, D. (1993) Engineered yeast cells as model to study coupling between human xenobiotic metabolizing enzymes. Simulation of the two first steps of benzo[a]pyrene activation. Eur. J. Biochem. 211, 63-72.
• Gonzalez, F.J. and Korzekwa, K.R. (1995) Cytochromes P450 expression systems. Annu. Rev. Pharmacol. Toxicol. 35, 369-390.
• Gonzalez, F.J. and Nebert, D.W. (1990) Evolution of the P450 gene superfamily: animal-plant 'warfare', molecular drive and human genetic differences in drug oxidation. Trends Genet. 6, 182-186.
• Gonzalez, F.J., Jaiswal, A.K. and Nebert, D.W. (1986) P450 genes: evolution, regulation, and relationship to human cancer and pharmacogenetics. Cold Spring Harbor Symp. Quant. Biol. 51 Pt 2, 879-890.
• Gruenke, L.D., Konopka, K., Cadieu, M. and Waskell, L. (1995) The stoichiometry of the cytochrome P-450-catalyzed metabolism of methoxyflurane and benzphetamine in the presence and absence of cytochrome b₅. J. Biol. Chem. 270, 24707-24718.
• Guengerich, F.P., Gillam, E.M., Ohmori, S., Sandhu, P., Brian, W.R., Sari, M.A. and Iwasaki, M. (1993) Expression of human cytochrome P450 enzymes in yeast and bacteria and relevance to studies on catalytic specificity. Toxicology 82, 21-37.
• Guengerich, F.P., Martin, M.V., Guo, Z. and Chun, Y.-J. (1996) Purification of functional recombinant P450s from bacteria. Methods Enzymol. 272, 35-44.
• Hanukoglu, I. (1996) Electron transfer proteins of cytochrome P450 systems. Adv. Mol. Cell Biol. 14, 29-56.
• Hanukoglu, I. and Hanukoglu, Z. (1986) Stoichiometry of mitochondrial cytochromes P-450, adrenodoxin and adrenodoxin reductase in adrenal cortex and corpus luteum. Implications for membrane organization and gene regulation. Eur. J. Biochem. 157, 27-31.
• Harayama, S., Kok, M. and Neidle, E.L. (1992) Functional and evolutionary relationships among diverse oxygenases. Annu. Rev. Microbiol. 46, 565-601.
• Jackson, C.J., Lamb, D.C., Marczylo, T.H., Warrilow, A.G.S., Manning, N.J., Lowe, D.J., Kelly, D.E. and Kelly, S.L. (2002) A novel sterol 14-demethylase/ferredoxin fusion protein (MCCYP51FX) from Methylococcus capsulatus represents a new class of the cytochrome P450 superfamily. J. Biol. Chem. 277, 46959-46965.
• Jenkins, C.M. and Waterman, M.R. (1994) Flavodoxin and NADPH-flavodoxin reductase from Escherichia coli support bovine cytochrome P450c17 hydroxylase activities. J. Biol. Chem. 269, 27401-27408.
• Jenkins, C.M. and Waterman, M.R. (1998) NADPH-flavodoxin reductase and flavodoxin from Escherichia coli: Characteristics as a soluble microsomal P450 reductase. Biochemistry 37, 6106-6113.
• Katagiri, M., Kagawa, N. and Waterman, M.R. (1995) The role of cytochrome b₅ in the biosynthesis of androgens by human P450c17. Arch. Biochem. Biophys. 317, 343-347.
• Kitazume, T., Takaya, N., Nakayama, N. and Shoun, H. (2000) Fusarium oxysporum fatty-acid subterminal hydroxylase (CYP505) is a membrane-bound eukaryotic counterpart of Bacillus megaterium cytochrome P450BM3. J. Biol. Chem. 275, 39734-39740.
• Koga, H., Yamaguchi, E., Matsunaga, K., Aramaki, H. and Horiuchi, T. (1989) Cloning and nucleotide sequences of NADH-putidaredoxin reductase gene (camA) and putidaredoxin gene (camB) involved in cytochrome P-450cam hydroxylase of Pseudomonas putida. J. Biochem. (Tokyo) 106, 831-836.
• Lecoeur, S., Gautier, J.-C., Belloc, C., Gauffre, A. and Beaune, P.H. (1996) Use of heterologous expression systems to study autoimmune drug-induced hepatitis. Methods Enzymol. 272, 76-85.
