Carboxylesterase inhibitors

Expert Opinion on Therapeutic Patents

Volumn 21, Issue 8, 2011, Pages 1159-1171

  Hatfield, M Jason ^a   Potter, Philip M ^a  

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

Author keywords

carboxylesterase; ester; hydrolysis; inhibitor

Indexed keywords

BENZIL; BIS(4 NITROPHENYL) PHOSPHATE; CARBOXYLESTERASE; CARBOXYLESTERASE INHIBITOR; CHOLESTEROL DERIVATIVE; ESTERASE INHIBITOR; HYRTIOSIN B; ISATIN DERIVATIVE; KETONE DERIVATIVE; LOPERAMIDE; PESTICIDE; SULFONAMIDE; TRIFLUOROKETONE DERIVATIVE; UNCLASSIFIED DRUG;

DRUG EFFECT; DRUG ISOLATION; DRUG MECHANISM; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; NONHUMAN; REVIEW;

ANIMALS; CARBOXYLIC ESTER HYDROLASES; DRUG INTERACTIONS; DRUG STABILITY; ENZYME INHIBITORS; HUMANS; HYDROLYSIS; PHARMACOKINETICS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79960687534     PISSN: 13543776     EISSN: 17447674     Source Type: Journal    
DOI: 10.1517/13543776.2011.586339     Document Type: Review

References (88)

