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Original Research

Multipotent cholinesterase/monoamine oxidase inhibitors for the treatment of Alzheimer’s disease: design, synthesis, biochemical evaluation, ADMET, molecular modeling, and QSAR analysis of novel donepezil-pyridyl hybrids

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Pages 1893-1910 | Published online: 13 Oct 2014

References

  • Goedert M Spillantini MG A Century of Alzheimer’s disease Science 2006 314 5800 777 781 17082447
  • Kung HF The β-amyloid hypothesis in Alzheimer’s disease: seeing is believing ACS Med Chem Lett 2012 3 4 265 267 24936237
  • Ballatore C Lee VM Trojanowski JQ Tau-mediated neurodegeneration in Alzheimer’s disease and related disorders Nat Rev Neurosci 2007 8 9 663 672 17684513
  • Gella A Durany N Oxidative stress in Alzheimer disease Cell Adh Migr 2009 3 1 88 93 19372765
  • Jakob-Roetne R Jacobsen H Alzheimer’s disease: from pathology to therapeutic approaches Angew Chem Int Ed Engl 2009 48 17 3030 3059 19330877
  • Sugimoto H Yamanishi Y Iimura Y Kawakami Y Donepezil hydrochloride (E2020) and other acetylcholinesterase inhibitors Curr Med Chem 2000 7 3 303 339 10637367
  • Marco-Contelles J do Carmo Carreiras M Rodríguez C Villarroya M Garcia AG Synthesis and pharmacology of galantamine Chem Rev 2006 106 1 116 133 16402773
  • Anand P Singh B A review on cholinesterase inhibitors for Alzheimer’s disease Arch Pharm Res 2013 36 4 375 399 23435942
  • Barbanti P Fabbrini G Ricci A Reduced density of dopamine D2-like receptors on peripheral blood lymphocytes in Alzheimer’s disease Mech Ageing Dev 2000 120 1–3 65 75 11087905
  • Thompson AJ Lummis SC The 5-HT3 receptor as a therapeutic target Expert Opin Ther Targets 2007 11 4 527 540 17373882
  • Shih JC Chen K Ridd MJ Monoamine oxidase: from genes to behavior Annu Rev Neurosci 1999 22 197 217 10202537
  • Riederer P Danielczyk W Grünblatt E Monoamine oxidase-B inhibition in Alzheimer’s disease Neurotoxicology 2004 25 1–2 271 277 14697902
  • Pizzinat N Copin N Vindis C Parini A Cambon C Reactive oxygen species production by monoamine oxidases in intact cells Naunyn Schmiedebergs Arch Pharmacol 1999 359 5 428 431 10498294
  • Kristal BS Conway AD Brown AM Selective dopaminergic vulnerability: 3,4-dihydroxyphenylacetaldehyde targets mitochondria Free Radical Biol Med 2001 30 8 924 931 11295535
  • Sterling J Herzig Y Goren T Novel dual inhibitors of AChE and MAO derived from hydroxy aminoindan and phenethylamine as potential treatment for Alzheimer’s disease J Med Chem 2002 45 24 5260 5279 12431053
  • Yogev-Falach M Bar-Am O Amit T Weinreb O Youdim MB A multifunctional, neuroprotective drug, ladostigil (TV3326), regulates holo-APP translation and processing FASEB J 2006 20 12 2177 2179 16935943
  • Youdim MB Weinstock M Molecular basis of neuroprotective activities of rasagiline and the anti-Alzheimer drug TV3326 [lpar;N-Propargyl-(3R) aminoindan-5-YL-ethyl methyl carbamate] Cell Mol Neurobiol 2002 21 6 555 573 12043833
  • Bar-Am O Amit T Weinreb O Youdim MB Mandel S Propargylamine containing Compounds as modulators of proteolytic cleavage of amyloid protein precursor: involvement of MAPK and PKC activation J Alzheimer’s Dis 2010 21 2 361 371 20555137
  • Bruehlmann C Ooms F Carrupt PA Coumarins derivatives as dual inhibitors of acetylcholinesterase and monoamine oxidase J Med Chem 2001 44 19 3195 3198 11543689
  • Zheng H Fridkin M Youdim MB Novel chelators targeting cell cycle arrest, acetylcholinesterase, and monoamine oxidase for Alzheimer’s therapy Curr Drug Targets 2012 13 8 1096 1113
