An orphan esterase ABHD10 modulates probenecid acyl glucuronidation in human liver

Drug Metabolism and Disposition

Volumn 42, Issue 12, 2014, Pages 2109-2116

  Ito, Yusuke ^a   Fukami, Tatsuki ^a   Yokoi, Tsuyoshi ^a,b   Nakajima, Miki ^a  

^a KANAZAWA UNIVERSITY   (Japan)

^b NAGOYA UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABHD10 PROTEIN; BENZYLSULFONYL FLUORIDE; CARBOXYLESTERASE; ESTERASE; GLUCURONOSYLTRANSFERASE 1A1; GLUCURONOSYLTRANSFERASE 1A9; GLUCURONOSYLTRANSFERASE 2B7; PROBENECID; PROBENECID ACYL GLUCURONIDE; UNCLASSIFIED DRUG; ABHD10 PROTEIN, HUMAN; GLUCURONIDE; GLUCURONOSYLTRANSFERASE; HYDROLASE;

ARTICLE; CATALYSIS; CONTROLLED STUDY; DRUG CLEARANCE; DRUG GLUCURONIDATION; ENZYME ACTIVITY; ENZYME INHIBITION; FEMALE; HUMAN; HUMAN TISSUE; LIVER; LIVER HOMOGENATE; MALE; PRIORITY JOURNAL; HYDROLYSIS; LIVER MICROSOME; METABOLISM;

ESTERASES; FEMALE; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HUMANS; HYDROLASES; HYDROLYSIS; LIVER; MALE; MICROSOMES, LIVER; PROBENECID;

EID: 84924952946     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.114.059485     Document Type: Article

References (48)