1. Potter PM, Wadkins RM. Carboxylesterases - detoxifying enzymes and targets for drug therapy. Curr Med Chem 2006;21:1045-54
2. Redinbo MR, Potter PM. Mammalian Carboxylesterases: From drug targets to protein therapeutics. Drug Discov Today 2005;10:313-25
3. Cashman J, Perroti B, Berkman C, et al. Pharmacokinetics and molecular detoxification. Environ Health Perspect 1996;104:23-40
4. Bencharit S, Edwards CC, Morton CL, et al. Multisite promiscuity in the processing of endogenous substrates by human carboxylesterase 1. J Mol Biol 2006;363:201-14 (Pubitemid 44414849)
5. Humerickhouse R, Lohrbach K, Li L, et al. Characterization of CPT-11 hydrolysis by human liver carboxylesterase isoforms hCE-1 and hCE-2. Cancer Res 2000;60:1189-92 (Pubitemid 30151980)
6. Khanna R, Morton CL, Danks MK, et al. Proficient metabolism of CPT-11 by a human intestinal carboxylesterase. Cancer Res 2000;60:4725-8
7. Satoh T, Hosokawa M, Atsumi R, et al. Metabolic activation of CPT-11, 7-ethyl- 10-[4-(1-piperidino)-1- piperidino] carbonyloxycamptothecin, a novel antitumor agent, by carboxylesterase. Biol Pharm Bull 1994;17:662-4 (Pubitemid 24186112)
8. Shi D, Yang J, Yang D, et al. Anti-influenza prodrug oseltamivir is activated by carboxylesterase human carboxylesterase 1, and the activation is inhibited by antiplatelet agent clopidogrel. J Pharmacol Exp Ther 2006;319:1477-84
9. Sun Z, Murry DJ, Sanghani SP, et al. Methylphenidate is stereoselectively hydrolyzed by human carboxylesterase CES1A1. J Pharmacol Exp Ther 2004;310:469-76 (Pubitemid 38988889)
10. Crow JA, Borazjani A, Potter PM, et al. Hydrolysis of pyrethroids by human and rat tissues: examination of intestinal, liver and serum carboxylesterases. Toxicol Appl Pharmacol 2007;221:1-12 (Pubitemid 46766564)
11. Crow JA, Middleton BL, Borazjani A, et al. Inhibition of carboxylesterase 1 is associated with cholesteryl ester retention in human THP-1 monocyte/macrophages. Biochim Biophys Acta 2008;1781:643-54
12. Stampfli HF Quon CY. Polymorphic metabolism of flestolol and other ester containing compounds by a carboxylesterase in New Zealand white rabbit blood and cornea. Res Commun Mol Pathol Pharmacol 1995;88:87-97
13. Tabata T, Katoh M, Tokudome S, et al. Identification of the cytosolic carboxylesterase catalyzing the 5¢-deoxy- 5-fluorocytidine formation from capecitabine in human liver. Drug Metab Dispos 2004;32:1103-10 (Pubitemid 39287584)
14. Quinney SK, Sanghani SP, Davis WI, et al. Hydrolysis of capecitabine to 5¢-deoxy-5-fluorocytidine by human carboxylesterases and inhibition by loperamide. J Pharmacol Exp Ther 2005;313:1011-16 (Pubitemid 40727004)
15. Kamendulis LM, Brzezinski MR, Pindel EV, et al. Metabolism of cocaine and heroin is catalyzed by the same human liver carboxylesterases. J Pharmacol Expt Therap 1996;279:713-17 (Pubitemid 27166843)
16. Alexson SE, Diczfalusy M, Halldin M, et al. Involvement of liver carboxylesterases in the in vitro metabolism of lidocaine. Drug Metab Dispos 2002;30:643-7 (Pubitemid 34579096)
17. Zhang J, Burnell JC, Dumaual N, et al. Binding and hydrolysis of meperidine byhuman liver carboxylesterase hCE-1. J Pharmacol Exp Ther 1999;290:314-18 (Pubitemid 29302337)
18. Hatfield MJ, Tsurkan L, Hyatt JL, et al. Biochemical and molecular analysis of carboxylesterase-mediated hydrolysis of cocaine and heroin. Br J Pharmacol 2010;160:1916-28
19. Hicks LD, Hyatt JL, Moak T, et al. Analysis of the inhibition of mammalian carboxylesterases by novel fluorobenzoins and fluorobenzils. Bioorg Med Chem 2007;15:3801-17 (Pubitemid 46635131)
20. Hicks LD, Hyatt JL, Stoddard S, et al. 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 2009;52:3742-52
21. Hyatt JL, Moak T, Hatfield JM, et al. Selective inhibition of carboxylesterases by isatins, indole-2,3-diones. J Med Chem 2007;50:1876-85 (Pubitemid 46626597)
22. Hyatt JL, Tsurkan L, Wierdl M, et al. Intracellular inhibition of carboxylesterases by benzil: Modulation of CPT-11 cytotoxicity. Mol Cancer Therap 2006;5:2281-8 (Pubitemid 44530465)
