Expression and functional characterization of cytochrome P450 26A1, a retinoic acid hydroxylase

Biochemical Pharmacology

Volumn 77, Issue 2, 2009, Pages 258-268

  Lutz, Justin D ^a   Dixit, Vaishali ^a   Yeung, Catherine K ^a   Dickmann, Leslie J ^a   Zelter, Alex ^b   Thatcher, Jayne E ^a   Nelson, Wendel L ^a   Isoherranen, Nina ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

^b UNIVERSITY OF WASHINGTON SCHOOL OF MEDICINE   (United States)

Author keywords

CYP26A1; Retinoic acid metabolism; Sequential metabolism; Vitamin A

Indexed keywords

18 HYDROXYRETINOIC ACID; 4 HYDROXYRETINOIC ACID; 4 OXORETINOIC ACID; 5,6 EPOXYRETINOIC ACID; CARBON MONOXIDE; CYTOCHROME P450 26A1; CYTOCHROME P450 REDUCTASE; HEME; HEXAHISTIDINE; OXYGENASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; RETINOIC ACID; RETINOIC ACID HYDROXYLASE; RETINOL; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CELL CYCLE REGULATION; CELL VIABILITY; CONTROLLED STUDY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME KINETICS; ENZYME METABOLISM; ENZYME PURIFICATION; INSECT CELL; LIGAND BINDING; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN EXPRESSION; VITAMIN METABOLISM; WESTERN BLOTTING;

BASE SEQUENCE; CELL CYCLE; CELL LINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; DNA PRIMERS; GENE AMPLIFICATION; GENE EXPRESSION REGULATION, DEVELOPMENTAL; GENE EXPRESSION REGULATION, ENZYMOLOGIC; HUMANS; KIDNEY; KINETICS; MOLECULAR SEQUENCE DATA; RECOMBINANT PROTEINS; TRETINOIN;

EID: 57249104707     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2008.10.012     Document Type: Article

References (38)

