Selected references on chemical models of P450 systems

Last modified: Thu Apr 15 09:25:19 BST 2004

• Aihara, K., Higuchi, T. and Hirobe, M. (1990) 3-Hydroxycoumarins: first direct preparation from coumarins using a Cu²⁺-ascorbic acid-O₂ system, and their potent bioactivities. Biochem. Biophys. Res. Commun. 168, 169-175.
• Akasaka, R., Mashino, T. and Hirobe, M. (1993) Cytochrome P450-like substrate oxidation catalyzed by cytochrome c and immobilized cytochrome c. Arch. Biochem. Biophys. 301, 355-360.
• Baciocchi, E., Belvedere, S., Bietti, M. and Lanzalunga, O. (1998) One electron oxidation of -alkylbenzyl alcohols induced by potassium 12-tungstocobalt(III)ate - comparison with the oxidation promoted by microsomal cytochrome P450. Eur. J. Org. Chem., 299-302.
• Battioni, P., Boucher, J.-L., Hart-Davis, J. and Mansuy, D. (1995) The dehydration of aldoximes to give nitriles: chemical modelling of a recently discovered enzymatic activity cytochromes P450. J. Inorg. Biochem. 59, 514.
• Breslow, R., Zhang, X. and Huang, Y. (1997a) Selective catalytic hydroxylation of a steroid by an artificial cytochrome P-450 enzyme. J. Am. Chem. Soc. 119, 4535-4536.
• Breslow, R., Huang, Y., Zhang, X. and Yang, J. (1997b) An artificial cytochrome P450 that hydroxylates unactivated carbons with regio- and stereoselectivity and useful catalytic turnovers. Proc. Natl. Acad. Sci. USA 94, 11156-11158.
• Choi, S.-Y., Eaton, P.E., Hollenberg, P.F., Liu, K.E., Lippard, S.J., Newcomb, M., Putt, D.A., Upadhyaya, S.P. and Xiong, Y. (1996) Regiochemical variations in reactions of methylcubane with tert-butoxyl radical, cytochrome P-450 enzymes, and a methane monooxygenase system. J. Am. Chem. Soc. 118, 6547-6555.
• Doi, T., Mori, T., Mashino, T. and Hirobe, M. (1993) Application of chemical cytochrome P-450 model systems to studies on drug metabolism. VI. N,N-coupling reaction of N-methylaniline catalyzed by polypeptide-bound porphyrinatoiron(III) and cytochrome P-450. Biochem. Biophys. Res. Commun. 191, 737-743.
• Dokoh, T., Suzuki, N., Higuchi, T., Urano, Y., Kikuchi, K. and Nagano, T. (2000) A new thioether-ligated iron porphyrin as a model of a protonated form of P450 active site. J. Inorg. Biochem. 82, 127-132.
• Evans, D.R., Drovetskaya, T., Bau, R., Reed, C.A. and Boyd, P.D.W. (1997) Heptane coordination to an iron(II) porphyrin. J. Am. Chem. Soc. 119, 3633-3634.
• Fujii, H., Yonetani, T., Miki, T. and Kakinuma, K. (1995) Modulation of the heme environment of neutrophil cytochrome b₅₅₈ to a "cytochrome P450-like" structure by pyridine. J. Biol. Chem. 270, 3193-3196.
• Gross, Z., Nimri, S., Barzilay, C.M. and Simkhovich, L. (1997) Reaction profile of the last step in cytochrome P-450 catalysis revealed by studies of model complexes. J. Biol. Inorg. Chem. 2, 492-506.
• Hart-Davis, J., Battioni, P., Boucher, J.-L. and Mansuy, D. (1998) New catalytic properties of iron porphyrins: Model systems for cytochrome P450-catalyzed dehydration of aldoximes. J. Am. Chem. Soc. 120, 12524-12530.
• Kim, C., Chen, K., Kim, J. and Que, L., Jr. (1997) Stereospecific alkane hydroxylation with H₂O₂ catalyzed by an iron(II)-tris(2-pyridylmethyl)amine complex. J. Am. Chem. Soc. 119, 5964-5965.
