Effect of carbonate anion on cytochrome P450 2D6-mediated metabolism in vitro: the potential role of multiple oxygenating species.

[1]  A. Nomeir,et al.  Stimulation of tolbutamide hydroxylation by acetone and acetonitrile in human liver microsomes and in a cytochrome P-450 2C9-reconstituted system. , 2000, Drug metabolism and disposition: the biological fate of chemicals.

[2]  D. Greenblatt,et al.  Human cytochromes mediating N-demethylation of fluoxetine in vitro , 1997, Psychopharmacology.

[3]  H. Yamazaki,et al.  Roles of Cytochrome b5in the Oxidation of Testosterone and Nifedipine by Recombinant Cytochrome P450 3A4 and by Human Liver Microsomes , 1996 .

[4]  M. J. Coon,et al.  Evidence for a role of a perferryl-oxygen complex, FeO3+, in the N-oxygenation of amines by cytochrome P450 enzymes. , 1997, Molecular pharmacology.

[5]  A. Y. Lu,et al.  Human cytochrome P450 3A4-catalyzed testosterone 6 beta-hydroxylation and erythromycin N-demethylation. Competition during catalysis. , 1997, Drug metabolism and disposition: the biological fate of chemicals.

[6]  F Peter Guengerich,et al.  Role of glutamic acid 216 in cytochrome P450 2D6 substrate binding and catalysis. , 2003, Biochemistry.

[7]  Jeffrey P. Jones,et al.  On isotope effects for the cytochrome P-450 oxidation of substituted N,N-dimethylanilines , 1993 .

[8]  H. Yamazaki,et al.  High rates of substrate hydroxylation by human cytochrome P450 3A4 in reconstituted membranous vesicles: influence of membrane charge. , 1996, Biochemical and biophysical research communications.

[9]  Aiming Yu,et al.  Comparative contribution to dextromethorphan metabolism by cytochrome P450 isoforms in vitro: can dextromethorphan be used as a dual probe for both CTP2D6 and CYP3A activities? , 2001, Drug metabolism and disposition: the biological fate of chemicals.

[10]  M. J. Coon,et al.  Epoxidation of olefins by cytochrome P450: evidence from site-specific mutagenesis for hydroperoxo-iron as an electrophilic oxidant. , 1998, Proceedings of the National Academy of Sciences of the United States of America.

[11]  H Koga,et al.  Uncoupling of the cytochrome P-450cam monooxygenase reaction by a single mutation, threonine-252 to alanine or valine: possible role of the hydroxy amino acid in oxygen activation. , 1989, Proceedings of the National Academy of Sciences of the United States of America.

[12]  K Chiba,et al.  Comparative studies on the catalytic roles of cytochrome P450 2C9 and its Cys- and Leu-variants in the oxidation of warfarin, flurbiprofen, and diclofenac by human liver microsomes. , 1998, Biochemical pharmacology.

[13]  J. Miners,et al.  Use of tolbutamide as a substrate probe for human hepatic cytochrome P450 2C9. , 1996, Methods in enzymology.

[14]  J. Venhorst,et al.  Design, synthesis, and characterization of 7-methoxy-4-(aminomethyl)coumarin as a novel and selective cytochrome P450 2D6 substrate suitable for high-throughput screening. , 1999, Chemical research in toxicology.

[15]  S. Wrighton,et al.  The human hepatic cytochromes P450 involved in drug metabolism. , 1992, Critical reviews in toxicology.

[16]  F. Guengerich,et al.  Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. , 2001, Chemical research in toxicology.

[17]  M. J. Coon,et al.  Multiple activated oxygen species in P450 catalysis: contributions To specificity in drug metabolism. , 1998, Drug metabolism and disposition: the biological fate of chemicals.

[18]  F. Guengerich,et al.  Oxidation of the antihistaminic drug terfenadine in human liver microsomes. Role of cytochrome P-450 3A(4) in N-dealkylation and C-hydroxylation. , 1993, Drug metabolism and disposition: the biological fate of chemicals.

[19]  J. Idle,et al.  POLYMORPHIC HYDROXYLATION OF DEBRISOQUINE IN MAN , 1977, The Lancet.

[20]  M. J. Coon,et al.  Oxygen activation by cytochrome P-450. , 1980, Annual review of biochemistry.

[21]  Metabolism of 7-benzyloxy-4-trifluoromethylcoumarin by human hepatic cytochrome P450 isoforms , 2000, Xenobiotica; the fate of foreign compounds in biological systems.

[22]  S. Shaik,et al.  Two-state reactivity mechanisms of hydroxylation and epoxidation by cytochrome P-450 revealed by theory. , 2002, Current opinion in chemical biology.

[23]  T. Hirose,et al.  Role of Thr-252 in cytochrome P450cam: a study with unnatural amino acid mutagenesis. , 1995, Biochemical and biophysical research communications.

[24]  M. Calder,et al.  Mechanistic studies on C-19 demethylation in oestrogen biosynthesis. , 1982, The Biochemical journal.

[25]  M. J. Coon,et al.  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. , 1996, Proceedings of the National Academy of Sciences of the United States of America.

[26]  M. J. Coon,et al.  Multiple mechanisms and multiple oxidants in P450-catalyzed hydroxylations. , 2003, Archives of biochemistry and biophysics.

[27]  L. Wienkers,et al.  Topological alteration of the CYP3A4 active site by the divalent cation Mg(2+). , 2000, Drug metabolism and disposition: the biological fate of chemicals.

[28]  J. Schenkman,et al.  Influence of ionic strength on the P450 monooxygenase reaction and role of cytochrome b5 in the process. , 1994, Archives of biochemistry and biophysics.