1. Blomhoff R., and Blomhoff H.K. Overview of retinoid metabolism and function. J Neurobiol 66 7 (2006) 606-630
2. Napoli J.L. Retinoid acid biosynthesis and metabolism. Faseb J 10 9 (1996) 993-1001
3. Napoli J.L. Biochemical pathways of retinoid transport, metabolism, and signal transduction. Clin Immunol Immunopathol 80 (1996) s52-62
4. Noy N. Retinoid binding proteins: mediators of retinoid action. Biochem J 348 (2000) 481-495
5. Ross A.C., and Ternus M.E. Vitamin A as a hormone: recent advances in understanding the actions of retinol, retinoic acid and beta-carotene. J Am Diet Assoc 93 11 (1993) 1285-1291
6. Lampen A., Meyer S., Arnhold T., and Nau H. Metabolism of vitamin A and its active metabolite, all-trans-retinoic acid, in small intestinal enterocytes. J Pharmacol Exp Ther 295 3 (2000) 979-985
7. Allenby G., Bocquel M.T., Saunders M., Kazmer S., Speck J., Rosenberger M., et al. Retinoic acid receptors and retinoid X receptors: interactions with endogenous retinoic acids. Proc Natl Acad Sci USA 90 (1993) 30-34
8. Allenb G., Janocha R., Kazner S., Speck J., Grippo J.F., and Levin A.A. Binding of 9-cis-retinoic acid and all-trans-retinoic acid to retinoic acid receptors alpha, beta, and gamma. Retinoic acid receptor gamma binds all-trans-retinoic acid preferentially over 9-cis-retinoic acid. J Biol Chem 269 24 (1994) 16689-16695
9. Tzimas G., and Nau N. The role of metabolism and toxicokinetics in retinoid teratogenesis. Curr Pharm Des 7 (2001) 803-831
10. Chithalen V., Luu L., Petkovich M., and Jones G. HPLC-MS/MS analysis of the products generated from all-trans-retinoic acid using recombinant human CYP26A. J Lipid Res 43 7 (2002) 1133-1142
11. Marill J., Cresteil T., Lanotte M., and Chabot G.G. Identification of human cytochrome P450s involved in the formation of all-trans retinoic acid principal metabolites. Mol Pharmacol 58 6 (2000) 1341-1348
12. Idres N., Marill J., Flexor M.A., and Chabot G.G. Activation of retinoic acid receptor-dependent transcription by all-trans retinoic acid metabolites and isomers. J Biol Chem 277 35 (2002) 31491-31498
13. Niederreither K., Abu-Abed S., Schuhbau B., Petkovich M., Chambon P., and Dolle P. Genetic evidence that oxidative derivatives of retinoic acid are not involved in retinoid signaling during mouse development. Nat Genet 31 1 (2002) 84-88
14. Nadin L., and Murray M. Participation of CYP2C8 in retinoic acid 4-hydroxylation in human hepatic microsomes. Biochem Pharmacol 58 7 (1999) 1201-1208
15. Chen H., Fantel A.G., and Juchau M.R. Catalysis of the 4-hydroxylation of retinoic acids by cyp3a7 in human fetal hepatic tissues. Drug Metab Dispos 28 9 (2000) 1051-1057
16. McSorley L.C., and Daly A.K. Identification of human cytochrome P450 isoforms that contribute to all-trans-retinoic acid 4-hydroxylation. Biochem Pharmacol 60 4 (2000) 517-526
17. Napoli J.L. Retinoid binding-proteins redirect retinoid metabolism: biosynthesis and metabolism of retinoic acid. Semin Cell Dev Biol 8 4 (1997) 403-415
18. Dong D., Ruuska S.E., Levinthal D.J., and Noy N. Distinct roles for cellular retinoic acid-binding proteins I and II in regulating signaling by retinoic acid. J Biol Chem 274 34 (1999) 23695-23698
19. White J.A., Guo Y.D., Baetz K., Beckett-Jones B., Bonasoro J., Hsu K.E., et al. Identification of the retinoic acid inducible all-trans-retinoic acid 4-hydroxylase. J Biol Chem 271 47 (1996) 29922-29927
20. White J.A., Beckett-Jones B., Guo Y.D., Dilworth F.J., Bonasoro J., Jones G., et al. cDNA cloning of human retinoic acid-metabolizing enzyme (hP450RAI) identifies a novel family of cytochromes P450. J Biol Chem 272 30 (1997) 18538-18541
21. White J.A., Ramshaw H., Taimi M., Stangle W., Zhang A., Everingham S., et al. Identification of the human cytochrome P450, P450RAI-2, which is predominantly expressed in the adult cerebellum and is responsible for all-trans-retinoic acid metabolism. Proc Natl Acad Sci USA 97 12 (2000) 6403-6408
22. Taimi M., Helvig C., Wisniewski J., Ramshaw H., White J., Amad M., et al. A novel human cytochrome P450, CYP26C1, involved in the metabolism of 9-cis and all-trans isomers of retinoic acid. J Biol Chem 279 1 (2004) 77-85
23. Lee S.J., Perera L., Coulter S.J., Mohrenweiser H.W., Jetten A., and Goldstein J.A. The discovery of new coding alleles of human CYP26A1 that are potentially defective in the metabolism of all-trans-retinoic acid and their assessment in a recombinant cDNA expression system. Pharmacogenet Genomics 17 3 (2007) 169-180
24. Sakai Y., Meno C., Fujii H., Nishino J., Shiratori H., Saijoh Y., et al. The retinoic acid-inactivating enzyme CYP26 is essential for establishing an uneven distribution of retinoic acid along the antero-posterior axis within the mouse embryo. Genes Dev 15 2 (2001) 213-225
25. Yashiro K., Zhao X., Uehara M., Yamashita K., Nishijima M., Nishino J.S., et al. Regulation of retinoic acid distribution is required for proximodistal patterning and outgrowth of the developing mouse limb. Dev Cell 6 3 (2004) 411-422
26. Abu-Abed S., Dolle P., Metzger D., Beckett B., and Chambon P. The retinoic acid-metabolizing enzyme, CYP26A1, is essential for normal hindbrain patterning, vertebral identity, and development of posterior structures. Genes Dev 15 (2001) 226-240
27. Trofimova-Griffin M.E., Brzezinski M.R., and Juchau M.R. Patterns of CYP26 expression in human prenatal cephalic and hepatic tissues indicate an important role during early brain development. Brain Res Dev Brain Res 120 1 (2000) 7-16
28. Samokyszyn V.M., Gall W.E., Zawada G., Freyaldenhoven M.A., Chen G., Mackenzie P.I., et al. 4-Hydroxyretinoic acid, a novel substrate for human liver microsomal UDP-glucuronosyltransferase(s) and recombinant UGT2B7. J Biol Chem 275 10 (2000) 6908-6914
29. 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
30. Andreola F., Hayhurst G.P., Luo G., Ferguson S.S., Gonzalez F.J., Goldstein J.A., et al. Mouse liver CYP2C39 is a novel retinoic acid 4-hydroxylase. Its down-regulation offers a molecular basis for liver retinoid accumulation and fibrosis in aryl hydrocarbon receptor-null mice. J Biol Chem 279 5 (2004) 3434-3438
31. Segel I.H. Enzyme kinetics (1993), Wiley, New York
32. Obach R.S., and Reed-Hagen A.E. Measurement of Michaelis constants for cytochrome P450-mediated biotransformation reactions using a substrate depletion approach. Drug Metab Dispos 30 7 (2002) 831-837
33. Nath A., and Atkins W.M. A theoretical validation of the substrate depletion approach to determining kinetic parameters. Drug Metab Dispos 34 9 (2006) 1433-1435
34. Gonzalez F.J., and Korzekwa K.R. Cytochromes P450 expression systems. Annu Rev Pharmacol Toxicol 35 (1995) 369-390
35. Barnes H.J., Arlotto M.P., and Waterman M.R. Expression enzymatic activity of recombinant cytochrome P450 17-alpha-hydroxylase in Escherichia coli. Proc Natl Acad Sci USA 88 13 (1991) 5597-5601
36. Grogan J., Shou M., Andruisak E.A., Tamura S., Buters J.T.M., Gonzalez F.J., et al. Cytochrome P450 2A1, 2E1, and 2C9 cDNA-expression by insect cells and partial purification using hydrophobic chromatography. Biochem Pharmacol 50 9 (1995) 1509-1515
37. Buters J.T.M., Shou M., Hardwick J.P., Kozekwa K.R., and Gonzalez F.J. cDNA-directed expression of human cytochrome P450 CYP1A1 using baculovirus. Purification, dependency on NADPH-P450 oxidoreductase, and reconstitution of catalytic properties without purification. Drug Metab Dispos 23 7 (1995) 696-701
38. Ross A.C. Cellular metabolism and activation of retinoids: roles of cellular retinoid-binding proteins. Faseb J 7 2 (1993) 317-327