Biochemical and molecular analysis of carboxylesterase-mediated hydrolysis of cocaine and heroin

British Journal of Pharmacology

Volumn 160, Issue 8, 2010, Pages 1916-1928

  Hatfield, M J ^a   Tsurkan, L ^a   Hyatt, J L ^a   Yu, X ^b   Edwards, C C ^a   Hicks, L D ^a   Wadkins, R M ^b   Potter, P M ^a  

^a ST JUDE CHILDREN S RESEARCH HOSPITAL   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

carboxylesterase; cocaine; CPT 11; heroin; inhibitor; molecular modelling

Indexed keywords

CARBOXYLESTERASE; COCAINE; DIAMORPHINE; IRINOTECAN; RECOMBINANT ENZYME; CAMPTOTHECIN; CES1 PROTEIN, HUMAN; CES2 PROTEIN, HUMAN; RECOMBINANT PROTEIN;

ARTICLE; CHEMICAL ANALYSIS; CHROMATOGRAPHY; CONTROLLED STUDY; DRUG STRUCTURE; ENZYME INHIBITION; ENZYME ISOLATION; ENZYME SUBSTRATE; HUMAN; HUMAN TISSUE; HYDROLYSIS; ION EXCHANGE CHROMATOGRAPHY; KINETICS; LIVER MICROSOME; MOLECULAR MODEL; PRIORITY JOURNAL; ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; ENZYME SPECIFICITY; ENZYMOLOGY; GENETICS; INTESTINE; ISOLATION AND PURIFICATION; LIVER; METABOLISM; PROTEIN CONFORMATION; STRUCTURE ACTIVITY RELATION;

CAMPTOTHECIN; CARBOXYLESTERASE; CARBOXYLIC ESTER HYDROLASES; CHROMATOGRAPHY; COCAINE; HEROIN; HUMANS; HYDROLYSIS; INTESTINES; KINETICS; LIVER; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN CONFORMATION; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 77954876834     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1111/j.1476-5381.2010.00700.x     Document Type: Article

References (40)

