Biological activity of sym-triazines with acetylcholine-like substitutions as multitarget modulators of Alzheimer's disease

ACS Chemical Neuroscience

Volumn 4, Issue 6, 2013, Pages 924-929

  Veloso, Anthony J ^a   Chow, Ari M ^a   Dhar, Devjani ^a   Tang, Derek W F ^a   Ganesh, Hashwin V S ^a   Mikhaylichenko, Svetlana ^a   Brown, Ian R ^a   Kerman, Kagan ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

acetylcholinesterase; Alzheimer's disease; Amyloid beta; human SH SY5Y neuronal cells; multitarget modulator; sym triazines

Indexed keywords

ACETYLCHOLINE; ACETYLCHOLINESTERASE; AMYLOID BETA PROTEIN; AMYLOID BETA PROTEIN[1-42]; MICROTUBULE ASSOCIATED PROTEIN 2; PENTAPEPTIDE; SYNAPTOPHYSIN; TAE 1; TAE 2; THIOFLAVINE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG; AMYLOID BETA-PROTEIN (1-42); BIOLOGICAL PRODUCT; PEPTIDE FRAGMENT;

ALZHEIMER DISEASE; ARTICLE; BIOLOGICAL ACTIVITY; CHOLINESTERASE INHIBITION; CONTROLLED STUDY; CYTOSOL; ENZYME ACTIVITY; ERYTHROCYTE; FLUORESCENCE ANALYSIS; HUMAN; HUMAN CELL; NERVE CELL DIFFERENTIATION; PRIORITY JOURNAL; PROTEIN EXPRESSION; SCANNING ELECTRON MICROSCOPY; CELL DIFFERENTIATION; CHEMISTRY; DRUG DELIVERY SYSTEM; DRUG EFFECTS; PATHOLOGY; PHYSIOLOGY; PROCEDURES; PROTEIN SECONDARY STRUCTURE; TUMOR CELL LINE;

ACETYLCHOLINE; ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; BIOLOGICAL PRODUCTS; CELL DIFFERENTIATION; CELL LINE, TUMOR; DRUG DELIVERY SYSTEMS; HUMANS; PEPTIDE FRAGMENTS; PROTEIN STRUCTURE, SECONDARY; TRIAZINES;

EID: 84879765371     PISSN: None     EISSN: 19487193     Source Type: Journal    
DOI: 10.1021/cn400028w     Document Type: Article

References (31)

