Donepezil structure-based hybrids as potential multifunctional anti-Alzheimer’s drug candidates

References

• a) Alzheimer’s Association. Alzheimer's disease facts and figures. Alzheimers Dement 2017;13:325–73. b) World Health Organization. Dementia, WHO fact sheet: 2017; http://www.who.int/mediacentre/factsheets/fs362/en/
   Google Scholar
• a) Grill JD, Cummings JL. Current therapeutic targets for the treatment of Alzheimer's disease. Expert Rev Neurother 2010;10:711–28. b) Cummings JL, Morstorf T, Zhong K. Alzheimer's disease drug-development pipeline: few candidates, frequent failures. Alzheimers Res Ther 2014;6:37.
   PubMed Web of Science ®Google Scholar
• Querfurth HW, LaFerla FM. Alzheimer's disease. N Engl J Med 2010;362:329–44.
   PubMed Web of Science ®Google Scholar
• Santos MA, Chand K, Chaves S. Recent progress in repositioning Alzheimer’s disease drugs based on a multitarget strategy. Future Med Chem 2016;8:2113–42.
   PubMed Web of Science ®Google Scholar
• a) Ghosh AK, Osswald HL. BACE1 (β-secretase) inhibitors for the treatment of Alzheimer's disease. Chem Soc Rev 2014;43:6765–813. b) Zheng H, Amit T, Bar-Am O, et al. From anti-Parkinson's drug rasagiline to novel multitarget iron chelators with acetylcholinesterase and monoamine oxidase inhibitory and neuroprotective properties for Alzheimer's disease. Alzheimer's Dis 2012;30:1–16.
   PubMed Web of Science ®Google Scholar
• a) Parsons CG, Stöffler A, Danysz W. Memantine: a NMDA receptor antagonist that improves memory by restoration of homeostasis in the glutamatergic system—too little activation is bad, too much is even worse. Neuropharmacol 2007;53:699–723. b) Bernardo A, Minghetti L. PPAR-gamma agonists as regulators of microglial activation and brain inflammation. Cur Pharm Des 2006;12:93–109. c) Piemontese L. New approaches for prevention and treatment of Alzheimer’s disease: a fascinating challenge. Neur Reg Res 2017;12:405–6.
   PubMed Web of Science ®Google Scholar
• Ansari MA, Scheff SW. Oxidative stress in the progression of Alzheimer disease in the frontal cortex. J Neuropathol Exp Neurol 2010;69:155–67.
   PubMed Web of Science ®Google Scholar
• Bush AI, Tanzi RE. Therapeutics for Alzheimer's disease based on the metal hypothesis. Neurotherapeutics 2008;5:421–32.
   PubMed Web of Science ®Google Scholar
• Santos MA, Chand K, Chaves S. Recent progress in multifunctional metal chelators as potential drugs for Alzheimer’s disease. Coord Chem Rev 2016;327–328:287–303.
   Web of Science ®Google Scholar
• a) Hiremathad A. A review: natural compounds as anti-Alzheimer´s Disease agents. Curr. Food Nutr. Sci 2017;13:247254. b) Piemontese L. Plant food supplements with antioxidant properties for the treatment of chronic and neurodegenerative diseases: benefits or risks? J Diet Suppl 2017;14:478–84.
   Web of Science ®Google Scholar
• Zemek F, Drtinova L, Nepovimova E, et al. Outcomes of Alzheimer's disease therapy with acetylcholinesterase inhibitors and memantine. Expert Opin Drug Saf 2014;13:759–74.
   PubMed Web of Science ®Google Scholar
• Cavalli A, Bolognesi ML, Minarini A, et al. Multi-target-directed ligands to combat neurodegenerative diseases. J Med Chem 2008;51:2326–72.
   Web of Science ®Google Scholar
• Guzior N, Ckowska AW, Panek D, Malawska B. Recent development of multifunctional agents as potential drug candidates for the treatment of Alzheimer's disease. Curr Med Chem 2015;22:373–404.
   PubMed Web of Science ®Google Scholar
• Unzeta M, Esteban G, Bolea I, et al. Multi-Target directed donepezil-like ligands for Alzheimer's disease. Front Neurosci 2016;10:205.
