Assessment of UDP-glucuronosyltransferase catalyzed formation of ethyl glucuronide in human liver microsomes and recombinant UGTs

Forensic Science International

Volumn 153, Issue 2-3, 2005, Pages 109-116

  Foti, Robert S ^a   Fisher, Michael B ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

Alcohol metabolism; Ethyl glucuronide; UDP glucuronosyltransferase

Indexed keywords

BILIRUBIN; ETHYL GLUCURONIDE; GLUCURONIDE; GLUCURONOSYLTRANSFERASE; ISOENZYME; RECOMBINANT ENZYME; UNCLASSIFIED DRUG; ZIDOVUDINE;

ARTICLE; CATALYSIS; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME KINETICS; HUMAN; HUMAN TISSUE; LIVER MICROSOME; PRIORITY JOURNAL;

EID: 24044431556     PISSN: 03790738     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.forsciint.2004.12.003     Document Type: Article

References (52)

1. F.M. Wurst, and J. Metzger The ethanol conjugate ethyl glucuronide is a useful marker of recent alcohol consumption Alcohol Clin. Exp. Res. 26 2002 1114 1119
2. H. Matsumoto, and Y. Fukui Pharmacokinetics of ethanol: a review of the methodology Addict. Biol. 7 2002 5 14
3. C.S. Lieber, and L.M. DeCarli Hepatic microsomal oxidizing system: in vitro characteristics and adaptive properties in vivo J. Biol. Chem. 245 1970 2505 2512
4. I.A. Kamil, J.N. Smith, and R.T. Williams A new aspect of ethanol metabolism: isolation of ethyl-glucuronide Biochem. J. 51 1952 32 33
5. P.I. Jaakonmaki, K.L. Knox, E.C. Horning, and M.G. Manning The characterization by gas-liquid chromatography of ethyl-β-d-glucosiduronic- acid as a metabolite of ethanol in rat and man Eur. J. Pharmacol. 1 1967 63 70
6. T. Kozu Gas chromatographic analysis of ethyl-β-d-glucuronide in human urine Shinzu Igaku Zasshi 21 1973 595 601
7. K. Besserer, and V. Schmidt Ein Beitrag zur renalen Ausscheidung von Äthylglucuronid nach oraler Alkoholaufnahme [a contribution on the renal excretion of ethyl glucuronide following oral ethanol intake] Zentralbl. Rechtsmed. 25 1983 369
8. G.J. Dutton G.J. Dutton Glucuronic Acid - Free and Combined 1966 Academic Press NY 349
9. P.J. Bosma, L. Roy Chowdhury, and C. Bakker The genetic basis of the reduced expression of bilirubin UDP-glucuronosyltransferase in Gilbert's syndrome N. Engl. J. Med. 333 1995 1171 1175
10. E. Beutler, T. Gelbart, and A. Demina Racial variability in the UDP-glucuronosyltransferase 1 (UGT1A1) promoter: a balanced polymorphism for regulation of bilirubin metabolism? Proc. Natl. Acad. Sci. U.S.A. 95 1998 8170 8174
11. B. Burchell, and R. Hume Molecular genetic basis of Gilbert syndrome J. Gastroenterol. Hepatol. 14 1999 960 966
12. M. Ciotti, A. Marrone, C. Potter, and I.S. Owens Genetic polymorphism in the human UGT1A6 (planar phenol) UDP-glucuronosyltransferase: pharmacological implications Pharmacogenetics 7 1997 485 495
13. J.W. Lampe, L. Bigler, N.K. Horner, and J.D. Potter UDP- glucuronosyltransferase (UGT1A1*28 and UGT1A6*2) polymorphisms in Caucasians and Asians: relationships to serum bilirubin concentrations Pharmacogenetics 9 1999 341 349
14. C. Guillemette, J.K. Ritter, D.J. Auyeung, F.K. Kessler, and D.E. Houseman Structural heterogeneity at the UDP-glucuronosyltransferase 1 locus: functional consequences of three novel missense mutations in the human UGT1A7 gene Pharmacogenetics 10 2000 629 644
15. E. Levesque, M. Beaulieu, D.W. Hum, and A. Belanger Characterisation and substrate specificity of UGT2B4(E458): a UDP-glucuronosyltransferase encoded by a polymorphic gene Pharmacogenetics 9 1999 207 216
