7-methoxytacrine-p-anisidine hybrids as novel dual binding site acetylcholinesterase inhibitors for Alzheimer's disease treatment

Molecules

Volumn 20, Issue 12, 2015, Pages 22084-22101

  Korabecny, Jan ^a,b,c   Andrs, Martin ^a,b   Nepovimova, Eugenie ^a,b   Dolezal, Rafael ^a   Babkova, Katerina ^a,b   Horova, Anna ^a,b   Malinak, David ^a   Mezeiova, Eva ^a   Gorecki, Lukas ^a,b   Sepsova, Vendula ^a,b   Hrabinova, Martina ^a,b   Soukup, Ondrej ^a,b,c   Jun, Daniel ^a,b   Kuca, Kamil ^a,b,c  

^a UNIVERSITY HOSPITAL HRADEC KRALOVE   (Czech Republic)

^b UNIVERSITY OF DEFENCE   (Czech Republic)

^c NATIONAL INSTITUTE OF MENTAL HEALTH   (Czech Republic)

Author keywords

7 methoxy tacrine; Acetylcholinesterase; Alzheimer's disease; Butyrylcholinesterase; MTDLs; Tacrine

Indexed keywords

ACETYLCHOLINESTERASE; AMYLOID BETA PROTEIN; ANILINE DERIVATIVE; CENTRAL NERVOUS SYSTEM AGENTS; CHOLINESTERASE INHIBITOR; RECOMBINANT PROTEIN; TACRINE;

ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; BINDING SITE; CHEMISTRY; HUMAN; KINETICS; MOLECULAR DOCKING; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ACETYLCHOLINESTERASE; AMYLOID BETA-PEPTIDES; ANILINE COMPOUNDS; BINDING SITES; CENTRAL NERVOUS SYSTEM AGENTS; CHOLINESTERASE INHIBITORS; HUMANS; KINETICS; MOLECULAR DOCKING SIMULATION; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; TACRINE;

EID: 84954356941     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules201219836     Document Type: Article

References (48)

