Molecular cloning of the baboon UDP-glucuronosyltransferase 2B gene family and their activity in conjugating morphine

Drug Metabolism and Disposition

Volumn 38, Issue 4, 2010, Pages 545-553

  Abildskov, Kirsten ^a   Weldy, Piper ^a   Garland, Marianne ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEMENTARY DNA; GLUCURONOSYLTRANSFERASE; GLUCURONOSYLTRANSFERASE 2B; GLUCURONOSYLTRANSFERASE 2B20; GLUCURONOSYLTRANSFERASE 2B39; GLUCURONOSYLTRANSFERASE 2B4; GLUCURONOSYLTRANSFERASE 2B40; GLUCURONOSYLTRANSFERASE 2B41; GLUCURONOSYLTRANSFERASE 2B42; GLUCURONOSYLTRANSFERASE 2B43; GLUCURONOSYLTRANSFERASE 2B44; GLUCURONOSYLTRANSFERASE 2B45; GLUCURONOSYLTRANSFERASE 2B46; GLUCURONOSYLTRANSFERASE 2B7; ISOLEUCINE; MORPHINE; MORPHINE 3 GLUCURONIDE; MORPHINE 6 GLUCURONIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG METABOLISM; GENETIC ANALYSIS; GLUCURONIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MACACA; MOLECULAR CLONING; NEWBORN; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOTIDE SEQUENCE; PERINATAL DEVELOPMENT; PHYLOGENY; PRIORITY JOURNAL; PROTEIN STRUCTURE; SEQUENCE ANALYSIS;

AMINO ACID SEQUENCE; ANALGESICS, OPIOID; ANIMALS; CELL MEMBRANE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CLONING, MOLECULAR; DNA, COMPLEMENTARY; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HUMANS; LIVER; MACACA FASCICULARIS; MOLECULAR SEQUENCE DATA; MORPHINE; PAPIO; PHYLOGENY; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION; RNA; SPECIES SPECIFICITY;

MACACA FASCICULARIS; PAPIO;

EID: 77950267766     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.109.030635     Document Type: Article

References (50)