23. Wadkins RM, Hyatt JL, Wei X, et al. Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem 2005;48:2905-15
24. Wadkins RM, Hyatt JL, Yoon KJ, et al. 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 2004;65:1336-43 (Pubitemid 38668292)
25. Material Safety Data Sheet - Lethal Nerve Agent Sarin (GB). >In: United States Senate, 103rd Congress (ed.). 1994. Available from: . gulfweb.org/bigdoc/report/appgb.html [Last accessed 3 March 2011]
26. Dvir H, Silman I, Harel M, et al. Acetylcholinesterase: from 3D structure to function. Chem Biol Interact 2010;187:10-22
27. Silman I, Sussman JL. Acetylcholinesterase: how is structure related to function? Chem Biol Interact 2008;175:3-10
28. Rogers SL, Friedhoff LT. The efficacy and safety of donepezil in patients with Alzheimers disease: results of a US multicentre, randomized, double-blind, placebo-controlled trial. The Donepezil Study Group. Dementia 1996;7:293-303 (Pubitemid 26341258)
29. Munoz-Torrero D. Acetylcholinesterase inhibitors as disease-modifying therapies for Alzheimers disease. Curr Med Chem 2008;15:2433-55
30. Sramek JJ, Anand R, Wardle TS, et al. Safety/tolerability trial of SDZ ENA 713 in patients with probable Alzheimers disease. Life Sci 1996;58:1201-7 (Pubitemid 26093988)
31. Greenblatt HM, Dvir H, Silman I, et al. Acetylcholinesterase: a multifaceted target for structure-based drug design of anticholinesterase agents for the treatment of Alzheimers disease. J Mol Neurosci 2003;20:369-83 (Pubitemid 38146996)
32. Morton CL, Iacono L, Hyatt JL, et al. Metabolism and antitumor activity of CPT-11 in plasma esterase-deficient mice. Cancer Chemother Pharmacol 2005;56:629-36 (Pubitemid 41425060)
33. Morton CL, Wierdl M, Oliver L, et al. Activation of CPT-11 in mice: Identification and analysis of a highly effective plasma esterase. Cancer Res 2000;60:4206-10 (Pubitemid 30636606)
34. Bencharit S, Morton CL, Howard-Williams EL, et al. Structural insights into CPT-11 activation by mammalian carboxylesterases. Nat Struct Biol 2002;9:337-42 (Pubitemid 34462550)
35. Bencharit S, Morton CL, Hyatt JL, et al. Crystal structure of human carboxylesterase 1 complexed with the Alzheimers drug tacrine. From binding promiscuity to selective inhibition. Chem & Biol 2003;10:341-9 (Pubitemid 36516652)
36. Bencharit S, Morton CL, Xue Y, et al. Structural basis of heroin and cocaine metabolism by a promiscuous human drug-processing enzyme. Nat Struct Biol 2003;10:349-56 (Pubitemid 36523269)
37. Fleming CD, Bencharit S, Edwards CC, et al. Structural insights into drug processing by human carboxylesterase 1: tamoxifen, mevastatin, and inhibition by benzil. J Mol Biol 2005;352:165-77 (Pubitemid 41207447)
38. Hemmert AC, Otto TC, Wierdl M, et al. Human carboxylesterase 1 stereoselectively binds the nerve agent cyclosarin and spontaneously hydrolyzes the nerve agent sarin. Mol Pharmacol 2010;77:508-16
39. Redinbo MR, Bencharit S, Potter PM. Human carboxylesterase 1: from drug metabolism to drug discovery. Biochem Soc Trans 2003;31:620-4 (Pubitemid 36750742)
40. Morton CL, Potter PM. 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 2000;16:193-202 (Pubitemid 32217198)
41. Beroza P, Damodaran K, Lum RT. Target-related affinity profiling: Teliks lead discovery technology. Curr Top Med Chem 2005;5:371-81 (Pubitemid 40753874)
42. Beroza P, Villar HO, Wick MM, et al. Chemoproteomics as a basis for post-genomic drug discovery. Drug Discov Today 2002;7:807-14 (Pubitemid 34876960)
43. Webb JL. Enzyme and Metabolic Inhibitors. Volume 1. General Principles of Inhibition. New York: Academic Press, Inc., 1963
44. Brandstetter H, Turk D, Hoeffken HW, et al. Refined 2.3 A X-ray crystal structure of bovine thrombin complexes formed with the benzamidine and arginine-based thrombin inhibitors NAPAP, 4-TAPAP and MQPA. A starting point for improving antithrombotics. J Mol Biol 1992;226:1085-99
