Synthesis and bioevaluation of new tacrine-cinnamic acid hybrids as cholinesterase inhibitors against Alzheimer’s disease

References

• Tumiatti V, Minarini A, Bolognesi ML, et al. Tacrine derivatives and Alzheimer’s disease. Curr Med Chem 2010;17:1825–38.
   PubMed Web of Science ®Google Scholar
• Tang H, Zhao HT, Zhong SM, et al. Novel oxoisoaporphine-based inhibitors of acetyl- and butyrylcholinesterase and acetylcholinesterase-induced beta-amyloid aggregation. Bioorg Med Chem Lett 2012;22:2257–61.
   PubMed Web of Science ®Google Scholar
• Spilovska K, Zemek F, Korabecny J, et al. Adamantane – a lead structure for drugs in clinical practice. Curr Med Chem 2016;23:3245–66.
   PubMed Web of Science ®Google Scholar
• Kuca K, Soukup O, Maresova P, et al. Current approaches against Alzheimer’s disease in clinical trials. J Braz Chem Soc 2016;27:641–9.
   Web of Science ®Google Scholar
• Selkoe DJ. Alzheimer’s disease: genes, proteins, and therapy. Physiol Rev 2001;81:741–66.
   PubMed Web of Science ®Google Scholar
• Francis PT, Palmer AM, Snape M, Wilcock GK. The cholinergic hypothesis of Alzheimer’s disease: a review of progress. J Neurol Neurosurg Psychiatry 1999;66:137–47.
   PubMed Web of Science ®Google Scholar
• Karran E, Mercken M, De Strooper B. The amyloid cascade hypothesis for Alzheimer’s disease: an appraisal for the development of therapeutics. Nat Rev Drug Discov 2011;10:698–712.
   PubMed Web of Science ®Google Scholar
• Ballatore C, Lee VM, Trojanowski JQ. Tau-mediated neurodegeneration in Alzheimer’s disease and related disorders. Nat Rev Neurosci 2007;8:663–72.
   PubMed Web of Science ®Google Scholar
• Webber KM, Raina AK, Marlatt MW, et al. The cell cycle in Alzheimer disease: a unique target for neuropharmacology. Mech Ageing Dev 2005;126:1019–25.
   PubMed Web of Science ®Google Scholar
• Tapia-Arancibia L, Aliaga E, Silhol M, Arancibia S. New insights into brain BDNF function in normal aging and Alzheimer disease. Brain Res Rev 2008;59:201–20.
   PubMed Web of Science ®Google Scholar
• Su B, Wang X, Nunomura A, et al. Oxidative stress signaling in Alzheimer’s disease. Curr Alzheimer Res 2008;5:525–32.
   PubMed Web of Science ®Google Scholar
• Barnham KJ, Masters CL, Bush AI. Neurodegenerative diseases and oxidative stress. Nat Rev Drug Discov 2004;3:205–14.
   PubMed Web of Science ®Google Scholar
• Jomova K, Valko M. Advances in metal-induced oxidative stress and human disease. Toxicology 2011;283:65–87.
   PubMed Web of Science ®Google Scholar
• Devi L, Anandatheerthavarada HK. Mitochondrial trafficking of APP and alpha synuclein: Relevance to mitochondrial dysfunction in Alzheimer’s and Parkinsons diseases. Biochim Biophys Acta 2010;1802:11–9.
   PubMed Web of Science ®Google Scholar
• De Jaeger X, Cammarota M, Prado MA, et al. Decreased acetylcholine release delays the consolidation of object recognition memory. Behav Brain Res 2013;238:62–8.
   PubMed 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
• Lemes LFN, de Andrade Ramos G, de Oliveira AS, et al. Cardanol-derived AChE inhibitors: towards the development of dual binding derivatives for Alzheimer’s disease. Eur J Med Chem 2016;108:687–700.
   PubMed Web of Science ®Google Scholar
• Holzgrabe U, Kapkova P, Alptuzun V, et al. Targeting acetylcholinesterase to treat neurodegeneration. Expert Opin Ther Targets 2007;11:161–79.
   PubMed Web of Science ®Google Scholar
• Korabecny J, Musilek K, Zemek F, et al. Synthesis and in vitro evaluation of 7-methoxy-N-(pent-4-enyl)-1,2,3,4-tetrahydroacridin-9-amine-new tacrine derivate with cholinergic properties. Bioorg Med Chem Lett 2011;21:6563–6.
   PubMed Web of Science ®Google Scholar
• Galimberti D, Scarpini E. Old and new acetylcholinesterase inhibitors for Alzheimer’s disease. Expert Opin Investig Drugs 2016;25:1181–7.
   PubMed Web of Science ®Google Scholar
• Giacobini E. Cholinesterases: new roles in brain function and in Alzheimer’s disease. Neurochem Res 2003;28:515–22.
   PubMed Web of Science ®Google Scholar
• Greig NH, Lahiri DK, Sambamurti K. Butyrylcholinesterase: an important new target in Alzheimer’s disease therapy. Int Psychogeriatr 2002;14:77–91.
   PubMed Web of Science ®Google Scholar
• Terry AV, Jr, Buccafusco JJ. The cholinergic hypothesis of age and Alzheimer’s disease-related cognitive deficits: recent challenges and their implications for novel drug development. J Pharmacol Exp Ther 2003;306:821–7.
   PubMed Web of Science ®Google Scholar
• Bajda M, Guzior N, Ignasik M, Malawska B. Multi-target-directed ligands in Alzheimer’s disease treatment. Curr Med Chem 2011;18:4949–75.
