Comparative modelling of the human UDP-glucuronosyltransferases: Insights into structure and mechanism

Xenobiotica

Volumn 37, Issue 2, 2007, Pages 155-168

  Locuson, C W ^a   Tracy, T S ^b  

^a PFIZER INC   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

Author keywords

Drug metabolism; Glucuronidation; Molecular modelling; UDP glucuronosyltranferase (UGT); UDP glucuronosyltransferase

Indexed keywords

GLUCURONOSYLTRANSFERASE;

ARTICLE; BINDING SITE; CATALYSIS; COMPARATIVE STUDY; ENZYME BINDING; ENZYME MECHANISM; ENZYME STRUCTURE; MODEL; SEQUENCE ANALYSIS;

AMINO ACID SEQUENCE; CATALYTIC DOMAIN; GLUCURONOSYLTRANSFERASE; HUMANS; LIGANDS; MICROSOMES, LIVER; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PLANTS; PROTEIN STRUCTURE, SECONDARY; PROTEIN STRUCTURE, TERTIARY; SEQUENCE HOMOLOGY, AMINO ACID; XENOBIOTICS;

MAMMALIA;

EID: 33847027327     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.1080/00498250601129109     Document Type: Article

References (41)

1. Baker D, Sali A. 2001. Protein structure prediction and structural genomics. Science 294:93-96.
2. Battaglia E, Senay C, Fournel-Gigleux S, Herber R, Siest G, Magdalou J. 1994. The chemical modification of human liver UDP-glucuronosyltransferase UGT1*6 reveals the involvement of a carboxyl group in catalysis. FEBS Letters 346:146-150.
3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE. 2000. The protein data bank. Nucleic Acids Research 28:235-242.
4. Bond CS. 2003. TopDraw: A sketchpad for protein structure topology cartoons. Bioinformatics 19:311-312.
5. Bowalgaha K, Elliot DJ, Mackenzie PI, Knights KM, Swedmark S, Miners JO. 2005. S-naproxen and desmethylnaproxen glucuronidation by human liver microsomes and recombinant human UDP-glucuronosyltransferases (UGT): Role of UGT2B7 in the elimination of naproxen. British Journal of Clinical Pharmacology 60:423-433.
6. Coffman BL, Rios GR, King CD, Tephly TR. 1997. Human UGT2B7 catalyzes morphine glucuronidation. Drug Metabolism and Disposition 25:1-4.
7. Cohen AF, Land GS, Breimer DD, Yuen WC, Winton C, Peck AW. 1987. Lamotrigine, a new anticonvulsant: Pharmacokinetics in normal humans. Clinical Pharmacology and Therapy 42:535-541.
8. Coutinho PM, Deleury E, Davies GJ, Henrissat B. 2003. An evolving hierarchical family classification for glycosyltransferases. Journal of Molecular Biology 328:307-317.
9. Ethell BT, Ekins S, Wang J, Burchell B. 2002. Quantitative structure-activity relationships for the glucuronidation of simple phenols by expressed human UGT1A6 and UGT1A9. Drug Metabolism and Disposition 30:734-738.
10. Fisher MB, Campanale K, Ackermann BL, VandenBranden M, Wrighton SA. 2000. In vitro glucuronidation using human liver microsomes and the pore-forming peptide alamethicin. Drug Metabolism and Disposition 28:560-566.
11. Fisher MB, Paine MF, Strelevitz TJ, Wrighton SA. 2001. The role of hepatic and extrahepatic UDP-glucuronosyltransferases in human drug metabolism. Drug Metabolism Reviews 33:273-297.
12. Franco OL, Rigden DJ. 2003. Fold recognition analysis of glycosyltransferase families: Further members of structural superfamilies. Glycobiology 13:707-712.
13. Green MD, Bishop WP, Tephly TR. 1995. Expressed human UGT1.4 protein catalyzes the formation of quaternary ammonium-linked glucuronides. Drug Metabolism and Disposition 23:299-302.
14. Hall TA. 1999. BioEdit: A user-friendly biological sequence alignment editor and analysis program for Windows 95/98/NT. Nucleic Acids Symposium Series 41:95-98.
15. Hulo N, Bairoch A, Bulliard V, Cerutti L, De Castro E, Langendijk-Genevaux PS, Pagni M, Sigrist CJ. 2006. The PROSITE database. Nucleic Acids Research 34:D227-D230.
16. Johnson EF, Stout CD. 2005. Structural diversity of human xenobiotic-metabolizing cytochrome P450 monooxygenases. Biochemistry and Biophysics Research Communications 338:331-336.
17. Kapitonov D, Yu RK. 1999. Conserved domains of glycosyltransferases. Glycobiology 9:961-978.
18. Kelley LA, MacCallum RM, Sternberg MJ. 2000. Enhanced genome annotation using structural profiles in the program 3D-PSSM. Journal of Molecular Biology 299:499-520.
19. Kurkela M, Morsky S, Hirvonen J, Kostiainen R, Finel M. 2004. An active and water-soluble truncation mutant of the human UDP-glucuronosyltransferase 1A9. Molecular Pharmacology 65:826-831.
