Hydroxylation of quinocetone and carbadox is mediated by CYP1As in the chicken (Gallus gallus)

Comparative Biochemistry and Physiology - C Toxicology and Pharmacology

Volumn 158, Issue 2, 2013, Pages 84-90

  Yang, Jiannan ^a,c   Liu, Zhaoying ^b   Li, Mei ^a   Qiu, Xinghui ^a,c  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^b HUNAN AGRICULTURAL UNIVERSITY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Carbadox; Cyadox; CYP1A4; CYP1A5; Gallus gallus

Indexed keywords

CARBADOX; CIADOX; CYTOCHROME P450 1A; CYTOCHROME P450 REDUCTASE; MEQUINDOX; QUINOCETONE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

AEROBIC METABOLISM; ARTICLE; CHEMICAL STRUCTURE; DRUG METABOLISM; ENZYME SPECIFICITY; GALLUS GALLUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; METABOLITE; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY;

ANIMALIA; GALLUS GALLUS;

EID: 84886910654     PISSN: 15320456     EISSN: 18781659     Source Type: Journal    
DOI: 10.1016/j.cbpc.2013.05.008     Document Type: Article

References (33)

1. Antonovic, L., Martinez, M., 2011. Role of the cytochrome P450 enzyme system in veterinary pharmacokinetics: where are we now? Where are we going? Future Med. Chem. 3, 855-879.
2. Bradford, M.M., 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem.72, 248-254.
3. Carta, A., Corona, P., Loriga, M., 2005. Quinoxaline 1, 4-dioxide: a versatile scaffold endowed with manifold activities. Curr. Med. Chem. 12, 2259-2272. (Pubitemid 41179711)
4. Chen, Q., Tang, S., Jin, X., Zou, J., Chen, K., Zhang, T., Xiao, X., 2009. Investigation of the genotoxicity of quinocetone, carbadox and olaquindox in vitro using Vero cells. Food Chem. Toxicol. 47, 328-334.
5. Diaz, G.J., Murcia, H.W., Cepeda, S.M., 2010. Cytochrome P450 enzymes involved in the metabolism of aflatoxin B1 in chickens and quail. Poult. Sci. 89 (11), 2461-2469.
6. Gilday, D., Gannon, M., Yutzey, K., Bader, D., Rifkind, A.B., 1996. Molecular cloning and expression of two novel avian cytochrome P450 1A induced by 2, 3, 7, 8- tetrachlorodibenzo-p-dioxin. J. Biol. Chem. 271, 33054-33059. (Pubitemid 27008744)
7. Head, J.A., Kennedy, S.W., 2007. Differential expression, induction, and stability of CYP1A4 and CYP1A5 mRNA in chicken and herring gull embryo hepatocytes. Comp. Biochem. Physiol. C 145, 617-624. (Pubitemid 46660755)
8. Ihsan, A., Wang, X., Liu, Z., Wang, Y., Huang, X., Liu, Y., Yu, H., Zhang, H., Li, T., Yang, C., 2011. Long-term mequindox treatment induced endocrine and reproductive toxicity via oxidative stress in male Wistar rats. Toxicol. Appl. Pharmacol. 252, 281-288.
9. Kojima, M., Sekimoto, M., Degawa, M., 2008. A novel gender-related difference in the constitutive expression of hepatic cytochrome P4501A subfamily enzymes in Meishan pigs. Biochem. Pharmacol. 75, 1076-1082.
10. Kupfer, D., Mani, C., Lee, C.A., Rifkind, A.B., 1994. Induction of tamoxifen-4-hydroxylation by 2,3,7,8-tetrachlorodibenzo-p-dioxin(TCDD), β-naphthoflavone (βNF), and phenobarbital (PB) in avian liver: identification of P450 TCDDAA as catalyst of 4- hydroxylation induced by TCDD and βNF. Cancer Res. 54, 3140-3144.
11. Li, J., Zhao, R., Miao, X., Zhang, J., Zhou, X., 2008. Study on residues of quinocetone in edible chicken tissues. Prog. Vet. Med. 4, 34-37.
12. Liu, Z.Y., Huang, L.L., Dai, M.H., Chen, D.M., Tao, Y.E., Wang, Y.L., Yuan, Z.H., 2009. Metabolism of cyadox in rat, chicken and pig liver microsomes and identification of metabolites by accurate mass measurements using electrospray ionization hybrid ion trap/time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 23, 2026-2034.
13. Liu, Z.Y., Huang, L.L., Chen, D.M., Dai, M.H., Tao, Y.F., Wang, Y.L., Yuan, Z.H., 2010a. Application of electrospray ionization hybrid ion trap/time-of-flight mass spectrometry in the rapid characterization of quinocetone metabolites formed in vitro. Anal. Bioanal. Chem. 396, 1259-1271.
14. Liu, Z.Y., Huang, L.L., Chen, D.M., Yuan, Z.H., 2010b. Metabolism of mequindox in liver microsomes of rats, chicken and pigs. Rapid Commun. Mass Spectrom. 24, 909-918.
15. Liu, J., Ge, X., Ouyang, M., Tang, X., Wu, J., Wang, J., Jiang, J., Huen, M.S.Y., Deng, Y., 2011. Catalytic characteristics of CYP3A22-dependent mequindox detoxification. Catal. Commun. 12, 637-643.