1. Barbier O and Bélanger A (2003) The cynomolgus monkey (Macaca fascicularis) is the best animal model for the study of steroid glucuronidation. J Steroid Biochem Mol Biol 85:235-245.
2. Barbier O, Bélanger A, and Hum DW (1999a) Cloning and characterization of a simian UDP-glucuronosyltransferase enzyme UGT2B20, a novel C19 steroid-conjugating protein. Biochem J 337:567-574.
3. Barbier O, Girard C, Breton R, Bélanger A, and Hum DW (2000b) N-Glycosylation and residue 96 are involved in the functional properties of UDP-glucuronosyltransferase enzymes. Biochemistry 39:11540-11552.
4. Barbier O, Lévesque E, Bélanger A, and Hum DW (1999b) UGT2B23, a novel uridine diphosphate-glucuronosyltransferase enzyme expressed in steroid target tissues that conjugates androgen and estrogen metabolites. Endocrinology 140:5538-5548.
5. Barbier O, Turgeon D, Girard C, Green MD, Tephly TR, Hum DW, and Bélanger A (2000a) 3′-azido-3′-deoxythimidine (AZT) is glucuronidated by human UDP-glucuronosyltransferase 2B7 (UGT2B7). Drug Metab Dispos 28:497-502.
6. Beaulieu M, Lévesque E, Barbier O, Turgeon D, Bélanger G, Hum DW, and Bélanger A (1998) Isolation and characterization of a simian UDP-glucuronosyltransferase UGT2B18 active on 3-hydroxyandrogens. J Mol Biol 275:785-794.
7. Bélanger G, Barbier O, Hum DW, and Bélanger A (1999) Molecular cloning, expression and characterization of a monkey steroid UDP-glucuronosyltransferase, UGT2B19, that conjugates testosterone. Eur J Biochem 260:701-708.
8. Bélanger G, Beaulieu M, Lévesque E, Hum DW, and Bélanger A (1997) Expression and characterization of a novel UDP-glucuronosyltransferase, UGT2B9, from cynomolgus monkey. DNA Cell Biol 16:1195-1205.
9. Caspersen CS, Reznik B, Weldy PL, Abildskov KM, Stark RI, and Garland M (2007) Molecular cloning of the baboon UDP-glucuronosyltransferase 1A gene family: evolution of the primate UGT1 locus and relevance for models of human drug metabolism. Pharmacogenet Genomics 17:11-24.
10. Chay PC, Duffy BJ, and Walker JS (1992) Pharmacokinetic-pharmacodynamic relationships of morphine in neonates. Clin Pharmacol Ther 51:334-342.
11. Chen JM, Cooper DN, Chuzhanova N, Férec C, and Patrinos GP (2007) Gene conversion: mechanisms, evolution and human disease. Nat Rev Genet 8:762-775.
12. Chimpanzee Sequencing and Analysis Consortium (2005) Initial sequence of the chimpanzee genome and comparison with the human genome. Nature 437:69-87.
13. Coffman BL, Kearney WR, Goldsmith S, Knosp BM, Tephly TR, Dean B, Arison B, Chang S, Thomas PE, and King C (2003) Opioids bind to the amino acids 84 to 118 of UDPglucuronosyltransferase UGT2B7. Mol Pharmacol 63:283-288.
14. Coffman BL, Rios GR, King CD, and Tephly TR (1997) Human UGT2B7 catalyzes morphine glucuronidation. Drug Metab Dispos 25:1-4.
15. Court MH, Duan SX, von Moltke LL, Greenblatt DJ, Patten CJ, Miners JO, and Mackenzie PI (2001) Interindividual variability in acetaminophen glucuronidation by human liver microsomes: identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms. J Pharmacol Exp Ther 299:998-1006.
16. Court MH, Krishnaswamy S, Hao Q, Duan SX, Patten CJ, Von Moltke LL, and Greenblatt DJ (2003) 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 31:1125-1133.
17. Cox LA, Mahaney MC, Vandeberg JL, and Rogers J (2006) A second-generation genetic linkage map of the baboon (Papio hamadryas) genome. Genomics 88:274-281.
18. de Wildt SN, Kearns GL, Leeder JS, and van den Anker JN (1999) Glucuronidation in humans. Pharmacogenetic and developmental aspects. Clin Pharmacokinet 36:439-452.
19. Dean B, Arison B, Chang S, Thomas PE, and King C (2004) Identification of UGT2B9*2 and UGT2B33 isolated from female rhesus monkey liver. Arch Biochem Biophys 426:55-62.
20. Drouin G, Prat F, Ell M, and Clarke GD (1999) Detecting and characterizing gene conversions between multigene family members. Mol Biol Evol 16:1369-1390.
21. Dutton GJ (1978) Developmental aspects of drug conjugation, with special reference to glucuronidation. Annu Rev Pharmacol Toxicol 18:17-35.
22. Dutton GJ and Leakey JE (1981) The perinatal development of drug-metabolizing enzymes: what factors trigger their onset? Prog Drug Res 25:189-273.
23. Fisher MB, Campanale K, Ackermann BL, VandenBranden M, and Wrighton SA (2000) In vitro glucuronidation using human liver microsomes and the pore-forming peptide alamethicin. Drug Metab Dispos 28:560-566.