• Lee, C.A., Kost, T. and Serabjit-Singh, C.J. (1996) Recombinant baculovirus strategy for coexpression of functional human cytochrome P450 and P450 reductase. Methods Enzymol. 272, 86-95.
• Lewis, D.F.V. and Hlavica, P. (2000) Interactions between redox partners in various cytochrome P450 systems: functional and structural aspects. Biochim. Biophys. Acta 1460, 353-374.
• Mason, J.R. and Cammack, R. (1992) The electron-transport proteins of hydroxylating bacterial dioxygenases. Annu. Rev. Microbiol. 46, 277-305.
• Miller, W.L., Auchus, R.J. and Geller, D.H. (1997) The regulation of 17,20 lyase activity. Steroids 62, 133-142.
• Nagy, I., Schoofs, G., Compernolle, F., Proost, P., Vanderleyden, J. and de Mot, R. (1995) Degradation of the thiocarbamate herbicide EPTC (S-ethyl dipropylcarbamothioate) and biosafening by Rhodococcus sp. strain NI86/21 involve an inducible cytochrome P-450 system and aldehyde dehydrogenase. J. Bacteriol. 177, 676-687.
• Nakayama, N. and Shoun, H. (1994) Fatty acid hydroxylase of the fungus Fusarium oxysporum is possibly a fused protein of cytochrome P-450 and its reductase. Biochem. Biophys. Res. Commun. 202, 586-590.
• Nakayama, N., Takemae, A. and Shoun, H. (1996) Cytochrome P450foxy, a catalytically self-sufficient fatty acid hydroxylase of the fungus Fusarium oxysporum. J. Biochem. (Tokyo) 119, 435-440.
• Nebert, D.W. (1991) Proposed role of drug-metabolizing enzymes: regulation of steady state levels of the ligands that effect growth, homeostasis, differentiation, and neuroendocrine functions. Mol. Endocrinol. 5, 1203-1214.
• Nebert, D.W. (1994) Drug-metabolizing enzymes in ligand-modulated transcription. Biochem. Pharmacol. 47, 25-37.
• O'Keefe, D.P. and Harder, P.A. (1991) Occurrence and biological function of cytochrome P450 monooxygenases in the actinomycetes. Mol. Microbiol. 5, 2099-2105.
• Patten, C.J. and Koch, P. (1995) Baculovirus expression of human P450 2E1 and cytochrome b₅: Spectral and catalytic properties and effect of b₅ on the stoichiometry of P450 2E1-catalyzed reactions. Arch. Biochem. Biophys. 317, 504-513.
• Pearce, R.E., McIntyre, C.J., Madan, A., Sanzgiri, U., Draper, A.J., Bullock, P.L., Cook, D.C., Burton, L.A., Latham, J., Nevins, C. and Parkinson, A. (1996) Effects of freezing, thawing, and storing human liver microsomes on cytochrome P450 activity. Arch. Biochem. Biophys. 331, 145-169.
• Perrin, A., Chambaz, E.M. and Defaye, G. (1995) Modulation of hydroxylase and lyase activities of bovine cytochrome P-450₁₇ in adrenal and testicular microsomes by a tissue-specific local membrane environment. J. Steroid Biochem. Mol. Biol. 54, 121-129.
• Peterson, J.A., Lorence, M.C. and Amarneh, B. (1990) Putidaredoxin reductase and putidaredoxin. Cloning, sequence determination, and heterologous expression of the proteins. J. Biol. Chem. 265, 6066-6073.
• Peterson, J.A., Lu, J.Y., Geisselsoder, J., Graham-Lorence, S., Carmona, C., Witney, F. and Lorence, M.C. (1992) Cytochrome P-450terp. Isolation and purification of the protein and cloning and sequencing of its operon. J. Biol. Chem. 267, 14193-14203.
• Pompon, D., Perret, A., Bellamine, A., Laine, R., Gautier, J.C. and Urban, P. (1995) Genetically engineered yeast cells and their applications. Toxicol. Lett. 82-83, 815-822.
• Pompon, D., Louerat, B., Bronine, A. and Urban, P. (1996) Yeast expression of animal and plant P450s in optimized redox environments. Methods Enzymol. 272, 51-64.
• Rapoport, R., Sklan, D. and Hanukoglu, I. (1995) Electron leakage from the adrenal cortex mitochondrial P450scc and P450c11 systems: NADPH and steroid dependence. Arch. Biochem. Biophys. 317, 412-416.
