Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes

Drug Metabolism and Disposition

Volumn 33, Issue 7, 2005, Pages 1027-1035

  Kuehl, Gwendolyn E ^a   Lampe, Johanna W ^a   Potter, John D ^a   Bigler, Jeannette ^a,b  

^a Fred Hutchinson Cancer Research Center   (United States)

^b M5 A864 ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DICLOFENAC; FLURBIPROFEN; GLUCURONOSYLTRANSFERASE; GLUCURONOSYLTRANSFERASE 1A1; IBUPROFEN; INDOMETACIN; KETOPROFEN; NAPROXEN; NONSTEROID ANTIINFLAMMATORY AGENT; SULINDAC; SULINDAC SULFONE;

ANALYTIC METHOD; ARTICLE; CATALYSIS; CATALYST; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG GLUCURONIDATION; ENZYME SPECIFICITY; HUMAN; HUMAN CELL; KINETICS; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; PRIORITY JOURNAL; PROTEIN EXPRESSION; TANDEM MASS SPECTROMETRY;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CHROMATOGRAPHY, LIQUID; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HUMANS; KINETICS; MASS SPECTROMETRY; MICROSOMES, LIVER;

EID: 22344442057     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: 10.1124/dmd.104.002527     Document Type: Article

References (48)

1. Bailey M and Dickinson R (2003) Acyl glucuronide reactivity in perspective: biological consequences. Chem Biol Interact 145:117-137.
2. Balram C, Sabapathy K, Fei G, Khoo KS, and Lee EJD (2002) Genetic polymorphisms of UDP-glucuronosyltransferase in Asians: UGT1A1*28 is a common allele in Indians. Pharmacogenetics 12:81-83.
3. Baron JA and Sandler RS (2000) Nonsteroidal anti-inflammatory drugs and cancer prevention. Annu Rev Med 51:511-523.
4. Basu NK, Kubota S, Meselhy MR, Ciotti M, Chowdhury B, Hartori M, and Owens IS (2004) Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation. J Biol Chem 279:28320-28329.
5. Bolze S, Lacombe O, Durand G, Chaimbault P, Massiere F, Gay-Feutry C, Bromet N, and Hulot T (2002) Standardization of a LC/MS/MS method for the determination of acyl glucuronides and their isomers. Curr Sep 20:55-59.
6. Bosma PJ, Seppen J, Goldhoorn B, Bakker C, Oude Elfrink RPJ, Chowdhury JR, Chowdhury NR, and Jansen PL (1994) Bilirubin UDP-glucuronosyltransferase 1 is the only relevant glucuronidating isoform in man. J Biol Chem 269:17960-17964.
7. 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.
8. Ciotti M, Marrone A, Potter C, and Owens IS (1997) Genetic polymorphism in the human UGT1A6 (planar phenol) UDP-glucuronosyltransferase: pharmacological implications. Pharmacogenetics 7:485-495.
9. Coffman BL, Rios GR, King CD, and Tephly TR (1997) Human UGT2B7 catalyzes morphine glucuronidation. Drug Metab Dispos 25:1-4.
10. Court MH, Duan SX, Guillemette C, Journault K, Krishnaswamy S, Von Moltke LL, and Greenblatt DJ (2002) Stereoselective conjugation of oxazepam by human UDPglucuronosyltransferases (UGTs): S-oxazepam is glucuronidated by UGT2B15, while Roxazepam is glucuronidated by UGT2B7 and UGT1A9. Drug Metab Dispos 30:1257-1265.
11. Cryer B and Feldman M (1998) Cyclooxygenase-1 and cyclooxygenase-2 selectivity of widely used nonsteriodal anti-inflammatory drugs. Am J Med 104:413-421.
12. Ehmer U, Vogel A, Schutte JK, Krone B, Manns MP, and Strassburg CP (2004) Variation of hepatic glucuronidation: novel functional polymorphisms of the UDP-glucuronosyltransferase UGT1A4. Hepatology 39:970-977.
13. Ethell BT, Ekins S, Wang J, and Burchell B (2002) Quantitative structure activity relationships for the glucuronidation of simple phenols by expressed human UGT1A6 and UGT1A9. Drug Metab Dispos 30:734-738.
14. Frölich JC (1997) A classification of NSAIDs according to the relative inhibition of cyclooxygenase isoenzymes. Trends Pharmacol Sci 18:30-34.