   PubMed Web of Science ®Google Scholar
• Benek O, Soukup O, Pasdiorova M, et al. Design, synthesis and in vitro evaluation of indolotacrine analogues as multitarget-directed ligands for the treatment of Alzheimer's disease. ChemMedChem 2016;11:1264–9.
   PubMed Web of Science ®Google Scholar
• Hiremathad A, Chand K, Esteves AR, et al. Tacrine-allyl/propargylcysteine-benzothiazole trihybrids as potential anti-Alzheimer´s drug candidates. RSC Adv 2016;6:53519–32.
   Web of Science ®Google Scholar
• Spilovska K, Korabecny J, Nepovimova E, et al. Multitarget tacrine hybrids with neuroprotective properties to confront Alzheimer's disease. Curr Top Med Chem 2017;17:1006–26.
   PubMed Web of Science ®Google Scholar
• Prati F, Bergamini C, Fato R, et al. Novel 8-hydroxyquinoline derivatives as multitarget compounds for the treatment of Alzheimer's disease. ChemMedChem 2016;11:1284–95.
   PubMed Web of Science ®Google Scholar
• Hiremathad A, Keri RS, Esteves AR, et al. Novel tacrine-hydroxyphenylbenzimidazole hybrids as potential multitarget drug candidates for Alzheimer's disease. Eur J Med Chem 2018;148:255–67.
   PubMed Web of Science ®Google Scholar
• Panek D, Więckowska A, Wichur T, et al. Design, synthesis and biological evaluation of new phthalimide and saccharin derivatives with alicyclic amines targeting cholinesterases, beta-secretase and amyloid beta aggregation. Eur J Med Chem 2017;125:676–95.
   PubMed Web of Science ®Google Scholar
• Mezeiova E, Spilovska K, Nepovimova E, et al. Profiling donepezil template into multipotent hybrids with antioxidant properties. J Enzyme Inhib Med Chem 2018;33:583–606.
   PubMed Web of Science ®Google Scholar
• Hiremathad A, Piemontese L. Heterocyclic compounds as key structures for the interaction with old and new targets in Alzheimer's disease therapy. Neural Regen Res 2017;12:1256–61.
   PubMed Web of Science ®Google Scholar
• Keri RS, Hiremathad A, Budagumpi S, Nagaraja BM. Comprehensive review in current developments of benzimidazole-based medicinal chemistry. Chem Biol Drug Des 2015;86:19–65.
   PubMed Web of Science ®Google Scholar
• Chand K, Rajeshwari, Hiremathad A, et al. A review on antioxidant potential of bioactive heterocycle benzofuran: natural and synthetic derivatives. Pharmacol Rep 2017;69:281–95.
   PubMed Web of Science ®Google Scholar
• Coban G, Carlino L, Tarikogullari AH, et al. 1H-benzimidazole derivatives as butyrylcholinesterase inhibitors: synthesis and molecular modeling studies. Med Chem Res 2016;25:2005–14.
   Web of Science ®Google Scholar
• Hiremathad A, Chand K, Tolayan L, et al. Hydroxypyridinone-benzofuran hybrids with potential protective roles for Alzheimer’s disease therapy. J Inorg Biochem 2018;179:82–96.
   PubMed Web of Science ®Google Scholar
• Korabecny J, Dolezal R, Cabelova P, et al. 7-MEOTA-donepezil like compounds as cholinesterase inhibitors: synthesis, pharmacological evaluation, molecular modeling and QSAR studies. Eur J Med Chem 2014;82:426–38.
   PubMed Web of Science ®Google Scholar
• a) Kryger G, Silman I, Sussman JL. Structure of acetylcholinesterase complexed with E2020 (Aricept): implications for the design of new anti-Alzheimer drugs. Structure 1999;7:297–307. b) Kryger G, Silman I, Sussman JL. The peripheral anionic site of acetylcholinesterase: structure, functions and potential role in rational drug design. Curr Pharm Des 1999;7:297–25.
   PubMed Web of Science ®Google Scholar
• Cheung J, Rudolph MJ, Burshteyn F, et al. Structures of human acetylcholinesterase in complex with pharmacologically important ligands. J Med Chem 2012;55:10282–6.