1. Alzheimer's Association. 2015 Alzheimer's disease facts and figures. Alzheimers Dement. 2015, 11, 332-384.
2. Maresova, P.; Mohelska, H.; Dolejs, J.; Kuca, K. Socio-economic aspects of Alzheimer's disease. Curr. Alzheimer Res. 2015, 12, 903-911. [CrossRef][PubMed]
3. Karran, E.; Mercken, M.; de Strooper, B. The amyloid cascade hypothesis for Alzheimer's disease: An appraisal for the development of therapeutics. Nat. Rev. Drug Discov. 2011, 10, 698-712. [CrossRef][PubMed]
4. Ballatore, C.; Lee, V.M.-Y.; Trojanowski, J.Q. Tau-mediated neurodegeneration in Alzheimer's disease and related disorders. Nat. Rev. Neurosci. 2007, 8, 663-672. [CrossRef][PubMed]
5. Rosini, M.; Simoni, E.; Milelli, A.; Minarini, A.; Melchiorre, C. Oxidative stress in Alzheimer's disease: Are we connecting the dots? J. Med. Chem. 2014, 57, 2821-2831. [CrossRef][PubMed]
6. Schrag, M.; Mueller, C.; Oyoyo, U.; Smith, M.A.; Kirsch, W.M. Iron, zinc and copper in the Alzheimer's disease brain: A quantitative meta-analysis. Some insight on the influence of citation bias on scientific opinion. Prog. Neurobiol. 2011, 94, 296-306. [CrossRef][PubMed]
7. Contestabile, A. The history of the cholinergic hypothesis. Behav. Brain Res. 2011, 221, 334-340. [CrossRef][PubMed]
8. Bartus, R.T.; Dean, R.L.; Beer, B.; Lippa, A.S. The cholinergic hypothesis of geriatric memory dysfunction. Science 1982, 217, 408-414. [CrossRef][PubMed]
9. Zemek, F.; Drtinova, L.; Nepovimova, E.; Sepsova, V.; Korabecny, J.; Klimes, J.; Kuca, K. Outcomes of Alzheimer's disease therapy with acetylcholinesterase inhibitors and memantine. Expert Opin. Drug Saf. 2014, 13, 759-774.[PubMed]
10. Johnson, J.W.; Glasgow, N.G.; Povysheva, N.V. Recent insights into the mode of action of memantine and ketamine. Curr. Opin. Pharmacol. 2015, 20, 54-63. [CrossRef][PubMed]
11. Summers, W.K.; Majovski, L.V.; Marsh, G.M.; Tachiki, K.; Kling, A. Oral tetrahydroaminoacridine in long-term treatment of senile dementia, Alzheimer type. N. Engl. J. Med. 1986, 315, 1241-1245. [CrossRef][PubMed]
12. Patocka, J.; Jun, D.; Kuca, K. Possible role of hydroxylated metabolites of tacrine in drug toxicity and therapy of Alzheimer's disease. Curr. Drug Metab. 2008, 9, 332-335. [CrossRef][PubMed]
13. Soukup, O.; Jun, D.; Zdarova-Karasova, J.; Patocka, J.; Musilek, K.; Korabecny, J.; Krusek, J.; Kaniakova, M.; Sepsova, V.; Mandikova, J.; et al. A resurrection of 7-MEOTA: A comparison with tacrine. Curr. Alzheimer Res. 2013, 10, 893-906. [CrossRef][PubMed]
14. Sepsova, V.; Karasova, J.Z.; Tobin, G.; Jun, D.; Korabecny, J.; Cabelova, P.; Janska, K.; Krusek, J.; Skrenkova, K.; Kuca, K.; et al. Cholinergic properties of new 7-methoxytacrine-donepezil derivatives. Gen. Physiol. Biophys. 2015, 34, 189-200. [CrossRef][PubMed]
15. Misik, J.; Korabecny, J.; Nepovimova, E.; Cabelova, P.; Kassa, J. The effects of novel 7-MEOTA-donepezil like hybrids and N-alkylated tacrine analogues in the treatment of quinuclidinyl benzilate-induced behavioural deficits in rats performing the multiple T-maze test. Biomed. Pap. Med. Fac. Univ. Palacky Olomouc Czechoslov. 2015. [CrossRef][PubMed]
16. Nepovimova, E.; Uliassi, E.; Korabecny, J.; Peña-Altamira, L.E.; Samez, S.; Pesaresi, A.; Garcia, G.E.; Bartolini, M.; Andrisano, V.; Bergamini, C.; et al. Multitarget drug design strategy: Quinone-tacrine hybrids designed to block amyloid-β aggregation and to exert anticholinesterase and antioxidant effects. J. Med. Chem. 2014, 57, 8576-8589. [CrossRef][PubMed]