• Mansuy, D. and Battioni, P. (1994) Cytochrome P450 model systems. In Sheldon, R.A., Ed. Metalloporphyrins in Catalytic Oxidations, Marcel Dekker, Inc., New York, pp. 99-132.
• Mansuy, D., Battioni, P. and Battioni, J.P. (1989) Chemical model systems for drug-metabolizing cytochrome-P-450-dependent monooxygenases. Eur. J. Biochem. 184, 267-285.
• Matsui, T., Nagano, S., Ishimori, K., Watanabe, Y. and Morishima, I. (1996) Preparation and reactions of myoglobin mutants bearing both proximal cysteine ligand and hydrophobic distal cavity: protein models for the active site of P-450. Biochemistry 35, 13118-13124.
• Murakami, Y., Kikuchi, J.-i., Hisaeda, Y. and Hayashida, O. (1996) Artificial enzymes. Chem. Rev. 96, 721-758.
• Nakano, R., Konami, H., Sato, H., Ito, O. and Shimizu, T. (1995) Marked detergents effects on safranine T-mediated photo-induced electron transfer in cytochrome P450 1A2. Biochim. Biophys. Acta 1252, 245-250.
• Nam, W., Goh, Y.M., Lee, Y.J., Lim, M.H. and Kim, C. (1999) Biomimetic alkane hydroxylations by an iron(III) porphyrin complex with H₂O₂ and by a high-valent iron(IV) oxo porphyrin cation radical complex. Inorg. Chem. 38, 3238-3240. [Electronic Supplementary Material]
• Ohe, T., Mashino, T. and Hirobe, M. (1994) Novel metabolic pathway of arylethers by cytochrome P450: cleavage of the oxygen-aromatic ring bond accompanying ipso-substitution by the oxygen atom of the active species in cytochrome P450 models and cytochrome P450. Arch. Biochem. Biophys. 310, 402-409.
• Onuoha, A.C., Zu, X. and Rusling, J.F. (1997) Electrochemical generation and reactions of ferrylmyoglobins in water and microemulsions. J. Am. Chem. Soc. 119, 3979-3986.
• Osman, A.M., Koerts, J., Boersma, M.G., Boeren, S., Veeger, C. and Rietjens, I.M.C.M. (1996) Microperoxidase/H₂O₂-catalyzed aromatic hydroxylation proceeds by a cytochrome-P-450-type oxygen-transfer reaction mechanism. Eur. J. Biochem. 240, 232-238.
• Parton, R.F., Vankelecom, I.F.J., Casselman, M.J.A., Bezoukhanova, C.P., Uytterhoeven, J.B. and Jacobs, P.A. (1994) An efficient mimic of cytochrome P-450 from a zeolite-encaged iron complex in a polymer membrane. Nature 370, 541-544.
• Ren, Q.-Z., Huang, J.-W., Zhu, Z.-A., Ji, L.-N. and Chen, Y.-T. (2001) Spectroscopic properties of p/p and o/o type iron(III)-metal-free porphyrin dimers and their catalysis as cytochrome P450 model. J. Porphyrins Phthalocyanines 5, 449-455.
• Sadeque, A.J.M., Shimizu, T. and Hatano, M. (1987) Thiol-coordinated heme octapeptides of cytochrome c: Model compounds of cytochrome P-450. Inorg. Chim. Acta 135, 109-113.
• Sakurai, H., Hatayama, E., Fujitani, K. and Kato, H. (1982) Occurrence of aromatic methyl migration (NIH-shift) during oxidation of p-methylanisole by hemin-thiolester complex as a cytochrome P-450 model. Biochem. Biophys. Res. Commun. 108, 1649-1654.
• Sakurai, H., Hatayama, E., Yoshimura, T., Maeda, M., Tamura, H. and Kawasaki, K. (1983) Thiol-containing peptide-hemin complexes as models of cytochrome P-450. Biochem. Biophys. Res. Commun. 115, 590-597.
