The induction of human UDP-glucuronosyltransferase 1A1 mediated through a distal enhancer module by flavonoids and xenobiotics

Biochemical Pharmacology

Volumn 67, Issue 5, 2004, Pages 989-1000

  Sugatani, Junko ^a   Yamakawa, Kasumi ^a   Tonda, Eri ^a   Nishitani, Shinichi ^a   Yoshinari, Kouichi ^a   Degawa, Masakuni ^a   Abe, Ikuro ^a   Noguchi, Hiroshi ^a   Miwa, Masao ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

Aryl hydrocarbon receptor (AhR); Constitutive androstane receptor (CAR); Flavonoids; Pregnane X receptor (PXR); UDP glucuronosyltransferase 1A1 (UGT1A1); Xenobiotics

Indexed keywords

3 METHYLCHOLANTHRENE; APIGENIN; AROMATIC HYDROCARBON RECEPTOR; BAICALEIN; BENZO[A]PYRENE; BETA NAPHTHOFLAVONE; CHRYSIN; CLOTRIMAZOLE; CONSTITUTIVE ANDROSTANE RECEPTOR; CYTOCHROME P450 2B6; CYTOCHROME P450 3A4; ETHOXYRESORUFIN DEETHYLASE; FLAVONOID; GALLOCATECHIN; GLUCURONOSYLTRANSFERASE; GLUCURONOSYLTRANSFERASE 1A1; KAEMPFEROL; LUTEOLIN; MESSENGER RNA; METHOXYCHLOR; METYRAPONE; PHENOBARBITAL; PINOCEMBRINE; PREGNANE X RECEPTOR; QUERCETIN; RIFAMPICIN; RUTOSIDE; TERT BUTYLHYDROQUINONE; UNCLASSIFIED DRUG; UNINDEXED DRUG; XENOBIOTIC AGENT;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; ENZYME INDUCTION; EXPRESSION VECTOR; GENE ACTIVATION; GENE FUNCTION; GENE MUTATION; HUMAN; HUMAN CELL; NONHUMAN; PRIORITY JOURNAL; PROTEIN MOTIF; REPORTER GENE; TRANSACTIVATION; WILD TYPE;

EID: 1042287037     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2003.11.002     Document Type: Article

References (39)

