Effect of D256N and Y483D on propofol glucuronidation by human uridine 5′-diphosphate glucuronosyltransferase (UGT1A9)

Basic and Clinical Pharmacology and Toxicology

Volumn 103, Issue 2, 2008, Pages 131-136

  Takahashi, Hiroko ^a   Maruo, Yoshihiro ^a   Mori, Asami ^a   Iwai, Masaru ^a   Sato, Hiroshi ^a   Takeuchi, Yoshihiro ^a  

^a SHIGA UNIVERSITY OF MEDICAL SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 NAPHTHOL; 7 ETHYL 10 HYDROXYCAMPTOTHECIN; ESTROGEN; GLUCURONOSYLTRANSFERASE; GLUCURONOSYLTRANSFERASE 1A9; IRINOTECAN; ISOENZYME; MYCOPHENOLIC ACID; NARINGENIN; PARACETAMOL; PHENOL DERIVATIVE; PROPOFOL; THYROID HORMONE; XENOBIOTIC AGENT;

ADULT; AMINO ACID SUBSTITUTION; ARTICLE; CONTROLLED STUDY; DRUG GLUCURONIDATION; DRUG METABOLISM; ENZYME MECHANISM; ENZYME POLYMORPHISM; EXON; GENE; GENE FREQUENCY; GENE LOCATION; GENETIC POLYMORPHISM; GENETIC VARIABILITY; HUMAN; HUMAN CELL; IN VITRO STUDY; JAPAN; NORMAL HUMAN; PRIORITY JOURNAL; RISK ASSESSMENT; UGT1 GENE; UGT1A9 GENE; WILD TYPE;

ANESTHETICS, INTRAVENOUS; ANIMALS; ASIAN CONTINENTAL ANCESTRY GROUP; BLOTTING, WESTERN; CERCOPITHECUS AETHIOPS; COS CELLS; GENE FREQUENCY; GLUCURONOSYLTRANSFERASE; HUMANS; JAPAN; METABOLIC DETOXICATION, PHASE II; MUTATION, MISSENSE; MYCOPHENOLIC ACID; POLYMORPHISM, SINGLE NUCLEOTIDE; PROPOFOL; SUBSTRATE SPECIFICITY; TRANSFECTION;

EID: 47649127415     PISSN: 17427835     EISSN: 17427843     Source Type: Journal    
DOI: 10.1111/j.1742-7843.2008.00247.x     Document Type: Article

References (41)

