2-Arylbenzofuran-based molecules as multipotent Alzheimer's disease modifying agents

European Journal of Medicinal Chemistry

Volumn 58, Issue , 2012, Pages 519-532

  Rizzo, Stefano ^a   Tarozzi, Andrea ^a   Bartolini, Manuela ^a   Da Costa, Gregory ^b   Bisi, Alessandra ^a   Gobbi, Silvia ^a   Belluti, Federica ^a   Ligresti, Alessia ^c   Allarà, Marco ^c   Monti, Jean Pierre ^b   Andrisano, Vincenza ^a   Di Marzo, Vincenzo ^c   Hrelia, Patrizia ^a   Rampa, Angela ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b Bordeaux Segalen University   (France)

^c CNR   (Italy)

Author keywords

2 Arylbenzofurans; A peptide; Alzheimer's disease; CB receptors; Drug design; Neuroprotection

Indexed keywords

2 [4 (3 CHLOROPROPOXY)PHENYL]BENZOFURAN; [2 [3 [7 (BENZYLMETHYLAMINO)HEPTYLOXY]PHENYL]BENZOFURAN 3 YL] 2,3 DIMETHOXYPHENYL METHANONE; [2 [3 [7 (BENZYLMETHYLAMINO)HEPTYLOXY]PHENYL]BENZOFURAN 3 YL] 3 METHOXYPHENYLMETHANONE; [2 [3 [7 (BENZYLMETHYLAMINO)HEPTYLOXY]PHENYL]BENZOFURAN 3 YL] 3,4 DIMETHOXYPHENYL METHANONE; [2 [3 [7 (BENZYLMETHYLAMINO)HEPTYLOXY]PHENYL]BENZOFURAN 3 YL] 3,5 DIMETHOXYPHENYL METHANONE; [2 [3 [7 (BENZYLMETHYLAMINO)HEPTYLOXY]PHENYL]BENZOFURAN 3 YL]2 METHOXYPHENYLMETHANONE; [2 [3 [7 (BENZYLMETHYLAMINO)HEPTYLOXY]PHENYL]BENZOFURAN 3 YL]M TOLYLMETHANONE; [2 [3 [7 (BENZYLMETHYLAMINO)HEPTYLOXY]PHENYL]BENZOFURAN 3 YL]PARA TOLYLMETHANONE; [2 [3 [7 (BENZYLMETHYLAMINO)HEPTYLOXY]PHENYL]BENZOFURAN 3 YL]PHENYLMETHANONE; [2 [4 [7 (BENZYLMETHYLAMINO)HEPTYL]PHENYL]BENZOFURAN 3 YL]NAPHTHALEN 1YL METHANONE; [2 [4 [7 (BENZYLMETHYLAMINO)HEPTYLOXY]PHENYL]BENZOFURAN 3 YL][3 (2 DIETHYLAMINOETHOXY)PHENYL]METHANONE; [2 [4 [7 (BENZYLMETHYLAMINO)HEPTYLOXY]PHENYL]BENZOFURAN 3 YL][3 (DIETHYLAMINOMETHYL)PHENYL]METHANONE; [2 [4 [7 (BENZYLMETHYLAMINO)HEPTYLOXY]PHENYL]BENZOFURAN 3 YL][4 (2 CHLOROETHOXY)PHENYL]METHANONE; [2 [4 [7 (BENZYLMETHYLAMINO)HEPTYLOXY]PHENYL]BENZOFURAN 3 YL][4 (2 MORPHOLINOETHOXY)PHENYL]METHANONE; [2 [4 [7 (BENZYLMETHYLAMINO)HEPTYLOXY]PHENYL]BENZOFURAN 3 YL][4 (DIETHYLAMINOMETHYL)PHENYL]METHANONE; [2 [4 [7 (BENZYLMETHYLAMINO)HEPTYLOXY]PHENYL]BENZOFURAN 3 YL]BIPHENYL 4YL METHANONE; [2 [4 [7 (BENZYLMETHYLAMINO)HEPTYLOXY]PHENYL]BENZOFURAN 3 YL]NAPHTHALEN 2YL METHANONE; [3 (4 BENZOFURAN 2 YL PHENOXY)PROPYL]BENZYLMETHYLAMINE; [5 (4 BENZOFURAN 2 YL PHENOXY)PENTYL]BENZYLMETHYLAMINE; [7 (3 BENZOFURAN 2 YL PHENOXY)HEPTYL]BENZYLMETHYLAMINE; [8 (4 BENZOFURAN 2 YL PHENOXY)OCTYL]BENZYLMETHYLAMINE; [9 (4 BENZOFURAN 2 YL PHENOXY)NONYL]BENZYLMETHYLAMINE; ANTHRACEN 9 YL [2 [4 [7 (BENZYLMETHYLAMINO)HEPTYLOXY]PHENYL]BENZOFURAN 3 YL]METHANONE; BENZOFURAN DERIVATIVE; GALANTAMINE; METHYLCARBAMIC ACID 3 [[METHYL [7 [4 [3 (4 METHYLBENZOYL)BENZOFURAN 2 YL]PENOXY]HEPTYL]AMINO]METHYL]PHENYL ESTER; NOOTROPIC AGENT; RIVASTIGMINE; TACRINE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CONTROLLED STUDY; ENZYME INHIBITION; HUMAN; HUMAN CELL; NEUROPROTECTION; NEUROTOXICITY; OXIDATIVE STRESS; PROTEIN AGGREGATION; TOXICITY TESTING; ULTRAVIOLET SPECTROSCOPY;

