Novel heterobivalent tacrine derivatives as cholinesterase inhibitors with notable selectivity toward butyrylcholinesterase

Journal of Medicinal Chemistry

Volumn 49, Issue 25, 2006, Pages 7540-7544

  Elsinghorst, Paul W ^a   González Tanarro, Camino M ^a   Gütschow, Michael ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLINESTERASE; CHOLINESTERASE INHIBITOR; HYDRAZIDE; TACRINE DERIVATIVE; TRIMETHOXYBENZOIC ACID DERIVATIVE; TRIMETHOXYPHENYLPROPIONIC ACID DERIVATIVE;

ALKYLATION; ARTICLE; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ELECTROPHORESIS; ENZYME INHIBITION; EVALUATION; IC 50; NONHUMAN; SUBSTITUTION REACTION; TORPEDO CALIFORNICA;

ACETYLCHOLINESTERASE; ANIMALS; BENZAMIDES; BUTYRYLCHOLINESTERASE; CHOLINESTERASE INHIBITORS; ELECTROPHORUS; HUMANS; HYDRAZINES; TACRINE;

EID: 33845480947     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060742o     Document Type: Article

References (26)

1. (a) Castro, A.; Martinez, A. Peripheral and dual binding site acetylcholinesterase inhibitors: implications in treatment of Alzheimer's disease. Mini-Rev. Med. Chem. 2001, 1, 267-272.
2. (b) Silman, I.; Sussman, J. L. Acetylcholinesterase: " classical" and "non-classical" functions and pharmacology. Curr. Opin. Pharmacol. 2005, 5, 293-302.
3. (c) Muñoz-Torrero, D.; Camps, P. Dimeric and hybrid anti-Alzheimer drug candidates. Curr. Med. Chem. 2006, 13, 399-422.
4. (a) Darvesh, S.; Hopkins, D. A.; Geula, C. Neurobiology of butyrylcholinesterase. Nat. Rev. Neurosci. 2003, 4, 131-138.
5. (b) Greig, N. H.; Utsuki, T.; Yu, Q.-S.; Zhu, X.; Holloway, H. W.; Perry, T.; Lee, B.; Ingram, D. K.; Lahiri, D. K. A new therapeutic target in Alzheimer's disease treatment: attention to butyrylcholinesterase. Curr. Med. Res. Opin. 2001, 17, 159-165.
6. Inestrosa, N. C.; Alvarez, A.; Prez, C. A.; Moreno, R. D.; Vicente, M.; Linker, C.; Casanueva, O. J.; Soto, C.; Garrido, J. Acetylcholinesterase accelerates assembly of amyloid-beta-peptides into Alzheimer's fibrils: possible role of the peripheral site of the enzyme. Neuron 1996, 16, 881-891.
7. Branduardi, D.; Gervasio, F. L.; Cavalli, A.; Recanatini, M.; Parrinello, M. The role of the peripheral anionic site and cation-π interactions in the ligand penetration of the human AChE gorge. J. Am. Chem. Soc. 2005, 127, 9147-9155.
8. Pang, Y. P.; Quiram, P.; Jelacic, T.; Hong, F.; Brimijoin, S. Highly potent, selective, and low cost bis-tetrahydroaminacrine inhibitors of acetylcholinesterase. Steps toward novel drugs for treating Alzheimer's disease. J. Biol. Chem. 1996, 271, 23646-23649.
9. (a) Carlier, P. R.; Chow, E. S.; Han, Y.; Liu, J.; Yazal, J. E.; Pang, Y. P. Heterodimeric tacrine-based acetylcholinesterase inhibitors: investigating ligand-peripheral site interactions. J. Med. Chem. 1999, 42, 4225-4231.
10. (b) Camps, P.; Formosa, X.; Munoz-Torrero, D.; Petrignet, J.; Badia, A.; Clos, M. V. Synthesis and pharmacological evaluation of huprine-tacrine heterodimers: subnanomolar dual binding site acetylcholinesterase inhibitors. J. Med. Chem. 2005, 48, 1701-1704.
11. (c) Rodríguez-Franco, M. I.; Fernández-Bachiller, M. I.; Pérez, C.; Hernández-Ledesma, B.; Bartolomé, B. Novel tacrine-melatonin hybrids as dual-acting drugs for Alzheimer disease, with improved acetylcholinesterase inhibitory and antioxidant properties. J. Med. Chem. 2006, 49, 459-462.
12. (a) 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 butyryl-cholinesterase recognition sites. Rational design of novel, selective, and highly potent cholinesterase inhibitors. J. Med. Chem. 2003, 46, 1-4.
