CYP2C76, a novel cytochrome P450 in cynomolgus monkey, is a major CYP2C in liver, metabolizing tolbutamide and testosterone

Molecular Pharmacology

Volumn 70, Issue 2, 2006, Pages 477-486

  Uno, Yasuhiro ^a,b   Fujino, Hideki ^c   Kito, Go ^a,b   Kamataki, Tetsuya ^a   Nagata, Ryoichi ^a,b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b SHIN NIPPON BIOMEDICAL LABORATORIES LTD   (Japan)

^c KOWA COMPANY LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; COMPLEMENTARY DNA; CYTOCHROME P450 2C; CYTOCHROME P450 2C76; PACLITAXEL; PHENYTOIN; TESTOSTERONE; TOLBUTAMIDE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; APE; ARTICLE; CONTROLLED STUDY; DRUG METABOLISM; FEMALE; GENE CLUSTER; GENE EXPRESSION; GENOME; IMMUNOBLOTTING; IMMUNOCHEMISTRY; LIVER; MALE; MONKEY; NONHUMAN; NUCLEOTIDE SEQUENCE; OPEN READING FRAME; ORTHOLOGY; PRIORITY JOURNAL; PROTEIN EXPRESSION; RHESUS MONKEY;

AMINO ACID SEQUENCE; ANIMALS; CHROMOSOME MAPPING; CYTOCHROME P-450 ENZYME SYSTEM; DNA, COMPLEMENTARY; FEMALE; HUMANS; IMMUNOBLOTTING; IMMUNOHISTOCHEMISTRY; LIVER; MACACA FASCICULARIS; MALE; MOLECULAR SEQUENCE DATA; TESTOSTERONE; TOLBUTAMIDE;

EID: 33746238122     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.106.022673     Document Type: Article

References (32)