ACETYLCHOLINESTERASE; ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; BENZOFURANS; BUTYRYLCHOLINESTERASE; CELL LINE, TUMOR; CELL SURVIVAL; CHOLINESTERASE INHIBITORS; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84869143950     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.10.045     Document Type: Article

References (37)

1. C. Ballard, S. Gauthier, A. Corbett, C. Brayne, D. Aarsland, and E. Jones Alzheimer's disease Lancet 377 2011 1019 1031
2. A.V. Terry, and J.J. Buccafusco 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. 306 2003 821 827
3. C.L. Masters, and D.J. Selkoe Biochemistry of amyloid β-protein and amyloid deposits in Alzheimer disease Cold Spring Harb. Perspect. Med. 2 2012 a006262
4. M. Jin, N. Shepardson, T. Yang, G. Chen, D. Walsh, and D.J. Selkoe Soluble amyloid β-protein dimers isolated from Alzheimer cortex directly induce Tau hyperphosphorylation and neuritic degeneration Proc. Natl. Acad. Sci. U. S. A. 108 2011 5819 5824
5. S. Darvesh, D.A. Hopkins, and C. Geula Neurobiology of butyrylcholinesterase Nat. Rev. Neurosci. 4 2003 131 138
6. N.H. Greig, T. Utsuki, D.K. Ingram, Y. Wang, G. Pepeu, C. Scali, Q.S. Yu, J. Mamczarz, H.W. Holloway, T. Giordano, D. Chen, K. Furukawa, K. Sambamurti, A. Brossi, and D.K. Lahir Selective butyrylcholinesterase inhibition elevates brain acetylcholine, augments learning and lowers Alzheimer beta-amyloid peptide in rodent Proc. Natl. Acad. Sci. U. S. A. 102 2005 17213 17218
7. T. Bisogno, and V. Di Marzo The role of the endocannabinoid system in Alzheimer's disease: facts and hypotheses Curr. Pharm. Des. 14 2008 2299 3305
8. T. Bisogno, and V. Di Marzo Cannabinoid receptors and endocannabinoids: role in neuroinflammatory and neurodegenerative disorders CNS Neurol. Disord. Drug Targets 9 2010 564 573
9. R. Morphy, and Z. Rankovic Designing multiple ligands - medicinal chemistry strategies and challenges Curr. Pharm. Des. 15 2009 587 600
10. A. Cavalli, M.L. Bolognesi, A. Minarini, M. Rosini, V. Tumiatti, M. Recanatini, and C. Melchiorre Multi-target-directed ligands to combat neurodegenerative diseases J. Med. Chem. 51 2008 347 372
11. S. Rizzo, C. Rivière, L. Piazzi, A. Bisi, S. Gobbi, M. Bartolini, V. Andrisano, F. Morroni, A. Tarozzi, J.P. Monti, and A. Rampa Benzofuran-based hybrid compounds for the inhibition of cholinesterase activity, β amyloid aggregation, and Aβ neurotoxicity J. Med. Chem. 51 2008 2883 2886
12. C.C. Felder, K.E. Joyce, E.M. Briley, M. Glass, K.P. Mackie, K.J. Fahey, G.J. Cullinan, D.C. Hunden, D.W. Johnson, M.O. Chaney, G.A. Koppel, and M. Brownstein LY320135, a novel cannabinoid CB1 receptor antagonist, unmasks coupling of the CB1 receptor to stimulation of cAMP accumulation J. Pharmacol. Exp. Ther. 284 1998 291 297