13. (b) Campiani, G.; Fattorusso, C.; Butini, S.; Gaeta, A.; Agnusdei, M.; Gemma, S.; Persico, M.; Catalanotti, B.; Savini, L.; Nacci, V.; Novellino, E.; Holloway, H. W.; Greig, N. H.; Belinskaya, T.; Fedorko, J. M.; Saxena, A. Development of molecular probes for the identification of extra interaction sites in the mid-gorge and peripheral sites of butyrylcholinesterase (BuChE). Rational design of novel, selective, and highly potent BuChE inhibitors. J. Med. Chem. 2005, 48, 1919-1929.
14. (a) Piazzi, L.; Rampa, A.; Bisi, A.; Gobbi, S.; Belluti, F.; Cavalli, A.; Bartolini, M.; Andrisano, V.; Valenti, P.; Recanatini, M. 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. 2003, 46, 2279-2282.
15. (b) Alonso, D.; Dorronsoro, I.; Rubio, L.; Muñoz, P.; García-Palomero, E.; Del Monte, M.; Bidon-Chanal, A.; Orozco, M.; Luque, F. J.; Castro, A.; Medina, M.; Martínez, A. Donepezil-tacrine hybrid related derivatives as new dual binding site inhibitors of AChE. Bioorg. Med. Chem. 2005, 13, 6588-6597.
16. Chen, J. W.; Luo, Y. L.; Hwang, M. J.; Peng, F. C.; Ling, K. H. Territrem B. a tremorgenic mycotoxin that inhibits acetylcholinesterase with a noncovalent yet irreversible binding mechanism. J. Biol. Chem. 1999, 274, 34916-34923.
17. Ucar, G.; Gokhan, N.; Yesilada, A.; Bilgin, A. A. 1-N-Substituted thiocarbamoyl-3-phenyl-5-thienyl-2-pyrazolines: a novel cholinesterase and selective monoamine oxidase B inhibitors for the treatment of Parkinson's and Alzheimer's diseases. Neurosci. Lett. 2005, 382, 327-331.
18. Michalson, E. T.; D'Andrea, S.; Freeman, J. P.; Szmuszkovicz, J. The synthesis of 9-(1-azetidinyl)-1,2,3,4-tetrahydroacridine. Heterocycles 1990, 30, 415-425.
19. Temple, C.; Elliott, R. D.; Montgomery, J. A. Potential anticancer agents: 5-(N-substituted-aminocarbonyl)- and 5-(N-substituted-aminothiocarbonyl) -5,6,7,8-tetrahydrofolic acids. J. Med. Chem. 1988, 31, 697-700.
20. Leone-Bay, A.; Paton, D. R.; Freeman, J.; Lercara, C.; O'Toole, D.; Gschneidner, D.; Wang, E.; Harris, E.; Rosado, C.; Rivera, T.; DeVincent, A.; Tai, M.; Mercogliano, F.; Agarwal, R.; Leipold, H.; Baughman, R. A. Synthesis and evaluation of compounds that facilitate the gastrointestinal absorption of heparin. J. Med. Chem. 1998, 41, 1163-1171.
21. Ellman, G. L.; Courtney, K. D.; Andres, V.; Feather-Stone, R. M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 1961, 7, 88-95.
22. Pietsch, M.; Gütschow, M. Synthesis of tricyclic 1,3-oxazin-4-ones and kinetic analysis of cholesterol esterase and acetylcholinesterase inhibition. J. Med. Chem. 2005, 48, 8270-8288.
23. Kronman, C.; Velan, B.; Gazes, Y.; Leitner, M.; Flashner, Y.; Lazarb, A.; Marcus, D.; Sery, T.; Papier, Y.; Grosfeld, H.; Cohen, S.; Shafferman, A. Production and secretion of high levels of recombinant human acetylcholinesterase in cultured cell lines: microheterogeneity of the catalytic subunit. Gene 1992, 121, 295-304.
24. Chatonnet, A.; Lockridge, O. Comparison of butyrylcholinesterase and acetylcholinesterase. Biochem. J. 1989, 260, 625-634.
25. Worek, F.; Mast, U.; Kiderlen, D.; Diepold, C.; Eyer, P. Improved determination of acetylcholinesterase activity in human whole blood. Clin. Chim. Acta. 1999, 288, 73-90.
26. Augustinsson, K. B.; Eriksson, H.; Faijersson, Y. A new approach to determining cholinesterase activities in samples of whole blood. Clin. Chim. Acta. 1978, 89, 239-252.