1. Barnes HJ (1996) Maximizing expression of eukaryotic cytochrome P450s in Escherichia coli. Methods Enzymol 272:3-14.
2. Barnes HJ, Arlotto MP, and Waterman MR (1991) Expression and enzymatic activity of recombinant cytochrome P450 17 alpha-hydroxylase in Escherichia coli. Proc Natl Acad Sci USA 88:5597-5601.
3. Bellino FL and Wise PM (2003) Nonhuman primate models of menopause workshop. Biol Reprod 68:10-18.
4. Bogaards JJ, Bertrand M, Jackson P, Oudshoorn MJ, Weaver RJ, van Bladeren PJ, and Walther B (2000) Determining the best animal model for human cytochrome P450 activities: a comparison of mouse, rat, rabbit, dog, micropig, monkey and man. Xenobiotica 30:1131-1152.
5. Busi F and Cresteil T (2005) CYP3A5 mRNA degradation by nonsense-mediated mRNA decay. Mol Pharmacol 68:808-815.
6. Christmas P, Jones JP, Patten CJ, Rock DA, Zheng Y, Cheng SM, Weber BM, Carlesso N, Scadden DT, Rettie AE, et al. (2001) Alternative splicing determines the function of CYP4F3 by switching substrate specificity. J Biol Chem 276:38166-38172.
7. Daigo S, Takahashi Y, Fujieda M, Ariyoshi N, Yamazaki H, Koizumi W, Tanabe S, Saigenji K, Nagayama S, Ikeda K, et al. (2002) A novel mutant allele of the CYP2A6 gene (CYP2A6*11) found in a cancer patient who showed poor metabolic phenotype towards tegafur. Pharmacogenetics 12:299-306.
8. Fujino H, Yamada I, Shimada S, and Yoneda M (2001) Simultaneous determination of taxol and its metabolites in microsomal samples by a simple thin-layer chromatography radioactivity assay - inhibitory effect of NK-104, a new inhibitor of HMG-CoA reductase. J Chromatogr B Biomed Sci Appl 757:143-150.
9. Goldstein JA (2001) Clinical relevance of genetic polymorphisms in the human CYP2C subfamily. Br J Clin Pharmacol 52:349-355.
10. Gotoh O (1992) Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. J Biol Chem 267:83-90.
11. Gray IC, Nobile C, Muresu R, Ford S, and Spurr NK (1995) A 2.4-megabase physical map spanning the CYP2C gene cluster on chromosome 10q24. Genomics 28:328-332.
12. Guengerich FP (1997) Comparisons of catalytic selectivity of cytochrome P450 subfamily enzymes from different species. Chem Biol Interact 106:161-182.
13. Holbrook JA, Neu-Yilik G, Hentze MW, and Kulozik AE (2004) Nonsense-mediated decay approaches the clinic. Nat Genet 36:801-808.
14. Iwata H, Fujita K, Kushida H, Suzuki A, Konno Y, Nakamura K, Fujino A, and Kamataki T (1998) High catalytic activity of human cytochrome P450 co-expressed with human NADPH-cytochrome P450 reductase in Escherichia coli. Biochem Pharmacol 55:1315-1325.
15. Komori M, Kikuchi O, Sakuma T, Funaki J, Kitada M, and Kamataki T (1992) Molecular cloning of monkey liver cytochrome P-450 cDNAs: similarity of the primary sequences to human cytochromes P-450. Biochim Biophys Acta 1171:141-146.
16. Kuehl P, Zhang J, Lin Y, Lamba J, Assem M, Schuetz J, Watkins PB, Daly A, Wrighton SA, Hall SD, et al. (2001) Sequence diversity in CYP3A promoters and characterization of the genetic basis of polymorphic CYP3A5 expression. Nat Genet 27:383-391.
17. Kumar S and Hedges SB (1998) A molecular timescale for vertebrate evolution. Nature (Lond) 392:917-920.
18. Lewis BP, Green RE, and Brenner SE (2003) Evidence for the widespread coupling of alternative splicing and nonsense-mediated mRNA decay in humans. Proc Natl Acad Sci USA 100:189-192.
19. Ludwig E, Wolfinger H, and Ebner T (1998) Assessment of microsomal tolbutamide hydroxylation by a simple thin-layer chromatography radioactivity assay. J Chromatogr B Biomed Sci Appl 707:347-350.
20. Magness CL, Fellin PC, Thomas MJ, Korth MJ, Agy MB, Proll SC, Fitzgibbon M, Scherer CA, Miner DG, Katze MG, et al. (2005) Analysis of the Macaca mulatta transcriptome and the sequence divergence between Macaca and human. Genome Biol 6:R60.
21. Matsunaga T, Ohmori S, Ishida M, Sakamoto Y, Nakasa H, and Kitada M (2002) Molecular cloning of monkey CYP2C43 cDNA and expression in yeast. Drug Metab Pharmacokinet 17:117-124.
22. Narimatsu S, Kobayashi N, Masubuchi Y, Horie T, Kakegawa T, Kobayashi H, Hardwick JP, Gonzalez FJ, Shimada N, Ohmori S, et al. (2000) Species difference in enantioselectivity for the oxidation of propranolol by cytochrome P450 2D enzymes. Chem Biol Interact 127:73-90.
23. Nelson DR, Koymans L, Kamataki T, Stegeman JJ, Feyereisen R, Waxman DJ, Waterman MR, Gotoh O, Coon MJ, Estabrook RW, et al. (1996) P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics 6:1-42.
24. Nelson DR, Zeldin DC, Hoffman SM, Maltais LJ, Wain HM, and Nebert DW (2004) Comparison of cytochrome P450 (CYP) genes from the mouse and human genomes, including nomenclature recommendations for genes, pseudogenes and alternativesplice variants. Pharmacogenetics 14:1-18.
25. Omura T and Sato R (1964) The carbon monoxide-binding pigment of liver microsomes. II. Solubilization, purification and properties. J Biol Chem 239:2379-2385.
26. Roth GS, Mattison JA, Ottinger MA, Chachich ME, Lane MA, and Ingram DK (2004) Aging in rhesus monkeys: relevance to human health interventions. Science (Wash DC) 305:1423-1426.
27. Saito T, Takahashi Y, Hashimoto H, and Kamataki T (2001) Novel transcriptional regulation of the human CYP3A7 gene by Sp1 and Sp3 through nuclear factor kappa B-like element. J Biol Chem 276:38010-38022.
28. Sharer JE, Shipley LA, Vandenbranden MR, Binkley SN, and Wrighton SA (1995) Comparisons of phase I and phase II in vitro hepatic enzyme activities of human, dog, rhesus monkey and cynomolgus monkey. Drug Metab Dispos 23:1231-1241.
29. Shimada T, Shea JP, and Guengerich FP (1985) A convenient assay for mephenytoin 4-hydroxylase activity of human liver microsomal cytochrome P-450. Anal Biochem 147:174-179.
30. Stevens JC, Shipley LA, Cashman JR, Vandenbranden M, and Wrighton SA (1993) Comparison of human and rhesus monkey in vitro phase I and phase II hepatic drug metabolism activities. Drug Metab Dispos 21:753-760.
31. Takagi Y, Takahashi J, Saiki H, Morizane A, Hayashi T, Kishi Y, Fukuda H, Okamoto Y, Koyanagi M, Ideguchi M, et al. (2005) Dopaminergic neurons generated from monkey embryonic stem cells function in a Parkinson primate model. J Clin Investig 115:102-109.
32. Weaver RJ, Dickins M, and Burke MD (1999) A comparison of basal and induced hepatic microsomal cytochrome P450 monooxygenase activities in the cynomolgus monkey (Macaca fascicularis) and man. Xenobiotica 29:467-482.