13. S. Rizzo, A. Bisi, M. Bartolini, F. Mancini, F. Belluti, S. Gobbi, V. Andrisano, and A. Rampa Multi-target strategy to address Alzheimer's disease: design, synthesis and biological evaluation of new tacrine-based dimers Eur. J. Med. Chem. 46 2011 4336 4343
14. G.L. Ellman, K.D. Courtney, V. Andres, and R.M. Featherstone A new rapid colorimetric determination of acetylcholinesterase activity Biochem. Pharmacol. 7 1961 88 95
15. C. Rivière, T. Richard, L. Quentin, S. Krisa, J.-M. Mérillon, and J.-P. Monti Inhibitory activity of stilbenes on Alzheimer's β-amyloid fibrils in vitro Bioorg. Med. Chem. 15 2007 1160 1167
16. A. Klegeris, D.G. Walker, and P.L. McGeer Activation of macrophages by Alzheimer beta amyloid peptide Biochem. Biophys. Res. Commun. 199 1994 984 991
17. C.J. Pike, A.J. Walencewicz-Wasserman, J. Kosmoski, D.H. Cribbs, C.G. Glabe, and C.W. Cotman Structure-activity analyses of beta-amyloid peptides: contributions of the beta 25-35 region to aggregation and neurotoxicity J. Neurochem. 64 1995 253 265
18. K. Ono, K. Hasegawa, H. Naiki, and M. Yamada Curcumin has potent anti-amyloidogenic effects for Alzheimer's beta-amyloid fibrils in vitro J. Neurosci. Res. 75 2004 742 750
19. A. Tarozzi, F. Morroni, A. Merlicco, C. Bolondi, G. Teti, M. Falconi, G. Cantelli-Forti, and P. Hrelia Neuroprotective effects of cyanidin 3-O-glucopyranoside on amyloid beta (25-35) oligomer-induced toxicity Neurosci. Lett. 473 2010 72 76
20. J. Wilhelm, R. Vytásek, I. Ostádalová, and L. Vajner Evaluation of different methods detecting intracellular generation of free radicals Mol. Cell. Biochem. 328 2009 167 176
21. A. Rampa, A. Bisi, P. Valenti, M. Recanatini, A. Cavalli, V. Andrisano, V. Cavrini, L. Fin, A. Buriani, and P. Giusti Acetylcholinesterase inhibitors: synthesis and structure-activity relationships of ω-[N-methyl-N-(3- alkylcarbamoyloxyphenyl)methyl]-aminoalkoxyheteroaryl derivatives J. Med. Chem. 41 1998 3976 3986
22. A. Rampa, L. Piazzi, F. Belluti, S. Gobbi, A. Bisi, M. Bartolini, V. Andrisano, V. Cavrini, A. Cavalli, M. Recanatini, and P. Valenti Acetylcholinesterase inhibitors: SAR and kinetic studies on ω-[N-methyl-N- (3-alkylcarbamoyloxyphenyl)-methyl]-aminoalkoxyaryl derivatives J. Med. Chem. 44 2001 3810 3820
23. M. Mesulam, A. Guillozet, P. Shaw, and B. Quinn Widely spread butyrylcholinesterase can hydrolyze acetylcholine in the normal and Alzheimer brain Neurobiol. Dis. 9 2002 88 93
24. Y. Furukawa-Hibi, T. Alkam, A. Nitta, A. Matsuyama, H. Mizoguchi, K. Suzuki, S. Moussaoui, Q.S. Yu, N.H. Greig, T. Nagai, and K. Yamada Butyrylcholinesterase inhibitors ameliorate cognitive dysfunction induced by amyloid-β peptide in mice Behav. Brain Res. 225 2011 222 229
