Nicotine glucuronidation and the human UDP-glucuronosyltransferase UGT2B10

Molecular Pharmacology

Volumn 72, Issue 3, 2007, Pages 761-768

  Kaivosaari, Sanna ^a,b   Toivonen, Päivi ^a,b   Hesse, Leah M ^c   Koskinen, Mikko ^a   Court, Michael H ^c   Finel, Moshe ^b  

^a ORION CORPORATION   (Finland)

^b UNIVERSITY OF HELSINKI   (Finland)

^c TUFTS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC NITRO COMPOUND; COTININE; GLUCURONIC ACID; GLUCURONOSYLTRANSFERASE; GLUCURONOSYLTRANSFERASE 1A9; GLUCURONOSYLTRANSFERASE 2B7; LIVER ENZYME; MESSENGER RNA; MICROSOME ENZYME; NICOTINE; UDP GLUCURONOSYLTRANSFERASE 1A4; UDP GLUCURONOSYLTRANSFERASE 2B10; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; ENZYME ACTIVITY; GLUCURONIDATION; HUMAN; HUMAN TISSUE; INTESTINE; KIDNEY PARENCHYMA; LIVER; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FOLDING; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION;

AMINO ACID SEQUENCE; BIOTRANSFORMATION; CONSERVED SEQUENCE; COTININE; FEMALE; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HUMANS; INTESTINES; ISOENZYMES; KINETICS; MALE; MICROSOMES; MICROSOMES, LIVER; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; NICOTINE; PROTEIN SORTING SIGNALS; RECOMBINANT PROTEINS; RNA, MESSENGER; SEQUENCE HOMOLOGY, AMINO ACID; STEREOISOMERISM;

EID: 34548311575     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.107.037093     Document Type: Article

References (28)

