Pharmacophore-based virtual screening and density functional theory approach to identifying novel butyrylcholinesterase inhibitors

Acta Pharmacologica Sinica

Volumn 33, Issue 7, 2012, Pages 964-978

  Sakkiah, Sugunadevi ^a   Lee, Keun Woo ^a  

^a Gyeongsang National University   (South Korea)

Author keywords

Alzheimer's disease; butyrylcholinesterase; cholinesterase; density functional theory; ligand based pharmacophore modeling theory; molecular docking; virtual screening

Indexed keywords

AMINO ACID DERIVATIVE; BTB 07807; CHOLINESTERASE INHIBITOR; KM 02281; KM 03101; LIGAND; RJC 03502; SPB 07954; UNCLASSIFIED DRUG;

ARTICLE; DATA BASE; DENSITY FUNCTIONAL THEORY; DRUG POTENCY; ENERGY TRANSFER; ENZYME ACTIVE SITE; ENZYME INHIBITION; FALSE POSITIVE RESULT; GEOMETRY; HYDROGEN BOND; HYDROPHOBICITY; IC 50; MOLECULAR DOCKING; MOLECULAR INTERACTION; MOLECULAR MODEL; PHARMACOPHORE; QUANTITATIVE ANALYSIS; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RELIABILITY; SCREENING; VALIDATION PROCESS; VIRTUAL REALITY;

BUTYRYLCHOLINESTERASE; CHOLINESTERASE INHIBITORS; DRUG DESIGN; HUMANS; MODELS, MOLECULAR; PROTEIN BINDING; QUANTUM THEORY;

EID: 84863693289     PISSN: 16714083     EISSN: 17457254     Source Type: Journal    
DOI: 10.1038/aps.2012.21     Document Type: Article

References (46)

