Alkoxyresorufin (methoxy-, ethoxy-, pentoxy- and benzyloxyresorufin) O-dealkylase activities by in vitro-expressed cytochrome P450 1A4 and 1A5 from common cormorant (Phalacrocorax carbo)

Comparative Biochemistry and Physiology - C Toxicology and Pharmacology

Volumn 149, Issue 4, 2009, Pages 544-551

  Kubota, Akira ^a   Kim, Eun Young ^a   Iwata, Hisato ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

AROD; Common cormorant; CYP1A4; CYP1A5; Heterologous expression; P450; Yeast

Indexed keywords

BENZYLOXYRESORUFIN O DEALKYLASE; CYTOCHROME P450 1A; CYTOCHROME P450 1A4; CYTOCHROME P450 1A5; ETHOXYRESORUFIN DEETHYLASE; METHOXYRESORUFIN O DEALKYLASE; PENTOXYRESORUFIN DEALKYLASE; PENTOXYRESORUFIN O DEPENTHYLASE; RECOMBINANT PROTEIN; UNCLASSIFIED DRUG; UNCLASSIFIED ENZYME;

ARTICLE; BIRD; CATALYSIS; ENZYME ACTIVITY; ENZYME SPECIFICITY; NONHUMAN; ORTHOLOGY; PARALOGY; PHALACROCORAX CARBO; PRIORITY JOURNAL; PROTEIN EXPRESSION; SACCHAROMYCES CEREVISIAE;

AVES; PHALACROCORAX CARBO; RATTUS; SACCHAROMYCES CEREVISIAE;

EID: 63449111785     PISSN: 15320456     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbpc.2008.12.004     Document Type: Article

References (38)

