Metabolism of the c-Fos/activator protein-1 inhibitor T-5224 by multiple human UDP-glucuronosyltransferase isoforms

Drug Metabolism and Disposition

Volumn 39, Issue 5, 2011, Pages 803-813

  Uchihashi, Shinsuke ^a,b   Fukumoto, Hiroyuki ^a   Onoda, Makoto ^a   Hayakawa, Hiroyoshi ^a   Ikushiro, Shinichi ^b   Sakaki, Toshiyuki ^b  

^a TOYAMA CHEMICAL CO LTD   (Japan)

^b TOYAMA PREFECTURAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 [5 [4 (CYCLOPENTYLOXY) 2 HYDROXYBENZOYL] 2 [(3 HYDROXY 1,2 BENZISOXAZOL 6 YL)METHOXYL]PHENYL]PROPIONIC ACID; ANTIRHEUMATIC AGENT; CYTOCHROME P450; ESTRADIOL; GLUCURONOSYLTRANSFERASE; GLUCURONOSYLTRANSFERASE 1A1; GLUCURONOSYLTRANSFERASE 1A3; T 5224; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG GLUCURONIDATION; DRUG METABOLISM; DRUG STRUCTURE; HAPLORHINI; HUMAN; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALS; ANTIRHEUMATIC AGENTS; ARTHRITIS, RHEUMATOID; BENZOPHENONES; CYTOCHROME P-450 ENZYME SYSTEM; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HAPLORHINI; HUMANS; HYDROLYSIS; INTESTINES; ISOENZYMES; ISOXAZOLES; LIVER; MICROSOMES; MICROSOMES, LIVER; RATS; RECOMBINANT PROTEINS; TRANSCRIPTION FACTOR AP-1;

RATTUS;

EID: 79954988600     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.110.037952     Document Type: Article

References (38)