• Roberts, G.A., Grogan, G., Greter, A., Flitsch, S.L. and Turner, N.J. (2002) Identification of a new class of cytochrome P450 from a Rhodococcus sp. J. Bacteriol. 184, 3898-3908.
• Roberts, G.A., Çelik, A., Hunter, D.J.B., Ost, T.W.B., White, J.H., Chapman, S.K., Turner, N.J. and Flitsch, S.L. (2003) A self-sufficient cytochrome P450 with a primary structural organisation that includes a flavin domain and a [2Fe-2S] redox center. J. Biol. Chem. 278, 48914-48920.
• Sakaki, T., Akiyoshi-Shibata, M., Yabusaki, Y., Manabe, K., Murakami, H. and Ohkawa, H. (1991) Progesterone metabolism in recombinant yeast simultaneously expressing bovine cytochromes P450c17 (CYP17A1) and P450c21 (CYP21B1) and yeast NADPH-P450 oxidoreductase. Pharmacogenetics , 86-93.
• Shafiee, A. and Hutchinson, C. R. (1988) Purification and reconstitution of the electron transport components for 6-deoxyerythronolide B hydroxylase, a cytochrome P-450 enzyme of macrolide antibiotic (erythromycin) biosynthesis. J. Bacteriol. 170, 1548-1553.
• Shimizu, T., Sogawa, K., Fujii-Kuriyama, Y., Takahashi, M., Ogoma, Y. and Hatano, M. (1986) Expression of cytochrome P-450d by Saccharomyces cerevisiae. FEBS Lett. 207, 217-221.
• Sligar, S.G., Filipovic, D. and Stayton, P.S. (1991) Mutagenesis of cytochromes P450cam and b₅. Methods Enzymol. 206, 31-49.
• Spurr, N.K., Gough, A.C., Smith, C.A. and Wolf, C.R. (1991) Genetic analysis of cytochrome P450 system. Methods Enzymol. 206, 149-166.
• Sugiyama, T., Miki, N. and Yamano, T. (1980) NADH- and NADPH-dependent reconstituted p-nitroanisole O-demethylation system containing cytochrome P-450 with high affinity for cytochrome b₅. J. Biochem. (Tokyo) 87, 1457-1467.
• Truan, G., Cullin, C., Reisdorf, P., Urban, P. and Pompon, D. (1993) Enhanced in vivo monooxygenase activities of mammalian P450s in engineered yeast cells producing high levels of NADPH-P450 reductase and human cytochrome b₅. Gene 125, 49-55.
• Ullah, A.J., Murray, R.I., Bhattacharyya, P.K., Wagner, G.C. and Gunsalus, I.C. (1990) Protein components of a cytochrome P-450 linalool 8-methyl hydroxylase. J. Biol. Chem. 265, 1345-1351.
• Urban, P., Mignotte, C., Kazmaier, M., Delorme, F. and Pompon, D. (1997) Cloning, yeast expression, and characterization of the coupling of two distantly related Arabidopsis thaliana NADPH-cytochrome P450 reductases with P450 CYP73A5. J. Biol. Chem. 272, 19176-19186.
• van der Meer, J.R., de Vos, W.M., Harayama, S. and Zehnder, A.J. (1992) Molecular mechanisms of genetic adaptation to xenobiotic compounds. Microbiol. Rev. 56, 677-694.
• White, K.A. and Marletta, M.A. (1992) Nitric oxide synthase is a cytochrome P-450 type hemoprotein. Biochemistry 31, 6627-6631.
• Yamazaki, H., Ueng, Y.-F., Shimada, T. and Guengerich, F.P. (1995) Roles of divalent metal ions in oxidations catalyzed by recombinant cytochrome P450 3A4 and replacement of NADPH-cytochrome P450 reductase with other flavoproteins, ferredoxin, and oxygen surrogates. Biochemistry 34, 8380-8389.
• Zhukov, A.A. and Archakov, A.I. (1982) Complete stoichiometry of free NADPH oxidation in liver microsomes. Biochem. Biophys. Res. Commun. 109, 813-818.
• Zimmer, T. and Schunck, W.-H. (1995) A deviation from the universal genetic code in Candida maltosa and consequences for heterologous expression of cytochromes P450 52A4 and 52A5 in Saccharomyces cerevisiae. Yeast 11, 33-41.

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