1. Mackenzie PI, Walter Bock K, Burchell B, Guillemette C, Ikushiro S, Iyanagi T et al. Nomenclature update for the mammalian UDP- glucuronosyltransferase (UGT) gene superfamily. Pharmacogenet Genomics 2005 15 : 677 85.
2. Gong QH, Cho JW, Huang T, Potter C, Gholami N, Basu NK et al. Thirteen UDP glucuronosyltransferase genes are encoded at the human UGT1 gene complex locus. Pharmacogenetics 2001 11 : 357 68.
3. Ritter JK, Chen F, Sheen YY, Tran HM, Kimura S, Yeatman MT et al. A novel complex locus UGT1 encodes human bilirubin, phenol, and other UDP-glucuronosyltransferase isozymes with identical carboxyl termini. J Biol Chem 1992 267 : 3257 61.
4. Strassburg CP, Manns MP, Tukey RH. Expression of the UDP- glucuronosyltransferase 1A locus in human colon. J Biol Chem 1998 273 : 8719 26.
5. Findlay KA, Kaptein E, Visser TJ, Burchell B. Characterization of the uridine diphosphate-glucuronosyltransferase-catalyzing thyroid hormone glucuronidation in man. J Clin Endocrinol Metab 2000 85 : 2879 83.
6. Court MH, Duan SX, von Moltke LL, Greenblatt DJ, Patten CJ, Miners JO et al. Interindividual variability in acetaminophen glucuronidation by human liver microsomes: identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms. J Pharmacol Exp Ther 2001 299 : 998 1006.
7. Gagne JF, Montminy V, Belanger P, Journault K, Gaucher G, Guillemette C. Common human UGT1A polymorphisms and the altered metabolism of irinotecan active metabolite 7-ethyl-10-hydroxycamptothecin (SN-38). Mol Pharmacol 2002 62 : 608 17.
8. Ebner T, Burchell B. Substrate specificities of two stably expressed human liver UDP-glucuronosyltransferases of the UGT1 gene family. Drug Metab Dispos 1993 21 : 50 55.
9. Wooster R, Sutherland L, Ebner T, Clarke D, Da Cruz e Silva O, Burchell B. Cloning and stable expression of a new member of the human liver phenol/bilirubin: UDP-glucuronosyltransferase cDNA family. Biochem J 1991 278 : 465 9.
10. Albert C, Vallee M, Beaudry G, Belanger A, Hum DW. The monkey and human uridine diphosphate-glucuronosyltransferase UGT1A9, expressed in steroid target tissues, are estrogen-conjugating enzymes. Endocrinology 1999 140 : 3292 302.
11. AI-Jahdari WS, Yamamoto K, Hiraoka H, Nakamura K, Goto F, Horiuch R. Prediction of total propofol clearance based on enzyme activities in microsomes from human kidney and liver. Eur J Clin Pharmacol 2006 62 : 527 33.
12. Maruo Y, Iwai M, Mori A, Sato H, Takeuchi Y. Polymorphism of UDP-glucuronosyltransferase and drug metabolism. Curr Drug Metab 2005 6 : 91 9.
13. Iwai M, Maruo Y, Ito M, Yamamoto K, Sato H, Takeuchi Y. Six novel UDP-glucuronosyltransferase (UGT1A3) polymorphisms with varying activity. J Human Genetics 2004 49 : 123 8.
14. Mori A, Maruo Y, Iwai M, Sato H, Takeuch Y. UDP-glucuronosyltransferase 1A4 polymorphisms in a Japanese population and kinetics of clozapine glucuronidation. Drug Metab Dispos 2005 33 : 672 5.
15. 14C-propofol. Xenobiotica 1998 18 : 429 40.
16. Court MH. Isoform-selective probe substrates for in vitro studies of human UDP-glucuronosyltransferases. Methods Enzymol 2005 400 : 104 16.
17. King CD, Rios GR, Green MD, Tephly TR. UDP-glucuronosyltransferases. Curr Drug Metab 2000 1 : 143 61.
18. Mano Y, Usui T, Kamimura H. Substrate-dependent modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1) by propofol in recombinant human UGT1A1 and human liver microsomes. Basic Clin Pharmacol Toxicol 2007 101 : 211 4
19. Wolf AR, Potter F. Propofol infusion in children: when does an anesthetic tool become an intensive care liability? Paediatr Anaesth 2004 14 : 435 8.
20. Parke TJ, Stevens JE, Rice AS, Greenaway CL, Bray RJ, Smith PJ et al. Metabolic acidosis and fatal myocardial failure after propofol infusion in children: five case reports. BMJ 1992 5 : 613 6.
21. Kato S, Hiura H, Kisaki O, Samori T, Sato H. Gene frequencies of G71R, TA(TA)7TAA and Y486D of UDP-glucuronosyltransferase (UGT1A1). Rinsho Byori 2006 54 (Suppl 151.
22. Yamamoto K, Sato H, Fujiyama Y, Doida Y, Bamba T. Contribution of two missense mutations (G71R and Y486D) of the bilirubin UDP glycosyltransferase (UGT1A1) gene to phenotypes of Gilbert's syndrome and Crigler-Najjar syndrome type II. Biochim Biophys Acta 1998 1406 : 267 73.
