P450 oxidoreductase: genetic polymorphisms and implications for drug metabolism and toxicity

Bibliography

• Evans WE, Relling MV. Pharmacogenomics: translating functional genomics into rational therapeutics. Science 1999;286:487-91
   PubMed Web of Science ®Google Scholar
• Meyer UA. Pharmacogenetics: five decades of therapeutic lessons from genetic diversity. Nat Rev Genet 2004;5:669-76
   PubMed Web of Science ®Google Scholar
• Eichelbaum M, Ingelman-Sundberg M, Evans WE. Pharmacogenomics and individualized drug therapy. Ann Rev Med 2006;57:119-37
   PubMed Web of Science ®Google Scholar
• Ozdemir V, Kalow W, Tang BK, et al. Evaluation of the genetic component of variability in CYP3A4 activity: a repeated drug administration method. Pharmacogenetics 2000;10:373-88
   PubMedGoogle Scholar
• Wadelius M, Pirmohamed M. Pharmacogenetics of warfarin: current status and future challenges. Pharmacogenomics J 2007;7:99-111
   PubMed Web of Science ®Google Scholar
• Sanderson S, Emery J, Higgins J. CYP2C9 gene variants, drug dose, and bleeding risk in warfarin-treated patients: a HuGEnet systematic review and meta-analysis. Genet Med 2005;7:97-104
   PubMed Web of Science ®Google Scholar
• Rettie AE, Wienkers LC, Gonzalez FJ, et al. Impaired (S)-warfarin metabolism catalysed by the R144C allelic variant of CYP2C9. Pharmacogenetics 1994;4:39-42
   PubMedGoogle Scholar
• Sullivan-Klose TH, Ghanayem BI, Bell DA, et al. The role of the CYP2C9-Leu359 allelic variant in the tolbutamide polymorphism. Pharmacogenetics 1996;6:341-9
   PubMedGoogle Scholar
• de Morais SM, Wilkinson GR, Blaisdell J, et al. The major genetic defect responsible for the polymorphism of S-mephenytoin metabolism in humans. J Biol Chem 1994;269:15419-22
   PubMed Web of Science ®Google Scholar
• De Morais SM, Wilkinson GR, Blaisdell J, et al. Identification of a new genetic defect responsible for the polymorphism of (S)-mephenytoin metabolism in Japanese. Mol Pharmacol 1994;46:594-8
   PubMed Web of Science ®Google Scholar
• Wolf CR, Smith CA, Bishop T, et al. CYP2D6 genotyping and the association with lung cancer susceptibility. Pharmacogenetics 1994;4:104-6
   PubMedGoogle Scholar
• Ingelman-Sundberg M, Sim SC, Gomez A, Rodriguez-Antona C. Influence of cytochrome P450 polymorphisms on drug therapies: pharmacogenetic, pharmacoepigenetic and clinical aspects. Pharmacol Ther 2007;116:496-526
   PubMed Web of Science ®Google Scholar
• Wrighton SA, Stevens JC. The human hepatic cytochromes P450 involved in drug metabolism. Crit Rev Toxicol 1992;22:1-21
   PubMed Web of Science ®Google Scholar
• Renwick AB, Mistry H, Ball SE, et al. Metabolism of Zaleplon by human hepatic microsomal cytochrome P450 isoforms. Xenobiotica 1998;28:337-48
   PubMed Web of Science ®Google Scholar
• Schellens JH, Soons PA, Breimer DD. Lack of bimodality in nifedipine plasma kinetics in a large population of healthy subjects. Biochem Pharmacol 1988;37:2507-10
   PubMed Web of Science ®Google Scholar
• Ingelman-Sundberg M, Nebert DW. Home page of the Human Cytochrome P450 (CYP) Allele Nomenclature Committee, 2007 March 27. Available from: URL:www.cypalleles.ki.se/ [Last accessed 10 October 2007]
   Google Scholar
• Koyano S, Kurose K, Saito Y, et al. Functional characterization of four naturally occurring variants of human pregnane X receptor (PXR): one variant causes dramatic loss of both DNA binding activity and the transactivation of the CYP3A4 promoter/enhancer region. Drug Metabol Dispos 2004;32:149-54
   PubMed Web of Science ®Google Scholar