16. J.W. Lampe, J. Bigler, A.C. Bush, and J.D. Potter Prevalence of polymorphisms in the human UDP-glucuronosyltransferase 2B family: UGT2B4(D458E), UGT2B7(H268Y), and UGT2B15(D85Y) Cancer Epidemiol. (Biomarkers Prev.) 9 2000 329 333
17. C.R. Bhasker, W. McKinnon, and A.N. Stone Genetic polymorphism of UDP-glucuronosyltransferase 2B7 (UGT2B7) at amino acid 268: ethnic diversity of alleles and potential clinical significance Pharmacogenetics 10 2000 679 685
18. E. Levesque, M. Beaulieu, M.D. Green, T.R. Tephly, A. Belanger, and D.W. Hum Isolation and characterisation of UGT2B15(Y85): a UDP- glucuronosyltransferase encoded by a polymorphic gene Pharmacogenetics 7 1997 317 325
19. J.O. Miners, R.A. McKinnon, and P.I. Mackenzie Genetic polymorphisms of UDP-glucuronosyltransferases and their functional significance Toxicology 181-182 2002 453 456
20. M.W.H. Coughtrie, and M.B. Fisher The role of sulfotransferases (SULTs) and UDP-glucuronosyltransferases (UGTs) in human drug clearance and bioactivation J.S. Lee R.S. Obach M.B. Fisher Drug Metabolizing Enzymes 2003 Marcel Dekker Inc. New York 558 560
21. H. Dahl, N. Stephanson, O. Beck, and A. Helander Comparison of urinary excretion characteristics of ethanol and ethyl glucuronide J. Anal. Toxicol. 26 2002 201 204
22. M. Goll, G. Schmitt, B. Gansmann, and R.E. Aderjan Excretion profiles of ethyl glucuronide in human urine after internal dilution J. Anal. Toxicol. 26 2002 262 266
23. G. Schmitt, R. Aderjan, T. Keller, and M. Wu Ethyl glucuronide: an unusual ethanol metabolite in humans. Synthesis, analytical data, and determination in serum and urine J. Anal. Toxicol. 19 1995 91 94
24. G. Schmitt, P. Droenner, G. Skopp, and R. Aderjan Ethyl glucuronide concentration in serum of human volunteers, teetotalers, and suspected drinking drivers J. Forensic Sci. 42 1997 1099 1102
25. F.M. Wurst, C. Kempter, S. Seidl, and A. Alt Ethyl glucuronide - a marker of alcohol consumption and a relapse marker with clinical and forensic implications Alcohol Alcohol. 34 1999 71 77
26. W. Weinmann, P. Schaefer, A. Thierauf, A. Schreiber, and F.M. Wurst Confirmatory analysis of ethylglucuronide in urine by liquid-chromatography/ electrospray ionization/tandem mass spectrometry according to forensic guidelines J. Am. Soc. Mass Spectrom. 15 2004 188 193
27. I. Janda, and A. Alt Improvement of ethyl glucuronide determination in human urine and serum samples by solid-phase extraction J. Chromatogr. B: Biomed. Sci. Appl. 758 2001 229 234
28. N. Stephanson, H. Dahl, A. Helander, and O. Beck Direct quantification of ethyl glucuronide in clinical urine samples by liquid chromatography-mass spectrometry Ther. Drug Monit. 24 2002 645 651
29. H. Riveros-Rosas, A. Julian-Sanchez, and E. Piña Enzymology of ethanol and acetaldehyde metabolism in mammals Arch. Med. Res. 28 1997 453 471
30. M. Nishikawa, H. Tsuchihashi, A. Miki, M. Katagi, G. Schmitt, H. Zimmer, Th. Keller, and R. Aderjan Determination of ethyl glucuronide, a minor metabolite of ethanol, in human serum by liquid chromatography-electrospray ionization mass spectrometry J. Chromatogr. B 726 1999 105 110
31. F.M. Wurst, C. Kempter, J. Metzger, S. Seidl, and A. Alt Ethyl glucuronide: a marker of recent alcohol consumption with clinical and forensic implications Alcohol 20 2000 111 116
32. J.C. Kalvass, D.A. Tess, C. Giragossian, M.C. Linhares, and T.S. Maurer Influence of microsomal concentration on apparent intrinsic clearance: implications for scaling in vitro data Drug Metab. Dispos. 29 2001 1332 1336
33. I. Jandi, W. Weinmann, T. Kuehnle, M. Lahode, and A. Alt Determination of ethyl glucuronide in human hair by SPE and LC-MS/MS Forensic Sci. Int. 128 2002 59 65
