Different inhibitory effects in rat and human carboxylesterases

Drug Metabolism and Disposition

Volumn 37, Issue 5, 2009, Pages 956-961

  Takahashi, Shiori ^a   Katoh, Miki ^a   Saitoh, Takashi ^a   Nakajima, Miki ^a   Yokoi, Tsuyoshi ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

7 ETHYL 10 HYDROXYCAMPTOTHECIN; ACEMETACIN; CAPECITABINE; CARBOXYLESTERASE; CARBOXYLESTERASE 1; CARBOXYLESTERASE 2; CARVEDILOL; CIPROFLOXACIN; DELAPRIL; DEXAMETHASONE; DOCETAXEL; IMIDAPRIL; IMIDAPRILAT; IRINOTECAN; MANIDIPINE; NIFEDIPINE; NORDIHYDROGUAIARETIC ACID; PHYSOSTIGMINE; PROCAINAMIDE; PROGLUMIDE; TEMOCAPRIL; TEMOCAPRILAT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG HYDROLYSIS; DRUG INHIBITION; ENZYME ACTIVITY; HUMAN; HUMAN TISSUE; JEJUNUM MUCOSA; LIVER CYTOSOL; LIVER MICROSOME METABOLISM; MALE; NONHUMAN; PRIORITY JOURNAL; RAT;

ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; ANIMALS; CAMPTOTHECIN; CARBOXYLIC ESTER HYDROLASES; CYTOSOL; ENZYME INHIBITORS; HUMANS; IMIDAZOLIDINES; JEJUNUM; LIVER; MICROSOMES, LIVER; PHARMACEUTICAL PREPARATIONS; RATS; RATS, WISTAR; SPECIES SPECIFICITY;

RATTUS;

EID: 66449112461     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.108.024331     Document Type: Article

References (28)

