Screening of specific inhibitors for human carboxylesterases or arylacetamide deacetylase

Drug Metabolism and Disposition

Volumn 42, Issue 7, 2014, Pages 1103-1109

  Shimizu, Mai ^a   Fukami, Tatsuki ^a   Nakajima, Miki ^a   Yokoi, Tsuyoshi ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLORO 3',4' DIMETHOXYBENZIL; 2,6 DICHLORO 4 NITROPHENOL; 3,3',5 TRIIODO LEVO THYROXINE FREE ACID; 4 CHLORO 1 NAPHTHOL; 4 HYDROXYBENZOIC ACID N HEXYL ESTER; 4 NITROPHENYL ACETATE; 4' HYDROXYDICLOFENAC; ACEMETACIN; ACETIC ACID; ARYLACETAMIDE DEACETYLASE; BENZBROMARONE; BENZYLSULFONYL FLUORIDE; CARBOXYLESTERASE; CARBOXYLESTERASE 1; CARBOXYLESTERASE 2; DICLOFENAC; DIGITONIN; ENZYME INHIBITOR; FLAVOXATE; HYDROLASE; IRINOTECAN; LEVOTHYROXINE; LIDOCAINE; LITHOCHOLIC ACID; NORDIHYDROGUAIARETIC ACID; PHENACETIN; SIMVASTATIN; TELMISARTAN; UNCLASSIFIED DRUG; UNINDEXED DRUG; VINBLASTINE; ACETYLESTERASE;

ARTICLE; CELL ORGANELLE; CONTROLLED STUDY; DRUG HYDROLYSIS; DRUG POTENCY; DRUG SCREENING; DRUG SPECIFICITY; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; LIVER MACROSOME; LIVER MICROSOME; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; ANTAGONISTS AND INHIBITORS; CHEMISTRY;

ACETYLESTERASE; CARBOXYLIC ESTER HYDROLASES; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; HUMANS;

EID: 84903190897     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.114.056994     Document Type: Article

References (41)

