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Research Paper

Novel tacrine–benzofuran hybrids as potential multi-target drug candidates for the treatment of Alzheimer’s Disease

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Pages 211-226 | Received 27 Aug 2019, Accepted 29 Oct 2019, Published online: 25 Nov 2019

References

  • a) Alzheimer’s Association, Alzheimer’s disease facts and figures, Alzheimer’s Dement. J Alzheimer’s Assoc 2017;13:325–73.; b) W.H. Organization in: The Global Dementia Observatory Reference Guide, World Health Organization. 2018; http://www.who.int/iris/handle/10665/272669.
  • Lillo-Crespo M, Riquelme J, Macrae R, et al. Experiences of advanced dementia care in seven European countries: implications for educating the workforce. Glob Health Action 2018;11:1478686.
  • Scheff SW, Price DA, Schmitt FA, et al. Hippocampal synaptic loss in early Alzheimer’s disease and mild cognitive impairment. Neurobiol Aging 2006;27:1372–84.
  • Bloom GS. Amyloid-β and tau: the trigger and bullet in Alzheimer disease pathogenesis. JAMA Neurol 2014;71:505–8.
  • Marco-Contelles J. Facts, results, and perspectives of the current Alzheimer’s disease research. ACS Chem Neurosci 2019;10:1127–8.
  • Tricco AC, Ashoor HM, Soobiah C, et al. Comparative effectiveness and safety of cognitive enhancers for treating Alzheimer's disease: systematic review and network metaanalysis. J Am Geriatr Soc 2018;66:170–8.
  • a) Panza F, Seripa D, Lozupone M, et al. The potential of solanezumab and gantenerumab to prevent Alzheimer's disease in people with inherited mutations that cause its early onset. Expert Opin Biol Ther 2018;18:25–35; b) Rinaldi A. Setbacks and promises for drugs against Alzheimer's disease: as pharmaceutical companies are retreating from drug development for Alzheimer's, new approaches are being tested in academia and biotech companies. EMBO Rep 2018;19:e46714.
  • Guzior N, Ckowska AW, Panek D, et al. Recent development of multifunctional agents as potential drug candidates for the treatment of alzheimer's disease. Curr Med Chem 2014;22:373–404.
  • Ramsay RR, Popovic-Nikolic MR, Nikolic K, et al. A perspective on multi-target drug discovery and design for complex diseases. Clin Trans Med 2018;7:3.
  • Oset-Gasque MJ, Marco-Contelles J. Alzheimer’s Disease, the “One-Molecule, One-Target” Paradigm, and the multitarget directed ligand approach. ACS Chem Neurosci 2018;9:401–3.
  • Santos MA, Chand K, Chaves S. Recent progress in repositioning Alzheimer’s disease drugs based on a multitarget strategy. Fut Med Chem 2016;8:2113–42.
  • Girek M, Szymański P. Tacrine hybrids as multi-target-directed ligands in Alzheimer’s disease: influence of chemical structures on biological activities. Chem Papers 2019;73:269–89.
  • Pérez-Areales FJ, Turcu AL, Barniol-Xicota M, et al. A novel class of multitarget anti-Alzheimer benzohomoadamantane‒chlorotacrine hybrids modulating cholinesterases and glutamate NMDA receptors. Eur J Med Chem 2019;180:613–626; b) Chalupova K, Korabeccny J, Bartolini M, et al. Novel tacrine-tryptophan hybrids: Multi-target directed ligands as potential treatment for Alzheimer's disease. Eur J Med Chem 2019;168:491–514.
  • 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.
  • Piemontese L, Tomás D, Hiremathad A, et al. Donepezil structure-based hybrids as potential multifunctional anti-Alzheimer´s drug candidates. J Enz Inhib Med Chem 2018;33:1212–24.
  • a) Chand K, Rajeshwari, Chaves S, et al. Tacrine–deferiprone hybrids as multi-target-directed metal chelators against Alzheimer's disease: a two-in-one drug. Metallomics, 2018;10:1460–5.; b) Rajeshwari , Chand K, Candeias E, et al. New multitarget hybrids bearing tacrine and phenylbenzothiazole motifs as potential drug candidates for Alzheimer's disease. Molecules 2019;24:587–601.
  • Chand K, Rajeshwari HA, et al. A review on antioxidant potential of bioactive heterocycle benzofuran: Natural and synthetic derivatives. Pharmacol Rep 2017;69:281–95.
  • a) Goyal D, Kaur A, Goyal B. Benzofuran and indole: Promising scaffolds for drug development in Alzheimer’s disease. Chem Med Chem 2018;13:1275–99.; b) Paudel P, Seong SH, Zhou Y, et al. Arylbenzofurans from the Root Bark of Morus alba as Triple Inhibitors of Cholinesterase, β-Site Amyloid Precursor Protein Cleaving Enzyme 1, and Glycogen Synthase Kinase-3β: Relevance to Alzheimer’s Disease. ACS Omega 2019;4:6283–6294.
  • 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.
