4-Hydroxylation of debrisoquine by human CYP1A1 and its inhibition by quinidine and quinine

Journal of Pharmacology and Experimental Therapeutics

Volumn 301, Issue 3, 2002, Pages 1025-1032

  Granvil, Camille P ^a   Krausz, Kristopher W ^a   Gelboin, Harry V ^c   Idle, Jeffrey R ^b   Gonzalez, Frank J ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b NORWEGIAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Norway)

^c NONE   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA NAPHTHOFLAVONE; BUFURALOL; CYTOCHROME P450 1A1; CYTOCHROME P450 2D6; DEBRISOQUINE; DEBRISOQUINE 4 HYDROXYLASE; DEXTROMETHORPHAN; ENZYME INHIBITOR; ETHOXYRESORUFIN; MONOCLONAL ANTIBODY; O DEMETHYLASE; OXIDOREDUCTASE; QUINIDINE; QUININE; RECOMBINANT ENZYME; SPARTEINE;

ARTICLE; B LYMPHOCYTE; CONTROLLED STUDY; DRUG HYDROXYLATION; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SPECIFICITY; GENOTYPE; HUMAN; HUMAN CELL; IC 50; METABOLIC INHIBITION; NONHUMAN; PRIORITY JOURNAL;

ADRENERGIC AGENTS; ANTIMALARIALS; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 CYP2D6; DEBRISOQUIN; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; HUMANS; HYDROXYLATION; MICROSOMES; QUINIDINE; QUININE;

EID: 0036264528     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: 10.1124/jpet.301.3.1025     Document Type: Article

References (78)