1. Bailey DN and Briggs JR (2003) Procainamide and quinidine inhibition of the human hepatic degradation of meperidine in vitro. J Anal Toxicol 27:142-144.
2. Bencharit S, Morton CL, Hyatt JL, Kuhn P, Danks MK, Potter PM, and Redinbo MR (2003a) Crystal structure of human carboxylesterase 1 complexed with the Alzheimer's drug tacrine: from binding promiscuity to selective inhibition. Chem Biol 10:341-349.
3. Bencharit S, Morton CL, Xue Y, Potter PM, and Redinbo MR (2003b) Structural basis of heroin and cocaine metabolism by a promiscuous human drug-processing enzyme. Nat Struct Biol 10:349-356.
4. Buratti FM and Testai E (2005) Malathion detoxification by human hepatic carboxylesterases and its inhibition by isomalathion and other pesticides. J Biochem Mol Toxicol 19:406-414.
5. Emoto C, Yamazaki H, Iketaki H, Yamasaki S, Satoh T, Shimizu R, Suzuki S, Shimada N, Nakajima M, and Yokoi T (2001) Cooperativity of a-naphthoflavone in cytochrome P450 3A-dependent drug oxidation activities in hepatic and intestinal microsomes from mouse and human. Xenobiotica 31:265-275.
6. Fleming CD, Bencharit S, Edwards CC, Hyatt JL, Tsurkan L, Bai F, Fraga C, Morton CL, Howard-Williams EL, Potter PM, et al. (2005) Structural insights into drug processing by human carboxylesterase 1: tamoxifen, mevastatin, and inhibition by benzil. J Mol Biol 352:165-177.
7. 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.
8. Imai T (2006) Human carboxylesterase isozymes: catalytic properties and rational drug design. Drug Metab Pharmacokinet 21:173-185.
9. Jaganathan L and Boopathy R (1998) Interaction of Triton X-100 with acyl pocket of butyryl- cholinesterase: effect on esterase activity and inhibitor sensitivity of the enzyme. Indian J Biochem Biophys 35:142-147.
10. Linke T, Dawson H, and Harrison EH (2005) Isolation and characterization of a microsomal acid retinyl ester hydrolase. J Biol Chem 280:23287-23294.
11. Masaki K, Hashimoto M, and Imai T (2007) Intestinal first-pass metabolism via carboxylesterase in rat jejunum and ileum. Drug Metab Dispos 35:1089 -1095.
12. Mesange F, Sebbar M, Capdevielle J, Guillemot JC, Ferrara P, Bayard F, Poirot M, and Faye JC (2002) Identification of two tamoxifen target proteins by photolabeling with 4-(2- morpholinoethoxy)benzophenone. Bioconjug Chem 13:766-772.
13. Murakami K, Takagi Y, Mihara K, and Omura T (1993) An isozyme of microsomal carboxyes terases, carboxyesterase Sec, is secreted from rat liver into the blood. J Biochem 113:61-66.
14. Pindel EV, Kedishvili NY, Abraham TL, Brzezinski MR, Zhang J, Dean RA, and Bosron WF (1997) Purification and cloning of a broad substrate specificity human liver carboxylesterase that catalyzes the hydrolysis of cocaine and heroin. J Biol Chem 272:14769 -14775.
15. 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.
16. Rush RS, Main AR, Kilpatrick BF, and Faulkner GD (1981) Inhibition of two monomeric butyrylcholinesterases from rabbit liver by chlorpromazine and other drugs. J Pharmacol Exp Ther 216:586 -591.
17. Sanghani SP, Davis WI, Dumaual NG, Mahrenholz A, and Bosron WF (2002) Identification of microsomal rat liver carboxylesterases and their activity with retinyl palmitate. Eur J Biochem 269:4387-4398.
18. Sanghani SP, Quinney SK, Fredenburg TB, Davis WI, Murry DJ, and Bosron WF (2004) Hydrolysis of irinotecan and its oxidative metabolites, 7-ethyl-10-[4-N-(5-aminopentanoic acid)-1-piperidino] carbonyloxycamptothecin and 7-ethyl-10-[4-(1-piperidino)-1-amino]- carbonyloxycamptothecin, by human carboxylesterases CES1A1, CES2, and a newly expressed carboxylesterase isoenzyme, CES3. Drug Metab Dispos 32:505-511.
19. Satoh T and Hosokawa M (1995) Molecular aspects of carboxylesterase isoforms in comparison with other esterases. Toxicol Lett 82-83:439-445.
20. Satoh T, Hosokawa M, Atsumi R, Suzuki W, Hakusui H, and Nagai E (1994) Metabolic activation of CPT-11, 7-ethyl-10-[4-(1-piperidino)-1-piperidino] carbonyloxycamptothecin, a novel antitumor agent, by carboxylesterase. Biol Pharm Bull 17:662-664.
21. Satoh T, Taylor P, Bosron WF, Sanghani SP, Hosokawa M, and La Du BN (2002) Current progress on esterases: from molecular structure to function. Drug Metab Dispos 30:488 -493.
22. Schegg KM and Welch W Jr (1984) The effect of nordihydroguaiaretic acid and related lignans on formyltetrahydrofolate synthetase and carboxylesterase. Biochim Biophys Acta 788:167180.
23. Schwer H, Langmann T, Daig R, Becker A, Aslanidis C, and Schmitz G (1997) Molecular cloning and characterization of a novel putative carboxylesterase, present in human intestine and liver. Biochem Biophys Res Commun 233:117-120.
24. 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 capecit- abine in human liver. Drug Metab Dispos 32:1103-1110.
25. Takahashi S, Katoh M, Saitoh T, Nakajima M, and Yokoi T (2008) Allosteric kinetics of human carboxylesterase 1: species differences and interindividual variability. J Pharm Sci 97:5434-5445.
26. Takai S, Matsuda A, Usami Y, Adachi T, Sugiyama T, Katagiri Y, Tatematsu M, and Hirano K (1997) Hydrolytic profile for ester- or amide-linkage by carboxylesterases pI 5.3 and 4.5 from human liver. Biol Pharm Bull 20:869 -873.
27. 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.
28. Wadkins RM, Morton CL, Weeks JK, Oliver L, Wierdl M, Danks MK, and Potter PM (2001) Structural constraints affect the metabolism of 7-ethyl-10-[4-(1- piperidino)-1-piperidino]car- bonyloxycamptothecin (CPT-11) by carboxylesterases. Mol Pharmacol 60:355-362.