  • Samadi A Marco-Contelles J Soriano E Multipotent drugs with cholinergic and neuroprotective properties for the treatment of Alzheimer and neuronal vascular diseases. I. Synthesis, biological assessment, and molecular modeling of simple and readily available 2-aminopyridine-, and 2-chloropyridine-3,5-dicarbonitriles Bioorg Med Chem 2010 18 16 5861 5872 20656495
  • Bolea I Juárez-Jiménez J de los Ríos C Synthesis, biological evaluation, and molecular modeling of donepezil and N-[(5-(benzyloxy)-1-methyl-1H-indol-2-yl)methyl]-N-methylprop-2-yn-1-amine hybrids as new multipotent cholinesterase/monoamine oxidase inhibitors for the treatment of Alzheimer’s disease J Med Chem 2011 54 24 8251 8270 22023459
  • Peŕez V Marco JL Fernańdez-Álvarez E Unzeta M Relevance of benzyloxy group in 2-indolyl methylamines in the selective MAO-B inhibition Brit J Pharmacol 1999 127 4 869 876 10433493
  • Samadi A Chioua M Bolea I Synthesis, biological assessment and molecular modeling of new multipotent MAO and cholinesterase inhibitors as potential drugs for the treatment of Alzheimer’s disease Eur J Med Chem 2011 46 9 4665 4668 21669479
  • Peinador C Veiga MC Vilar J Quintela A synthesis of heterocyclic ring systems. Pyrido[3′,2′:4,5]thieno[2,3-b]pyrrolizine and pyrido[6′,5′:4,5][3′,2′:4,5]dithieno[2,3-b‘:2,3-b]dipyrrolizine Heterocycles 1994 38 6 1299 1305
  • Vilarelle DV Peinador C Quintela JM Synthesis of pyrido and pyrazinodithienodipyrimidine-4,8(3H,9H)-dione derivatives by the aza-Wittig methodology Tetrahedron 2004 60 2 275 283
  • Murray TJ Zimmerman SC Kolotuchin SV Synthesis of heterocyclic compounds containing three contiguous hydrogen bonding sites in all possible arrangements Tetrahedron 1995 51 2 635 648
  • Piper JR McCaleb GS Montgomery JA Kisliuk RL Gaumont Y Sirotnak FM Syntheses and antifolate activity of 5-methyl-5-deaza analogs of aminopterin, methotrexate, folic acid, and N10-methylfolic acid J Med Chem 1986 29 6 1080 1087 2423690
  • Samadi A Estrada M Peŕez C Pyridonepezils, new dual AChE inhibitors as potential drugs for the treatment of Alzheimer’s disease: Synthesis, biological assessment, and molecular modelling Eur J Med Chem 2012 57 296 301 23078965
  • Atsushi K Mitsuru O Hisashi Tinventors Fujisawa Pharmaceutical Co.; applicant Oxadiazole derivatives having acetylcholinesterase-inhibitory and muscarinic agonist activity Patent publication number WO9313083A1 1993 7 8
  • Contreras JM Rival YM Chayer S Bourguignon JJ Wermuth CG Aminopyridazines as acetylcholinesterase inhibitors J Med Chem 1999 42 4 730 741 10052979
  • Ellman GL Courtney KD Andres VJr Feather-stone RM A new and rapid colorimetric determination of acetylcholinesterase activity Biochem Pharmacol 1961 7 2 88 95 13726518
  • Zhou M Panchuk-Valashina N A one-step fluorometric method for the continuous measurement of monoamine oxidase activity Anal Biochem 1997 253 2 169 174 9367499
  • León R Marco-Contelles J A step further towards multitarget drugs for Alzheimer and neuronal vascular diseases: targeting the cholinergic system, amyloid-β aggregation and Ca2+ dyshomeostasis Curr Med Chem 2011 18 4 552 576 21143111
  • Trott O Olson AJ AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading J Comput Chem 2010 31 2 455 461 19499576
  • Arnold K Bordoli L Kopp J Schwede T The SWISS-MODEL workspace: a web-based environment for protein structure homology modelling Bioinformatics 2006 22 2 195 201 16301204
  • Kiefer F Arnold K Künzli M Bordoli L Schwede T The SWISS-MODEL Repository and associated resources Nucl Acids Res 2009 37 Database issue D387 D392 18931379
  • Guex N Peitsch MC Schwede T Automated comparative protein structure modeling with SWISS-MODEL and Swiss-PdbViewer: a historical perspective Electrophoresis 2009 30 Suppl 1 S162 S173 19517507