1. Massoulié J, Sussman J, Bon S, Silman I. Chapter 15: Structure and functions of acetylcholinesterase and butyrylcholinesterase. In: Cuello AC editor. Progress in Brain Research: Elsevier; 1993. p 139-46.
2. Sun H, El Yazal J, Lockridge O, Schopfer LM, Brimijoin S, Pang YP. Predicted michaelis-menten complexes of cocaine-butyrylcholinesterase. J Biol Chem 2001; 276: 9330-6.
3. Massoulié J, Pezzementi L, Bon S, Krejci E, Vallette FM. Molecular and cellular biology of cholinesterases. Prog Neurobiol 1993; 41: 31-91.
4. Valle AM, Radi Z, Rana BK, Whitfield JB, O'Connor DT, Martin NG, et al. The cholinesterases: Analysis by pharmacogenomics in man. Chem Biol Interact 2008; 175: 343-45.
5. Quinn DM. Acetylcholinesterase: enzyme structure, reaction dynamics, and virtual transition states. Chem Rev 1987; 87: 955-79.
6. Li B, Sedlacek M, Manoharan I, Boopathy R, Duysen EG, Masson P, et al. Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma. Biochem Pharmacol 2005; 70: 1673-84.
7. Satoh T, Hosokawa M. Structure, function and regulation of carboxylesterases. Chem Biol Interact 2006; 162: 195-211.
8. Duysen EG, Li B, Darvesh S, Lockridge O. Sensitivity of butyrylcholinesterase knockout mice to (-)-huperzine A and donepezil suggests humans with butyrylcholinesterase deficiency may not tolerate these Alzheimer's disease drugs and indicates butyrylcholinesterase function in neurotransmission. Toxicology 2007; 233: 60-69.
9. Gardiner Sj, Begg EJ. Pharmacogenetics, drug-metabolizing enzymes, and clinical practice. Pharm Rev 2006; 58: 521-90.
10. Doctor BP, Saxena A. Bioscavengers for the protection of humans against organophosphate toxicity. Chem Biol Interact 2005; 157-158: 167-71.
11. Masson P, Froment MT, Gillon E, Nachon F, Darvesh S, Schopfer LM. Kinetic analysis of butyrylcholinesterase-catalyzed hydrolysis of acetanilides. Biochim Biophys Acta 2007; 1774: 1139-47.
12. Vitorovic-Todorovic Md, Juranic Io, Mandic Lm, Drakulic BJ. 4-Aryl-4-oxo-N-phenyl-2-aminylbutyramides as acetyl-and butyrylcholinesterase inhibitors. Preparation, anticholinesterase activity, docking study, and 3D structure-activity relationship based on molecular interaction fields. Bioorg Med Chem 2010; 18: 1181-93.
13. Burgen AS. The mechanism of action of anticholinesterase drugs. Pharmac Ther 1979; 6: 579-628.
14. Mesulam MM, Guillozet A, Shaw P, Levey A, Duysen EG, Lockridge O. Acetylcholinesterase knockouts establish central cholinergic pathways and can use butyrylcholinesterase to hydrolyze acetylcholine. Neuroscience 2002; 110: 627-39.
15. Li B, Stribley JA, Ticu A, Xie W, Schopfer LM, Hammond P, et al. Abundant tissue butyrylcholinesterase and its possible function in the acetylcholinesterase knockout mouse. J Neurochem 2000; 75: 1320-31.
16. Jhee SS, Shiovitz T, Hartman RD, Messina J, Anand R, Sramek J, Cutler NR, et al. Centrally acting antiemetics mitigate nausea and vomiting in patients with Alzheimer's disease who receive rivastigmine. Neuropharmacology 2002; 25: 122.
17. Perry EK, Perry RH, Blessed G, Tomlinson BE. Changes in brain cholinesterases in senile dementia of Alzheimer type. Neuropathol Appl Neurobiol 1978; 4: 273-7.
18. Geula C, Nagykery N. Butyrylcholinesterase activity in the rat forebrain and upper brainstem: postnatal development and adult distribution. Exp Neurol 2007; 204: 640-57.
19. Mehrani H. Protective effect of polyurethane immobilized human butyrylcholinesterase against parathion inhalation in rat. Environmental Toxicol Pharmacol 2004; 16: 179-85.
20. Schumacher I, Arad A, Margalit R. Butyrylcholinesterase formulated in liposomes. Biotechnol Appl Biochem 1999; 30: 225-30.
21. Lockridge O, Bartels CF, Vaughan TA, Wong CK, Norton SE, Johnson LL. Complete amino acid sequence of human serum cholinesterase. J Biol Chem 1987; 262: 549-57.
22. Nicolet Y, Lockridge O, Masson P, Fontecilla-Camps, Nachon F. Crystal structure of human butyrylcholinesterase and of its complexes with substrate and products. J Biol Chem 2003; 278: 41141-7.
23. Altamirano CV, Lockridge O. Association of tetramers of human butyrylcholinesterase is mediated by conserved aromatic residues of the carboxy terminus. Chem Biol Interac 1999; 120: 53-60.