1. Bernard P, Goudonnet H, Artur Y, Desvergne B, and Wahli W (1999) Activation of the mouse TATA-less and human TATA-containing UDP-glucuronosyltransferase 1A1 promoters by hepatocyte nuclear factor 1. Mol Pharmacol 56:526-536.
2. Dubois-Presle N, Lapicque F, Maurice MH, Fournel-Gigleux S, Magdalou J, Abiteboul M, Siest G, and Netter P (1995) Stereoselective esterase activity of human serum albumin toward ketoprofen glucuronide. Mol Pharmacol 47:647-653.
3. Fallon JK, Neubert H, Hyland R, Goosen TC, and Smith PC (2013) Targeted quantitative proteomics for the analysis of 14 UGT1As and -2Bs in human liver using NanoUPLC-MS/MS with selected reaction monitoring. J Proteome Res 12:4402-4413.
4. Fujiwara R, Nakajima M, Oda S, Yamanaka H, Ikushiro S, Sakaki T, and Yokoi T (2010) Interactions between human UDP-glucuronosyltransferase (UGT) 2B7 and UGT1A enzymes. J Pharm Sci 99:442-454.
5. Fukami T, Takahashi S, Nakagawa N, Maruichi T, Nakajima M, and Yokoi T (2010) In vitro evaluation of inhibitory effects of antidiabetic and antihyperlipidemic drugs on human carboxylesterase activities. Drug Metab Dispos 38:2173-2178.
6. Fukami T and Yokoi T (2012) The emerging role of human esterases. Drug Metab Pharmacokinet 27:466-477.
7. Gregory PA, Lewinsky RH, Gardner-Stephen DA, and Mackenzie PI (2004) Coordinate regulation of the human UDP-glucuronosyltransferase 1A8, 1A9, and 1A10 genes by hepatocyte nuclear factor 1a and the caudal-related homeodomain protein 2. Mol Pharmacol 65:953-963.
8. Heymann E and Krisch K (1967) [Phosphoric acid-bis-(p-nitro-phenylester), a new inhibitor of microsomal carboxylesterases]. Hoppe Seylers Z Physiol Chem 348:609-619.
9. Hillecke NA (1965) Acute anaphylactoid reaction to probenecid. JAMA 193:740.
10. Hioki T, Fukami T, Nakajima M, and Yokoi T (2011) Human paraoxonase 1 is the enzyme responsible for pilocarpine hydrolysis. Drug Metab Dispos 39:1345-1352.
11. Ishii Y, Hansen AJ, and Mackenzie PI (2000) Octamer transcription factor-1 enhances hepatic nuclear factor-1a-mediated activation of the human UDP glucuronosyltransferase 2B7 promoter. Mol Pharmacol 57:940-947.
12. Israili ZH, Percel JM, Cunningham RF, Dayton PG, Yü TF, Gutman AB, Long KR, Long RC, Jr, and Goldstein JH (1972) Metabolites of probenecid. Chemical, physical, and pharmacological studies. J Med Chem 15:709-713.
13. Iwamura A, Fukami T, Higuchi R, Nakajima M, and Yokoi T (2012) Human α/β hydrolase domain containing 10 (ABHD10) is responsible enzyme for deglucuronidation of mycophenolic acid acyl-glucuronide in liver. J Biol Chem 287:9240-9249.
14. Iwatsubo K (1965) Studies on the classification of the enzymes hydrolysing ester-form drugs in liver microsomes. Jpn J Pharmacol 15:244-265.
15. Jinno N, Ohashi S, Tagashira M, Kohira T, and Yamada S (2013) A simple method to evaluate reactivity of acylglucuronides optimized for early stage drug discovery. Biol Pharm Bull 36:1509-1513.
16. Johnson G and Moore SW (2000) Cholinesterase-like catalytic antibodies: reaction with substrates and inhibitors. Mol Immunol 37:707-719.
17. Kato Y, Nakajima M, Oda S, Fukami T, and Yokoi T (2012) Human UDP-glucuronosyltransferase isoforms involved in haloperidol glucuronidation and quantitative estimation of their contribution. Drug Metab Dispos 40:240-248.
18. Kobayashi Y, Fukami T, Shimizu M, Nakajima M, and Yokoi T (2012) Contributions of arylacetamide deacetylase and carboxylesterase 2 to flutamide hydrolysis in human liver. Drug Metab Dispos 40:1080-1084.
19. Kuehl GE, Lampe JW, Potter JD, and Bigler J (2005) Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab Dispos 33:1027-1035.
20. Labar G, Bauvois C, Muccioli GG, Wouters J, and Lambert DM (2007) Disulfiram is an inhibitor of human purified monoacylglycerol lipase, the enzyme regulating 2-arachidonoylglycerol signaling. ChemBioChem 8:1293-1297.
21. Lass A, Zimmermann R, Haemmerle G, Riederer M, Schoiswohl G, Schweiger M, Kienesberger P, Strauss JG, Gorkiewicz G, and Zechner R (2006) Adipose triglyceride lipase-mediated lipolysis of cellular fat stores is activated by CGI-58 and defective in Chanarin-Dorfman Syndrome. Cell Metab 3:309-319.
22. Levvy GA (1952) The preparation and properties of β-glucuronidase. IV. Inhibition by sugar acids and their lactones. Biochem J 52:464-472.
23. 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.
24. Marrs WR, Blankman JL, Horne EA, Thomazeau A, Lin YH, Coy J, Bodor AL, Muccioli GG, Hu SS, and Woodruff G, et al. (2010) The serine hydrolase ABHD6 controls the accumulation and efficacy of 2-AG at cannabinoid receptors. Nat Neurosci 13:951-957.
25. Minagawa T, Kohno Y, Suwa T, and Tsuji A (1995) Species differences in hydrolysis of isocarbacyclin methyl ester (TEI-9090) by blood esterases. Biochem Pharmacol 49:1361-1365.
26. Miners JO, Bowalgaha K, Elliot DJ, Baranczewski P, and Knights KM (2011) Characterization of niflumic acid as a selective inhibitor of human liver microsomal UDP-glucuronosyltransferase 1A9: application to the reaction phenotyping of acetaminophen glucuronidation. Drug Metab Dispos 39:644-652.