34. M.B. Fisher, M.F. Paine, T.J. Strelevitz, and S.A. Wrighton The role of hepatic and extrahepatic UDP-glucuronosyltransferases in human drug metabolism Drug Metab. Rev. 33 2001 273 297
35. J.A. Williams, B.J. Ring, V.E. Cantrell, K. Campanale, D.R. Jones, S.D. Hall, and S.A. Wrighton 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
36. S.S. Dehal, P.V. Gagne, C.L. Crespi, and C.J. Patten Characterization of a probe substrate and an inhibitor of UDP glucuronosyl transferase (UGT) 1A4 activity in human liver microsomes (HLM) and cDNA-expressed UGT enzymes AAPS PharmSci 3 2001
37. S. Krishnaswamy, Q. Hao, L.L. von Moltke, D.J. Greenblatt, and M.H. Court Evaluation of 5-hydroxytryptophol and other endogenous serotonin (5-hydroxytryptamine) analogs as substrates for UDP-glucuronosyltransferase 1A6 Drug Metab. Dispos. 32 2004 862 869
38. M. Nakajima, N. Sakata, N. Ohashi, T. Kume, and T. Yokoi Involvement of multiple UDP-glucuronosyltransferase 1A isoforms in glucuronidation of 5-(4′-hydroxyphenyl)-5-phenylhydantoin in human liver microsomes Drug Metab. Dispos. 30 2002 1250 1256
39. M.H. Court, S. Krishnaswamy, Q. Hao, S.X. Duan, C.J. Patten, L.L. von Moltke, and D.J. Greenblatt Evaluation of 3′-azido-3′- deoxythymidine, morphine, and codeine as probe substrates for UDP-glucuronosyltransferase 2B7 (UGT2B7) in human liver microsomes: specificity and influence of the UGT2B7*2 polymorphism Drug Metab. Dispos. 31 2003 1125 1133
40. F.M. Wurst, G.E. Skipper, and W. Weinmann Ethyl glucuronide - the direct ethanol metabolite on the threshold from science to routine use Addiction 98 2003 51 61
41. B.L. Soderberg, and M. Laposata Fatty acid ethyl esters: markers of ethanol intake Am. Clin. Lab. 20 2001 18 20
42. F.M. Wurst, R. Vogel, K. Jachau, A. Varga, C. Alling, A. Alt, and G.E. Skipper Ethyl glucuronide discloses recent covert alcohol use not detected by standard testing forensic psychiatric inpatients Alcohol Clin. Exp. Res. 27 2003 471 476
43. R.S. Obach, J.G. Baxter, T.E. Liston, B.M. Silber, B.C. Jones, F. MacIntyre, D.J. Rance, and P. Wastall The prediction of human pharmacokinetic parameters from preclinical and in vitro metabolism data J. Pharmacol. Exp. Ther. 283 1997 46 58
44. J.G. Hardman L.E. Limbird Goodman and Gilman's The Pharmaceutical Basis of Therapeutics 10th ed. 2001 McGraw-Hill Companies Inc. NY
45. D.S. Dwyer, and R.J. Bradley Chemical properties of alcohols and their protein binding sites Cell. Mol. Life Sci. 57 2000 265 275
46. C. Ha, C.E. Peterson, D.S. Park, K. Harohalli, and N.V. Bhagavan Investigations of the effects of ethanol on warfarin binding to human serum albumin J. Biomed. Sci. 7 2000 114 121
47. T. Kardon, M.J. Coffey, G. Bánhegyi, A.A. Conley, B. Burchell, J. Mandl, and L. Braun Transcriptional induction of bilirubin UDP- glucuronosyltransferase by ethanol in rat liver Alcohol 21 2000 251 257
48. A. Radominska-Pandya, J.M. Little, and P.J. Czernik Human UDP-glucuronosyltransferase 2B7 Curr. Drug Metab. 2 2001 283 298
49. J.J. Fremont, R.W. Wang, and C.D. King Co-immunoprecipitation of UDP-glucuronosyltransferase isoforms and cytochrome P4503A4 Mol. Pharmacol. 67 2005 260 262
50. R. Meech, and P.I. Mackenzie UDP-glucuronosyltransferase, the role of the amino terminus in dimerization J. Biol. Chem. 272 1997 26913 26917
51. T.A. Aasmundstad, B. Lillekjendlie, and J. Morland Ethanol interference with morphine metabolism in isolated guinea pig hepatocytes Phamacol. Toxicol. 79 1996 114 119
52. S.B. Senafi, D.J. Clarke, and B. Burchell 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 1994 233 240