24. Mack A, Robitzki A. The key role of butyrylcholinesterase during neurogenesis and neural disorders: an antisense-5? butyrylcholinesterase-DNA study. Prog Neurobiol 2000; 60: 607-28.
25. Darvesh S, Hopkins DA, Geula C. Neurobiology of butyrylcholinesterase [10.1038/nrn1035]. Nat Rev Neurosci 2003; 4: 131-8.
26. Guillozet AI, Smiley JF, Mash DC, Mesulam MM. Butyrylcholinesterase in the life cycle of amyloid plaques. Ann Neurol 1997; 42: 909-18.
27. Giacobini E. Cholinesterases: New roles in brain function and in Alzheimer's disease. Neurochem Res 2003; 28: 515-22.
28. Bisi A, Belluti F, Gobbi S, Valenti P, Andrisano V, Cavrini V, et al. Acetylcholinesterase inhibitors for potential use in Alzheimer's disease: molecular modeling, synthesis and kinetic evaluation of 11H-indeno-[1,2-b]- quinolin-10-ylamine derivatives. Bioorg Med Chem 2000; 8: 497-506.
29. Wadkins RM, Tsurkan L, Hicks LD, Hatfield MJ, Edwards CC, Ross CR 2nd, 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.
30. Moak T, Hatfield MJ, Tsurkan L, Edwards CC, Wierdl M, Danks MK, et al. Selective inhibition of carboxylesterases by isatins, indole-2,3-diones. J Med Chem 2007; 50: 1876-85.
31. Luo W, Yu QS, Kulkarni SS, Parrish DA, Holloway HW, Tweedie D, et al. Inhibition of human acetyl-and butyrylcholinesterase by novel carbamates of -and (+)-tetrahydrofurobenzofuran and methanobenzodioxepine. J Med Chem 2006; 49: 2174-85.
32. Fernandez-Bachiller MI, Perez C, Hernandez-Ledesma B, Bartolome B, Novel tacrine-melatonin hybrids as dual-acting drugs for Alzheimer disease, with improved acetylcholinesterase inhibitory and antioxidant properties. J Med Chem 2006; 49: 459-62.
33. Sakkiah S, Thangapandian S, John S, Kwon YJ, Lee KW. 3D QSAR pharmacophore based virtual screening and molecular docking for identification of potential HSP90 inhibitors. Eur J Med Chem 2010; 45: 2132-40.
34. Debnath AK. Pharmacophore mapping of a series of 2,4-diamino-5- deazapteridine inhibitors of mycobacterium avium complex dihydrofolate reductase. J Med Chem 2002; 45: 41-53.
35. Kansal N, Silakari O, Ravikumar M. Three dimensional pharmacophore modelling for c-kit receptor tyrosine kinase inhibitors. Eur J Med Chem 2010; 45: 393-404.
36. Brogi S, Kladi M, Vagias C, Papazafiri P, Roussis V, Tafi A. Pharmacophore modeling for qualitative prediction of antiestrogenic activity. J Chem Inf Model 2009; 49: 2489-97.
37. Sakkiah S, Thangapandian S, John S, Lee KW. Identification of critical chemical features for aurora kinase-B inhibitors using Hip-Hop, virtual screening and molecular docking. J Mol Struct 2011; 985: 14-26.
38. Lipinski A, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Delivery Rev 1997; 23: 3-25.
39. Venkatachalam CM, Jiang X, Oldfield T, Waldan M, LigandFit n. LigandFit: a novel method for the shape-directed rapid docking of ligands to protein active sites. J Mol Graphics Model 2003; 21: 289-307.
40. Brooks B, Bruccoleri R, Olafson B, States D, Swaminathan S, Karplus M. CHARMM: A program for macromolecular energy, minimization, and dynamics calculations. J Comput Chem 1983; 4: 187-217.
41. Bartolott LJ, Flurchick K. (2007) An Introduction to Density Functional Theory, in Reviews in Computational Chemistry, Volume 7 (eds Lipkowitz KB and Boyd DB), John Wiley & Sons, Inc, Hoboken, NJ, USA. doi: 10.1002/9780470125847.ch4.
42. Debnath AK. Generation of predictive pharmacophore models for CCR5 antagonists: study with piperidine-and piperazine-based compounds as a new class of HIV-1 entry inhibitors. J Med Chem 2003; 46: 4501-15.
43. Cokugras AN. Butyrylcholinestrase: structure and physiological importance. Turk J Biochem 2003; 28: 54-61.
44. Darvesh KV, McDonald RS, Mataija D, Walsh R, Mothana S, Lockridge O, et al. Carbamates with differential mechanism of inhibition toward acetylcholinesterase and butyrylcholinesterase. J Med Chem 2008; 51: 4200-12.
45. Li Y, Wang Y, Li W, Dong P, Ge G, Yang L, et al. Investigation of binding features: effects on the interaction between CYP2A6 and inhibitors. J Comput Chem 2010; 31: 1822-31.
46. Queiroz AN, Gomes BAQ, Moraes WM Jr, Borges RS. A theoretical antioxidant pharmacophore for resveratrol. Eur J Med Chem 2009; 44: 1644-49.