27. Oda S, Nakajima M, Hatakeyama M, Fukami T, and Yokoi T (2012) Preparation of a specific monoclonal antibody against human UDP-glucuronosyltransferase (UGT) 1A9 and evaluation of UGT1A9 protein levels in human tissues. Drug Metab Dispos 40:1620-1627.
28. Ohtsuki S, Schaefer O, Kawakami H, Inoue T, Liehner S, Saito A, Ishiguro N, Kishimoto W, Ludwig-Schwellinger E, and Ebner T, et al. (2012) Simultaneous absolute protein quantification of transporters, cytochromes P450, and UDP-glucuronosyltransferases as a novel approach for the characterization of individual human liver: comparison with mRNA levels and activities. Drug Metab Dispos 40:83-92.
29. Perel JM, Cunningham RF, Fales HM, and Dayton PG (1970) Identification and renal excretion of probenecid metabolites in man. Life Sci I 9:1337-1343.
30. Preuss CV and Svensson CK (1996) Arylacetamide deacetylase activity towards monoacetyldapsone. Species comparison, factors that influence activity, and comparison with 2-acetylaminofluorene and p-nitrophenyl acetate hydrolysis. Biochem Pharmacol 51:1661-1668.
31. Ramírez J, Mirkov S, Zhang W, Chen P, Das S, Liu W, Ratain MJ, and Innocenti F (2008) Hepatocyte nuclear factor-1 alpha is associated with UGT1A1, UGT1A9 and UGT2B7 mRNA expression in human liver. Pharmacogenomics J 8:152-161.
32. Rowe BJ and Meffin PJ (1984) Diisopropylfluorophosphate increases clofibric acid clearance: supporting evidence for a futile cycle. J Pharmacol Exp Ther 230:237-241.
33. Rowland A, Miners JO, and Mackenzie PI (2013) The UDP-glucuronosyltransferases: their role in drug metabolism and detoxification. Int J Biochem Cell Biol 45:1121-1132.
34. Sakaguchi K, Green M, Stock N, Reger TS, Zunic J, and King C (2004) Glucuronidation of carboxylic acid containing compounds by UDP-glucuronosyltransferase isoforms. Arch Biochem Biophys 424:219-225.
35. Sallustio BC, Fairchild BA, and Pannall PR (1997) Interaction of human serum albumin with the electrophilic metabolite 1-O-gemfibrozil-β-D-glucuronide. Drug Metab Dispos 25:55-60.
36. Sato Y, Nagata M, Tetsuka K, Tamura K, Miyashita A, Kawamura A, and Usui T (2014) Optimized methods for targeted peptide-based quantification of human uridine 5′-diphosphate-glucuronosyltransferases in biological specimens using liquid chromatography-tandem mass spectrometry. Drug Metab Dispos 42:885-889.
37. Satoh T and Hosokawa M (1998) The mammalian carboxylesterases: from molecules to functions. Annu Rev Pharmacol Toxicol 38:257-288.
38. Sawamura R, Okudaira N, Watanabe K, Murai T, Kobayashi Y, Tachibana M, Ohnuki T, Masuda K, Honma H, and Kurihara A, et al. (2010) Predictability of idiosyncratic drug toxicity risk for carboxylic acid-containing drugs based on the chemical stability of acyl glucuronide. Drug Metab Dispos 38:1857-1864.
39. Smith PC, McDonagh AF, and Benet LZ (1990) Effect of esterase inhibition on the disposition of zomepirac glucuronide and its covalent binding to plasma proteins in the guinea pig. J Pharmacol Exp Ther 252:218-224.
40. Smith PC, Song WQ, and Rodriguez RJ (1992) Covalent binding of etodolac acyl glucuronide to albumin in vitro. Drug Metab Dispos 20:962-965.
41. 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 301:382-390.
42. Southwood HT, DeGraaf YC, Mackenzie PI, Miners JO, Burcham PC, and Sallustio BC (2007) Carboxylic acid drug-induced DNA nicking in HEK293 cells expressing human UDP-glucuronosyltransferases: role of acyl glucuronide metabolites and glycation pathways. Chem Res Toxicol 20:1520-1527.
43. Spahn-Langguth H and Benet LZ (1992) Acyl glucuronides revisited: is the glucuronidation process a toxification as well as a detoxification mechanism? Drug Metab Rev 24:5-47.
44. Suzuki E, Yamamura N, Ogura Y, Nakai D, Kubota K, Kobayashi N, Miura S, and Okazaki O (2010) Identification of valproic acid glucuronide hydrolase as a key enzyme for the interaction of valproic acid with carbapenem antibiotics. Drug Metab Dispos 38:1538-1544.
45. Tachibana M, Tanaka M, Masubuchi Y, and Horie T (2005) Acyl glucuronidation of fluoroquinolone antibiotics by the UDP-glucuronosyltransferase 1A subfamily in human liver microsomes. Drug Metab Dispos 33:803-811.
46. Thomas G, Betters JL, Lord CC, Brown AL, Marshall S, Ferguson D, Sawyer J, Davis MA, Melchior JT, and Blume LC, et al. (2013) The serine hydrolase ABHD6 Is a critical regulator of the metabolic syndrome. Cell Reports 5:508-520.
47. Volland C, Sun H, Dammeyer J, and Benet LZ (1991) Stereoselective degradation of the fenoprofen acyl glucuronide enantiomers and irreversible binding to plasma protein. Drug Metab Dispos 19:1080-1086.
48. Yamaori S, Fujiyama N, Kushihara M, Funahashi T, Kimura T, Yamamoto I, Sone T, Isobe M, Ohshima T, and Matsumura K, et al. (2006) Involvement of human blood arylesterases and liver microsomal carboxylesterases in nafamostat hydrolysis. Drug Metab Pharmacokinet 21:147-155.