[29]  W. Busby,et al.  Effect of methanol, ethanol, dimethyl sulfoxide, and acetonitrile on in vitro activities of cDNA-expressed human cytochromes P-450. , 1999, Drug metabolism and disposition: the biological fate of chemicals.

[30]  Gordon C K Roberts,et al.  Residues Glutamate 216 and Aspartate 301 Are Key Determinants of Substrate Specificity and Product Regioselectivity in Cytochrome P450 2D6* , 2003, The Journal of Biological Chemistry.

[31]  Jeffrey P. Jones,et al.  Evidence for two different active oxygen species in cytochrome P450 BM3 mediated sulfoxidation and N-dealkylation reactions. , 2002, Journal of the American Chemical Society.

[32]  F. Guengerich,et al.  Evidence for a 1-Electron Oxidation Mechanism in N-Dealkylation of N,N-Dialkylanilines by Cytochrome P450 2B1 , 1996, The Journal of Biological Chemistry.

[33]  A. D. Rodrigues,et al.  [O-ethyl 14C]phenacetin O-deethylase activity in human liver microsomes. , 1997, Drug metabolism and disposition: the biological fate of chemicals.

[34]  H. Yamazaki,et al.  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. , 1995, Biochemistry.

[35]  Y Wang,et al.  Evaluation of the selectivity of In vitro probes and suitability of organic solvents for the measurement of human cytochrome P450 monooxygenase activities. , 1998, Drug metabolism and disposition: the biological fate of chemicals.

[36]  F. Guengerich,et al.  Mechanisms of cytochrome P‐450 catalysis , 1990, FASEB journal : official publication of the Federation of American Societies for Experimental Biology.

[37]  S. Devito,et al.  Electronic models for cytochrome P450 oxidations. , 1996, Advances in experimental medicine and biology.

[38]  Ortiz de Montellano,et al.  Cytochrome P-450: Structure, Mechanism, and Biochemistry , 1986 .

[39]  S. Imaoka,et al.  Role of phospholipids in reconstituted cytochrome P450 3A form and mechanism of their activation of catalytic activity. , 1992, Biochemistry.

[40]  F. Guengerich,et al.  Mechanism of cytochrome P-450 catalysis. Mechanism of N-dealkylation and amine oxide deoxygenation , 1985 .

[41]  Serge Léger,et al.  Diversity in the oxidation of substrates by cytochrome P450 2D6: lack of an obligatory role of aspartate 301-substrate electrostatic bonding. , 2002, Biochemistry.

[42]  Michael M. Mysinger,et al.  Computational models for cytochrome P450: a predictive electronic model for aromatic oxidation and hydrogen atom abstraction. , 2002, Drug metabolism and disposition: the biological fate of chemicals.

[43]  J. Clèdes,et al.  Cytochrome P450 4A and 2E1 expression in human kidney microsomes. , 1997, Biochemical pharmacology.

[44]  M. Eichelbaum,et al.  Defective N-oxidation of sparteine in man: A new pharmacogenetic defect , 1979, European Journal of Clinical Pharmacology.

[45]  S. Shaik,et al.  Electronic Structure Makes a Difference: Cytochrome P‐450 Mediated Hydroxylations of Hydrocarbons as a Two‐State Reactivity Paradigm , 1998 .

[46]  S D Hall,et al.  Regioselective and stereoselective metabolism of ibuprofen by human cytochrome P450 2C. , 1997, Biochemical pharmacology.

[47]  B. W. Penman,et al.  Microtiter plate assays for inhibition of human, drug-metabolizing cytochromes P450. , 1997, Analytical biochemistry.

[48]  L. Wienkers,et al.  Multiple cytochrome P450 enzymes responsible for the oxidative metabolism of the substituted (S)-3-phenylpiperidine, (S,S)-3-[3-(methylsulfonyl)phenyl]-1-propylpiperidine hydrochloride, in human liver microsomes. , 2002, Drug metabolism and disposition: the biological fate of chemicals.

[49]  D. Smith,et al.  Human cytochrome P450s: selectivity and measurement in vivo. , 1998, Xenobiotica; the fate of foreign compounds in biological systems.

[50]  G. L. Kedderis,et al.  The use of intramolecular isotope effects to distinguish between deprotonation and hydrogen atom abstraction mechanisms in cytochrome P-450- and peroxidase-catalyzed N-demethylation reactions. , 1983, The Journal of biological chemistry.

[51]  H. Yamazaki,et al.  Roles of NADPH-P450 reductase and apo- and holo-cytochrome b5 on xenobiotic oxidations catalyzed by 12 recombinant human cytochrome P450s expressed in membranes of Escherichia coli. , 2002, Protein expression and purification.

[52]  M. J. Coon,et al.  Ipso-substitution by cytochrome P450 with conversion of p-hydroxybenzene derivatives to hydroquinone: evidence for hydroperoxo-iron as the active oxygen species. , 2002, Archives of biochemistry and biophysics.

[53]  D. Greenblatt,et al.  CYP2C9 is a principal low-affinity phenacetin O-deethylase: fluvoxamine is not a specific CYP1A2 inhibitor. , 1999, Drug metabolism and disposition: the biological fate of chemicals.

[54]  J. P. Dinnocenzo,et al.  On the mechanism of amine oxidations by P450. , 1995, Xenobiotica; the fate of foreign compounds in biological systems.

[55]  N. Chauret,et al.  Effect of common organic solvents on in vitro cytochrome P450-mediated metabolic activities in human liver microsomes. , 1998, Drug metabolism and disposition: the biological fate of chemicals.