24. Garland M, Abildskov KM, Kiu TW, Daniel SS, and Stark RI (2005) The contribution of fetal metabolism to the disposition of morphine. Drug Metab Dispos 33:68-76.
25. Garland M, Abildskov KM, Taylor S, Benzeroual K, Caspersen CS, Arroyo SE, Kiu TW, Reznik B, Weldy P, Daniel SS, et al. (2006) Fetal morphine metabolism and clearance are constant during late gestation. Drug Metab Dispos 34:636-646.
26. Garland M, Szeto HH, Daniel SS, Tropper PJ, Myers MM, and Stark RI (1996) Zidovudine kinetics in the pregnant baboon. J Acquir Immune Defic Syndr Hum Retrovirol 11:117-127.
27. Garland M, Szeto HH, Daniel SS, Tropper PJ, Myers MM, and Stark RI (1998a) Placental transfer and fetal metabolism of zidovudine in the baboon. Pediatr Res 44:47-53.
28. Garland M, Szeto HH, Daniel SS, Tropper PJ, Myers MM, and Stark RI (1998b) Implications of the kinetics of zidovudine in the pregnant baboon following oral administration. J Acquir Immune Defic Syndr Hum Retrovirol 19:433-440.
29. Girard C, Barbier O, Turgeon D, and Bélanger A (2002) Isolation and characterization of the monkey UGT2B30 gene that encodes a uridine diphosphate-glucuronosyltransferase enzyme active on mineralocorticoid, glucocorticoid, androgen and oestrogen hormones. Biochem J 365:213-222.
30. 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.
31. Hartley R, Green M, Quinn M, and Levene MI (1993) Pharmacokinetics of morphine infusion in premature neonates. Arch Dis Child 69:55-58.
32. Karere GM, Froenicke L, Millon L, Womack JE, and Lyons LA (2008) A high-resolution radiation hybrid map of rhesus macaque chromosome 5 identifies rearrangements in the genome assembly. Genomics 92:210-218.
33. Li C and Wu Q (2007) Adaptive evolution of multiple-variable exons and structural diversity of drug-metabolizing enzymes. BMC Evol Biol 7:69.
34. Mackenzie PI, Bock KW, 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.
35. 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.
36. Marques-Bonet T, Sànchez-Ruiz J, Armengol L, Khaja R, Bertranpetit J, Lopez-Bigas N, Rocchi M, Gazave E, and Navarro A (2007) On the association between chromosomal rearrangements and genic evolution in humans and chimpanzees. Genome Biol 8:R230.
37. Ménard V, Eap O, Harvey M, Guillemette C, and Lévesque E (2009) Copy-number variations (CNVs) of the human sex steroid metabolizing genes UGT2B17 and UGT2B28 and their associations with a UGT2B15 functional polymorphism. Hum Mutat 30:1310-1319.
38. Nebert DW and Dieter MZ (2000) The evolution of drug metabolism. Pharmacology 61:124-135.
39. Nei M and Rooney AP (2005) Concerted and birth-and-death evolution of multigene families. Annu Rev Genet 39:121-152.
40. Ohno S, Kawana K, and Nakajin S (2008) Contribution of UDP-glucuronosyltransferase 1A1 and 1A8 to morphine-6-glucuronidation and its kinetic properties. Drug Metab Dispos 36:688-694.
41. Posada D, Crandall KA, and Holmes EC (2002) Recombination in evolutionary genomics. Annu Rev Genet 36:75-97.
42. Rogers J, Mahaney MC, Witte SM, Nair S, Newman D, Wedel S, Rodriguez LA, Rice KS, Slifer SH, Perelygin A, et al. (2000) A genetic linkage map of the baboon (Papio hamadryas) genome based on human microsatellite polymorphisms. Genomics 67:237-247.
43. Sawyer S (1989) Statistical tests for detecting gene conversion. Mol Biol Evol 6:526-638.
44. Scott CS, Riggs KW, Ling EW, Fitzgerald CE, Hill ML, Grunau RV, Solimano A, and Craig KD (1999) Morphine pharmacokinetics and pain assessment in premature newborns. J Pediatr 135:423-429.
45. 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.
46. Strassburg CP, Strassburg A, Kneip S, Barut A, Tukey RH, Rodeck B, and Manns MP (2002) Developmental aspects of human hepatic drug glucuronidation in young children and adults. Gut 50:259-265.
47. Tamura K, Dudley J, Nei M, and Kumar S (2007) MEGA4: Molecular Evolutionary Genetics Analysis (MEGA) software version 4.0. Mol Biol Evol 24:1596-1599.
48. Tephly TR and Burchell B (1990) UDP-glucuronosyltransferases: a family of detoxifying enzymes. Trends Pharmacol Sci 11:276-279.
49. Thomas JH (2007) Rapid birth-death evolution specific to xenobiotic cytochrome P450 genes in vertebrates. PLoS Genet 3:e67.
50. Yunis JJ and Prakash O (1982) The origin of man: a chromosomal pictorial legacy. Science 215:1525-1530.