45. Kiyama R, Tamura Y, Watanabe F, et al. Homology modeling of gelatinase catalytic domains and docking simulations of novel sulfonamide inhibitors. J Med Chem 1999;42:1723-38 (Pubitemid 29244966)
46. Hyatt JL, Stacy V, Wadkins RM, et al. Inhibition of carboxylesterases by benzyl (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 2005;48:5543-50 (Pubitemid 41209252)
47. Stoddard SV, Yu X, Potter PM, et al. In silico design and evaluation of carboxylesterase inhibitors. J Pestic Sci 2010;35:240-9
48. Siegel H, Eggersdorfer M. Ketones. In: Ullmanns Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, 2000
49. Hyatt JL, Wadkins RM, Tsurkan L, et al. Planarity and constraint of the carbonyl groups in 1,2-diones are determinants for selective inhibition of human carboxylesterase 1. J Med Chem 2007;50:5727-34 (Pubitemid 350106027)
50. Mukai M, Yamauchi S, Hirota N. Time-resolved EPR study on the photochemical reactions of benzil. J Phys Chem 1992;96:3305-11
51. McKay MJ, Carroll AR, Quinn RJ, et al. 1,2-bis(1H-indol-3-yl)ethane-1,2- dione, an indole alkaloid from the marine sponge Smenospongia sp. J Nat Prod 2002;65:595-7 (Pubitemid 34456953)
52. Salmoun M, Devijver C, Daloze D, et al. 5-hydroxytryptamine-derived alkaloids from two marine sponges of the genus Hyrtios. J Nat Prod 2002;65:1173-6 (Pubitemid 34976499)
53. Young BM, Hyatt JL, Bouck DC, et al. Structure-activity relationships of substituted 1-pyridyl-2-phenyl-1,2- ethanediones: potent, selective carboxylesterase inhibitors. J Med Chem 2010;53:8709-15
54. Wheelock CE, Severson TF, Hammock BD. Synthesis of new carboxylesterase inhibitors and evaluation of potency and water solubility. Chem Res Toxicol 2001;14:1563-72 (Pubitemid 34016619)
55. Wadkins RM, Hyatt JL, Edwards CC, et al. Analysis of mammalian carboxylesterase inhibition by trifluoromethylketone-containing compounds. Mol Pharmacol 2007;71:713-23 (Pubitemid 46294082)
56. Szekacs A, Bordas B, Hammock BD. Transition state analog enzyme inhibitors: Structure-activity relationships of trifluoromethyl ketones. In: Draber W, Fujita T, editors, Rational Approaches to Structure, Activity, and Ecotoxicology of Agrochemicals. CRC Press, Boca Raton, Florida; 1992. p. 219-49
57. Wolfenden R. Transition state analogues for enzyme catalysis. Nature 1969;223:704-5
58. Lienhard GE. Enzymatic catalysis and transition-state theory. Science 1973;180:149-54
59. Gelb MH, Svaren JP, Abeles RH. Fluoro ketone inhibitors of hydrolytic enzymes. Biochemistry 1985;24:1813-17 (Pubitemid 15019770)
60. Imperiali B, Abeles RH. Inhibition of serine proteases by peptidyl fluoromethyl ketones. Biochemistry 1986;25:3760-7
61. Brady K, Abeles RH. Inhibition of chymotrypsin by peptidyl trifluoromethyl ketones: determinants of slow-binding kinetics. Biochemistry 1990;29:7608-17 (Pubitemid 20279177)
62. Penning TD, Talley JJ, Bertenshaw SR, et al. Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3- (trifluoromethyl)-1H-pyrazol-1-yl] benzenesulfonamide (SC-58635, celecoxib). J Med Chem 1997;40:1347-65 (Pubitemid 27198082)
63. Wong DT, Perry KW, Bymaster FP. Case history: the discovery of fluoxetine hydrochloride (Prozac). Nat Rev Drug Discov 2005;4:764-74 (Pubitemid 43090497)
64. Thornberry NA, Weber AE. Discovery of JANUVIA (Sitagliptin), a selective dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes. Curr Top Med Chem 2007;7:557-68 (Pubitemid 46488280)
65. Armand JP, Extra YM, Catimel G, et al. Rationale for the dosage and schedule of CPT-11 (irinotecan) selected for Phase II studies, as determined by European Phase I studies. Ann Oncol 1996;7:837-42 (Pubitemid 26345875)
66. Armand JP. Irinotecan (CPT11): recent clinical development and future direction. Ann Oncol 1994;5:A360
67. Berg D. Irinotecan hydrochloride: drug profile and nursing implications of a topoisomerase I inhibitor in patients with advanced colorectal cancer. Oncol Nurs Forum 1998;25:535-43
68. Crow JA, Herring KL, Xie S, et al. Inhibition of carboxylesterase activity of THP1 monocytes/macrophages and recombinant human carboxylesterase 1 by oxysterols and fatty acids. Biochim Biophys Acta 2010;1801:31-41