1. Selkoe, D. J. (2001) Alzheimer's disease results from the cerebral accumulation and cytotoxicity of amyloid beta-protein J. Alzheimer's Dis. 3, 75-81
2. da Silva, G. F. Z. and Ming, L. J. (2007) Metallo-ROS in Alzheimer's disease: Oxidation of neurotransmitters by Cu-II-beta-amyloid and neuropathology of the disease Angew. Chem., Int. Ed. 46, 3337-3341
3. Qin, L. Y., Liu, Y. X., Cooper, C., Liu, B., Wilson, B., and Hong, J. S. (2002) Microglia enhance beta-amyloid peptide-induced toxicity in cortical and mesencephalic neurons by producing reactive oxygen species J. Neurochem. 83, 973-983
4. Scheidt, H. A., Morgado, I., Rothemund, S., Huster, D., and Fäendrich, M. (2011) Solid-state NMR spectroscopic investigation of A beta protofibrils: Implication of a beta-sheet remodeling upon maturation into terminal amyloid fibrils Angew. Chem., Int. Ed. 50, 2837-2840
5. Walsh, D. M. and Selkoe, D. J. (2007) A beta oligomers-A decade of discovery J. Neurochem. 101, 1172-1184
6. Nakagami, Y., Nishimura, S., Murasugi, T., Kubo, T., Kaneko, I., Meguro, M., Marumoto, S., Kogen, H., Koyama, K., and Oda, T. (2002) A novel compound RS-0466 reverses beta-amyloid-induced cytotoxicity through the Akt signaling pathway in vitro Eur. J. Pharmacol. 457, 11-17
7. Kim, W., Kim, Y., Min, J., Kim, D. J., Chang, Y. T., and Hecht, M. H. (2006) A high-throughput screen for compounds that inhibit aggregation of the Alzheimer's peptide ACS Chem. Biol. 1, 461-469
8. Schliebs, R. and Arendt, T. (2006) The significance of the cholinergic system in the brain during aging and in Alzheimer's disease J. Neural. Transm. 113, 1625-1644
9. Ibach, B. and Haen, E. (2004) Acetylcholinesterase inhibition in Alzheimer's disease Curr. Pharm. Des. 10, 231-251
10. Piazzi, L., Rampa, A., Bisi, A., Gobbi, S., Belluti, F., Cavalli, A., Bartolini, M., Andrisano, V., Valenti, P., and Recanatini, M. (2003) 3-(4-{ benzyl(methyl)amino methyl}-phenyl)-6,7-dimethoxy-2H-2-chromenone (AP2238) inhibits both acetylcholinesterase and acetylcholinesterase-induced beta-amyloid aggregation: A dual function lead for Alzheimer's disease therapy J. Med. Chem. 46, 2279-2282
11. Cavalli, A., Bolognesi, M. L., Minarini, A., Rosini, M., Tumiatti, V., Recanatini, M., and Melchiorre, C. (2008) Multi-target-directed ligands to combat neurodegenerative diseases J. Med. Chem. 51, 347-372
12. Huang, Y. D. and Mucke, L. (2012) Alzheimer mechanisms and therapeutic strategies Cell 148, 1204-1222
13. Cavalli, A., Bolognesi, M. L., Capsoni, S., Andrisano, V., Bartolini, M., Margotti, E., Cattaneo, A., Recanatini, M., and Melchiorre, C. (2007) A small molecule targeting the multifactorial nature of Alzheimer's disease Angew. Chem., Int. Ed. 46, 3689-3692
14. Dantoine, T., Auriacombe, S., Sarazin, M., Becker, H., Pere, J. J., and Bourdeix, I. (2006) Rivastigmine monotherapy and combination therapy with memantine in patients with moderately severe Alzheimer's disease who failed to benefit from previous cholinesterase inhibitor treatment Int. J. Clin. Pract. 60, 110-118
15. Veloso, A. J., Dhar, D., Chow, A. M., Zhang, B., Tang, D. W. F., Ganesh, H. V. S., Mikhaylichenko, S., Brown, I. R., and Kerman, K. (2013) Sym-triazines for directed multitarget modulation of cholinesterases and amyloid-beta in Alzheimer's disease ACS Chem. Neurosci. 4, 339-349
16. Pallitto, M. M., Ghanta, J., Heinzelman, P., Kiessling, L. L., and Murphy, R. M. (1999) Recognition sequence design for peptidyl modulators of beta-amyloid aggregation and toxicity Biochemistry 38, 3570-3578
17. Ehrnhoefer, D. E., Bieschke, J., Boeddrich, A., Herbst, M., Masino, L., Lurz, R., Engemann, S., Pastore, A., and Wanker, E. E. (2008) EGCG redirects amyloidogenic polypeptides into unstructured, off-pathway oligomers Nat. Struct. Mol. Biol. 15, 558-566
18. Bieschke, J., Russ, J., Friedrich, R. P., Ehrnhoefer, D. E., Wobst, H., Neugebauer, K., and Wanker, E. E. (2010) EGCG remodels mature alpha-synuclein and amyloid-beta fibrils and reduces cellular toxicity Proc. Natl. Acad. Sci. U.S.A. 107, 7710-7715
19. Okabe, S., Miwa, A., and Okado, H. (2001) Spine formation and correlated assembly of presynaptic and postsynaptic molecules J. Neurosci. 21, 6105-6114
20. Brewer, G. J., Boehler, M. D., Pearson, R. A., DeMaris, A. A., Ide, A. N., and Wheeler, B. C. (2009) Neuron network activity scales exponentially with synapse density J. Neural Eng. 6, 014001
21. Dinsmore, J. H. and Solomon, F. (1991) Inhibition of MAP2 expression affects both morphological and cell-division phenotypes of neuronal differentiation Cell 64, 817-826
22. Fraichard, A., Chassande, O., Bilbaut, G., Dehay, C., Savatier, P., and Samarut, J. (1995) In-vitro differentiation of embryonic stem-cells into glial-cells and functional-neurons J. Cell Sci. 108, 3181-3188
23. Abrous, D. N., Koehl, M., and Le Moal, M. (2005) Adult neurogenesis: From precursors to network and physiology Physiol. Rev. 85, 523-569
24. Dounin, V., Veloso, A. J., Schulze, H., Bachmann, T. T., and Kerman, K. (2010) Disposable electrochemical printed gold chips for the analysis of acetylcholinesterase inhibition Anal. Chim. Acta 669, 63-67
25. Somji, M., Dounin, V., Muench, S. B., Schulze, H., Bachmann, T. T., and Kerman, K. (2012) Electroanalysis of amino acid substitutions in bioengineered acetylcholinesterase Bioelectrochemistry 88, 110-113
26. Chow, A. M. and Brown, I. R. (2007) Induction of heat shock proteins in differentiated human and rodent neurons by celastrol Cell Stress Chaperones 12, 237-244
27. Ellman, G. L., Courtney, K. D., Andres, V., and Featherstone, R. M. (1961) A new and rapid colorimetric determination of acetylcholinesterase activity Biochem. Pharmacol. 7, 88
28. Rizzo, S., Bartolini, M., Ceccarini, L., Piazzi, L., Gobbi, S., Cavalli, A., Recanatini, M., Andrisano, V., and Rampa, A. (2010) Targeting Alzheimer's disease: Novel indanone hybrids bearing a pharmacophoric fragment of AP2238 Bioorg. Med. Chem. 18, 1749-1760
29. Hansen, R. A., Gartlehner, G., Webb, A. P., Morgan, L. C., Moore, C. G., and Jonas, D. E. (2008) Efficacy and safety of donepezil, galantamine, and rivastigmine for the treatment of Alzheimer's disease: A systematic review and meta-analysis Clin. Interventions Aging 3, 211-225
30. Das, J. R. and Tizabi, Y. (2009) Additive protective effects of Donepezil and nicotine against salsolinol-induced cytotoxicity in SH-SY5Y cells Neurotoxic. Res. 16, 194-204
31. Belluti, F., Piazzi, L., Bisi, A., Gobbi, S., Bartolini, M., Cavalli, A., Valenti, P., and Rampa, A. (2009) Design, synthesis, and evaluation of benzophenone derivatives as novel acetylcholinesterase inhibitors Eur. J. Med. Chem. 44, 1341-1348