23. Jinno H, Tanaka-Kagawa T, Hanioka N, Saeki M, Ishida S, Nishimura T et al. Glucuronidation of 7-ethyl-10-hydroxycamptothecin (SN-38), an active metabolite of irinotecan (CPT-11), by human UGT1A1 variants, G71R, P229Q, and Y486D. Drug Metab Dispos 2003 31 : 108 13.
24. Ito M, Yamamoto K, Maruo Y, Sato H, Fujiyama Y, Bamba T. Effect of a conserved mutation in uridine diphosphate glucuronosyltransferase 1A1 and 1A6 on glucuronidation of a metabolite of flutamide. Eur J Clin Pharmacol 2002 58 : 11 4.
25. Kurkela M, Hirvonen J, Kostiainen R, Finel M. The interactions between the N-terminal and C-terminal domains of the human UDP-glucuronosyltransferases are partly isoform-specific, and may involve both monomers. Biochem Pharmacol 2004 68 : 2443 50.
26. Kraemer D, Klinker H. Crigler-Najjar syndrome type II in a Caucasian patient resulting from two mutations in the bilirubin uridine 5′-diphosphate-glucuronosyltransferase (UGT1A1) gene. J Hepatol 2002 36 : 706 7.
27. Jinno H, Saeki M, Saito Y, Tanaka-Kagawa T, Hanioka N, Sai K et al. Functional characterization of human UDP-glucuronosyltransferase 1A9 variant, D256N, found in Japanese cancer patients. J Pharmacol Exp Ther 2003 306 : 688 93.
28. Bosma PJ, Chowdhury JR, Bakker C, Gantla S, de Boer A, Oostra BA et al. The genetic basis of the reduced expression of bilirubin UDP- glucuronosyltransferase 1in Gilbert's syndrome. N Engl J Med 1995 333 : 1171 5.
29. Monaghan G, Ryan M, Seddon R, Hume R, Burchell B. Genetic variation in bilirubin UDP-glucuronosyltransferase gene promoter and Gilbert's syndrome. Lancet 1996 347 : 578 81.
30. Sato H, Adachi Y, Koiwai O. The genetic basis of Gilbert's syndrome. Lancet 1996 347 : 557 8.
31. Maruo Y, Nishizawa K, Sato H, Doida Y, Shimada M. Association of neonatal hyperbilirubinemia with bilirubin UDP-glucuronosyltransferase polymorphism. Pediatrics 1999 103 : 1224 7.
32. Maruo Y, Nishizawa K, Sato H, Sawa H, Shimada M. Prolonged unconjugated hyperbilirubinemia associated with breast milk and mutations of the bilirubin uridine diphosphate-glucuronosyltransferase gene. Pediatrics 2000 55 : 126 32.
33. Villeneuve L, Girard H, Fortier LC, Gagne JF, Guillemette C. 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 2003 307 : 117 28.
34. Thibaudeau J, Lepine J, Tojcic J, Duguay Y, Pelletier G, Plante M et al. Characterization of common UGT1A8, UGT1A9, and UGT2B7 variants with different capacities to inactivate mutagenic 4-hydroxylated metabolites of estradiol and estrone. Cancer Res 2006 66 : 125 33.
35. Paoluzzi L, Singh AS, Price DK, Danesi R, Mathijssen RH, Verweij J et al. Influence of genetic variants in UGT1A1 and UGT1A9 on the in vivo glucuronidation of SN-38. J Clin Pharmacol 2004 44 : 854 60.
36. Fujita K, Ando Y, Nagashima F, Yamamo, A-Y, Endo H, Kodama K et al. Novel single nucleotide polymorphism of UGT1A9 gene in Japanese. Drug Metab Pharmacokinet 2006 21 : 79 81.
37. Mehlotra RK, Bockarie MJ, Zimmerman PA. Prevalence of UGT1A9 and UGT2B7 nonsynonymous single nucleotide polymorphisms in West African, Papua New Guinean, and North American populations. Eur J Clin Pharmacol 2007 63 : 1 8.
38. Aono S, Yamada Y, Keino H, Hanada N, Nakagawa T, Sasaoka Y et al. Identification of defect in the genes for bilirubin UDP-glucuronosyltransferase in a patient with Crigler-Najjar syndrome type II. Biochem Biophys Res Commun 1993 197 : 1239 44.
39. Maruo Y, Sato H, Yamano T, Doida Y, Shimada M. Gilbert syndrome caused by a homozygous missense mutation (Tyr486Asp) of bilirubin UDP- glucuronosyltransferase gene. J Pediatr 1998 132 : 1045 7.
40. Yamamoto K, Soeda Y, Kamisako Y, Hosaka H, Fukano M, Sato H et al. Analysis of bilirubin uridine 5′-diphosphate (UDP)-glucuronosyltransferase gene mutations in seven patients with Crigler-Najjar syndrome type II. J Hum Genet 1998 43 : 111 4.
41. Bernard O, Guillemette C. The main role of UGT1A9 in the hepatic metabolism of mycophenolic acid and the effects of naturally occurring variants. Drug Metab Dispos 2004 32 : 775 8.