1. Aikawa Y, Morimoto K, Yamamoto T, Chaki H, Hashiramoto A, Narita H, Hirono S, and Shiozawa S (2008) Treatment of arthritis with a selective inhibitor of c-Fos/activator protein-1. Nat Biotechnol 26:817-823. (Pubitemid 351961451)
2. Ando Y, Saka H, Asai G, Sugiura S, Shimokata K, and Kamataki T (1998) UGT1A1 genotypes and glucuronidation of SN-38, the active metabolite of irinotecan. Ann Oncol 9:845-847. (Pubitemid 28440442)
3. Cheng Z, Radominska-Pandya A, and Tephly TR (1998) Cloning and expression of human UDP-glucuronosyltransferase (UGT) 1A8. Arch Biochem Biophys 356:301-305. (Pubitemid 28387735)
4. Congiu M, Mashford ML, Slavin JL, and Desmond PV (2002) UDP glucuronosyltransferase mRNA levels in human liver disease. Drug Metab Dispos 30:129-134. (Pubitemid 34106530)
5. Court MH (2005) Isoform-selective probe substrates for in vitro studies of human UDPglucuronosyltransferases. Methods Enzymol 400:104-116. (Pubitemid 43052418)
6. Court MH (2010) Interindividual variability in hepatic drug glucuronidation: Studies into the role of age, sex, enzyme inducers, and genetic polymorphism using the human liver bank as a model system. Drug Metab Rev 42:209-224.
7. Cubitt HE, Houston JB, and Galetin A (2009) Relative importance of intestinal and hepatic glucuronidation-impact on the prediction of drug clearance. Pharm Res 26:1073-1083.
8. Fenselau C and Johnson LP (1980) Analysis of intact glucuronides by mass spectrometry and gas chromatography-mass spectrometry. A review. Drug Metab Dispos 8:274-283. (Pubitemid 10034560)
9. Fisher MB, Paine MF, Strelevitz TJ, and Wrighton SA (2001) The role of hepatic and extrahepatic UDP-glucuronosyltransferases in human drug metabolism. Drug Metab Rev 33:273-297. (Pubitemid 33136266)
10. Gagní JF, 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. (Pubitemid 36329379)
11. Houston JB and Kenworthy KE (2000) In vitro-in vivo scaling of CYP kinetic data not consistent with the classical Michaelis-Menten model. Drug Metab Dispos 28:246-254. (Pubitemid 30137047)
12. Ikushiro S, Emi Y, and Iyanagi T (1995) Identification and analysis of drug-responsive expression of UDP-glucuronosyltransferase family 1 (UGT1) isozyme in rat hepatic microsomes using anti-peptide antibodies. Arch Biochem Biophys 324:267-272.
13. Ikushiro S, Emi Y, Kato Y, Yamada S, and Sakaki T (2006) Monospecific antipeptide antibodies against human hepatic UDP-glucuronosyltransferase 1A subfamily (UGT1A) isoforms. Drug Metab Pharmacokinet 21:70-74.
14. Ikushiro S, Sahara M, Emi Y, Yabusaki Y, and Iyanagi T (2004) Functional co-expression of xenobiotic metabolizing enzymes, rat cytochrome P450 1A1 and UDP-glucuronosyltransferase 1A6, in yeast microsomes. Biochim Biophys Acta 1672:86-92. (Pubitemid 38515859)
15. Iyer L, King CD, Whitington PF, Green MD, Roy SK, Tephly TR, Coffman BL, and Ratain MJ (1998) Genetic predisposition to the metabolism of irinotecan (CPT-11). Role of uridine diphosphate glucuronosyltransferase isoform 1A1 in the glucuronidation of its active metabolite (SN-38) in human liver microsomes. J Clin Invest 15:847-854. (Pubitemid 28096082)
16. Izukawa T, Nakajima M, Fujiwara R, Yamanaka H, Fukami T, Takamiya M, Aoki Y, Ikushiro S, Sakaki T, and Yokoi T (2009) Quantitative analysis of UDP-glucuronosyltransferase (UGT) 1A and UGT2B expression levels in human livers. Drug Metab Dispos 37:1759-1768.
17. Jaggi R, Addison RS, King AR, Suthers BD, and Dickinson RG (2002) Conjugation of desmethylnaproxen in the rat-a novel acyl glucuronide-sulfate diconjugate as a major biliary metabolite. Drug Metab Dispos 30:161-166. (Pubitemid 34106534)
18. Kasai N, Sakaki T, Shinkyo R, Ikushiro S, Iyanagi T, Kamao M, Okano T, Ohta M, and Inouye K (2004) Sequential metabolism of 2,3,7-trichlorodibenzo-p- dioxin (2,3,7-triCDD) by cytochrome P450 and UDP-glucuronosyltransferase in human liver microsomes. Drug Metab Dispos 32:870-875. (Pubitemid 38955617)
19. Kiang TK, Ensom MH, and Chang TK (2005) UDP-glucuronosyltransferases and clinical drug-drug interactions. Pharmacol Ther 106:97-132. (Pubitemid 40386722)
20. Lin JH and Wong BK (2002) Complexities of glucuronidation affecting in vitro-in vivo extrapolation. Curr Drug Metab 3:623-646. (Pubitemid 35331663)
