Tacrine-based dual binding site acetylcholinesterase inhibitors as potential disease-modifying anti-Alzheimer drug candidates

Chemico-Biological Interactions

Volumn 187, Issue 1-3, 2010, Pages 411-415

  Camps, Pelayo ^a   Formosa, Xavier ^a   Galdeano, Carles ^a   Gómez, Tània ^a   Muñoz Torrero, Diego ^a   Ramírez, Lorena ^a   Viayna, Elisabet ^a   Gómez, Elena ^b   Isambert, Nicolás ^b   Lavilla, Rodolfo ^a,b   Badia, Albert ^c   Clos, M Victòria ^c   Bartolini, Manuela ^d   Mancini, Francesca ^d   Andrisano, Vincenza ^d   Bidon Chanal, Axel ^a   Huertas, Óscar ^a   Dafni, Thomai ^a   Luque, F Javier ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

^c INSTITUT DE NEUROCIÈNCIES   (Spain)

^d UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Acetylcholinesterase; Dual binding site inhibitors; Amyloid; Secretase

Indexed keywords

ACETYLCHOLINESTERASE; AMYLOID BETA PROTEIN; CHOLINESTERASE INHIBITOR; DONEPEZIL; PHENYLPYRANOL[3,2 C]QUINOLINE; PROPIDIUM IODIDE; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG BINDING SITE; DRUG DESIGN; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; IN VITRO STUDY; PROTEIN AGGREGATION;

EID: 77955510495     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2010.02.013     Document Type: Article

References (23)