  • PDB Protein Data Base, entry 1ODC, http://www.rcsb.org/structure/1ODC.
  • 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.
  • Dvir H, Silman I, Harel M, et al. Acetylcholinesterase: from 3D structure to function. Chem Biol Interact 2010;187:10–22.
  • Ceshi MA, Costa JS, Lopes JPB, et al. Novel series of tacrine-tianeptine hybrids: Synthesis, cholinesterase inhibitory activity, S100B secretion and a molecular modeling approach. Eur J Med Chem 2016;121:758–72.
  • Campos P, Formosa X, Galdeano C, et al. Tacrine-based dual binding site acetylcholinesterase inhibitors as potential disease-modifying anti-Alzheimer drug candidates. Chem Biol Interact 2010;187:411–515.
  • Zha X, Lamba D, Zhang L, et al. Novel tacrine − benzofuran hybrids as potent multitarget-directed ligands for the treatment of Alzheimer’s disease: design, synthesis, biological evaluation, and X-ray crystallography. J Med Chem 2016;59:114–31.
  • Keri RS, Quintanova C, Chaves S, et al. New tacrine hybrids with natural based cysteine derivatives as multi-targeted drugs for potential treatment of Alzheimer’s disease. Chem Biol Drug Des 2016;87:101–11.
  • Brooks PR, Wirtz MC, Vetelino MG, et al. Boron trichloride/tetra-n-butylammonium iodide: a mild, selective combination reagent for the cleavage of primary alkyl aryl ethers. J Org Chem 1999;64:9719–21.
  • Quintanova C, Keri RS, Marques SM, et al. Design, synthesis and bioevaluation of tacrine-cinnamate based hybrids as potential bifunctional anti-Alzheimer drug candidates. Med Chem Comm 2015;6:1969–77.
  • Sebestík J, Marques SM, Falé PL, et al. Bifunctional phenolic-choline conjugates as anti-oxidants and acetylcholinesterase inhibitors. J Enz Inhib Med Chem 2011;26:485–97.
  • Marques SM, Abate CC, Chaves S, et al. New bifunctional metalloproteinase inhibitors: an integrated approach towards biological improvements and cancer therapy. J Inorg Biochem 2013;127:188–202.
  • Chaves S, Hiremathad A, Tomás D, el al. Exploring the chelating capacity of 2-hydroxyphenylbenzimidazole based hybrids with multi-target ability as anti-Alzheimer’s agents. New J Chem 2018;42:16503–15.
  • Ellman GL, Courtney KD, Andres V, Jr, et al. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88–95.
  • Seeman P, Seeman N. Alzheimer's disease: β-amyloid plaque formation in human brain. Synapse 2011;65:1289–97.
  • Gleichmann M, Mattson MP. Alzheimer’s disease and neuronal network activity. Neuromol Med 2010;12:44–7.
  • Hudson SA, Ecroyd H, Kee TW, et al. The thioflavin T fluorescence assay for amyloid fibril detection can be biased by the presence of exogenous compounds. FEBS J 2009;276:5960–72.
  • Biancalana M, Koide S. Molecular mechanism of Thioflavin-T binding to amyloid fibrils. Biochim Biophys Acta 2010;1804:1405–12.
  • Gestwicki JE, Ranke A. Structure-activity relationships of amyloid beta-aggregation inhibitors based on curcumin: influence of linker length and flexibility. Chem Biol Drug Des 2007;70:206–15.
  • Jones MR, Service EL, Thompson JR, et al. Dual-function triazole–pyridine derivatives as inhibitors of metal-induced amyloid-β aggregation. Metallomics 2012;4:910–20.
  • QikProp, version 2.5, Schrödinger. New York: LLC; 2005.
  • Cheignon C, Tomas M, Bonnefont-Rousselot DP, et al. Oxidative stress and the amyloid beta peptide in Alzheimer’s disease. Redox Biol 2018;14:450–64.
  • Armarego WLF, Perring DD (Eds). Purification of laboratory chemicals. 4th ed. Oxford: Butterworth–Heinemann Press; 1999.
  • Rossotti FJC, Rossotti H. H,Potentiometric titrations using Gran plots: A textbook omission. J Chem Ed 1965;42:375–8.
  • Taylor RD, Jewsbury PJ, Essex PJ. A review of protein-small molecule docking methods. J Comp-Aided Mol Des 2002;16:151–66.
  • Maestro, Version 9.3, Portland: Schrödinger Inc; 2012.
  • Hassinen T, Peräkylä MJ. New energy terms for reduced protein models implemented in an off-lattice force field. Comput Chem 2001;22:1229–42.
  • 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.
  • Gans P, Sabatini A, Vacca A. Investigation of equilibria in solution. Determination of equilibrium constants with the HYPERQUAD suite of programs. Talanta 1996;43:1739–53.
  • Zékány L, Nagypál I, Peintler G. PSEQUAD for Chemical Equilibria, Update 5.01; 2001.
  • 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.
  • 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.
  • Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55–63.