• Lamba J, Lamba V, Schuetz E. Genetic variants of PXR (NR1I2) and CAR (NR1I3) and their implications in drug metabolism and pharmacogenetics. Curr Drug Metab 2005;6:369-83
   PubMed Web of Science ®Google Scholar
• Ikeda S, Kurose K, Jinno H, et al. Functional analysis of four naturally occurring variants of human constitutive androstane receptor. Mol Genet Metab 2005;86:314-9
   PubMed Web of Science ®Google Scholar
• Lamba J, Strom S, Venkataramanan R, et al. MDR1 genotype is associated with hepatic cytochrome P450 3A4 basal and induction phenotype. Clin Pharmacol Ther 2006;79:325-38
   PubMed Web of Science ®Google Scholar
• Letschert K, Keppler D, Konig J. Mutations in the SLCO1B3 gene affecting the substrate specificity of the hepatocellular uptake transporter OATP1B3 (OATP8). Pharmacogenetics 2004;14:441-52
   PubMedGoogle Scholar
• Michalski C, Cui Y, Nies AT, et al. A naturally occurring mutation in the SLC21A6 gene causing impaired membrane localization of the hepatocyte uptake transporter. J Biol Chem 2002;277:43058-63
   PubMed Web of Science ®Google Scholar
• Nozawa T, Nakajima M, Tamai I, et al. Genetic polymorphisms of human organic anion transporters OATP-C (SLC21A6) and OATP-B (SLC21A9): allele frequencies in the Japanese population and functional analysis. J Pharmacol Exp Ther 2002;302:804-13
   PubMed Web of Science ®Google Scholar
• Tirona RG, Leake BF, Merino G, Kim RB. Polymorphisms in OATP-C: identification of multiple allelic variants associated with altered transport activity among European- and African-Americans. J Biol Chemi 2001;276:35669-75
   PubMed Web of Science ®Google Scholar
• Horecker B. Triphosphopyridine nucleotide-cytochrome c reductase in liver. J Biol Chem 1950;183:593-605
   Web of Science ®Google Scholar
• Williams CH Jr, Kamin H. Microsomal triphosphopyridine nucleotide-cytochrome c reductase of liver. J Biol Chem 1962;237:587-95
   PubMed Web of Science ®Google Scholar
• Schacter BA, Nelson EB, Marver HS, Masters BS. Immunochemical evidence for an association of heme oxygenase with the microsomal electron transport system. J Biol Chem 1972;247:3601-7
   PubMed Web of Science ®Google Scholar
• Ono T, Bloch K. Solubilization and partial characterization of rat liver squalene epoxidase. J Biol Chem 1975;250:1571-9
   PubMed Web of Science ®Google Scholar
• Nishino H, Ishibashi T. Evidence for requirement of NADPH-cytochrome P450 oxidoreductase in the microsomal NADPH-sterol Delta7-reductase system. Arch Biochem Biophys 2000;374:293-8
   PubMed Web of Science ®Google Scholar
• Enoch HG, Strittmatter P. Cytochrome b5 reduction by NADPH-cytochrome P-450 reductase. J Biol Chem 1979;254:8976-81
   PubMed Web of Science ®Google Scholar
• Vermilion JL BD, Massey V, Coon MJ. Separate roles for FMN and FAD in catalysis by liver microsomal NADPH-cytochrome P-450 reductase. J Biol Chem 1981;256:266-77
   PubMed Web of Science ®Google Scholar
• Guengerich FP, Johnson WW. Kinetics of ferric cytochrome P450 reduction by NADPH-cytochrome P450 reductase: rapid reduction in the absence of substrate and variations among cytochrome P450 systems. Biochemistry 1997;36:14741-50
   PubMed Web of Science ®Google Scholar
• Hildebrandt A, Estabrook RW. Evidence for the participation of cytochrome b 5 in hepatic microsomal mixed-function oxidation reactions. Arch Biochem Biophys 1971;143:66-79
   PubMed Web of Science ®Google Scholar
• Noshiro M, Ullrich V, Omura T. Cytochrome b5 as electron donor for oxy-cytochrome P-450. Eur J Biochem 1981;116:521-6
   PubMedGoogle Scholar
• Guengerich FP. Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem Res Toxicol 2001;14:611-50