1. Nordberg A. Mechanisms behind the neuroprotective actions of cholinesterase inhibitors in Alzheimer's disease. Alzheimer Dis. Assoc. Disord. 2006, 20(Suppl. 1):S12-S18.
2. Relkin N.R. Beyond symptomatic therapy: a re-examination of acetylcholinesterase inhibitors in Alzheimer's disease. Expert Rev. Neurother. 2007, 7:735-748.
3. Muñoz-Torrero D. Acetylcholinesterase inhibitors as disease-modifying therapies for Alzheimer's disease. Curr. Med. Chem. 2008, 15:2433-2455.
4. Skovronsky D.M., Lee V.M.-Y., Trojanowski J.Q. Neurodegenerative diseases: new concepts of pathogenesis and their therapeutic implications. Annu. Rev. Pathol. Mech. Dis. 2006, 1:151-170.
5. Hardy J., Selkoe D.J. The amyloid hypothesis of Alzheimer's disease: progress and problems on the road to therapeutics. Science 2002, 297:353-356.
6. Inestrosa N.C., Alvarez A., Pérez C.A., Moreno R.D., Vicente M., Linker C., Casanueva O.I., Soto C., Garrido J. Acetylcholinesterase accelerates assembly of amyloid-β-peptides into Alzheimer's fibrils: possible role of the peripheral site of the enzyme. Neuron 1996, 16:881-891.
7. Rees T.M., Berson A., Sklan E.H., Younkin L., Younkin S., Brimijoin S., Soreq H. Memory deficits correlating with acetylcholinesterase splice shift and amyloid burden in doubly transgenic mice. Curr. Alzheimer Res. 2005, 2:291-300.
8. De Ferrari G.V., Canales M.A., Shin I., Weiner L.M., Silman I., Inestrosa N.C. A structural motif of acetylcholinesterase that promotes amyloid β-peptide fibril formation. Biochemistry 2001, 40:10447-10457.
9. García-Palomero E., Muñoz P., Usan P., Garcia P., De Austria C., Valenzuela R., Rubio L., Medina M., Martínez A. Potent β-amyloid modulators. Neurodegener. Dis. 2008, 5:153-156.
10. Cavalli A., Bolognesi M.L., Capsoni S., Andrisano V., Bartolini M., Margotti E., Cattaneo A., Recanatini M., Melchiorre C. A small molecule targeting the multifactorial nature of Alzheimer's disease. Angew. Chem. Int. Ed. 2007, 46:3689-3692.
11. C. Spuch, D. Antequera, M.I. Fernandez-Bachiller, M.I. Rodríguez-Franco, E. Carro, A new tacrine-melatonin hybrid reduces amyloid burden and behavioral deficits in a mouse model of Alzheimer's disease, Neurotoxicol. Res., in press, doi:10.1007/s12640-009-9121-2.
12. http://www.noscira.com/.
13. Camps P., Formosa X., Galdeano C., Muñoz-Torrero D., Ramírez L., Gómez E., Isambert N., Lavilla R., Badia A., Clos M.V., Bartolini M., Mancini F., Andrisano V., Arce M.P., Rodríguez-Franco M.I., Huertas O., Dafni T., Luque F.J. Pyrano[3,2-c]quinoline-6-chlorotacrine hybrids as a novel family of acetylcholinesterase- and β-amyloid-directed anti-Alzheimer compounds. J. Med. Chem. 2009, 52:5365-5379.
14. Camps P., Formosa X., Galdeano C., Gómez T., Muñoz-Torrero D., Scarpellini M., Viayna E., Badia A., Clos M.V., Camins A., Pallàs M., Bartolini M., Mancini F., Andrisano V., Estelrich J., Lizondo M., Bidon-Chanal A., Luque F.J. Novel donepezil-based inhibitors of acetyl- and butyrylcholinesterase and acetylcholinesterase-induced β-amyloid aggregation. J. Med. Chem. 2008, 51:3588-3598.
15. Ellman G.L., Courtney K.D., Andres B., Featherstone R.M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 1961, 7:88-95.
16. Bartolini M., Bertucci C., Cavrini V., Andrisano V. β-Amyloid aggregation induced by human acetylcholinesterase: inhibition studies. Biochem. Pharmacol. 2003, 65:407-416.
17. Bartolini M., Bertucci C., Bolognesi M.L., Cavalli A., Melchiorre C., Andrisano V. Insight into the kinetic of amyloid beta (1-42) peptide self-aggregation: elucidation of inhibitors' mechanism of action. ChemBioChem 2007, 8:2152-2161.
18. Hanessian S., Yun H., Hou Y., Yang G., Bayrakdarian M., Therrien E., Moitessier N., Roggo S., Veenstra S., Tintelnot-Blomley M., Rondeau J.-M., Ostermeier C., Strauss A., Ramage P., Paganetti P., Neumann U., Betschart C. Structure-based design, synthesis, and memapsin 2 (BACE) inhibitory activity of carbocyclic and heterocyclic peptidomimetics. J. Med. Chem. 2005, 48:5175-5190.
19. Savini L., Gaeta A., Fattorusso C., Catalanotti B., Campiani G., Chiasserini L., Pellerano C., Novellino E., McKissic D., Saxena A. Specific targeting of acetylcholinesterase and butyrylcholinesterase recognition sites. Rational design of novel, selective, and highly potent cholinesterase inhibitors. J. Med. Chem. 2003, 46:1-4.
20. Giacobini E. Cholinesterase inhibitors: new roles and therapeutic alternatives. Pharmacol. Res. 2004, 50:433-440.
21. Hong L., Koelsch G., Lin X., Wu S., Terzyan S., Ghosh A.K., Zhang X.C., Tang J. Structure of the protease domain of memapsin 2 (β-secretase) complexed with inhibitor. Science 2000, 290:150-153.
22. Fu H., Li W., Luo J., Lee N.T.K., Li M., Tsim K.W.K., Pang Y., Youdim M.B.H., Han Y. Promising anti-Alzheimer's dimer bis(7)-tacrine reduces β-amyloid generation by directly inhibiting BACE-1 activity. Biochem. Biophys. Res. Commun. 2008, 366:631-636.
23. Ryan A.J., Gray N.M., Lowe P.N., Chung C.W. Effect of detergents on " promiscuous" inhibitors. J. Med. Chem. 2003, 46:3448-3451.