1. Metabolism of debrisoquine sulfate. Identification of some urinary metabolites in rat and man
2. Comparative effects of the diastereoisomers, quinine and quinidine in producing phenocopy debrisoquine poor metabolisers (PMs) in healthy volunteers
3. Attempts to phenotype human liver samples in vitro for debrisoquine 4-hydroxylase activity
4. In vivo modulation of CYP enzymes by quinidine and rifampin
5. High-throughput cytochrome P450 inhibition screening via cassette probe-dosing strategy. IV. Validation of a direct injection on-line guard cartridge extraction/tandem mass spectrometry method for simultaneous CYP3A4, 2D6 and 2E1 inhibition assessment
6. Enantioselectivity of debrisoquine 4-hydroxylation in Brazilian Caucasian hypertensive patients phenotyped as extensive metabolizers
7. Differential inhibition of human CYP1A1 and CYP1A2 by quinidine and quinine
8. The CYP2D6 humanized mouse: Effect of the human CYP2D6 transgene and HNF4α on the disposition of debrisoquine in the mouse
9. Inhibition of debrisoquine hydroxylation with quinidine in subjects with three or more functional CYP2D6 genes
10. Genetic and metabolic criteria for the assignment of debrisoquine 4-hydroxylation (cytochrome P4502D6) phenotypes
11. The genetic control of bufuralol metabolism in man
12. A comparative study of hepatic and colonic metabolic enzymes in inbred mouse lines before and after treatment with the colon carcinogen, 1,2-dimethylhydrazine
13. Enantioselectivity of 4-hydroxylation in extensive and poor metabolizers of debrisoquine
14. Defective N-oxidation of sparteine in man: A new pharmacogenetic defect
15. 1- and 3-hydroxylations, in addition to 4-hydroxylation, of debrisoquine are catalyzed by cytochrome P450 2D6 in humans
16. Evidence that aspartic acid 301 is a critical substrate-contact residue in the active site of cytochrome P450 2D6
17. The application of monoclonal antibodies for studies on cytochrome P-450
18. Monoclonal antibody-directed phenotyping of cytochrome P-450-dependent aryl hydrocarbon hydroxylase and 7-ethoxycoumarin deethylase in mammalian tissues
19. A monoclonal antibody inhibitory to human P450 2D6: A paradigm for use in combinatorial determination of individual P450 role in specific drug tissue metabolism
20. On the assessment of drug metabolism by assays of codeine and its main metabolites
21. Expression of xenobiotic-metabolizing cytochrome P450 forms in human full-term placenta
22. Diversity in mechanisms of substrate oxidation by cytochrome P450 2D6, Lack of an allosteric role of NADPH-cytochrome P450 reductase in catalytic regioselectivity
23. Genotyping of poor metabolizers of debrisoquine by allele-specific PCR amplification
24. Porcine microsomal vitamin D(3) 25-hydroxylase (CYP2D25). Catalytic properties, tissue distribution, and comparison with human CYP2D6
25. The metabolism of [14C]-debrisoquine in man
26. Assay and characterisation of debrisoquine 4-hydroxylase activity of microsomal fractions of human liver
27. The specificity of inhibition of debrisoquine 4-hydroxylase activity by quinidine and quinine in the rat is the inverse of that in man
28. Preferential inhibition of CYP1A enzymes in hepatic microsomes by mexiletine
29. CYP2D6 polymorphism in systemic lupus erythematosus patients
30. High-performance liquid chromatographic assays for bufuralol 1′-hydroxylase, debrisoquine 4-hydroxylase, and dextromethorphan O-demethylase in microsomes and purified cytochrome P-450 isozymes of human liver
31. Dextromethorphan as a safe probe for debrisoquine hydroxylation polymorphism
32. CYP2D6 gene polymorphism in Caucasian smokers: Lung cancer susceptibility and phenotype-genotype relationships
33. Role of residue 382 in determining substrate specificity of P450 1A1: Molecular modeling and site-directed mutagenesis studies
34. Characterisation of xenobiotic-metabolising enzyme expression in human bronchial mucosa and peripheral lung tissues
35. Polymorphic hydroxylation of debrisoquine in man
36. The role of CYP2C19 in the metabolism of(+/-) bufuralol, the prototypic substrate of CYP2D6
37. Selective deficiency of debrisoquine 4-hydroxylase activity in mouse liver microsomes
38. A study of the debrisoquine hydroxylation polymorphism in a Nigerian population
39. CYP2D6 genotyping as an alternative to phenotyping for determination of metabolic status in a clinical trial setting
40. Metoprolol metabolism and debrisoquine oxidation polymorphism-population and family studies
41. Oxidation of phenethylamine derivatives by cytochrome P450 2D6: The issue of substrate protonation in binding and catalysis
42. Human hepatic CYP1A1 and CYP1A2 content, determined with specific anti-peptide antibodies, correlates with the mutagenic activation of PhIP
43. Selectivity in the inhibition of mammalian cytochromes P-450 by chemical agents
44. Coumarin substrates for cytochrome P450 2D6 fluorescence assays
45. A radiometric assay for debrisoquine 4-hydroxylase in human liver microsomes
46. The high performance liquid chromatography electrospray ionization mass spectrometry analysis of diverse basic pharmaceuticals on cyanopropyl and pentafluorophenylpropyl stationary phases
47. In vitro metabolism of quinidine: The (3S)-3-hydroxylation of quinidine is a specific marker reaction for cytochrome P-4503A4 activity in human liver microsomes
48. Detection and localization of CYP1A1/CYP1A2 in murine liver: Electrophoresis, immunoblotting and immunocytochemistry
49. Use of quinidine inhibition to define the role of the sparteine/debrisoquine cytochrome P450 in metoprolol oxidation by human liver microsomes
50. In vitro metabolism of sparteine by human liver: Competitive inhibition by debrisoquine
51. Cytochrome P-450 1A1 expression in human small bowel: Interindividual variation and inhibition by ketoconazole
52. The effect of cigarette smoking on 7-ethoxyresorufin O-deethylase and other monooxygenase activities in human liver: Analyses with monoclonal antibodies
53. Development of a human lymphoblastoid cell line constitutively expressing human CYP1A1 cDNA: Substrate specificity with model substrates and promutagens
54. A micromethod for quantitation of debrisoquine and 4-hydroxydebrisoquine in urine by liquid chromatography
55. Induction of cytochromes P450IA1 and P450IA2 and measurement of catalytic activities
56. Meta-analysis of studies of the CYP2D6 polymorphism in relation to lung cancer and Parkinson's disease
57. Polymorphic debrisoquine 4-hydroxylase activity in the rat is due to differences in CYP2D2 expression
58. Allelic variants of human cytochrome P450 1A1 (CYP1A1): Effect of T461N and I462V substitutions on steroid hydroxylase specificity
59. Expression of CYP1A1 and CYP1A2 genes in human liver
60. Determination of a 'GW cocktail' of cytochrome P450 probe substrates and their metabolites in plasma and urine using automated solid phase extraction and fast gradient liquid chromatography tandem mass spectrometry
61. Influence of the CYP2D6*10 allele on the metabolism of mexiletine by human liver microsomes
62. Major role of the CYP2C isozymes in deamination of amphetamine and benzphetamine: Evidence for the quinidine-specific inhibition of the reactions catalysed by rabbit enzyme
63. Polymorphism of carbon oxidation of drugs and clinical implications
64. Quinidine and the identification of drugs whose elimination is impaired in subjects classified as poor metabolizers of debrisoquine
65. Stereoselective hydroxylation of mexiletine in human liver microsomes: Implication of P450IID6 - A preliminary report
66. Modulation of drug-metabolising enzyme expression by condensation products of indole-3-ylcarbinol, an inducer in cruciferous vegetables
67. Inhibition of desmethylimipramine 2-hydroxylation by drugs in human liver microsomes
68. Multiple human cytochromes contribute to biotransformation of dextromethorphan in-vitro: Role of CYP2C9, CYP2C19, CYP2D6, and CYP3A
69. Expression of four rat CYP2D isoforms in Saccharomyces cerevisiae and their catalytic specificity
70. CYP1A2 is expressed along with CYP1A1 in the human lung
71. Xenobiotic metabolism enzyme gene expression in human bronchial epithelial and alveolar macrophage cells
72. Quantitative RT-PCR measurement of cytochromes P450 1A1, 1B1, and 2B7, microsomal epoxide hydrolase, and NADPH oxidoreductase expression in lung cells of smokers and nonsmokers
73. Cytochrome P450 CYP2D6
74. Substrate specificity of human liver cytochrome P-450 debrisoquine 4-hydroxylase probed using immunochemical inhibition and chemical modeling
75. Debrisoquin hydroxylation polymorphism among Ghanaians and Caucasians
76. Codeine O-demethylation co-segregates with polymorphic debrisoquine hydroxylation
77. Evidence for involvement of human CYP3A in the 3-hydroxylation of quinine
78. Characterization of human small intestinal cytochromes P-450