1. Anderson RN (1999). Deaths: leading causes for 1999. Natl Vital Stat Rep 49 : 1 88.
2. Beaufay H, Amar-Costesec A, Feytmans E, Thines-Sempoux D, Wibo M, Robbi M et al 1974). Analytical study of microsomes and isolated subcellular membranes from rat liver. I. Biochemical methods. J Cell Biol 61 : 188 200.
3. Bencharit S, Morton CL, Hyatt JL, Kuhn P, Danks MK, Potter PM et al 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.
4. Bencharit S, Morton CL, Xue Y, Potter PM, Redinbo MR (2003b). Structural basis of heroin and cocaine metabolism by a promiscuous human drug-processing enzyme. Nat Struct Biol 10 : 349 356.
5. Bencharit S, Edwards CC, Morton CL, Howard-Williams EL, Kuhn P, Potter PM et al 2006). Multisite promiscuity in the processing of endogenous substrates by human carboxylesterase 1. J Mol Biol 363 : 201 214.
6. Brzezinski MR, Spink BJ, Dean RA, Berkman CE, Cashman JR, Bosron WF (1997). Human liver carboxylesterase hCE-1: binding specificity for cocaine, heroin, and their metabolites and analogs. Drug Metab Dispos 25 : 1089 1096.
7. Chen H, Lyne PD, Giordanetto F, Lovell T, Li J (2006). On evaluating molecular-docking methods for pose prediction and enrichment factors. J Chem Inf Model 46 : 401 415.
8. Danks MK, Morton CL, Pawlik CA, Potter PM (1998). Overexpression of a rabbit liver carboxylesterase sensitizes human tumor cells to CPT-11. Cancer Res 58 : 20 22.
9. Danks MK, Morton CL, Krull EJ, Cheshire PJ, Richmond LB, Naeve CW et al 1999). Comparison of activation of CPT-11 by rabbit and human carboxylesterases for use in enzyme/prodrug therapy. Clin Cancer Res 5 : 917 924.
10. Dodds HM, Rivory LP (1999). The mechanism for the inhibition of acetylcholinesterases by irinotecan (CPT-11). Mol Pharmacol 56 : 1346 1353.
11. Fleming CF, Bencharit S, Edwards CC, Hyatt JL, Tsurkan L, Bai F et al 2005). Structural insights into drug processing by human carboxylesterase 1: tamoxifen, mevastatin, and inhibition by benzil. J Mol Biol 352 : 165 177.
12. Gatley SJ (1990). Rapid stereoselective hydrolysis of (+)-cocaine in baboon plasma prevents its uptake in the brain: implications for behavioral studies. J Neurochem 54 : 720 723.
13. Girardin F, Rentsch KM, Schwab MA, Maggiorini M, Pauli-Magnus C, Kullak-Ublick GA et al 2003). Pharmacokinetics of high doses of intramuscular and oral heroin in narcotic addicts. Clin Pharmacol Ther 74 : 341 352.
14. Hicks LD, Hyatt JL, Stoddard S, Tsurkan L, Edwards CC, Wadkins RM et al 2009). Improved, selective, human intestinal carboxylesterase inhibitors designed to modulate 7-ethyl-10-[4-(1-piperidino)-1-piperidino] carbonyloxycamptothecin (Irinotecan; CPT-11) toxicity. J Med Chem 52 : 3742 3752.
15. Humerickhouse R, Lohrbach K, Li L, Bosron W, Dolan M (2000). Characterization of CPT-11 hydrolysis by human liver carboxylesterase isoforms hCE-1 and hCE-2. Cancer Res 60 : 1189 1192.
16. Hyatt JL, Stacy V, Wadkins RM, Yoon KJ, Wierdl M, Edwards CC et al 2005). Inhibition of carboxylesterases by benzil (diphenylethane-1,2-dione) and heterocyclic analogues is dependent upon the aromaticity of the ring and the flexibility of the dione moiety. J Med Chem 48 : 5543 5550.
17. Hyatt JL, Wadkins RM, Tsurkan L, Hicks LD, Hatfield MJ, Edwards CC et al 2007). Planarity and constraint of the carbonyl groups in 1,2-diones are determinants for selective inhibition of human carboxylesterase 1. J Med Chem 50 : 5727 5734.
18. Kamendulis LM, Brzezinski MR, Pindel EV, Bosron WF, Dean RA (1996). Metabolism of cocaine and heroin is catalyzed by the same human liver carboxylesterases. J Pharmacol Expt Ther 279 : 713 717.
19. Khanna R, Morton CL, Danks MK, Potter PM (2000). Proficient metabolism of CPT-11 by a human intestinal carboxylesterase. Cancer Res 60 : 4725 4728.
20. Lockridge O, LaDu BN (1980). Diacetylmorphine (heroin) hydrolysis by human-serum cholinesterase (pseudocholinesterase or butyrylcholinesterase). Fed Proc 39 : 1754.
21. Mori M, Hosokawa M, Ogasawara Y, Tsukada E, Chiba K (1999). cDNA cloning, characterization and stable expression of novel human brain carboxylesterase. FEBS Lett 458 : 17 22.
22. Morton CL, Potter PM (2000). Comparison of Escherichia coli, Saccharomyces cerevisiae, Pichia pastoris, Spodoptera frugiperda and COS7 cells for recombinant gene expression: application to a rabbit liver carboxylesterase. Mol Biotechnol 16 : 193 202.
23. Morton CL, Wadkins RM, Danks MK, Potter PM (1999). CPT-11 is a potent inhibitor of acetylcholinesterase but is rapidly catalyzed to SN-38 by butyrylcholinesterase. Cancer Res 59 : 1458 1463.
24. Munger JS, Shi GP, Mark EA, Chin DT, Gerard C, Chapman HA (1991). A serine esterase released by human alveolar macrophages is closely related to liver microsomal carboxylesterases. J Biol Chem 266 : 18832 18838.
25. Pindel EV, Kedishvili NY, Abraham TL, Brzezinski MR, Zhang J, Dean RA et al 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. (Pubitemid 27251744)
26. Potter PM, Wadkins RM (2006). Carboxylesterases - detoxifying enzymes and targets for drug therapy. Curr Med Chem 13 : 1045 1054.
27. Potter PM, Wolverton JS, Morton CL, Wierdl M, Danks MK (1998). Cellular localization domains of a rabbit and a human carboxylesterase: influence on irinotecan (CPT-11) metabolism by the rabbit enzyme. Cancer Res 58 : 3627 3632.
28. Redinbo MR, Potter PM (2005). Mammalian carboxylesterases: from drug targets to protein therapeutics. Drug Discov Today 10 : 313 325.
29. Sali A, Blundell TJ (1993). Comparitive protein modelling by satisfaction of spatial restraints. J Mol Biol 234 : 779 815.
30. Schwer H, Langmann T, Daig R, Becker A, Aslanidis C, Schmitz G (1997). Molecular cloning and characterization of a novel putative carboxylesterase, present in human intestine and liver. Biochem Biophys Res Comm 233 : 117 120.
31. Stewart DJ, Inaba T, Tang BK, Kalow W (1977). Hydrolysis of cocaine in human plasma by cholinesterase. Life Sci 20 : 1557 1563.
32. Tabata T, Katoh M, Tokudome S, Nakajima M, 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.
33. Wadkins RM, Morton CL, Weeks JK, Oliver L, Wierdl M, Danks MK et al 2001). Structural constraints affect the metabolism of 7-ethyl-10-[4-(1- piperidino)-1-piperidino]carbonyloxycamptothecin (CPT-11) by carboxylesterases. Mol Pharmacol 60 : 355 362.
34. Wadkins RM, Hyatt JL, Yoon KJ, Morton CL, Lee RE, Damodaran K et al 2004). Identification of novel selective human intestinal carboxylesterase inhibitors for the amelioration of irinotecan-induced diarrhea: synthesis, quantitative structure-activity relationship analysis, and biological activity. Mol Pharmacol 65 : 1336 1343.
35. Wadkins RM, Hyatt JL, Wei X, Yoon KJ, Wierdl M, Edwards CC et al 2005). Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem 48 : 2905 2915.
36. Webb JL (1963). Enzyme and Metabolic Inhibitors. Volume 1. General Principles of Inhibition. Academic Press Inc
37. Wierdl M, Tsurkan L, Hyatt JL, Hatfield MJ, Edwards CC, Danks MK et al 2008). An improved human carboxylesterase for use in enzyme/prodrug therapy with CPT-11. Cancer Gene Ther 15 : 183 192.
38. Wu MH, Chen P, Remo BF, Cook EH Jr., Das S, Dolan ME (2003). Characterization of multiple promoters in the human carboxylesterase 2 gene. Pharmacogenetics 13 : 425 435.
39. Zhang J, Burnell JC, Dumaual N, Bosron WF (1999). Binding and hydrolysis of meperidine by human liver carboxylesterase hCE-1. J Pharmacol Exp Ther 290 : 314 318.
40. Zhu HJ, Patrick KS, Yuan HJ, Wang JS, Donovan JL, DeVane CL et al 2008). Two CES1 gene mutations lead to dysfunctional carboxylesterase 1 activity in man: clinical significance and molecular basis. Am J Hum Genet 82 : 1241 1248.