16. Liu, Z.Y., Tao, Y.F., Chen, D.M., Wang, X., Yuan, Z.H., 2011. Identification of carbadox metabolites formed by liver microsomes from rats, pigs and chickens using highperformance liquid chromatography combined with hybrid ion trap/time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 25, 341-348.
17. Mahajan, S.S., Rifkind, A.B., 1999. Transcriptional activation of avian CYP1A4 and CYP1A5 by 2,3,7,8-tetrachlorodibenzo-pdioxin: differences in gene expression and regulation compared to mammalian CYP1A1 and CYP1A2. Toxicol. Appl. Pharmacol. 155, 96-106. (Pubitemid 29102765)
18. Markovic, B., Stanimirovic, Z., Vucinic, M., Cupic, V., 2000. Examination of carbadox genotoxicity in vitro and in vivo. Acta Vet. (Beogr) 50, 387-395.
19. Meunier, B., De Visser, S.P., Shaik, S., 2004. Mechanism of oxidation reactions catalyzed by cytochrome P450 enzymes. Chem. Rev. - Columbus 104, 3947-3980.
20. Nakai, K., Ward, A.M., Gannon, M., Rifkind, A.B., 1992. β-Naphthoflavone induction of a cytochrome P450 arachidonic acid epoxygenase in chick embryo liver distinct from the arylhydrocarbon hydroxylase and from phenobarbital-induced arachidonic epoxygenase. J. Biol. Chem. 267, 19503-19512.
21. Nishihara, K., Kanemori, M., Kitagawa, M., Yanagi, H., Yura, T., 1998. Chaperone coexpression plasmids: Differential and synergistic roles of DnaK-DnaJ-GrpE and GroEL-GroES in assisting folding of an allergen of japanese cedar pollen, Cryj2, in Escherichia coli. Appl. Environ. Microbiol. 64, 1694-1699. (Pubitemid 28234771)
22. Omura, T., Sato, R., 1964. The carbon monoxide-binding pigment of liver microsomes. J. Biol. Chem. 239, 2370-2378.
23. Plant, N., 2004. Strategies for using in vitro screens in drug metabolism. Drug Discov. Today 9 (7), 328-336. (Pubitemid 38373652)
24. Pritchard, M., McLaughlin, L., Friedberg, T., Pritchard, M., McLaughlin, L., Friedberg, T., 2004. Establishment of functional human cytochrome P450 monooxygenase systems in Escherichia coli, In: Phillips, I.R., Elizabeth, A.S. (Eds.), Methods Mol Biol.: Cytochrome P450 protocols, 2nd ed. Human Press, New Jersey, pp. 19-29.
25. Rifkind, A.B., Kanetoshi, A., Orlinick, J., Capdevila, J.H., Lee, C., 1994. Purification and biochemical characterization of two major cytochrome P-450 isoforms induced by 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin in chick embryo liver. J. Biol. Chem. 269, 3387-3396.
26. Tang, X., Mu, P., Wu, J., Jiang, J., Zhang, C., Zheng, M., Deng, Y., 2012. Carbonyl reduction of requindox by chicken and porcine cytosol and cloned CBR1. Drug Metab. Dispos. 40 (4), 788-795.
27. Verbrugge, L., Giesy, J., Verbrugge, D., Woodin, B., Stegeman, J., 2001. Catalytic and immunochemical properties of hepatic cytochrome P450 1A in three avian species treated with β-naphthoflavone or isosafrole. Comp. Biochem. Physiol. C 130, 67-83. (Pubitemid 32816890)
28. Wang, X., Zhang, W., Wang, Y., Peng, D., Ihsan, A., Huang, X., Huang, L., Liu, Z., Dai, M., Zhou, W., Yuan, Z.H., 2010. Acute and sub-chronic oral toxicological evaluations of quinocetone in Wistar rats. Regul. Toxicol. Pharmacol. 58, 421-427.
29. Wu, Z.L., Qiao, J., Zhang, Z.G., Guengerich, F.P., Liu, Y., Pei, X.Q., 2009. Enhanced bacterial expression of several mammalian cytochrome P450s by codon optimization and chaperone coexpression. Biotechnol. Lett. 31, 1589-1593.
30. Yang, J., An, J., Li, M., Hou, X., Qiu, X., 2013. Characterization of chicken cytochrome P450 1A4 and 1A5: inter-paralog comparisons of substrate preference and inhibitor selectivity. Comp. Biochem. Physiol. C 157, 337-343.
31. Yip, S.S.M., Coulombe Jr., R.A., 2006. Molecular cloning and expression of a novel cytochrome P450 from turkey liver with aflatoxin B1 oxidizing activity. Chem. Res. Toxicol. 19, 30-37. (Pubitemid 43185459)
32. Yoshimura, H., 2002. Teratogenic assessment of carbadox in rats. Toxicol. Lett. 129, 115-118. (Pubitemid 34203801)
33. Zhou, X., Li, M., Sheng, C., Qiu, X., 2011. NADPH-cytochrome P450 oxidoreductase from the chicken (Gallus gallus): sequence characterization, functional expression and kinetic study. Comp. Biochem. Physiol. C 153, 53-59.