1. Bencharit S, Edwards CC, Morton CL, Howard-Williams EL, Kuhn P, Potter PM, and Redinbo MR (2006) Multisite promiscuity in the processing of endogenous substrates by human carboxylesterase 1. J Mol Biol 363:201-214.
2. Chang JW, Nomura DK, and Cravatt BF (2011) A potent and selective inhibitor of KIAA1363/AADACL1 that impairs prostate cancer pathogenesis. Chem Biol 18:476-484.
3. Fukami T, Nakajima M, Maruichi T, Takahashi S, Takamiya M, Aoki Y, McLeod HL, and Yokoi T (2008) Structure and characterization of human carboxylesterase 1A1, 1A2, and 1A3 genes. Pharmacogenet Genomics 18:911-920.
4. 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.
5. Fukami T and Yokoi T (2012) The emerging role of human esterases. Drug Metab Pharmacokinet 27:466-477.
6. Frick C, Atanasov AG, Arnold P, Ozols J, and Odermatt A (2004) Appropriate function of 11β-hydroxysteroid dehydrogenase type 1 in the endoplasmic reticulum lumen is dependent on its N-terminal region sharing similar topological determinants with 50-kDa esterase. J Biol Chem 279:31131-31138.
7. Gonzalvo MC, Gil F, Hernandez AF, Rodrigo L, Villanueva E, and Pla A (1998) Human liver paraoxonase (PON1): subcellular distribution and characterization. J Biochem Mol Toxicol 12: 61-69.
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. Higuchi R, Fukami T, Nakajima M, and Yokoi T (2013) Prilocaine- and lidocaine-induced methemoglobinemia is caused by human carboxylesterase-, CYP2E1-, and CYP3A4-mediated metabolic activation. Drug Metab Dispos 41:1220-1230.
10. Holmes RS, Wright MW, Laulederkind SJ, Cox LA, Hosokawa M, Imai T, Ishibashi S, Lehner R, Miyazaki M, and Perkins EJ, et al. (2010) Recommended nomenclature for five mammalian carboxylesterase gene families: human, mouse, and rat genes and proteins. Mamm Genome 21: 427-441.
11. Hosokawa M, Endo T, Fujisawa M, Hara S, Iwata N, Sato Y, and Satoh T (1995) Interindividual variation in carboxylesterase levels in human liver microsomes. Drug Metab Dispos 23: 1022-1027.
12. Humerickhouse R, Lohrbach K, Li L, Bosron WF, and Dolan ME (2000) Characterization of CPT-11 hydrolysis by human liver carboxylesterase isoforms hCE-1 and hCE-2. Cancer Res 60:1189-1192.
13. Ishiguro N, Maeda K, Kishimoto W, Saito A, Harada A, Ebner T, Roth W, Igarashi T, and Sugiyama Y (2006) Predominant contribution of OATP1B3 to the hepatic uptake of telmisartan, an angiotensin II receptor antagonist, in humans. Drug Metab Dispos 34: 1109-1115.
14. Iwatsubo K (1965) Studies on the classification of the enzymes hydrolyzing ester-form drugs in liver microsomes. Jpn J Pharmacol 15:244-265.
15. Jbilo O, Bartels CF, Chatonnet A, Toutant JP, and Lockridge O (1994) Tissue distribution of human acetylcholinesterase and butyrylcholinesterase messenger RNA. Toxicon 32: 1445-1457.
16. Karanth S and Pope C (2000) Carboxylesterase and A-esterase activities during maturation and aging: relationship to the toxicity of chlorpyrifos and parathion in rats. Toxicol Sci 58:282-289.
17. Kobayashi Y, Fukami T, Higuchi R, Nakajima M, and Yokoi T (2012a) Metabolic activation by human arylacetamide deacetylase, CYP2E1, and CYP1A2 causes phenacetin-induced methemoglobinemia. Biochem Pharmacol 84:1196-1206.
18. Kobayashi Y, Fukami T, Shimizu M, Nakajima M, and Yokoi T (2012b) Contributions of arylacetamide deacetylase and carboxylesterase 2 to flutamide hydrolysis in human liver. Drug Metab Dispos 40:1080-1084.
19. Kuo CL and La Du BN (1998) Calcium binding by human and rabbit serum paraoxonases. Structural stability and enzymatic activity. Drug Metab Dispos 26:653-660.
20. Nakajima A, Fukami T, Kobayashi Y, Watanabe A, Nakajima M, and Yokoi T (2011) Human arylacetamide deacetylase is responsible for deacetylation of rifamycins: rifampicin, rifabutin, and rifapentine. Biochem Pharmacol 82:1747-1756.
21. Nakamori F, Naritomi Y, Hosoya K, Moriguchi H, Tetsuka K, Furukawa T, Kadono K, Yamano K, Terashita S, and Teramura T (2012) Quantitative prediction of human intestinal glucuronidation effects on intestinal availability of UDP-glucuronosyltransferase substrates using in vitro data. Drug Metab Dispos 40:1771-1777.
22. Ng CJ, Wadleigh DJ, Gangopadhyay A, Hama S, Grijalva VR, Navab M, Fogelman AM, and Reddy ST (2001) Paraoxonase-2 is a ubiquitously expressed protein with antioxidant properties and is capable of preventing cell-mediated oxidative modification of low density lipoprotein. J Biol Chem 276:44444-44449.