   PubMed Web of Science ®Google Scholar
• Karthikeyan C, Solomon VR, Lee H, Trivedi P. Synthesis and biological evaluation of 2-(phenyl)-3H-benzo[d]imidazole-5-carboxylic acids and its methyl esters as potent anti-breast cancer agents. Arab J Chem 2017;10:S1788–S94.
   Web of Science ®Google Scholar
• Quintanova C, Keri RS, Marques SM, et al. Design, synthesis and bioevaluation of tacrine hybrids with cinnamate and cinnamylidene acetate derivatives as potential anti-Alzheimer drugs. MedChemComm 2015;6:1969–77.
   Web of Science ®Google Scholar
• Zagidullin RN. Reactions of N-(β-aminoethyl)piperazine and its derivatives. Chem Heterocycl Comp 1991;27:309–12.
   Google Scholar
• Porcelli L, Gilardi F, Laghezza A, et al. Synthesis, characterization and biological evaluation of ureidofibrate-like derivatives endowed with peroxisome proliferator-activated receptor activity. J Med Chem 2012;55:37–54.
   PubMed Web of Science ®Google Scholar
• Chaves S, Hiremathad A, Tomás D, et al. Exploring the chelating capacity of 2-hydroxyphenylbenzimidazole based hybrids with multi-target ability as anti-Alzheimer´s agents [unpublished results]
   Google Scholar
• Faller P, Hureau C, La Penna G. Metal ions and intrinsically disordered proteins and peptides: from Cu/Zn amyloid-β to general principles. Acc Chem Res 2014;47:2252–9.
   PubMed Web of Science ®Google Scholar
• Fancellu G, MSc Thesis. Pisa: University of Pisa; 2018.
   Google Scholar
• Tepe B, Daferera D, Sokmen A, et al. Antimicrobial and antioxidant activities of the essential oil and various extracts of Salvia tomentosa Miller (Lamiaceae). J Agric Food Chem 2005;90:333–40.
   Web of Science ®Google Scholar
• Valko M, Rhodes CJ, Moncol J, et al. Free radicals, metals and antioxidants in oxidative stress-induced cancer. Chem Biol Interact 2006;160:1–40.
   PubMed Web of Science ®Google Scholar
• Šebestík J, Marques SM, Falé PL, et al. Bifunctional phenolic-choline conjugates as anti-oxidants and acetylcholinesterase inhibitors. J Enzyme Inhib Med Chem 2011;26:485–97.
   PubMed Web of Science ®Google Scholar
• Schrödinger L. QikProp version 2.5. New York, NY: Schrödinger, LLC; 2005.
   Google Scholar
• 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 2012;64:4–17.
   Web of Science ®Google Scholar
• Armarego WLF, Perring DD, Purification of laboratory chemicals, 4th ed. Oxford: Butterworth–Heinemann Press; 1999.
   Google Scholar
• Keri RS, Quintanova C, Marques SM, et al. Design, synthesis and neuroprotective evaluation of novel tacrine-benzothiazole hybrids as multi-targeted compounds against Alzheimer’s disease. Bioorg Med Chem 2013;21:4559–69.
   PubMed Web of Science ®Google Scholar
• Maestro version 9.3. Portland, OR: Schrödinger Inc.; 2012.
   Google Scholar
• Hassinen T, Peräkylä M. New energy terms for reduced protein models implemented in an off-lattice force field. J Comput Chem 2001;22:1229–42.
   Web of Science ®Google Scholar
• Acton A, Banck M, Bréfort J, et al. Ghemical version 3.0 2011.
   Google Scholar
• Jones G, Willett P, Glen RC, et al. Development and validation of a genetic algorithm for flexible docking. J Mol Biol 1997;267:727–48.
   PubMed Web of Science ®Google Scholar
• Bartolini M, Bertucci C, Bolognesi ML, et al. Insight into the kinetic of amyloid beta (1–42) peptide self-aggregation: elucidation of inhibitors' mechanism of action. ChemBioChem 2007;8:2152–61.
   PubMed Web of Science ®Google Scholar
• Chao X, He X, Yang Y, et al. Design, synthesis and pharmacological evaluation of novel tacrine-caffeic acid hybrids as multi-targeted compounds against Alzheimer's disease. Bioorg Med Chem Lett 2012;22:6498–502.
   PubMed Web of Science ®Google Scholar
• Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55–63.
   PubMed Web of Science ®Google Scholar