21. Nakamura A, Nakajima M, Yamanaka H, Fujiwara R, and Yokoi T (2008) Expression of UGT1A and UGT2B mRNA in human normal tissues and various cell lines. Drug Metab Dispos 36:1461-1464.
22. Niemeijer NR, Gerding TK, and De Zeeuw RA (1991) Glucuronidation of labetalol at the two hydroxy positions by bovine liver microsomes. Isolation, purification, and structure elucidation of the glucuronides of labetalol. Drug Metab Dispos 19:20-23.
23. 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.
24. Oeda K, Sakaki T, and Ohkawa H (1985) Expression of rat liver cytochrome P-450MC cDNA in Saccharomyces cerevisiae. DNA 4:203-210. (Pubitemid 15027392)
25. Ohno S and Nakajin S (2009) Determination of mRNA expression of human UDPglucuronosyltransferases and application for localization in various human tissues by real-time reverse transcriptase-polymerase chain reaction. Drug Metab Dispos 37:32-40.
26. Plumb RS, Rainville PD, Potts WB 3rd, Castro-Perez JM, Johnson KA, and Wilson ID (2007) High-temperature ultra-performance liquid chromatography coupled to hybrid quadrupole time-of-flight mass spectrometry applied to ibuprofen metabolites in human urine. Rapid Commun Mass Spectrom 21:4079-4085.
27. Ramchandani RP, Wang Y, Booth BP, Ibrahim A, Johnson JR, Rahman A, Mehta M, Innocenti F, Ratain MJ, and Gobburu JV (2007) The role of SN-38 exposure, UGT1A1.*28 polymorphism, and baseline bilirubin level in predicting severe irinotecan toxicity. J Clin Pharmacol 47:78-86. (Pubitemid 44974001)
28. Ritter JK, Kessler FK, Thompson MT, Grove AD, Auyeung DJ, and Fisher RA (1999) Expression and inducibility of the human bilirubin UDP- glucuronosyltransferase UGT1A1 in liver and cultured primary hepatocytes: Evidence for both genetic and environmental influences. Hepatology 30:476-484. (Pubitemid 29357514)
29. Senafi SB, Clarke DJ, and Burchell B (1994) Investigation of the substrate specificity of a cloned expressed human bilirubin UDP- glucuronosyltransferase: UDP-sugar specificity and involvement in steroid and xenobiotic glucuronidation. Biochem J 303:233-240. (Pubitemid 24302924)
30. Soars MG, Burchell B, and Riley RJ (2002) In vitro analysis of human drug glucuronidation and prediction of in vivo metabolic clearance. J Pharmacol Exp Ther 30:382-390. (Pubitemid 34250317)
31. Strassburg CP, Manns MP, and Tukey RH (1998) Expression of the UDP-glucuronosyltransferase 1A locus in human colon. Identification and characterization of the novel extrahepatic UGT1A8. J Biol Chem 273:8719-8726. (Pubitemid 28176150)
32. Tsuchida K, Chaki H, Takakura T, Kotsubo H, Tanaka T, Aikawa Y, Shiozawa S, and Hirono S (2006) Discovery of nonpeptidic small-molecule AP-1 inhibitors: Lead hopping based on a three-dimensional pharmacophore model. J Med Chem 49:80-91. (Pubitemid 43077324)
33. Tsuchida K, Chaki H, Takakura T, Yokotani J, Aikawa Y, Shiozawa S, Gouda H, and Hirono S (2004) Design, synthesis, and biological evaluation of new cyclic disulfide decapeptides that inhibit the binding of AP-1 to DNA. J Med Chem 47:4239-4246. (Pubitemid 39045429)
34. Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, and Ball SE (2004) Drug-drug interactions for UDP- glucuronosyltransferase substrates: A pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos 32:1201-1208. (Pubitemid 39410902)
35. Williams JA, Ring BJ, Cantrell VE, Campanale K, Jones DR, Hall SD, and Wrighton SA (2002) Differential modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1)-catalyzed estradiol- 3-glucuronidation by the addition of UGT1A1 substrates and other compounds to human liver microsomes. Drug Metab Dispos 30:1266-1273. (Pubitemid 35265835)
36. Zhang W, Liu W, Innocenti F, and Ratain MJ (2007) Searching for tissue-specific expression pattern-linked nucleotides of UGT1A isoforms. PLoS ONE 2:e396.
37. Zhou D, Guo J, Linnenbach AJ, Booth-Genthe CL, and Grimm SW (2010a) Role of human UGT2B10 in N-glucuronidation of tricyclic antidepressants, amitriptyline, imipramine, clomipramine, and trimipramine. Drug Metab Dispos 38:863-870.
38. Zhou J, Tracy TS, and Remmel RP (2010b) Glucuronidation of dihydrotestosterone and transandrosterone by recombinant UDP- glucuronosyltransferase (UGT) 1A4: Evidence for multiple UGT1A4 aglycone binding sites. Drug Metab Dispos 38:431-440.