UDP-glucuronosyltransferase 1A1 is the principal enzyme responsible for etoposide glucuronidation in human liver and intestinal microsomes: Structural characterization of phenolic and alcoholic glucuronides of etoposide and estimation of enzyme kinetics

Drug Metabolism and Disposition

Volumn 35, Issue 3, 2007, Pages 371-380

  Wen, Zhiming ^a   Tallman, Melanie N ^a   Ali, Shazia Y ^a   Smith, Philip C ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA GLUCURONIDASE; DRUG METABOLITE; ETOPOSIDE; ETOPOSIDE GLUCURONIDE; ETOPOSIDE GLUCURONIDE 1; ETOPOSIDE GLUCURONIDE 2; GLUCURONIDE; GLUCURONOSYLTRANSFERASE 1A1; GLUCURONOSYLTRANSFERASE 1A3; GLUCURONOSYLTRANSFERASE 1A8; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONTROLLED STUDY; DRUG GLUCURONIDATION; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; ENZYME ACTIVITY; ENZYME KINETICS; HUMAN; HUMAN CELL; IN VITRO STUDY; INTESTINE MICROSOME; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MICROSOME; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

ALCOHOLS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; BILIRUBIN; ESTRADIOL; ETHINYL ESTRADIOL; ETOPOSIDE; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HUMANS; INTESTINES; KINETICS; LIVER; MICROSOMES; PHENOLS;

EID: 33847358669     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.106.012732     Document Type: Article

References (40)

