Tacrine–propargylamine derivatives with improved acetylcholinesterase inhibitory activity and lower hepatotoxicity as a potential lead compound for the treatment of Alzheimer’s disease

References

• Burns A, Iliffe S. Alzheimer's disease. BMJ 2009;338:467–71
   Google Scholar
• Iqbal K, del C. Alonso A, Chen S, et al. Tau pathology in Alzheimer disease and other tauopathies. BBA – Mol Basis Dis 2005;1739:198–210
   PubMed Web of Science ®Google Scholar
• Praticò D. Oxidative stress hypothesis in Alzheimer’s disease: a reappraisal. Trends Pharmacol Sci 2008;29:609–15
   PubMed Web of Science ®Google Scholar
• Querfurth HW, LaFerla FM. Alzheimer's disease. New Engl J Med 2010;362:329–44
   PubMed Web of Science ®Google Scholar
• Bartus RT, Dean RL, Pontecorvo MJ, Flicker C. The cholinergic hypothesis: a historical overview, current perspective, and future directions. Ann NY Acad Sci 1985;444:332–58
   PubMed Web of Science ®Google Scholar
• 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;21:381–96
   PubMed Web of Science ®Google Scholar
• Chianella C, Gragnaniello D, Maisano Delser P, et al. BCHE and CYP2D6 genetic variation in Alzheimer's disease patients treated with cholinesterase inhibitors. Eur J Clin Pharmacol 2011;67:1147–57
   PubMed Web of Science ®Google Scholar
• Ballard CG. Advances in the treatment of Alzheimer's disease: benefits of dual cholinesterase inhibition. Eur Neurol 2002;47:64–70
   PubMed Web of Science ®Google Scholar
• Rogers SL, Farlow MR, Doody RS, et al. A 24-week, double-blind, placebo-controlled trial of donepezil in patients with Alzheimer's disease. Donepezil Study Group. Neurology 1998;50:136–45
   PubMed Web of Science ®Google Scholar
• Cummings JL. Cholinesterase inhibitors: a new class of psychotropic compounds. Am J Psychiat 2000;157:4–15
   PubMed Web of Science ®Google Scholar
• Giacobini E, Spiegel R, Enz A, et al. Inhibition of acetyl- and butyryl-cholinesterase in the cerebrospinal fluid of patients with Alzheimer's disease by rivastigmine: correlation with cognitive benefit. J Neural Transm 2002;109:1053–65
   PubMed Web of Science ®Google Scholar
• Tariot PN, Federoff HJ. Current treatment for Alzheimer disease and future prospects. Alz Dis Assoc Dis 2003;17:S105–13
   PubMed Web of Science ®Google Scholar
• Lo D, Grossberg GT. Use of memantine for the treatment of dementia. Expert Rev Neurother 2011;11:1359–70
   PubMed Web of Science ®Google Scholar
• Watkins PB, Zimmerman HJ, Knapp MJ, et al. Hepatotoxic effects of tacrine administration in patients with Alzheimer's disease. JAMA – J Am Med Assoc 1994;271:992–8
   PubMed Web of Science ®Google Scholar
• Marco-Contelles J, León R, de los Ríos C, et al. Novel multipotent tacrine–dihydropyridine hybrids with improved acetylcholinesterase inhibitory and neuroprotective activities as potential drugs for the treatment of Alzheimer's disease. J Med Chem 2006;49:7607–10
   PubMed Web of Science ®Google Scholar
• Fernandez-Bachiller MI, Perez C, Gonzalez-Munoz GC, et al. Novel tacrine-8-hydroxyquinoline hybrids as multifunctional agents for the treatment of Alzheimer's disease, with neuroprotective, cholinergic, antioxidant, and copper-complexing properties. J Med Chem 2010;53:4927–37
   PubMed Web of Science ®Google Scholar
• Fernandez-Bachiller MI, Perez C, Campillo NE, et al. Tacrine-melatonin hybrids as multifunctional agents for Alzheimer's disease, with cholinergic, antioxidant, and neuroprotective properties. Chem Med Chem 2009;4:828–41