1. Ostrow J.D., Murphy N.H. Isolation and properties of conjugated bilirubin from bile. Biochem. J. 120:1970;311-327.
2. Iyanagi T., Emi Y., Ikushiro S. Biochemical and molecular aspects of genetic disorders of bilirubin metabolism. Biochim. Biophys. Acta. 1407:1998;173-184.
3. Tukey R.H., Strassburg C.P. Human UDP-glucuronosyltransferases: metabolism, expression, and disease. Annu. Rev. Pharmacol. Toxicol. 40:2000;581-616.
4. Dutton GJ. Glucuronidation of drugs and other compounds. Boca Raton: CRC Press; 1980.
5. Crigler J.F. Jr., Najjar V.A. Congenital familial non-hemolitic jaundice with kernicterus. Pediatrics. 10:1952;169-180.
6. Mackenzie P.I., Owens I.S., Burchell B., Bock K.W., Bairoch A., Belanger A., Fournel-Gigleux S., Green M., Hum D.W., Iyanagi T., Lancet D., Louisot P., Magdalou J., Chowdhury J.R., Ritter J.K., Schachter H., Tephly T.R., Tipton K.F., Nebert D.W. The UDP glycosyltransferase gene superfamily: recommended nomenclature update based on evolutionary divergence. Pharmacogenetics. 7:1997;255-269.
7. Gagne J.F., Montminy V., Belanger P., Journault K., Gaucher G., Guillemette C. Common human UGT1A polymorphisms and the altered metabolism of irinotecan active metabolite 7-ethyl-10-hydroxycamptothecin (SN-38). Mol. Pharmacol. 62:2002;608-617.
8. Yaffe S.J., Levy G., Matsuzawa T., Baliah T. Enhancement of glucuronide-conjugating capacity in a hyperbilirubinemic infant due to apparent enzyme induction by phenobarbital. N. Engl. J. Med. 275:2003;1461-1466.
9. Sueyoshi T., Kawamoto T., Zelko I., Honkakoski P., Negishi M. The repressed nuclear receptor CAR responds to phenobarbital in activating the human CYP2B6 gene. J. Biol. Chem. 274:1999;6043-6046.
10. Sugatani J., Kojima H., Ueda A., Kakizaki S., Yoshinari K., Gong Q.H., Owens I.S., Negishi M., Sueyoshi T. The phenobarbital response enhancer module in the human bilirubin UDP-glucuronosyltransferase UGT1A1 gene and regulation by the nuclear receptor CAR. Hepatology. 33:2001;1232-1238.
11. Xie W., Yeuh M.-F., Radminska-Pndy A., Saini S.P.S., Negishi Y., Bottroff B.S., Cabrera G.Y., Tukey R.H., Evans R.M. Control of steroid, heme, and carcinogen metabolism by nuclear pregnane X receptor and constitutive androstane receptor. Proc. Natl. Acad. Sci. U.S.A. 100:2003;4150-4155.
12. Yueh M.-F., Huang Y.-H., Chen S., Nguyen N., Tukey R.H. Involvement of the xenobotic response element (XRE) in Ah-receptor mediated induction of human UDP-glucuronosyltransferase 1A1. J. Biol. Chem. 278:2003;15001-15006.
13. Sugatani J., Yamakawa K., Yoshinari K., Machida T., Takagi H., Mori M., Kakizaki S., Sueyoshi T., Negishi M., Miwa M. Identification of a defect in the UGT1A1 gene promoter and its association with hyperbilirubinemia. Biochem. Biophys. Res. Commun. 292:2002;492-497.
14. Galijatovic A., Otake Y., Walle U.K., Walle T. Induction of UDP-glucuronosyltransferase UGT1A1 by the flavonoid chrysin in Caco-2cells - potential role in carcinogen bioinactivation. Pharm. Res. 18:2001;374-379.
15. Walle T., Otake Y., Galijatovic A., Ritter J.K., Walle U.K. Induction of UDP-glucuronosyltransferase UGT1A1 by the flavonoid chrysin in the human hepatoma cell line Hep G2. Drug Metab. Dispos. 28:2000;1077-1082.
16. Walle U.K., Walle T. Induction of human UDP-glucuronosyltransferase UGT1A1 by flavonoids-structural requirements. Drug Metab. Dispos. 30:2002;564-569.
17. Abe I., Umehara K., Morita R., Nemoto K., Degawa M., Noguchi H. Green tea polyphenols as potent enhancers of glucocorticoid-induced mouse mammary tumor virus gene expression. Biochem. Biophys. Res. Commun. 2819:2001;122-125.
18. Ciotti M., Chen F., Rubaltelli F.F., Owens I.S. Coding defect and a TATA box mutation at the bilirubin UDP-glucuronosyltransferase gene cause Crigler-Najjar type I disease. Biochim. Biophys. Acta. 1407:1998;40-50.
19. Maglich J.M., Stoltz C.M., Goodwin B., Hawkins-Brown D., Moore J.T., Kliewer S.A. Nuclear pregnane X receptor and constitutive androstane receptor regulate overlapping but distinct sets of genes involved in xenobiotic detoxification. Mol. Pharmacol. 62:2002;638-646.
20. Chen J., Lin H., Hu M. Metabolism of flavonoids via enteric recycling: role of intestinal disposition. J. Pharmacol. Exp. Ther. 304:2003;1228-1235.