   PubMed Web of Science ®Google Scholar
• Wang M, Roberts DL, Paschke R, et al. Three-dimensional structure of NADPH-cytochrome P450 reductase: prototype for FMN- and FAD-containing enzymes. Proc Natl Acad Sci USA 1997;94:8411-6
   PubMed Web of Science ®Google Scholar
• Hubbard PA, Shen AL, Paschke R, et al. NADPH-cytochrome P450 oxidoreductase. Structural basis for hydride and electron transfer. J Biol Chem 2001;276:29163-70
   PubMed Web of Science ®Google Scholar
• Gutierrez A, Lian LY, Wolf CR, et al. Stopped-flow kinetic studies of flavin reduction in human cytochrome P450 reductase and its component domains. Biochemistry 2001;40:1964-75
   PubMed Web of Science ®Google Scholar
• Gutierrez A, Paine M, Wolf CR, et al. Relaxation kinetics of cytochrome P450 reductase: internal electron transfer is limited by conformational change and regulated by coenzyme binding. Biochemistry 2002;41:4626-37
   PubMed Web of Science ®Google Scholar
• Grunau A, Paine MJ, Ladbury JE, Gutierrez A. Global effects of the energetics of coenzyme binding: NADPH controls the protein interaction properties of human cytochrome P450 reductase. Biochemistry 2006;45:1421-34
   PubMed Web of Science ®Google Scholar
• Sue Masters B, Marohnic CC. Cytochromes P450: a family of proteins and scientists understanding their relationships. Drug Metab Rev 2006;38:209-25
   PubMed Web of Science ®Google Scholar
• Gutierrez A, Grunau A, Paine M, et al. Electron transfer in human cytochrome P450 reductase. Biochem Soc Trans 2003;31:497-501
   PubMed Web of Science ®Google Scholar
• Gigon PL, Gram TE, Gillette JR. Studies on the rate of reduction of hepatic microsomal cytochrome P-450 by reduced nicotinamide adenine dinucleotide phosphate: effect of drug substrates. Mol Pharmacol 1969;5:109-22
   PubMed Web of Science ®Google Scholar
• Ullrich V. On the hydroxylation of cyclohexane in rat liver microsomes. Hoppe Seyler's Zeitschrift fur physiologische Chemie 1969;350:357-65
   PubMedGoogle Scholar
• Otto DM, Henderson CJ, Carrie D, et al. Identification of novel roles of the cytochrome p450 system in early embryogenesis: effects on vasculogenesis and retinoic acid homeostasis. Mol Cell Biol 2003;23:6103-16
   PubMed Web of Science ®Google Scholar
• Shen AL, O'Leary KA, Kasper CB. Association of multiple developmental defects and embryonic lethality with loss of microsomal NADPH-cytochrome P450 oxidoreductase. J Biol Chem 2002;277:6536-41
   PubMed Web of Science ®Google Scholar
• Ribes V, Otto DM, Dickmann L, et al. Rescue of cytochrome P450 oxidoreductase (Por) mouse mutants reveals functions in vasculogenesis, brain and limb patterning linked to retinoic acid homeostasis. Dev Biol 2007;303:66-81
   PubMed Web of Science ®Google Scholar
• Gu J, Weng Y, Zhang QY, et al. Liver-specific deletion of the NADPH-cytochrome P450 reductase gene: impact on plasma cholesterol homeostasis and the function and regulation of microsomal cytochrome P450 and heme oxygenase. J Biol Chem 2003;278:25895-901
   PubMed Web of Science ®Google Scholar
• Henderson CJ, Otto DM, Carrie D, et al. Inactivation of the hepatic cytochrome P450 system by conditional deletion of hepatic cytochrome P450 reductase. J Biol Chem 2003;278:13480-6
   PubMed Web of Science ®Google Scholar
• Mutch DM, Klocke B, Morrison P, et al. The disruption of hepatic cytochrome P450 reductase alters mouse lipid metabolism. J Proteome Res 2007;6:3976-84
   PubMed Web of Science ®Google Scholar
• Shephard EA, Phillips IR, Santisteban I, et al. Isolation of a human cytochrome P-450 reductase cDNA clone and localization of the corresponding gene to chromosome 7q11.2. Ann Hum Genet 1989;53:291-301