1. Burke M.D., Thompson S., Weaver R.J., Wolf C.R., and Mayer R.T. Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat liver. Biochem. Pharmacol. 48 (1994) 923-936
2. Chung W.G., Sen A., Wang-Buhler J.L., Yang Y.H., Lopez N., Merrill G.F., Miranda C.L., Hu C.H., and Buhler D.R. cDNA-directed expression of a functional zebrafish CYP1A in yeast. Aquat. Toxicol. 70 (2004) 111-121
3. Elliott J.E., Wilson L.K., Henny C.J., Trudeau S.F., Leighton F.A., Kennedy S.W., and Cheng K.M. Assessment of biological effects of chlorinated hydrocarbons in osprey chicks. Environ. Toxicol. Chem. 20 (2001) 866-879
4. Eugster H.P., Probst M., Wurgler F.E., and Sengstag C. Caffeine, estradiol, and progesterone interact with human CYP1A1 and CYP1A2. Evidence from cDNA-directed expression in Saccharomyces cerevisiae. Drug Metab. Dispos. 21 (1993) 43-49
5. Gilday D., Gannon M., Yutzey K., Bader D., and Rifkind A.B. Molecular cloning and expression of two novel avian cytochrome P450 1A enzymes induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. J. Biol. Chem. 271 (1996) 33054-33059
6. Goldstone H.M.H., and Stegeman J.J. A revised evolutionary history of the CYP1A subfamily: gene duplication, gene conversion, and positive selection. J. Mol. Evol. 62 (2006) 708-717
7. Hirakawa S., Iwata H., Takeshita Y., Kim E.Y., Sakamoto T., Okajima Y., Amano M., Miyazaki N., Petrov E.A., and Tanabe S. Molecular characterization of cytochrome P450 1A1, 1A2, and 1B1, and effects of polychlorinated dibenzo-p-dioxin, dibenzofuran, and biphenyl congeners on their hepatic expression in Baikal seal (Pusa sibirica). Toxicol. Sci. 97 (2007) 318-335
8. Kennedy S.W., Lorenzen A., Jones S.P., Hahn M.E., and Stegeman J.J. Cytochrome P4501A induction in avian hepatocyte cultures: a promising approach for predicting the sensitivity of avian species to toxic effects of halogenated aromatic hydrocarbons. Toxicol. Appl. Pharmacol. 141 (1996) 214-230
9. Kennedy S.W., Jones S.P., and Elliott J.E. Sensitivity of bald eagle (Haliaeetus leucocephalus) hepatocyte cultures to induction of cytochrome P4501A by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Ecotoxicology 12 (2003) 163-170
10. Kubota A., Iwata H., Tanabe S., Yoneda K., and Tobata S. Levels and toxicokinetic behaviors of PCDD, PCDF, and coplanar PCB congeners in common cormorants from Lake Biwa, Japan. Environ. Sci. Technol. 38 (2004) 3853-3859
11. Kubota A., Iwata H., Tanabe S., Yoneda K., and Tobata S. Hepatic CYP1A induction by dioxin-like compounds, and congener-specific metabolism and sequestration in wild common cormorants from Lake Biwa, Japan. Environ. Sci. Technol. 39 (2005) 3611-3619
12. Kubota A., Iwata H., Goldstone H.M.H., Kim E.Y., Stegeman J.J., and Tanabe S. Cytochrome P450 1A4 and 1A5 in common cormorant (Phalacrocorax carbo): evolutionary relationships and functional implications associated with dioxin and related compounds. Toxicol. Sci. 92 (2006) 394-408
13. Kubota A., Iwata H., Tanabe S., Yoneda K., and Tobata S. Congener-specific toxicokinetics of polychlorinated dibenzo-p-dioxins, polychlorinated dibenzofurans, and coplanar polychlorinated biphenyls in black-eared kites (Milvus migrans): cytochrome P4501A-dependent hepatic sequestration. Environ. Toxicol. Chem. 25 (2006) 1007-1016
14. Kubota A., Iwata H., and Kim E.Y. Catalytic function of avian cytochrome P450 1A4 and 1A5 (CYP1A4 and CYP1A5) enzymes heterologously expressed using in vitro yeast system. Mar. Environ. Res. 66 (2008) 154-155
15. Lee J.S., Kim E.Y., Iwata H., and Tanabe S. Molecular characterization and tissue distribution of aryl hydrocarbon receptor nuclear translocator isoforms, ARNT1 and ARNT2, and identification of novel splice variants in common cormorant (Phalacrocorax carbo). Comp. Biochem. Physiol. C 145 (2007) 379-393
16. Lee, J.S., Kim, E.Y., Iwata, H., 2009. Dioxin activation of CYP1A5 promoter/ enhancer regions from two avian species, common cormorant (Phalacrocorax carbo) and chicken (Gallus gallus): association with aryl hydrocarbon receptor 1 and 2 isoforms. Toxicol. Appl. Pharmacol. 234, 1-13.
17. Liu J., Ericksen S.S., Besspiata D., Fisher C.W., and Szklarz G.D. Characterization of substrate binding to cytochrome P450 1A1 using molecular modeling and kinetic analyses: case of residue 382. Drug Metab. Dispos. 31 (2003) 412-420
18. Liu J., Ericksen S.S., Sivaneri M., Besspiata D., Fisher C.W., and Szklarz G.D. The effect of reciprocal active site mutations in human cytochromes P450 1A1 and 1A2 on alkoxyresorufin metabolism. Arch. Biochem. Biophys. 424 (2004) 33-43