15. Gagné J-F, Montminy V, Belanger P, Journault K, Gaucher G, and Guillemette C (2002) Common human UGT1A polymorphisms and the altered metabolism of irinotecan active metabolite 7-ethyl-10-hydroxycamptothecin (SN-38). Mol Pharmacol 62:608-617.
16. Green MD, King CD, Mojarrabi B, Mackenzie PI, and Tephly TR (1998) Glucuronidation of amines and other xenobiotics catalyzed by expressed human UDP-glucuronosyltransferase 1A3. Drug Metab Dispos 26:507-512.
17. Hanioka N, Ozawa S, Jinno H, Ando M, Saito Y, and Sawada J (2001) Human liver UDP-glucuronosyltransferase isoforms involved in the glucuronidation of 7-ethyl-10-hydroxycamptothecin. Xenobiotica 31:687-699.
18. Huang YH, Galijatovic A, Nguyen N, Geske D, Beaton D, Green J, Peters WH, and Tukey RH (2002) Identification and functional characterization of UDP-glucuronosyltransferases UGT1A8*1, UGT1A8*2 and UGT1A8*3. Pharmacogenetics 12:287-297.
19. Iwai M, Maruo Y, Ito M, Yamamoto K, Sato H, and Takeuchi Y (2004) Six novel UDPglucuronosyltransferase (UGT1A3) polymorphisms with varying activity. J Hum Genet 49:123-128.
20. 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.
21. Kuehl GE and Murphy SE (2003) N-glucuronidation of nicotine and cotinine by human liver microsomes and heterologously expressed UDP- glucuronosyltransferases. Drug Metab Dispos 31:1361-1368.
22. Lampe JW, Bigler J, Bush A, and Potter JD (2000) Prevalence of polymorphisms in the human UDP-glucuronosyltransferase 2B family: UGT2B4(D458E), UGT2B7(H268Y) and UGT2B15(D85Y). Cancer Epidemiol Biomarkers Prev 9:329-333.
23. Lampe JW, Bigler J, Horner NK, and Potter JD (1999) UDP- glucuronosyltransferase (UGT1A1*28 and UGT1A6*2) polymorphisms in Caucasians and Asians: relationships to serum bilirubin concentrations. Pharmacogenetics 9:341-349.
24. Lautala P, Ethell BT, Taskinen J, and Burchell B (2000) The specificity of glucuronidation of entacapone and tolcapone by recombinant human UDP-glucuronosyltransferases. Drug Metab Dispos 28:1385-1389.
25. Lepine J, Bernard O, Plante M, Tetu B, Pelletier G, Labrie F, Belanger A, and Guillemette C (2004) Specificity and regioselectivity of the conjugation of estradiol, estrone and their catecholestrogen and methoxyestrogen metabolites by human uridine diphosphoglucuronosyltransferases expressed in endometrium. J Clin Endocrinol Metab 89:5222-5232.
26. Levesque E, Beaulieu M, Hum DW, and Belanger A (1999) Characterization and substrate specificity of UGT2B4(E458): a UDP-glucuronosyltransferase encoded by a polymorphic gene. Pharmacogenetics 9:207-216.
27. Levesque E, Beaulieu M, Green MD, Tephly TR, Belanger A, and Hum DW (1997) Isolation and characterization of UGT2B15(Y85): a UDP- glucuronosyltransferase encoded by a polymorphic gene. Pharmacogenetics 7:317-325.
28. Mackenzie PI, Little JM, and Radominska-Pandya A (2003) Glucosidation of hyodeoxycholic acid by UDP-glucuronosyltransferase 2B7. Biochem Pharmacol 65:417-421.
29. Mackenzie PI, Owens IS, Burchell B, Bock KW, Bairoch A, Belanger 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.
30. Mano Y, Usui T, and Kamimura H (2005) In vitro inhibitory effects of nonsteriodal antiinflammatory drugs on UDP-glucuronosyltransferase 1A1-catalyzed estradiol 3-betaglucuronidation in human liver microsomes. Biopharm Drug Dispos 26:35-39.
31. Miners JO, Lillywhite KJ, Matthews AP, Jones ME, and Birkett DJ (1988) Kinetic and inhibitor studies of 4-methylumbelliferone and 1-naphthol glucuronidation in human liver microsomes. Biochem Pharmacol 37:665-671.
32. Mojarrabi B and Mackenzie PI (1998) Characterization of two UDP glucuronosyltransferases that are predominantly expressed in human colon. Biochem Biophys Res Commun 247:704-709.