   PubMed Web of Science ®Google Scholar
• Zhao Z, Fu YX, Hewett-Emmett D, Boerwinkle E. Investigating single nucleotide polymorphism (SNP) density in the human genome and its implications for molecular evolution. Gene 2003;312:207-13
   PubMed Web of Science ®Google Scholar
• Available from: http://www.ncbi.nlm.nih.gov/SNP/snp_ref.cgi?locusId=5447&chooseRs=all [Build 128, revised by May 25, 2006]
   Google Scholar
• Flck CE, Miller WL. P450 oxidoreductase deficiency: a new form of congenital adrenal hyperplasia. Curr Opin Pediatr 2006;18:435-41
   PubMed Web of Science ®Google Scholar
• Huang N, Pandey AV, Agrawal V, et al. Diversity and function of mutations in p450 oxidoreductase in patients with Antley-Bixler syndrome and disordered steroidogenesis. Am J Hum Genet 2005;76:729-49
   PubMed Web of Science ®Google Scholar
• Krone N, Dhir V, Ivison HE, Arlt W. Congenital adrenal hyperplasia and P450 oxidoreductase deficiency. Clin Endocrinol 2007;66:162-72
   PubMed Web of Science ®Google Scholar
• Arlt W. P450 oxidoreductase deficiency and Antley-Bixler syndrome. Rev Endocr Metab Dis 2007;8:301-7
   PubMed Web of Science ®Google Scholar
• Adachi M, Tachibana K, Asakura Y, et al. A male patient presenting with major clinical symptoms of glucocorticoid deficiency and skeletal dysplasia, showing a steroid pattern compatible with 17alpha-hydroxylase/17,20-lyase deficiency, but without obvious CYP17 gene mutations. Endocr J 1999;46:285-92
   PubMed Web of Science ®Google Scholar
• Reardon W, Smith A, Honour JW, et al. Evidence for digenic inheritance in some cases of Antley-Bixler syndrome? J Med Genet 2000;37:26-32
   PubMed Web of Science ®Google Scholar
• Miller WL. Congenital adrenal hyperplasia. N Engl J Med 1986;314:1321-2
   PubMed Web of Science ®Google Scholar
• Flck CE, Tajima T, Pandey AV, et al. Mutant P450 oxidoreductase causes disordered steroidogenesis with and without Antley-Bixler syndrome. Nature Genet 2004;36:228-30
   PubMed Web of Science ®Google Scholar
• Arlt W, Walker EA, Draper N, et al. Congenital adrenal hyperplasia caused by mutant P450 oxidoreductase and human androgen synthesis: analytical study. Lancet 2004;363:2128-35
   PubMed Web of Science ®Google Scholar
• Fukami M, Horikawa R, Nagai T, et al. Cytochrome P450 oxidoreductase gene mutations and Antley-Bixler syndrome with abnormal genitalia and/or impaired steroidogenesis: molecular and clinical studies in 10 patients. J Clin Endocrin Metab 2005;90:414-26
   PubMed Web of Science ®Google Scholar
• Haiman CA, Setiawan VW, Xia LY, et al. A variant in the cytochrome p450 oxidoreductase gene is associated with breast cancer risk in African Americans. Cancer Res 2007;67:3565-8
   PubMed Web of Science ®Google Scholar
• Wu L, Gu J, Cui H, et al. Transgenic mice with a hypomorphic NADPH-cytochrome P450 reductase gene: effects on development, reproduction, and microsomal cytochrome P450. J Pharmacol Exp Ther 2005;312:35-43
   PubMed Web of Science ®Google Scholar
• Hart SN, Li Y, Nakamoto K, et al. Novel SNPs in cytochrome P450 oxidoreductase. Drug Metab Pharmacokinet 2007;22:322-6
   PubMed Web of Science ®Google Scholar
• Hart S, Wang S, Nakamoto K, et al. Genetic polymorphisms in cytochrome P450 oxidoreductase influence microsomal P450-catalyzed drug metabolism. Pharmacogenet Genom 2008;18:11-24
   PubMed Web of Science ®Google Scholar
• Huang N, Agrawal V, Giacomini KM, Miller WL. Genetics of P450 oxidoreductase: sequence variation in 842 individuals of four ethnicities and activities of 15 missense mutations. Proc Natl Acad Sci USA 2008;105:1733-8