69. Buch H, Buzello W, Heymann E, et al. Inhibition of phenacetin- and acetanilide-induced methemoglobinemia in the rat by the carboxylesterase inhibitor bis-[p-nitrophenyl] phosphate. Biochem Pharmacol 1969;18:801-11
70. Fujita Y, Yaegashi T, Sawada S, et al. Partial purification and characterization of an esterase acting on the anticancer pro-drugs, 7-ethylcamptothecin derivatives. Biol Pharm Bull 1995;18:648-52
71. Eng H, Niosi M, McDonald TS, et al. Utility of the carboxylesterase inhibitor bis-para-nitrophenylphosphate (BNPP) in the plasma unbound fraction determination for a hydrolytically unstable amide derivative and agonist of the TGR5 receptor. Xenobiotica 2010;40:369-80
72. Chekhlov AN, Solovev VN, Makhaeva GF, et al. Molecular structure and hydrolysis of 2-alkoxy-2-oxo-3H- 1,4,2-benzodioxaphosphorines. J Gen Chem USSR 1988;58:1456-61
73. Tsvetkov EN, Degtyarev AN, Bovin AN. Method for the synthesis of alpha-phosphorus-containing monoalkylated pyrocatechols J Gen Chem USSR 1986;56:2542-53
74. Tsvetkov EN, Degtyarev AN, Bovin AN, et al. 2-Alkoxy-2-oxo-5,6-benzo- 1,4,2-dioxaphosphorine and phenyl substituted analogues as selective inhibitors of nonspecific esterases of warm-blooded animals. RU1187444; 1985
75. Yang ZP, Dettbarn WD. Prevention of tolerance to the organophosphorus anticholinesterase paraoxon with carboxylesterase inhibitors. Biochem Pharmacol 1998;55:1419-26 (Pubitemid 28298523)
76. Wu SY, Casida JE. Neuropathy target esterase inhibitors: 2-alkyl-, 2-alkoxy-, and 2-(aryloxy)-4H- 1,3,2-benzodioxaphosphorin 2-oxides. Chem Res Toxicol 1992;5:680-4
77. Kristoff G, Guerrero NR, Cochon AC. Inhibition of cholinesterases and carboxylesterases of two invertebrate species, Biomphalaria glabrata and Lumbriculus variegatus, by the carbamate pesticide carbaryl. Aquat Toxicol 2010;96:115-23
78. Arufe MI, Arellano JM, Albendin G, et al. Toxicity of parathion on embryo and yolk-sac larvae of gilthead seabream (Sparus aurata l.): effects on survival, cholinesterase, and carboxylesterase activity. Environ Toxicol 2010;25:601-7
79. Arufe MI, Arellano JM, Garcia L, et al. Cholinesterase activity in gilthead seabream (Sparus aurata) larvae: Characterization and sensitivity to the organophosphate azinphosmethyl. Aquat Toxicol 2007;84:328-36 (Pubitemid 47260732)
80. Casida JE, Quistad GB. Serine hydrolase targets of organophosphorus toxicants. Chem Biol Interact 2005;157-8:277-283
81. Satoh T, Hosokawa M. Organophosphates and their impact on the global environment. Neurotoxicology 2000;21:223-7
82. Li B, Sedlacek M, Manoharan I, et al. Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma. Biochem Pharmacol 2005;70:1673-84 (Pubitemid 41540360)
83. Augmentin - Prescribing Information. GlaxoSmithKline, 2009. Available from: http://us.gsk.com/products/assets/us-augmentin.pdf [Last accessed 5 March 2011]
84. Pindel EV, Kedishvili NY, Abraham TL, et al. Purification and cloning of a broad substrate specificity human liver carboxylesterase that catalyzes the hydrolysis of cocaine and heroin. J Biol Chem 1997;272:14769-75 (Pubitemid 27251744)
85. Wang L, Zhang Y, Han Z, et al. Cross-resistance and possible mechanisms of chlorpyrifos resistance in Laodelphax striatellus (Fallen). Pest Manag Sci 2010;66:1096-100
86. Zhang L, Shi J, Shi X, et al. Quantitative and qualitative changes of the carboxylesterase associated with beta-cypermethrin resistance in the housefly, Musca domestica (Diptera: Muscidae). Comp Biochem Physiol B Biochem Mol Biol 2010;156:6-11
87. Alon M, Alon F, Nauen R, et al. Organophosphates resistance in the B-biotype of Bemisia tabaci (Hemiptera: Aleyrodidae) is associated with a point mutation in an ace1-type acetylcholinesterase and overexpression of carboxylesterase. Insect Biochem Mol Biol 2008;38:940-9
88. Whyard S, Russell RJ, Walker VK. Insecticide resistance and malathion carboxylesterase in the sheep blowfly, Lucilia cuprina. Biochem Genet 1994;32:9-24 (Pubitemid 24127309)