19. Lorenzen A., Shutt J.L., and Kennedy S.W. Sensitivity of common tern (Sterna hirundo) embryo hepatocyte cultures to CYP1A induction and porphyrin accumulation by halogenated aromatic hydrocarbons and common tern egg extracts. Arch. Environ. Contam. Toxicol. 32 (1997) 126-134
20. Mahajan S.S., and Rifkind A.B. Transcriptional activation of avian CYP1A4 and CYP1A5 by 2,3,7,8-tetrachlorodibenzo-p-dioxin: differences in gene expression and regulation compared to mammalian CYP1A1 and CYP1A2. Toxicol. Appl. Pharmacol. 155 (1999) 96-106
21. Nebert D.W., and Dalton T.P. The role of cytochrome P450 enzymes in endogenous signalling pathways and environmental carcinogenesis. Nat. Rev. Cancer 6 (2006) 947-960
22. Omura T., and Sato R. The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J. Biol. Chem. 239 (1964) 2370-2378
23. Rattner B.A., Melancon M.J., Custer T.W., Hothem R.L., King K.A., LeCaptain L.J., Spann J.W., Woodin B.R., and Stegeman J.J. Biomonitoring environmental contamination with pipping black-crowned night-heron embryos: induction of cytochrome P450. Environ. Toxicol. Chem. 12 (1993) 1719-1732
24. Rattner B.A., Hatfield J.S., Melancon M.J., Custer T.W., and Tillitt D.E. Relation among cytochrome P450, Ah-active PCB congeners and dioxin equivalents in pipping black-crowned night-heron. Environ. Toxicol. Chem. 13 (1994) 1805-1812
25. Rifkind A.B., Kanetoshi A., Orlinick J., Capdevila J.H., and Lee C. 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 (1994) 3387-3396
26. Ryan D.E., Thomas P.E., and Levin W. Hepatic microsomal cytochrome P-450 from rats treated with isosafrole. Purification and characterization of four enzymic forms. J. Biol. Chem. 255 (1980) 7941-7955
27. Sakaki T., Kominami S., Takemori S., Ohkawa H., Akiyoshi-Shibata M., and Yabusaki Y. Kinetic studies on a genetically engineered fused enzyme between rat cytochrome P4501A1 and yeast NADPH-P450 reductase. Biochemistry 33 (1994) 4933-4939
28. Sanderson J.T., Norstrom R.J., Elliott J.E., Hart L.E., Cheng K.M., and Bellward G.D. Biological effects of polychlorinated dibenzo-p-dioxins, dibenzofurans, and biphenyls in double-crested cormorant chicks (Phalacrocorax auritus). J. Toxicol. Environ. Health 41 (1994) 247-265
29. Schlezinger J.J., Keller J., Verbrugge L.A., and Stegeman J.J. 3,3',4,4'-Tetrachlorobiphenyl oxidation in fish, bird and reptile species: relationship to cytochrome P450 1A inactivation and reactive oxygen production. Comp. Biochem. Physiol. C 125 (2000) 273-286
30. Sinclair P.R., Gorman N., Walton H.S., Sinclair J.F., Lee C.A., and Rifkind A.B. Identification of CYP1A5 as the CYP1A enzyme mainly responsible for uroporphyrinogen oxidation induced by AH receptor ligands in chicken liver and kidney. Drug Metab. Dispos. 25 (1997) 779-783
31. Sinclair P.R., Gorman N., Tsyrlov I.B., Fuhr U., Walton H.S., and Sinclair J.F. Uroporphyrinogen oxidation catalyzed by human cytochromes P450. Drug Metab. Dispos. 26 (1998) 1019-1025
32. Smith P.K., Krohn R.I., Hermanson G.T., Mallia A.K., Gartner F.H., Provenzano M.D., Fujimoto E.K., Goeke N.M., Olson B.J., and Klenk D.C. Measurement of protein using bicinchoninic acid. Anal. Biochem. 150 (1985) 76-85
33. Tanaka N., Miyasho T., Shinkyo R., Sakaki T., and Yokota H. cDNA cloning and characterization of feline CYP1A1 and CYP1A2. Life Sci. 79 (2006) 2463-2473
34. Thomas P.E., Reidy J., Reik L.M., Ryan D.E., Koop D.R., and Levin W. Use of monoclonal antibody probes against rat hepatic cytochromes P-450c and P-450d to detect immunochemically related isozymes in liver microsomes from different species. Arch. Biochem. Biophys. 235 (1984) 239-253
35. Verbrugge L.A., Giesy J.P., Verbrugge D.A., Woodin B.R., and Stegeman J.J. Catalytic and immunochemical properties of hepatic cytochrome P450 1A in three avian species treated with beta-naphthoflavone or isosafrole. Comp. Biochem. Physiol. C 130 (2001) 67-83
36. Watanabe M.X., Iwata H., Okamoto M., Kim E.Y., Yoneda K., Hashimoto T., and Tanabe S. Induction of cytochrome P450 1A5 mRNA, protein and enzymatic activities by dioxin-like compounds, and congener-specific metabolism and sequestration in the liver of wild jungle crow (Corvus macrorhynchos) from Tokyo, Japan. Toxicol. Sci. 88 (2005) 384-399
37. Yasui T., Kim E.Y., Iwata H., and Tanabe S. Identification of aryl hydrocarbon receptor 2 in aquatic birds; cDNA cloning of AHR1 and AHR2 and characteristics of their amino acid sequences. Mar. Environ. Res. 58 (2004) 113-118
38. Yasui T., Kim E.Y., Iwata H., Franks D.G., Karchner S.I., Hahn M.E., and Tanabe S. Functional characterization and evolutionary history of two aryl hydrocarbon receptor isoforms (AhR1 and AhR2) from avian species. Toxicol. Sci. 99 (2007) 101-117