   PubMed Web of Science ®Google Scholar
• Marohnic CC, Panda SP, Martasek P, Masters BS. Diminished FAD binding in the Y459H and V492E Antley-Bixler syndrome mutants of human cytochrome P450 reductase. J Biol Chemi 2006;281:35975-82
   PubMed Web of Science ®Google Scholar
• Dhir V, Ivison HE, Krone N, et al. Differential inhibition of CYP17A1 and CYP21A2 activities by the P450 oxidoreductase mutant A287P. Mol Endocrinol 2007;21:1958-68
   PubMed Web of Science ®Google Scholar
• Han JF, Wang SL, He XY, et al. Effect of genetic variation on human cytochrome p450 reductase-mediated paraquat cytotoxicity. Toxicol Sci 2006;91:42-8
   PubMed Web of Science ®Google Scholar
• Lu AY, Junk KW, Coon MJ. Resolution of the cytochrome P-450-containing omega-hydroxylation system of liver microsomes into three components. J Biol Chemi 1969;244:3714-21
   PubMed Web of Science ®Google Scholar
• Misaka E, Nakanishi K. Studies on menadione reductase of bakers' yeast. II. Inhibition of the enzyme activity by NAD and stimulation of that by p-chloromercuribenzoate. J Biochem 1965;58:1-6
   PubMed Web of Science ®Google Scholar
• Bachur NR GS, Gee MV, Kon H. NADPH cytochrome P-450 reductase activation of quinone anticancer agents to free radicals. Proc Natl Acad Sci USA 1979;76:954-7
   PubMed Web of Science ®Google Scholar
• Walton MI, Wolf CR, Workman P. Molecular enzymology of the reductive bioactivation of hypoxic cell cytotoxins. Int J Radiat Oncol Biol Phys 1989;16:983-6
   PubMed Web of Science ®Google Scholar
• Saunders MP, Jaffar M, Patterson AV, Nolan J, et al. The relative importance of NADPH: cytochrome c (P450) reductase for determining the sensitivity of human tumour cells to the indolequinone EO9 and related analogues lacking functionality at the C-2 and C-3 positions. Biochem Pharmacol 2000;59:993-6
   PubMed Web of Science ®Google Scholar
• Patterson AV, Barham HM, Chinje EC, et al. Importance of P450 reductase activity in determining sensitivity of breast tumour cells to the bioreductive drug, tirapazamine (SR 4233). Br J Cancer 1995;72:1144-50
   PubMed Web of Science ®Google Scholar
• Walton MI, Wolf CR, Workman P. The role of cytochrome P450 and cytochrome P450 reductase in the reductive bioactivation of the novel benzotriazine di-N-oxide hypoxic cytotoxin 3-amino-1,2,4-benzotriazine-1,4-dioxide (SR 4233, WIN 59075) by mouse liver. Biochem Pharmacol 1992;44:251-9
   PubMed Web of Science ®Google Scholar
• Elwell JH, Siim BG, Evans JW, Brown JM. Adaptation of human tumor cells to tirapazamine under aerobic conditions: implications of increased antioxidant enzyme activity to mechanism of aerobic cytotoxicity. Biochem Pharmacol 1997;54:249-57
   PubMed Web of Science ®Google Scholar
• Denny WA, Wilson WR. Tirapazamine: a bioreductive anticancer drug that exploits tumour hypoxia. Expert Opin Investig Drugs 2000;9:2889-901
   PubMed Web of Science ®Google Scholar
• Wang SL, Han JF, He XY, et al. Genetic variation of human cytochrome p450 reductase as a potential biomarker for mitomycin C-induced cytotoxicity. Drug Metab Dispos 2007;35:176-9
   PubMed Web of Science ®Google Scholar
• Benedetti A, Comporti M, Esterbauer H. Identification of 4-hydroxynonenal as a cytotoxic product originating from the peroxidation of liver microsomal lipids. Biochim Biophys Acta 1980;620:281-96
   PubMed Web of Science ®Google Scholar
• Saito M, Thomas CE, Aust SD. Paraquat and ferritin-dependent lipid peroxidation. J Free Rad Biol Med 1985;1:179-85
   PubMedGoogle Scholar