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 Metabolism and Disposition

Volumn 30, Issue 11, 2002, Pages 1266-1273

  Andrew Williams, J ^a,c   Ring, Barbara J ^a   Cantrell, Varon E ^a   Campanale, Kristina ^a   Jones, David R ^b   Hall, Stephen D ^b   Wrighton, Steven A ^a  

^a ELI LILLY AND COMPANY   (United States)

^b INDIANA UNIVERSITY   (United States)

^c PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 1 METHYL 6 PHENYLIMIDAZO[4,5 B]PYRIDINE; ALAMETHICIN; ANTHRAFLAVIC ACID; BILIRUBIN; CHRYSIN; ESTRADIOL; ESTRIOL; ETHINYLESTRADIOL; FLAVANONE; FLAVONE; FLAVONOID; GLUCURONOSYLTRANSFERASE; GLUCURONOSYLTRANSFERASE 1A1; IBUPROFEN; MORPHINE; NARINGENIN; NOBILETIN; QUERCETIN; RETINOIC ACID; SILYMARIN; TANGERETIN; UNCLASSIFIED DRUG; BILIRUBIN URIDINE DIPHOSPHOGLUCURONOSYL TRANSFERASE 1A1; BILIRUBIN URIDINE-DIPHOSPHOGLUCURONOSYL TRANSFERASE 1A1; ESTROGEN; GLUCURONIDE;

ARTICLE; CATALYSIS; COMPETITIVE INHIBITION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG GLUCURONIDATION; DRUG POTENCY; DRUG STRUCTURE; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME REGULATION; ENZYME SUBSTRATE; HUMAN; HUMAN TISSUE; LIVER MICROSOME; MICHAELIS MENTEN KINETICS; PRIORITY JOURNAL; ALGORITHM; ENZYME SPECIFICITY; ENZYMOLOGY; IN VITRO STUDY; KINETICS; METABOLISM; STRUCTURE ACTIVITY RELATION;

ALGORITHMS; BILIRUBIN; ESTRADIOL; ESTROGENS; FLAVONOIDS; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HUMANS; KINETICS; MICROSOMES, LIVER; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 0036843701     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: 10.1124/dmd.30.11.1266     Document Type: Article

References (25)