23. Ohura K, Tasaka K, Hashimoto M, and Imai T (2014) Distinct patterns of aging effects on the expression and activity of carboxylesterases in rat liver and intestine. Drug Metab Dispos 42:264-273.
24. Parkinson EI, Jason Hatfield M, Tsurkan L, Hyatt JL, Edwards CC, Hicks LD, Yan B, and Potter PM (2011) Requirements for mammalian carboxylesterase inhibition by substituted ethane-1,2-diones. Bioorg Med Chem 19:4635-4643.
25. Quinney SK, Sanghani SP, Davis WI, Hurley TD, Sun Z, Murry DJ, and Bosron WF (2005) Hydrolysis of capecitabine to 5′-deoxy-5-fluorocytidine by human carboxylesterases and inhibition by loperamide. J Pharmacol Exp Ther 313:1011-1016.
26. Sato Y, Miyashita A, Iwatsubo T, and Usui T (2012) Simultaneous absolute protein quantification of carboxylesterases 1 and 2 in human liver tissue fractions using liquid chromatographytandem mass spectrometry. Drug Metab Dispos 40:1389-1396.
27. Shimizu M, Fukami T, Kobayashi Y, Takamiya M, Aoki Y, Nakajima M, and Yokoi T (2012) A novel polymorphic allele of human arylacetamide deacetylase leads to decreased enzyme activity. Drug Metab Dispos 40:1183-1190.
28. Stewart DJ, Lu K, Benjamin RS, Leavens ME, Luna M, Yap HY, and Loo TL (1983) Concentration of vinblastine in human intracerebral tumor and other tissues. J Neurooncol 1: 139-144.
29. Tabata T, Katoh M, Tokudome S, Nakajima M, and Yokoi T (2004) Identification of the cytosolic carboxylesterase catalyzing the 5′-deoxy-5-fluorocytidine formation from capecitabine in human liver. Drug Metab Dispos 32:1103-1110.
30. Takahashi S, Katoh M, Saitoh T, Nakajima M, and Yokoi T (2009) Different inhibitory effects in rat and human carboxylesterases. Drug Metab Dispos 37:956-961.
31. Takusagawa S, Yajima K, Miyashita A, Uehara S, Iwatsubo T, and Usui T (2012) Identification of human cytochrome P450 isoforms and esterases involved in the metabolism of mirabegron, a potent and selective b3-adrenoceptor agonist. Xenobiotica 42:957-967.
32. Wadkins RM, Hyatt JL, Edwards CC, Tsurkan L, Redinbo MR, Wheelock CE, Jones PD, Hammock BD, and Potter PM (2007) Analysis of mammalian carboxylesterase inhibition by trifluoromethylketone-containing compounds. Mol Pharmacol 71:713-723.
33. Wadkins RM, Hyatt JL, Wei X, Yoon KJ, Wierdl M, Edwards CC, Morton CL, Obenauer JC, Damodaran K, and Beroza P, et al. (2005) Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem 48:2906-2915.
34. Wadkins RM, Hyatt JL, Yoon KJ, Morton CL, Lee RE, Damodaran K, Beroza P, Danks MK, and Potter PM (2004) Discovery of novel selective inhibitors of human intestinal carboxylesterase for the amelioration of irinotecan-induced diarrhea: synthesis, quantitative structure-activity relationship analysis, and biological activity. Mol Pharmacol 65: 1336-1343.
35. Wang J, Williams ET, Bourgea J, Wong YN, and Patten CJ (2011) Characterization of recombinant human carboxylesterases: fluorescein diacetate as a probe substrate for human carboxylesterase 2. Drug Metab Dispos 39:1329-1333.
36. Watanabe A, Fukami T, Nakajima M, Takamiya M, Aoki Y, and Yokoi T (2009) Human arylacetamide deacetylase is a principal enzyme in flutamide hydrolysis. Drug Metab Dispos 37:1513-1520.
37. Watanabe A, Fukami T, Takahashi S, Kobayashi Y, Nakagawa N, Nakajima M, and Yokoi T (2010) Arylacetamide deacetylase is a determinant enzyme for the difference in hydrolase activities of phenacetin and acetaminophen. Drug Metab Dispos 38:1532-1537.
38. Xie M, Yang D, Liu L, Xue B, and Yan B (2002) Human and rodent carboxylesterases: immunorelatedness, overlapping substrate specificity, differential sensitivity to serine enzyme inhibitors, and tumor-related expression. Drug Metab Dispos 30:541-547.
39. Xu G, Zhang W, Ma MK, and McLeod HL (2002) Human carboxylesterase 2 is commonly expressed in tumor tissue and is correlated with activation of irinotecan. Clin Cancer Res 8:2605-2611.
40. 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.
41. Yanjiao X, Chengliang Z, Xiping L, Tao W, Xiuhua R, and Dong L (2013) Evaluation of the inhibitory effects of antihypertensive drugs on human carboxylesterase in vitro. Drug Metab Pharmacokinet 28:468-474.