  • Edmonson DE Mattevi A Binda C Li M Hubalek F Structure and mechanism of Monoamine Oxidase Curr Med Chem 2004 11 15 1983 1993 15279562
  • Jones TZ Balsa D Unzeta M Ramsay RR Variations in activity and inhibition with pH: the protonated amine is the substrate for monoamine oxidase, but uncharged inhibitors bind better J Neural Transm 2007 114 6 707 712 17401535
  • Wang J Edmonson DE 2H kinetic isotope effects and pH dependence of catalysis as mechanistic probes of rat Monoamine Oxidase A: comparisons with the human enzyme Biochemistry 2011 50 35 7710 7717 21819071
  • Scerrer RA Leo AJ Multi-pH QSAR: a method to differentiate the activity of neutral and ionized species and obtain true correlations when both species are involved Molecular Informatics 2010 29 10 687 693
  • Samadi A de los Ríos C Bolea I Multipotent MAO and cholinesterase inhibitors for the treatment of Alzheimer’s disease: synthesis, pharmacological analysis and molecular modeling of heterocyclic substituted alkyl and cycloalkyl propargyl amine Eur J Med Chem 2012 52 251 262 22503231
  • ACD/Percepta 14.0.0, Advanced Chemistry Development 2013
  • Kragh-Hansen U Molecular aspects of ligand binding to serum albumin Pharmacol Rev 1981 33 17 53 7027277
  • Moriguchi I Hirono S Liu Q Nakagome I Matsushita Y Simple method of calculating octanol/water partition coefficient Chem Pharm Bull 1992 40 1 127 130
  • Lipinski CA Lombardo F Dominy BW Feeney PJ Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv Drug Deliv Rev 2001 46 1–3 3 26 11259830
  • Pajouhesh H Lenz GR Medicinal chemical properties of successful central nervous system drugs NeuroRx 2005 2 4 541 553 16489364
  • Ma XL Chen C Yang Y Predictive model of blood-brain barrier penetration of organic compounds Acta Pharmacol Sin 2005 26 4 500 512 15780201
  • Cheng F Li W Zhou Y admetSAR: a comprehensive source and free tool for assessment of chemical ADMET properties J Chem Inf Model 2012 52 11 3099 3105 23092397
  • Lennernas H Human intestinal permeability J Pharm Sci 1998 87 4 403 410 9548891
  • Yee S In vitro permeability across caco-2 cells (Colonic) can predict in vivo (small intestinal) absorption in man – Fact or myth Pharm Res 1997 14 6 763 766 9210194
  • Yamashita S Furubayashi T Kataoka M Sakane T Sezaki H Tokuda H Optimized conditions for prediction of intestinal drug permeability using Caco-2 cells Eur J Pharm Sci 2000 10 3 195 204 10767597
  • Gold LS Manley NB Slone TH Rohrbach L Supplement to the Carcinogenic Potency Database (CPDB): results of animal bioassays published in the general literature in 1993 to 1994 and by the National Toxicology Program in 1995 to 1996 Enviro Health Perspect 1999 107 Suppl 4 527 600
  • Matthews EJ Kruhlak NL Benz RD Contrera JF Assessment of the health effects of chemicals in humans: I. QSAR estimation of the maximum recommended therapeutic dose (MRTD) and no effect level (NOEL) of organic chemicals based on clinical trial aata1 Curr Drug Discov Technol 2004 1 1 61 76 16472220
  • Arendt T Bruckner MK Lange M Bigl V Changes in acetylcholinesterase and butyrylcholinesterase in Alzheimer’s disease resemble embryonic development. A study of molecular forms Neurochem Int 1992 21 3 381 396 1303164
  • Darvesh S Hopkins DA Geula C Neurobiology of butyrylcholinesterase Nat Rev Neurosci 2003 4 2 131 138 12563284
  • Greig NH Utsuki T Ingram DK Selective butyrylcholinesterase inhibition elevates brain acetylcholine, augments learning and lowers Alzheimer β-amyloid peptide in rodent Proc Natl Acad Sci U S A 2005 102 47 17213 17218 16275899
  • Saura J Bleuel Z Ultrich J Molecular neuroanatomy of human monoamine oxidases A and B revealed by quantitative enzyme radioautography and in situ hybridization histochemistry Neuroscience 1996 70 3 755 774 9045087