20. Laskowski RA, MacArthur MW, Moss DS, Thornton JM. 1993. PROCHECK: A program to check the stereochemical quality of protein structures. Journal of Applied Crystallography 26:283-291.
21. Luukkanen L, Taskinen J, Kurkela M, Kostiainen R, Hirvonen J, Finel M. 2005. Kinetic characterization of the 1A subfamily of recombinant human UDP-glucuronosyltransferases. Drug Metabolism and Disposition 33:1017-1026.
22. Mackenzie PI, Walter BK, Burchell B, Guillemette C, Ikushiro S, Iyanagi T, Miners JO, Owens IS, Nebert DW. 2005. Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily. Pharmacogenetics and Genomics 15:677-685.
23. Marchler-Bauer A, Anderson JB, Cherukuri PF, DeWeese-Scott C, Geer LY, Gwadz M, He S, Hurwitz DI, Jackson JD, Ke Z, et al. 2005. CDD: A conserved domain database for protein classification. Nucleic Acids Research 33:D192-D196.
24. McGuffin LJ, Bryson K, Jones DT. 2000. The PSIPRED protein structure prediction server. Bioinformatics 16:404-405.
25. Meech R, Mackenzie PI. 1997. UDP-glucuronosyltransferase, the role of the amino terminus in dimerization. Journal of Biology and Chemistry 272:26913-26917.
26. Miners JO, Mackenzie PI. 1991. Drug glucuronidation in humans. Pharmacology and Therapy 51:347-369.
27. Ouzzine M, Antonio L, Burchell B, Netter P, Fournel-Gigleux S, Magdalou J. 2000. Importance of histidine residues for the function of the human liver UDP-glucuronosyltransferase UGT1A6: Evidence for the catalytic role of histidine 370. Molecular Pharmacology 58:1609-1615.
28. Qasba PK, Ramakrishnan B, Boeggeman E. 2005. Substrate-induced conformational changes in glycosyltransferases. Trends in Biochemistry Science 30:53-62.
29. Radominska-Pandya A, Czernik PJ, Little JM, Battaglia E, Mackenzie PI. 1999. Structural and functional studies of UDP-glucuronosyltransferases. Drug Metabolism Reviews 31:817-899.
30. Ross J, Li Y, Lim E, Bowles DJ. 2001. Higher plant glycosyltransferases. Genome Biology 2: Reviews, 2:3004.1-3004.6.
31. Rossman MG, Moras D, Olsen KW. 1974. Chemical and biological evaluation of a nucleotide-binding protein. Nature 250:194-199.
32. Schwede T, Kopp J, Guex N, Peitsch MC. 2003. SWISS-MODEL: An automated protein homology-modeling server. Nucleic Acids Research 31:3381-3385.
33. Senay C, Ouzzine M, Battaglia E, Pless D, Cano V, Burchell B, Radominska A, Magdalou J, Fournel-Gigleux S. 1997. Arginine 52 and histidine 54 located in a conserved amino-terminal hydrophobic region (LX2-R52-G-H54-X3-V-L) are important amino acids for the functional and structural integrity of the human liver UDP-glucuronosyltransferase UGT1*6. Molecular Pharmacology 51:406-413.
34. Shao H, He X, Achnine L, Blount JW, Dixon RA, Wang X. 2005. Crystal structures of a multifunctional triterpene/flavonoid glycosyltransferase from Medicago truncatula. Plant Cell 17:3141-3154.
35. Smith PA, Sorich MJ, Low LS, McKinnon RA, Miners JO. 2004. Towards integrated ADME prediction: Past, present and future directions for modelling metabolism by UDP-glucuronosyltransferases. Journal of Molecular Graphics and Modelling 22:507-517.
36. Stone AN, Mackenzie PI, Galetin A, Houston JB, 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 Metabolism and Disposition 31:1086-1089.
37. Thompson JD, Higgins DG, Gibson TJ. 1994. CLUSTAL W: Improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Research 22:4673-4680.
38. Tsoutsikos P, Miners JO, Stapleton A, Thomas A, Sallustio BC, Knights KM. 2004. Evidence that unsaturated fatty acids are potent inhibitors of renal UDP-glucuronosyltransferases (UGT): Kinetic studies using human kidney cortical microsomes and recombinant UGT1A9 and UGT2B7. Biochemistry and Pharmacology 67:191-199.
39. Tukey RH, Strassburg CP. 2000. Human UDP-glucuronosyltransferases: Metabolism, expression, and disease. Annual Reviews in Pharmacology and Toxicology 40:581-616.
40. Upton RA, Buskin JN, Williams RL, Holford NH, Riegelman S. 1980. Negligible excretion of unchanged ketoprofen, naproxen, and probenecid in urine. Journal of Pharmacology Science 69:1254-1257.
41. Zakim D, Hochman Y, Kenney WC. 1983. Evidence for an active site arginine in UDP-glucuronyltransferase. Journal of Biology and Chemistry 258:6430-6434.