   Web of Science ®Google Scholar
• Kochi A, Eckroat TJ, Green KD, et al. A novel hybrid of 6-chlorotacrine and metal-amyloid-β modulator for inhibition of acetylcholinesterase and metal-induced amyloid-β aggregation. Chem Sci 2013;4:4137–45
   Web of Science ®Google Scholar
• Hamulakova S, Janovec L, Hrabinova M, et al. Synthesis, design and biological evaluation of novel highly potent tacrine congeners for the treatment of Alzheimer's disease. Eur J Med Chem 2012;55:23–31
   PubMed Web of Science ®Google Scholar
• Chen X, Zenger K, Lupp A, et al. Tacrine–silibinin codrug shows neuro- and hepatoprotective effects in vitro and pro-cognitive and hepatoprotective effects in vivo. J Med Chem 2012;55:5231–42
   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
• Mao F, Chen J, Zhou Q, et al. Novel tacrine–ebselen hybrids with improved cholinesterase inhibitory, hydrogen peroxide and peroxynitrite scavenging activity. Bioorg Med Chem Lett 2013;23:6737–42
   PubMed Web of Science ®Google Scholar
• Youdim MBH, Wadia A, Tatton W, Weinstock M. The anti-Parkinson drug rasagiline and its cholinesterase inhibitor derivatives exert neuroprotection unrelated to MAO inhibition in cell culture and in vivo. Ann NY Acad Sci 2001;939:450–8
   PubMed Web of Science ®Google Scholar
• Yogev-Falach M, Amit T, Bar-Am O, Youdim MBH. The importance of propargylamine moiety in the anti-Parkinson drug rasagiline and its derivatives in MAPK-dependent amyloid precursor protein processing. FASEB J 2003;17:2325–7
   PubMed Web of Science ®Google Scholar
• Bar-Am O, Weinreb O, Amit T, Youdim MB. Regulation of Bcl-2 family proteins, neurotrophic factors, and APP processing in the neurorescue activity of propargylamine. FASEB J 2005;19:1899–901
   PubMed Web of Science ®Google Scholar
• Sagi Y, Mandel S, Amit T, Youdim MBH. Activation of tyrosine kinase receptor signaling pathway by rasagiline facilitates neurorescue and restoration of nigrostriatal dopamine neurons in post-MPTP-induced parkinsonism. Neurobiol Dis 2007;25:35–44
   PubMed Web of Science ®Google Scholar
• Kupershmidt L, Amit T, Bar-Am O, et al. Multi-target, neuroprotective and neurorestorative M30 improves cognitive impairment and reduces Alzheimer's-like neuropathology and age-related alterations in mice. Mol Neurobiol 2012;46:217–20
   PubMed Web of Science ®Google Scholar
• Tang J, Li J, Zhang L, et al. The divergent transformations of aromatic o-aminonitrile with carbonyl compound. J Heterocyclic Chem 2012;49:533–42
   Web of Science ®Google Scholar
• Mao F, Huang L, Luo Z, et al. O-hydroxyl- or o-amino benzylamine-tacrine hybrids: multifunctional biometals chelators, antioxidants, and inhibitors of cholinesterase activity and amyloid-beta aggregation. Bioorgan Med Chem 2012;20:5884–92
   PubMed Web of Science ®Google Scholar
• Ellman GL, Courtney KD, Andres V, Featherstone RM. Biochem Pharmacol 1961;7:88–95
   Google Scholar
• Bolognesi ML, Andrisano V, Bartolini M, et al. Propidium-based polyamine ligands as potent inhibitors of acetylcholinesterase and acetylcholinesterase-induced amyloid-beta aggregation. J Med Chem 2005;48:24–7
   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
• Schnabl B, Choi YH, Olsen JC, et al. Immortal activated human hepatic stellate cells generated by ectopic telomerase expression. Lab Invest 2002;82:323–33
   PubMed Web of Science ®Google Scholar