25. D.J. Selkoe Soluble oligomers of the amyloid beta-protein impair synaptic plasticity and behavior Behav. Brain Res. 192 2008 106 113
26. L. Wicklund, R.N. Leao, A.M. Stromberg, M. Mousavi, O. Hovatta, A. Nordberg, and A. Marutle Beta-amyloid 1-42 oligomers impair function of human embryonic stem cell-derived forebrain cholinergic neurons PLoS One 5 2010 e15600
27. M. Bartolini, and V. Andrisano Strategies for the inhibition of protein aggregation in human diseases Chembiochem 11 2010 1018 1035
28. A.S. Johansson, J. Bergquist, C. Volbracht, A. Päiviö, M. Leist, L. Lannfelt, and A. Westlind-Danielsson Attenuated amyloid-beta aggregation and neurotoxicity owing to methionine oxidation Neuroreport 18 2007 559 563
29. M.E. Clementi, S. Marini, M. Coletta, F. Orsini, B. Giardina, and F. Misiti Abeta(31-35) and Abeta(25-35) fragments of amyloid beta-protein induce cellular death through apoptotic signals: role of the redox state of methionine-35 FEBS Lett. 579 2005 2913 2918
30. C.G. Glabe Common mechanisms of amyloid oligomer pathogenesis in degenerative disease Neurobiol. Aging 27 2006 570 575
31. A. Rauk Why is the amyloid beta peptide of Alzheimer's disease neurotoxic? Dalton Trans. 14 2008 1273 1282
32. M. Bjerke, E. Portelius, L. Minthon, A. Wallin, H. Anckarsater, R. Anckarsater, N. Andreasen, H. Zetterberg, U. Andreasson, and K. Blennow Confounding factors influencing amyloid beta concentration in cerebrospinal fluid Int. J. Alzheimers Dis. 2010 986310
33. M.S. Garcia-Ayllon, I. Riba-Llena, C. Serra-Basante, J. Alom, R. Boopathy, and J. Saez-Valero Altered levels of acetylcholinesterase in Alzheimer plasma PLoS One 5 2010 e8701
34. B.S. Harvey, K.S. Ohlsson, J.L. Mååg, I.F. Musgrave, and S.D. Smid Contrasting protective effects of cannabinoids against oxidative stress and amyloid-β evoked neurotoxicity in vitro Neurotoxicology 33 2012 138 146
35. P. Marini, A.S. Moriello, L. Cristino, M. Palmery, L. De Petrocellis, and V. Di Marzo Cannabinoid CB1 receptor elevation of intracellular calcium in neuroblastoma SH-SY5Y cells: interactions with muscarinic and delta-opioid receptors Biochim. Biophys. Acta 1793 2009 1289 1303
36. M. Haghani, M. Shabani, M. Javan, F. Motamedi, and M. Janahmadi CB1 cannabinoid receptor activation rescues amyloid β-induced alterations in behaviour and intrinsic electrophysiological properties of rat hippocampal CA1 pyramidal neurons Cell. Physiol. Biochem. 29 2012 391 406
37. M.L. Bolognesi, R. Banzi, M. Bartolini, A. Cavalli, A. Tarozzi, V. Andrisano, A. Minarini, M. Rosini, V. Tumiatti, C. Bergamini, R. Fato, G. Lenaz, P. Hrelia, A. Cattaneo, M. Recanatini, and C. Melchiorre Novel class of quinone-bearing polyamines as multi-target-directed ligands to combat Alzheimer's disease J. Med. Chem. 50 2007 4882 4897