1. Borlak J, Gasparic A, Locher M, Schupke H, and Hermann R (2006) N-Glucuronidation of the antiepileptic drug retigabine: results from studies with human volunteers, heterologously expressed human UGTs, human liver, kidney, and liver microsomal membranes of Crigler-Najjar type II. Metabolism 55:711-721.
2. 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.
3. Ghosheh O and Hawes EM (2002a) Microsomal N-glucuronidation of nicotine and cotinine: human hepatic interindividual, human intertissue, and interspecies hepatic variation. Drug Metab Dispos 30:1478-1483.
4. Ghosheh O and Hawes EM (2002b) N-glucuronidation of nicotine and cotinine in human: formation of cotinine glucuronide in liver microsomes and lack of catalysis by 10 examined UDP-glucuronosyltransferases. Drug Metab Dispos 30:991-996.
5. Ghosheh O, Vashishtha SC, and Hawes EM (2001) Formation of the quaternary ammonium-linked glucuronide of nicotine in human liver microsomes: identification and stereoselectivity in the kinetics. Drug Metab Dispos 29:1525-1528.
6. Girard H, Thibaudeau J, Court MH, Fortier LC, Villeneuve L, Caron P, Hao Q, von Moltke LL, Greenblatt DJ, and Guillemette C (2005) UGT1A1 polymorphisms are important determinants of dietary carcinogen detoxification in the liver. Hepatology 42:448-457.
7. Green MD and Tephly TR (1998) Glucuronidation of amine substrates by purified and expressed UDP-glucuronosyltransferase proteins. Drug Metab Dispos 26:860-867.
8. Hawes EM (1998) N+-glucuronidation, a common pathway in human metabolism of drugs with a tertiary amine group. Drug Metab Dispos 26:830-837.
9. Hukkanen J, Jacob P 3rd, and Benowitz NL (2005) Metabolism and disposition kinetics of nicotine. Pharmacol Rev 57:79-115.
10. 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.
11. Kurkela M, Garcia-Horsman JA, Luukkanen L, Morsky S, Taskinen J, Baumann M, Kostiainen R, Hirvonen J, and Finel M (2003) Expression and characterization of recombinant human UDP-glucuronosyltransferases (UGTs). UGT1A9 is more resistant to detergent inhibition than other UGTs and was purified as an active dimeric enzyme. J Biol Chem 278:3536-3544.
12. Kurkela M, Patana AS, Mackenzie PI, Court MH, Tate CG, Hirvonen J, Goldman A, and Finel M (2007) Interactions with other human UDP- glucuronosyltransferases attenuate the consequences of the Y485D mutation on the activity and substrate affinity of UGT1A6. Pharmacogenet Genomics 17:115-126.
13. Lévesque E, Turgeon D, Carrier JS, Montminy V, Beaulieu M, and Belanger A (2001) Isolation and characterization of the UGT2B28 cDNA encoding a novel human steroid conjugating UDP-glucuronosyltransferase. Biochemistry 40:3869-3881.
14. Mackenzie PI, Gregory PA, Gardner-Stephen DA, Lewinsky RH, Jorgensen BR, Nishiyama T, Xie W, and Radominska-Pandya A (2003) Regulation of UDP glucuronosyltransferase genes. Curr Drug Metab 4:249-257.
15. Mackenzie PI, Walter Bock K, Burchell B, Guillemette C, Ikushiro S, Iyanagi T, Miners JO, Owens IS, and Nebert DW (2005) Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily. Pharmacogenet Genomics 15:677-685.
16. Miley MJ, Zielinska AK, Keenan JE, Bratton SM, Radominska-Pandya A, and Redinbo MR (2007) Crystal structure of the cofactor-binding domain of the human phase II drug-metabolism enzyme UDP-glucuronosyltransferase 2B7. J Mol Biol 369:498-511.
17. Nakajima M, Tanaka E, Kwon JT, and Yokoi T (2002) Characterization of nicotine and cotinine N-glucuronidations in human liver microsomes. Drug Metab Dispos 30:1484-1490.
18. Nakajima M and Yokoi T (2005) Interindividual variability in nicotine metabolism: C-oxidation and glucuronidation. Drug Metab Pharmacokinet 20:227-235.
19. Nishimura M and Naito S (2006) Tissue-specific mRNA expression profiles of human phase I metabolizing enzymes except for cytochrome P450 and phase II metabolizing enzymes. Drug Metab Pharmacokinet 21:357-374.
20. 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.
21. Strassburg CP, Kneip S, Topp J, Obermayer-Straub P, Barut A, Tukey RH, and Manns MP (2000) Polymorphic gene regulation and interindividual variation of UDP-glucuronosyltransferase activity in human small intestine. J Biol Chem 275:36164-36171.
22. Tukey RH and Strassburg CP (2000) Human UDP-glucuronosyltransferases: metabolism, expression, and disease. Annu Rev Pharmacol Toxicol 40:581-616.
23. Turgeon D, Chouinard S, Belanger P, Picard S, Labbe JF, Borgeat P, and Belanger A (2003) Glucuronidation of arachidonic and linoleic acid metabolites by human UDP-glucuronosyltransferases. J Lipid Res 44:1182-1191.
24. Uchaipichat V, Mackenzie PI, Guo XH, Gardner-Stephen D, Galetin A, Houston JB, Miners JO (2004) Human UDP-glucuronosyltransferases: isoform selectivity and kinetics of 4-methylumbelliferone and 1-naphthol glucuronidation, effects of organic solvents, and inhibition by diclofenac and probenecid. Drug Metab Dispos 32:413-423.
25. Wells PG, Mackenzie PI, Chowdhury JR, Guillemette C, Gregory PA, Ishii Y, Hansen AJ, Kessler FK, Kim PM, Chowdhury NR, et al. (2004) Glucuronidation and the UDP-glucuronosyltransferases in health and disease. Drug Metab Dispos 32:281-290.
26. Xu L, Krenitsky DM, Seacat AM, Butenhoff JL, Tephly TR, and Anders MW (2006) N-glucuronidation of perfluorooctanesulfonamide by human, rat, dog, and monkey liver microsomes and by expressed rat and human UDP- glucuronosyltransferases. Drug Metab Dispos 34:1406-1410.
27. Zenser TV, Lakshmi VM, Hsu FF, and Davis BB (2002) Metabolism of N-acetylbenzidine and initiation of bladder cancer. Mutat Res 506-507:29-40.
28. Zhang D, Zhao W, Roongta VA, Mitroka JG, Klunk LJ, and Zhu M (2004) Amide N-glucuronidation of MaxiPost catalyzed by UDP-glucuronosyltransferase 2B7 in humans. Drug Metab Dispos 32:545-551.