   PubMed Web of Science ®Google Scholar
• Babkova K, Korabecny J, Soukup O, et al. Prolyl oligopeptidase and its role in the organism: attention to the most promising and clinically relevant inhibitors. Future Med Chem 2017;9:1015–38.
   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;51:347–72.
   PubMed Web of Science ®Google Scholar
• Wang Y, Wang H, Chen HZ. AChE inhibition-based multi-target-directed ligands, a novel pharmacological approach for the symptomatic and disease-modifying therapy of Alzheimer’s disease. Curr Neuropharmacol 2016;14:364–75.
   PubMed Web of Science ®Google Scholar
• Bolognesi ML, Rosini M, Andrisano V, et al. MTDL design strategy in the context of Alzheimer’s disease: from lipocrine to memoquin and beyond. Curr Pharm Design 2009;15:601–13.
   PubMed Web of Science ®Google Scholar
• Bolognesi ML, Minarini A, Rosini M, et al. From dual binding site acetylcholinesterase inhibitors to multi-target-directed ligands (MTDLs): a step forward in the treatment of Alzheimer’s disease. Mini-Rev Med Chem 2008;8:960–7.
   PubMed Web of Science ®Google Scholar
• Gazova Z, Soukup O, Sepsova V, et al. Multi-target-directed therapeutic potential of 7-methoxytacrine-adamantylamine heterodimers in the Alzheimer’s disease treatment. Biochim Biophys Acta 2017;1863:607–19.
   PubMed Web of Science ®Google Scholar
• Spilovska K, Korabecny J, Sepsova V, et al. Novel tacrine-Scutellarin hybrids as multipotent anti-Alzheimer’s agents: design, synthesis and biological evaluation. Molecules 2017;22:1006–27.
   PubMed Web of Science ®Google Scholar
• Bourne Y, Taylor P, Radic Z, Marchot P. Structural insights into ligand interactions at the acetylcholinesterase peripheral anionic site. EMBO J 2003;22:1–12.
   PubMed Web of Science ®Google Scholar
• Nordberg A, Ballard C, Bullock R, et al. A review of butyrylcholinesterase as a therapeutic target in the treatment of Alzheimer’s disease. Prim Care Companion CNS Disord 2013;15:PCC.12r01412.
   PubMedGoogle Scholar
• Li Q, Yang H, Chen Y, Sun H. Recent progress in the identification of selective butyrylcholinesterase inhibitors for Alzheimer’s disease. Eur J Med Chem 2017;132:294–309.
   PubMed Web of Science ®Google Scholar
• Inestrosa NC, Sagal JP, Colombres M. Acetylcholinesterase interaction with Alzheimer amyloid beta. Subcell Biochem 2005;38:299–317.
   PubMedGoogle Scholar
• Horak M, Holubova K, Nepovimova E, et al. The pharmacology of tacrine at N-methyl-d-aspartate receptors. Prog Neuropsychopharmacol Biol Psychiatry 2017;75:54–62.
   PubMed 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
• Chen Y, Sun J, Fang L, et al. Tacrine-ferulic acid-nitric oxide (NO) donor trihybrids as potent, multifunctional acetyl- and butyrylcholinesterase inhibitors. J Med Chem 2012;55:4309–21.
   PubMed Web of Science ®Google Scholar
• Spilovska K, Korabecny J, Horova A, et al. Design, synthesis and in vitro testing of 7-methoxytacrine-amantadine analogues: a novel cholinesterase inhibitors for the treatment of Alzheimer’s disease. Med Chem Res 2015;24:2645–55.
   Web of Science ®Google Scholar
• Ellman GL, Courtney KD, Andres V, Jr, Feather SRM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88–95.
   PubMed Web of Science ®Google Scholar
• Korabecny J, Holas O, Musilek K, et al. Synthesis and in vitro evaluation of new tacrine derivates-BIS-alkylene linked 7-MEOTA. Lett Org Chem 2010;7:327–31.
   Web of Science ®Google Scholar
• Nepovimova E, Korabecny J, Dolezal R, et al. Tacrine-trolox hybrids: a novel class of centrally active, nonhepatotoxic multi-target-directed ligands exerting anticholinesterase and antioxidant activities with low in vivo toxicity. J Med Chem 2015;58:8985–9003.
   PubMed Web of Science ®Google Scholar
• Chen Y, Lin H, Zhu J, et al. Design, synthesis, in vitro and in vivo evaluation of tacrine-cinnamic acid hybrids as multi-target acetyl- and butyrylcholinesterase inhibitors against Alzheimer’s disease. RSC Adv 2017;7:33851–67.
   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
• Chen Y, Lin H, Yang H, et al. Discovery of new acetylcholinesterase and butyrylcholinesterase inhibitors through structure-based virtual screening. RSC Adv 2017;7:3429–38.
   Web of Science ®Google Scholar
• Chen Y, Sun J, Huang Z, et al. Design, synthesis and evaluation of tacrine-flurbiprofen-nitrate trihybrids as novel anti-Alzheimer’s disease agents. Bioorg Med Chem 2013;21:2462–70.
   PubMed Web of Science ®Google Scholar
• Li SY, Jiang N, Xie SS, et al. Design, synthesis and evaluation of novel tacrine-rhein hybrids as multifunctional agents for the treatment of Alzheimer’s disease. Org Biomol Chem 2014;12:801–14.
   PubMed Web of Science ®Google Scholar
• Chen Y, Xu X, Fu T, et al. Discovery of new scaffolds from approved drugs as acetylcholinesterase inhibitors. RSC Adv 2015;5:90288–94.
   Web of Science ®Google Scholar