• Sakurai, H., Uchikubo, H., Yoshimura, T., Maeda, M. and Kawasaki, K. (1985) Synthetic analogs of the active site of cytochrome P-450cam characterization of thiolpeptide fragment-hemin complexes by optical and ESR spectrometries. Biochem. Biophys. Res. Commun. 130, 1254-1260.
• Sakurai, H., Shibuya, M., Shimizu, C., Akimoto, S., Maeda, M. and Kawasaki, K. (1986) DNA strand scission by hemin-thiolate complexes as models of cytochrome P-450. Biochem. Biophys. Res. Commun. 136, 645-650.
• Sakurai, H., Tsuchiya, K., Sugasaki, N. and Shibuya, M. (1990) Unusual hyperporphyrin spectrum by bis(glutathione dimethyl ester)-hemin complex, a model of cytochrome P-450-thiolate complexes. Biochem. Biophys. Res. Commun. 169, 22-29.
• Sawyer, D.T., Sugimoto, H. and Calderwood, T.S. (1984) Base (O₂·^-, e^-, or OH^-)-induced autoxygenation of organic substrates: A model chemical system for cytochrome P-450-catalyzed monoxygenation and dehydrogenation by dioxygen. Proc. Natl. Acad. Sci. USA 81, 8025-8027.
• Schappacher, M., Ricard, L., Fischer, J., Weiss, R., Bill, E., Montiel-Montoya, R., Winkler, H. and Trautwein, A.X. (1987) Synthesis, structure and spectroscopic properties of two models for the active site of the oxygenated state of cytochrome P450. Eur. J. Biochem. 168, 419-429.
• Schenning, A.P.H.J., Hubert, D.H.W., Feiters, M.C. and Nolte, R.J.M. (1996) Control of aggregation and tuning of the location of porphyrins in synthetic membranes as mimics for cytochrome P450. Langmuir 12, 1572-1577.
• Schenning, A.P.H.J., Spelberg, J.H.L., Hubert, D.H.W., Feiters, M.C. and Nolte, R.J.M. (1998) A supramolecular cytochrome P450 mimic. Chem. Eur. J. 4, 871-880.
• Selke, M. and Valentine, J.S. (1998) Switching on the nucleophilic reactivity of a ferric porphyrin peroxo complex. J. Am. Chem. Soc. 120, 2652-2653.
• Sheldon, R.A. (1994) Oxidation catalysis by metalloporphyrins: A historical perspective. In Sheldon, R.A., Ed. Metalloporphyrins in Catalytic Oxidations, Marcel Dekker, Inc., New York, pp. 1-27.
• Shumyantseva, V.V., Uvarov, V.Yu., Byakova, O.E. and Archakov, A.I. (1996a) Reductase and oxygenase activities of semisynthetic flavocytochromes based on cytochrome P450 2B4. Biochem. Mol. Biol. Int. 38, 829-838.
• Shumyantseva, V.V., Bulko, T.V., Zimin, A.G., Uvarov, V.Yu. and Archakov, A.I. (1996b) Design of an artificial hemoprotein based on human serum albumin. Biochem. Mol. Biol. Int. 39, 503-510.
• Shumyantseva, V.V., Uvarov, V.Yu., Byakova, O.E. and Archakov, A.I. (1998a) Semisynthetic flavocytochromes based on cytochrome P450 2B4: reductase and oxygenase activities. Arch. Biochem. Biophys. 354, 133-138.
• Shumyantseva, V.V., Avdeenko, Yu.L., Moskvitina, T.L., Bulko, T.V. and Archakov, A.I. (1998b) Hydrogen peroxide-supported activities of semisynthetic flavocytochrome 2B4. Biochem. Mol. Biol. Int. 45, 171-179.
• Shumyantseva, V.V., Avdeenko, Yu.L., Moskvitina, T.L., Bulko, T.V., Osipov, A.N. and Archakov, A.I. (1998c) Peroxide-dependent oxidation of substrates of semisynthetic flavocytochrome 2B4. Vopr. Med. Khim. (Moscow) 44, 369-375.