1. Berrino F, Bellati C, Secreto G, Camerini E, Pala V, Panico S, Allegro G, and Kaaks R (2001) Reducing bioavailable sex hormones through a comprehensive change in diet: The diet and androgens (DIANA) randomized trial. Cancer Epidemiol Biomarkers Prev 10:25-33.
2. Bruni S and Chang TMS (1999) Kinetic studies of hepatocyte UDP-glucuronosyltransferase: Evidence of an allosteric enzyme. Artif Cells Blood Substit Immobil Biotechnol 27:343-356.
3. Carrier JS, Turgeon D, Journault K, Hum DW, and Belanger A (2000) Isolation and characterization of the human UGT2B7 gene. Biochem Biophys Res Commun 272:616-621.
4. Ciotti M and Owens IS (1996) Evidence for overlapping active sites for 17 alpha-ethynlestradiol and bilirubin in the human major bilirubin UDPglucuronosyltransferase. Biochemistry 35:10119-10124.
5. Coffman BL, Rios GR, King CD, and Tephly TR (1997) Human UGT2B7 catalyzes morphine glucuronidation. Drug Metab Dispos 25:1-4.
6. Ebner TR, Remmel P, and Burchell B (1993) Human bilirubin UDP-glucuronosyltransferase catalyzes the glucuronidation of ethinylestradiol. Mol Pharmacol 43:649-654.
7. Ekins S, Ring BJ, Binkley SN, Hall SD, and Wrighton SA (1998) Autoactivation and activation of the cytochrome P450s. Int J Clin Pharmacol Ther 36:642-651.
8. Fisher MB, Campanale K, Ackermann BL, VandenBranden M, and Wrighton SA (2000a) In vitro glucuronidation using human liver microsomes and the pore-forming peptide alamethicin. Drug Metab Dispos 28:560-566.
9. Fisher MB, Vandenbranden M, Findlay K, Burchell B, Thummel KE, Hall SD, and Wrighton SA (2000b) Tissue distribution and interindividual variation in human UDP-glucuronosyltransferase activity: Relationship between UGT1A1 promoter genotype and variability in a liver bank. Pharmacogenetics 10:727-739.
10. Gall WE, Zawada G, Mojarrabi B, Tephly TR, Green MD, Coffman BL, Mackenzie PI, and Radominska-Pandya A (1999). Differential glucuronidation of bile acids androgens and estrogens by human UGT1A3 and 2B7. J Steroid Biochem Mol Biol 70:101-108.
11. Jin C, Miners JO, Lillywhite KJ, and Mackenzie PI (1993) Complementary, deoxyribonucleic acid cloning and expression of a human liver uridine diphosphate-glucuronosyltransferase glucuronidating carboxylic acid-containing drugs. J Pharmacol Exp Ther 264:475-479.
12. Korzekwa KR, Krishnamachary N, Shou M, Ogai A, Parise RA, Rettie AE, Gonzalez FJ. and Tracy TS (1998) Evaluation of atypical cytochrome P450 kinetics with two-substrate models: Evidence that multiple substrates can simultaneously bind to cytochrome P450 active sites. Biochemistry 37:4137-4147.
13. Mackenzie PI, Miners JO, and McKinnon RA (2000) Polymorphisms in UDP glucuronosyltransferase genes: Functional consequences and clinical relevance. Clin Chem Lab Med 38:889-892.
14. Maenpaa J, Hall SD, Ring BJ, Strom SC, and Wrighton SA (1998) Human cytochrome P450 3A (CYP3A) mediated midazolam metabolism: The effect of assay conditions and regioselective stimulation by alpha-naphthoflavone, terfenadine and testosterone. Pharmacogenetics 8:137-155.
15. Malfatti MA and Felton JS (2001) N-glucuronidation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and N-hydroxy-PHIP by specific human UDP-glucuronosyl-transferase. Carcinogenesis 22:1087-1093.
16. Meech R and Mackenzie PI (1997) UDP-glucuronosyltransferase, the role of the amino terminus in dimerization. J Biol Chem 272:26913-26917.
17. Peters WH and Jansen PL (1986) Microsomal UDP-glucuronyltransferase-catalyzed bilirubin diglucuronide formation in human liver. J Hepatol 2:182-194.
18. Ring BJ, Parli CJ, George MC, and Wrighton SA (1994) In vitro metabolism of zatosetron. Interspecies comparison and role of CYP 3A. Drug Metab Dispos 22:352-357.
19. Ritter JK, Chen F, Sheen YY, Tran HM, Kimura S, Yeatman MT, and Owens IS (1992) A novel complex locus UGT1 encodes human bilirubin, phenol and other UDP-glucuronosyltransferase isozymes with identical carboxyl termini. J Biol Chem 267:3257-3261.
20. Segel IH (1975) Enzyme Kinetics: Behavior and Analysis of Rapid Equilibrium and Steady-State Enzyme Systems. John Wiley & Sons Inc., New York.
21. Senafi SB, Clarke DJ, and Burchell B (1994) Investigation of the substrate specificity of a cloned expressed human bilirubin UDP-glucuronosyltransferase: UDP-sugar specificity and involvement in steroid and xenobiotic glucuronidation. Biochem J 303:233-240.
22. Stresser DM, Blanchard AP, Turner SD, Erve JC, Dandeneau AA, Miller VP, and Crespi CL (2000) Substrate-dependent modulation of CYP3A4 catalytic activity: Analysis of 27 test compounds with four fluorometric substrates. Drug Metab Dispos 28:1440-1448.
23. Tephly TR and Green MD (2000) UDP-glucuronosyltransferases, in Metabolic Drug Interactions (Levy RH, Thummel EE, Trager WF, Hansten PD, and Eichelbaum M eds) pp 160-173. Lippincott Williams and Wilkins, Philadelphia.
24. Ueng YF, Kuwabara T, Chun YJ, and Guengerich FP (1997) Cooperativity in oxidations catalyzed by cytochrome P450 3A4. Biochemistry 36:370-381.
25. van der Hoeven TA and Coon MJ (1974) Preparation and properties of partially purified cytochrome P-450 and reduced nicotinamide adenine dinucleotide phosphate-cytochrome P-450 reductase from rabbit liver microsomes. J Biol Chem 249:6302-6310.