21. Blizard D., Sueyoshi T., Negishi M., Dehal S.S., Kupfer D. Mechanism of induction of cytochrome P450 enzymes by the proestrogenic endocrine disruptor pesticide-methoxychlor: interactions of methoxychlor metabolites with the constitutive androstane receptor system. Drug Metab. Dispos. 29:2001;781-785.
22. Moore L.B., Parks D.J., Jones S.A., Bledsoe R.K., Consler T.G., Stimmel J.B., Goodwin B., Liddle C., Blanchard S.G., Willson T.M., Collins J.L., Kliewer S.A. Orphan nuclear receptors constitutive androstane receptor and pregnane X receptor share xenobiotic and steroid ligands. J. Biol. Chem. 275:2000;15122-15127.
23. Ciolino H.P., Yeh G.C. Inhibition of aryl hydrocarbon-induced cytochrome P-450 1A1 enzyme activity and CYP1A1 expression by resveratrol. Mol. Pharmacol. 56:1999;760-767.
24. Ciolino H.P., Daschner P.J., Yeh G.C. Dietary flavonols quercetin and kaempferol are ligands of the aryl hydrocarbon receptor that affect CYP1A1 transcription differentially. Biochem. J. 340:1999;715-722.
25. Munzel P.A., Schmohl S., Heel H., Kalberer K., Bock-Hennig B.S., Bock K.W. Induction of human UDP glucuronosyltransferases (UGT1A6, UGT1A9, and UGT2B7) by t-butylhydroquinone and 2,3,7,8-tetrachlorodibenzo-p-dioxin in Caco-2 cells. Drug Metab. Dispos. 27:1999;569-573.
26. Burchell B., Soars M., Monaghan G., Cassidy A., Smith D., Ethell B. Drug-mediated toxicity caused by genetic deficiency of UDP- glucuronosyltransferases. Toxicol. Lett. 112/113:2000;333-340.
27. Tukey R.H., Strassburg C.P., Mackenzie P.I. Pharmacogenomics of human UDP-glucuronosyltransferases and irinotecan toxicity. Mol. Pharmacol. 62:2002;446-450.
28. Jemnitz K., Lengyel G., Vereczkey L. In vitro induction of bilirubin conjugation in primary rat hepatocyte culture. Biochem. Biophys. Res. Commun. 291:2002;29-33.
29. Honkakoski P., Moore R., Washburn K.A., Negishi M. Activation by diverse xenochemicals of the 51-base pair phenobarbital-responsive enhancer module in the CYP2B10 gene. Mol. Pharmacol. 53:1998;597-601.
30. Goodwin B., Moore L.B., Stoltz C.M., McKee D.D., Kliewer S.A. Regulation of the human CYP2B6 gene by the nuclear pregnane X receptor. Mol. Pharmacol. 60:2001;427-431.
31. Gerbal-Chaloin S., Daujat M., Pascussi J.M., Pichard-Garcia L., Vilarem M.J., Maurel P. Transcriptional regulation of CYP2C9 gene. Role of glucocorticoid receptor and constitutive androstane receptor. J. Biol. Chem. 277:2002;209-217.
32. Goodwin B., Hodgson E., D'Costa D.J., Robertson G.R., Liddle C. Transcriptional regulation of the human CYP3A4 gene by the constitutive androstane receptor. Mol. Pharmacol. 62:2002;359-365.
33. Kim J., Min G., Kemper B. Chromatin assembly enhances binding to the CYP2B1 phenobarbital-responsive unit (PBRU) of nuclear factor-1 which binds simultaneously with constitutive androstane receptor (CAR)/retinoid X receptor (RXR) and enhances CAR/RXR-mediated activation of the PBRU. J. Biol. Chem. 276:2001;7559-7567.
34. Smirlis D., Muangmoonchai R., Edwards M., Phillips I.R., Shephard E.A. Orphan receptor promiscuity in the induction of cytochromes P450 by xenobiotics. J. Biol. Chem. 276:2001;12822-12826.
35. Adachi Y., Nanno T., Yamashita M., Ueshima S., Yamamoto T. Induction of rat liver bilirubin-conjugating enzymes and glutathione S-transferase by rifampicin. Gastroenterol. Jpn. 20:1985;104-110.
36. Hirsch-Ernst K.I., Schlaefer K., Bauer D., Heder A.F., Kahl G.F. Repression of phenobarbital-dependent CYP2B1 mRNA induction by reactive oxygen species in primary rat hepatocyte cultures. Mol. Pharmacol. 59:2001;1402-1409.
37. Zhu B.T., Taneja N., Loder D.P., Balentine D.A., Conney A.H. Effects of tea polyphenols and flavonoids on liver microsomal glucuronidation of estradiol and estrone. J. Steroid Biochem. Mol. Biol. 64:1998;207-215.
38. Williams J.A., Ring B.J., Cantrell V.E., Campanale K., Jones D.R., Hall S.D., Wrighton S.A. Differential modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1)-catalyzed estradiol-3-glucuronidation by the addition of UGT1A1 substrates and other compounds to human liver microsomes. Drug Metab. Dispos. 30:2002;1266-1273.
39. Phelan D., Winter G.M., Rogers W.J., Lam J.C., Denison M.S. Activation of the Ah receptor signal transduction pathway by bilirubin and biliverdin. Arch. Biochem. Biophys. 357:1998;155-163.