1. Alkharfy KM and Frye RF (2002) Sensitive liquid chromatographic method using fluorescence detection for the determination of estradiol 3- and 17-glucuronides in rat and human liver microsomal incubations: formation kinetics. J Chromatogr B 774:33-38.
2. Bosma PJ, Seppen J, Goldhoorn B, Bakker C, Oude Elferink RP, Chowdhury JR, Chowdhury NR, and Jansen PL (1994) Bilirubin UDP-glucuronosyltransferase 1 is the only relevant bilirubin glucuronidating isoform in man. J Biol Chem 269:17960-17964.
3. Burchell B, Brierley CH, and Rance D (1995) Specificity of human UDP-glucuronosyltransferases and xenobiotic glucuronidation. Life Sci 57:1819-1831.
4. Chen CL and Uckun FM (2000) Highly sensitive liquid chromatography- electrospray mass spectrometry (LC-MS) method for the determination of etoposide levels in human serum and plasma. J Chromatogr B 744:91-98.
5. Cheng Z, Radominska-Pandya A, and Tephly TR (1999) Studies on the substrate specificity of human intestinal UDP-glucuronosyltransferases 1A8 and 1A10. Drug Metab Dispos 27:1165-1170.
6. Chowdhury JR, Chowdhury NR, Wu G, Shouval R, and Arias IM (1981) Bilirubin mono- and diglucuronide formation by human liver in vitro: assay by high-pressure liquid chromatography. Hepatology 1:622-627.
7. Colombo T, D'Incalci M, Donelli MG, Bartosek I, Benfenati E, Farina P, and Guaitani A (1985) Metabolic studies of a podophyllotoxin derivative (VP16) in the isolated perfused liver. Xenobiotica 15:343-350.
8. D'Incalci M, Rossi C, Zucchetti M, Urso R, Cavalli F, Mangioni C, Willems Y, and Sessa C (1986) Pharmacokinetics of etoposide in patients with abnormal renal and hepatic function. Cancer Res 46:2566-2571.
9. Ebner T, Remmel RP, and Burchell B (1993) Human bilirubin UDP-glucuronosyltransferase catalyzes the glucuronidation of ethinylestradiol. Mol Pharmacol 43:649-654.
10. Fenselau C and Johnson LP (1980) Analysis of intact glucuronides by mass spectrometry and gas chromatography-mass spectrometry: a review. Drug Metab Dispos 8:274-283.
11. Finel M, Li X, Gardner-Stephen D, Bratton S, Mackenzie PI, and Radominska-Pandya A (2005) Human UDP-glucuronosyltransferase 1A5: identification, expression and activity. J Pharmacol Exp Ther 315:1143-1149.
12. Fisher MB, Paine MF, Strelevitz TJ, and Wrighton SA (2001) The role of hepatic and extrahepatic UDP-glucuronosyltransferases in human drug metabolism. Drug Metab Rev 33:273-297.
13. Fleming RA, Miller AA, and Stewart CF (1989) Etoposide: an update. Clin Pharm 8:274-293.
14. 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.
15. Ghosal A, Hapangama N, Yuan Y, Achanfuo-Yeboah J, Iannucci R, Chowdhury S, Alton K, Patrick JE, and Zbaida S (2004) Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of posaconazole (Noxafil). Drug Metab Dispos 32:267-271.
16. Gordon ER, Meier PJ, Goresky CA, and James BL (1984) Mechanism and subcellular site of bilirubin diglucuronide formation in rat liver. J Biol Chem 259:5500-5506.
17. Gu J, Zhong D, and Chen X (1999) Analysis of O-glucuronide conjugates in urine by electrospray ion trap mass spectrometry. Fresenius J Anal Chem 365:553-558.
18. Hande K, Anthony L, Hamilton R, Bennett R, Sweetman B, and Branch R (1988a) Identification of etoposide glucuronide as a major metabolite of etoposide in the rat and rabbit. Cancer Res 48:1829-1834.
19. Hande K, Bennett R, Hamilton R, Grote T, and Branch R (1988b) Metabolism and excretion of etoposide in isolated, perfused rat liver models. Cancer Res 48:5692-5695.
20. Houston JB and Kenworthy KE (2000) In vitro-in vivo scaling of CYP kinetic data not consistent with the classical Michaelis-Menten model. Drug Metab Dispos 28:246-254.
21. Jansen PLM, Chowdhury JR, Fischberg EB, and Arias IM (1977) Enzymatic conversion of bilirubin monoglucuronide to diglucuronide by rat liver plasma membranes. J Biol Chem 252:2710-2716.
22. Kaji H and Kume T (2005) Regioselective glucuronidation of denopamine: marked species differences and identification of human UDP- glucuronosyltransferase isoform. Drug Metab Dispos 33:403-412.
23. Kiang TKL, Ensom MHH, and Chang TKH (2005) UDP-glucuronosyltransferases and clinical drug-drug interactions. Pharmacol Ther 106:97-132.
24. King CD, Rios GR, Green MD, and Tephly TR (2000) UDP- glucuronosyltransferases. Curr Drug Metab 1:143-161.
25. Levsen K, Schiebel HM, Behnke B, Dötzer R, Dreher W, Elend M, and Thiele H (2005) Structure elucidation of phase II metabolites by tandem mass spectrometry: an overview. J Chromatogr A 1067:55-72.
26. Mackenzie PI, Owens IS, Burchell B, Bock KW, Bairoch A, Bélanger A, Fournel-Gigleux S, Green M, Hum DW, Iyanagi T, et al. (1997) The UDP glycosyltransferase gene superfamily: recommended nomenclature update based on evolutionary divergence. Pharmacogenetics 7:255-269.
27. Miners JO, Knights KM, Houston JB, and Mackenzie PI (2006) In vitro-in vivo correlation for drugs and other compounds eliminated by glucuronidation in humans: pitfalls and promises. Biochem Pharmacol 71:1531-1539.
28. Miners JO, Smith PA, Sorich MJ, McKinnon RA, and Mackenzie PI (2004) Predicting human drug glucuronidation parameters: application of in vitro and in silico modeling approaches. Annu Rev Pharmacol Toxicol 44:1-25.
29. Niemeijer NR, Gerding TK, and de Zeeuw RA (1991) Glucuronidation of labetalol at the two hydroxyl positions by bovine liver microsomes: isolation, purification, and structure elucidation of the glucuronides of labetalol. Drug Metab Dispos 19:20-23.
30. Pang S, Zheng N, Felix CA, Scavuzzo J, Boston R, and Blair IA (2001) Simultaneous determination of etoposide and its catechol metabolite in the plasma of pediatric patients by liquid chromatography/tandem mass spectrometry. J Mass Spectrom 36:771-781.
31. Radominska-Pandya A, Czernik PJ, Little JM, Battaglia E, and Mackenzie PI (1999) Structural and functional studies of UDP-glucuronosyltransferases. Drug Metab Rev 31:817-899.
32. Ritter JK (2000) Role of glucuronidation and UDP-glucuronosyltransferases in xenobiotic bioactivation reactions. Chem-Biol Interact 129:171-193.
33. 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.
34. Soars MG, Petullo DM, Eckstein JA, Kasper SC, and Wrighton SA (2004) An assessment of UDP-glucuronosyltransferase induction using primary human hepatocytes. Drug Metab Dispos 32:140-148.
35. Soars MG, Ring BJ, and Wrighton SA (2003) The effect of incubation conditions on the enzyme kinetics of UDP-glucuronosyltransferases. Drug Metab Dispos 31:762-767.
36. Tukey RH and Strassburg CP (2000) Human UDP-glucuronosyltransferases: metabolism, expression and disease. Annu Rev Pharmacol Toxicol 40:581-616.
37. Watanabe Y, Nakajima M, Ohashi N, Kume T, and Yokoi T (2003) Glucuronidation of etoposide in human liver microsomes in specifically catalyzed by UDP-glucuronosyltransferase 1A1. Drug Metab Dispos 31:589-595.
38. Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, and Ball SE (2004) Drug-drug interactions for UDP- glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos 32:1201-1208.
39. Yan Z, Caldwell GW, Jones WJ, and Masucci JA (2003) Cone voltage induced in-source dissociation of glucuronides in electrospray and implications in biological analyses. Rapid Commun Mass Spectrom 17:1433-1442.
40. Zhang D, Chando TJ, Everett DW, Patten CJ, Dehal SS, and Humphreys WG (2005) In vitro inhibition of UDP-glucuronosyltransferases by atazanavir and other HIV protease inhibitors and the relationship of this property to in vivo bilirubin glucuronidation. Drug Metab Dispos 33:1729-1739.