33. Nakajima M, Sakata N, Ohashi N, Kume T, and Yokoi T (2002a) Involvement of multiple UDP-glucuronosyltransferase 1A isoforms in glucuronidation of 5-(4′-hydroxyphenyl)-5-phenylhydantoin in human liver microsomes. Drug Metab Dispos 30:1250-1256.
34. Nakajima M, Tanaka E, Kobayashi T, Ohashi N, Kume T, and Yokoi T (2002b) Imipramine N-glucuronidation in human liver microsomes: biphasic kinetics and characterization of UDP-glucuronosyltransferase isoforms. Drug Metab Dispos 30:636-642.
35. Nakajima M, Tanaka E, Kwon J-T, and Yokoi T (2002c) Characterization of nicotine and cotinine N-glucuronidations in human liver microsomes. Drug Metab Dispos 30:1484-1490.
36. Piazza GA, Alberts DS, Hixson LJ, Paranka NS, Li H, Finn T, Bogert C, Guillen JM, Brendel K, Gross PH, et al. (1997) Sulindac sulfone inhibits azoxymethane-induced colon carcinogenesis in rats without reducing prostaglandin levels. Cancer Res 57:2909-2915.
37. Pillot T, Ouzzine M, Fournel-Gigleux S, Lafaurie C, Radominska A, Burchell B, Siest G, and Magdalou J (1993) Glucuronidation of hyodeoxycholic acid: evidence for a selective role of UDP-glucuronosyltransferase 2B4. J Biol Chem 268:25636-25642.
38. Sabolovic N, Magdalou J, Netter P, and Abid A (2000) Nonsteroidal anti-inflammatory drugs and phenols glucuronidation in Caco-2 cells: identification of the UDP-glucuronosyltransferases UGT1A6, 1A3 and 2B7. Life Sci 67:185-196.
39. Sakaguchi K, Green M, Stock N, Reger TS, Zunic J, and King CD (2004) Glucuronidation of carboxylic acid containing compounds by UDP- glucuronosyltransferase isoforms. Arch Biochem Biophys 424:219-225.
40. Shipkova M, Armstrong VW, Oellerich M, and Wieland E (2003) Acyl glucuronide drug metabolites: toxicological and analytical implications. Ther Drug Monit 25:1-16.
41. Soars MG, Mattiuz EL, Jackson DA, Kulanthaivel P, Ehlhardt WJ, and Wrighton SA (2002) Biosynthesis of drug glucuronides for use as authentic standards. J Pharmacol Toxicol Methods 47:161-168.
42. Spahn H, Iwakawa S, Lin ET, and Benet LZ (1989) Procedures to characterize in vivo and in vitro enantioselective glucuronidation properly: studies with benoxaprofen glucuronides. Pharm Res 6:125-132.
43. Stone AN, Mackenzie PI, Galetin A, Houston JB, and Miners JO (2003) Isoform selectivity and kinetics of morphine 3- and 6-glucuronidation by human UDP-glucuronosyltransferases: evidence for atypical glucuronidation kinetics by UGT2B7. Drug Metab Dispos 31:1086-1089.
44. Tukey RH and Strassburg CP (2000) Human UDP-glucuronosyltransferases: metabolism, expression and disease. Annu Rev Pharmacol Toxicol 40:581-616.
45. Turgeon D, Carrier J, Levesque E, Hum D, and Belanger A (2001) Relative enzymatic activity, protein stability and tissue distribution of human steroid-metabolizing UGT2B subfamily members. Endocrinology 142:778-787.
46. Verlaan M, te Morsche RHM, Pap A, Laheij RJF, Jansen JBMJ, Peters WHM, and Drenth JPH (2004) Functional polymorphisms of UDP-glucuronosyltransferases 1A1, 1A6 and 1A8 are not involved in chronic pancreatitis. Pharmacogenetics 14:351-357.
47. Villeneuve L, Girard H, Fortier L-C, Gagné J-F, and Guillemette C (2003) Novel functional polymorphisms in the UGT1A7 and UGT1A9 glucuronidating enzymes in Caucasian and African American subjects and their impact on the metabolism of 7-ethyl-10-hydroxycamptothecin and flavopiridol anticancer drugs. J Pharmacol Exp Ther 307:117-128.
48. Yamanaka H, Nakajima M, Katoh M, Hara Y, Tachibana O, Yamashita J, McLeod HL, and Yokoi T (2004) A novel polymorphism in the promoter region of human UGT1A9 gene (UGT1A9*22) and its effects on the transcriptional activity. Pharmacogenetics 14:329-332.