• Shumyantseva, V.V., Moskvitina, T.L., Bulko, T.V. and Archakov, A.I. (1998d) The use of alternative sources of electrons in mono-oxygenase reactions catalyzed by cytochrome P450. Physico-chemical methods as factors acting on enzymatic activity of proteins. Vopr. Med. Khim. (Moscow) 44, 423-436.
• Shumyantseva, V.V., Bulko, T.V., Alexandrova, S.A., Sokolov, N.N., Schmid, R.D., Bachmann, T. and Archakov, A.I. (1999) N-terminal truncated cytochrome P450 2B4: catalytic activities and reduction with alternative electron sources. Biochem. Biophys. Res. Commun. 263, 678-680.
• Smolinka, K. and Göber, B. (1999) Biomimetic oxidation of denaverine hydrochloride. Eur. J. Org. Chem., 679-683.
• Sugimoto, H., Spencer, L. and Sawyer, D.T. (1987) Ferric chloride-catalyzed activation of hydrogen peroxide for the demethylation of N,N-dimethylaniline, the epoxidation of olefins, and the oxidative cleavage of vicinal diols in acetonitrile: a reaction mimic for cytochrome P-450. Proc. Natl. Acad. Sci. USA 84, 1731-1733.
• Suzuki, N., Higuchi, T. and Nagano, T. (2002) Multiple active intermediates in oxidation reaction catalyzed by synthetic heme-thiolate complex relevant to cytochrome P450. J. Am. Chem. Soc. 124, 9622-9628. [Supplementary Material]
• Tani, F., Matsu-ura, M., Nakayama, S., Ichimura, M., Nakamura, N. and Naruta, Y. (2001) Synthesis and characterization of alkanethiolate-coordinated iron porphyrins and their dioxygen adducts as models for the active center of cytochrome P450: Direct evidence for hydrogen bonding to bound dioxygen. J. Am. Chem. Soc. 123, 1133-1142. [Supplementary Material]
• Ueno, T., Kousumi, Y., Yoshizawa-Kumagaye, K., Nakajima, K., Ueyama, N., Okamura, T.-a. and Nakamura, A. (1998) Role of -helix conformation cooperating with NH···S hydrogen bond in the active site of cytochrome P-450 and chloroperoxidase: Synthesis and properties of [M^III(OEP)(Cys-helical peptide)] (M = Fe and Ga). J. Am. Chem. Soc. 120, 12264-12273.
• Ueno, T., Nishikawa, N., Moriyama, S., Adachi, S., Lee, K., Okamura, T.-a., Ueyama, N. and Nakamura, A. (1999) Role of the invariant peptide fragment forming NH···S hydrogen bonds in the active site of cytochrome P-450 and chloroperoxidase: Synthesis and properties of Cys-containing peptide Fe(III) and Ga(III) (octaethylporphinato) complexes as models. Inorg. Chem. 38, 1199-1210.
• Ueyama, N., Nishikawa, N., Yamada, Y., Okamura, T.-a. and Nakamura, A. (1996) Cytochrome P-450 model (porphinato)(thiolato)iron(III) complexes with single and double NH···S hydrogen bonds at the thiolate site. J. Am. Chem. Soc. 118, 12826-12827.
• Ullrich, V., Ruf, H.H. and Mimoun, H. (1972) Model systems for mono-oxygenases. Biochem. Soc. Symp. 34, 11-19.
• Uvarov, V.Yu., Shumyantseva, V.V., Bykhovskaya, E.A., Kolyada, L.N. and Archakov, A.I. (1994) Semi-artificial hydroxylating enzymes created by flavins binding to cytochrome P450 2B4 and by bleomycin binding to NADPH-cytochrome P450 reductase. Biochem. Biophys. Res. Commun. 200, 722-725.
• Wood, M.L., Smith, J.R. and Garner, R.C. (1987) Aflatoxin B1 activation to a plasmid mutagen by a chemical model of cytochrome P-450. Mutat. Res. 176, 11-20.
• Zbaida, S. and Kariv, R. (1989) Biomimetic models for monooxygenases. Biopharm. Drug Dispos. 10, 431-442.

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