17. Korabecny, J.; Dolezal, R.; Cabelova, P.; Horova, A.; Hruba, E.; Ricny, J.; Sedlacek, L.; Nepovimova, E.; Spilovska, K.; Andrs, M.; et al. 7-MEOTA-donepezil like compounds as cholinesterase inhibitors: Synthesis, pharmacological evaluation, molecular modeling and QSAR studies. Eur. J. Med. Chem. 2014, 82, 426-438. [CrossRef][PubMed]
18. Korabecny, J.; Musilek, K.; Holas, O.; Binder, J.; Zemek, F.; Marek, J.; Pohanka, M.; Opletalova, V.; Dohnal, V.; Kuca, K. Synthesis and in vitro evaluation of N-alkyl-7-methoxytacrine hydrochlorides as potential cholinesterase inhibitors in Alzheimer disease. Bioorg. Med. Chem. Lett. 2010, 20, 6093-6095. [CrossRef][PubMed]
19. Korabecny, J.; Musilek, K.; Zemek, F.; Horova, A.; Holas, O.; Nepovimova, E.; Opletalova, V.; Hroudova, J.; Fisar, Z.; Jung, Y.-S.; et al. Synthesis and in vitro evaluation of 7-methoxy-N-(pent-4-enyl)-1,2,3,4-tetrahydroacridin-9-amine-New tacrine derivate with cholinergic properties. Bioorg. Med. Chem. Lett. 2011, 21, 6563-6566. [CrossRef][PubMed]
20. Hamulakova, S.; Janovec, L.; Hrabinova, M.; Spilovska, K.; Korabecny, J.; Kristian, P.; Kuca, K.; Imrich, J. Synthesis and biological evaluation of novel tacrine derivatives and tacrine-coumarin hybrids as cholinesterase inhibitors. J. Med. Chem. 2014, 57, 7073-7084. [CrossRef][PubMed]
21. Korabecny, J.; Musilek, K.; Holas, O.; Nepovimova, E.; Jun, D.; Zemek, F.; Opletalova, V.; Patocka, J.; Dohnal, V.; Nachon, F.; et al. Synthesis and in vitro evaluation of N-(Bromobut-3-en-2-yl)-7-methoxy-1,2,3,4-tetrahydroacridin-9-amine as a cholinesterase inhibitor with regard to Alzheimer's disease treatment. Mol. Basel Switz. 2010, 15, 8804-8812. [CrossRef][PubMed]
22. Minarini, A.; Milelli, A.; Simoni, E.; Rosini, M.; Bolognesi, M.L.; Marchetti, C.; Tumiatti, V. Multifunctional tacrine derivatives in Alzheimer's disease. Curr. Top. Med. Chem. 2013, 13, 1771-1786. [CrossRef][PubMed]
23. Carlier, P.R.; Chow, E.S.; Han, Y.; Liu, J.; el Yazal, J.; Pang, Y.P. Heterodimeric tacrine-based acetylcholinesterase inhibitors: Investigating ligand-peripheral site interactions. J. Med. Chem. 1999, 42, 4225-4231. [CrossRef][PubMed]
24. Lee, S.K.; Park, M.K.; Jhang, H.E.; Yi, J.; Nahm, K.; Cho, D.W.; Ra, C.S.; Musilek, K.; Horova, A.; Korabecny, J.; et al. Preparation of 7-Methoxy Tacrine Dimer Analogs and Their in vitro/in silico Evaluation as Potential Cholinesterase Inhibitors. Bull. Korean Chem. Soc. 2015, 36, 1654-1660. [CrossRef]
25. Silman, I.; Sussman, J.L. Acetylcholinesterase: How is structure related to function? Chem. Biol. Interact. 2008, 175, 3-10. [CrossRef][PubMed]
26. Spilovska, K.; Korabecny, J.; Kral, J.; Horova, A.; Musilek, K.; Soukup, O.; Drtinova, L.; Gazova, Z.; Siposova, K.; Kuca, K. 7-Methoxytacrine-adamantylamine heterodimers as cholinesterase inhibitors in Alzheimer's disease treatment-Synthesis, biological evaluation and molecular modeling studies. Mol. Basel Switz. 2013, 18, 2397-2418. [CrossRef][PubMed]
27. Spilovska, K.; Korabecny, J.; Horova, A.; Musilek, K.; Nepovimova, E.; Drtinova, L.; Gazova, Z.; Siposova, K.; Dolezal, R.; Jun, D.; et al. Design, synthesis and in vitro testing of 7-methoxytacrine-amantadine analogues: A novel cholinesterase inhibitors for the treatment of Alzheimer's disease. Med. Chem. Res. 2015, 24, 2645-2655. [CrossRef]
28. Recanatini, M.; Cavalli, A.; Hansch, C. A comparative QSAR analysis of acetylcholinesterase inhibitors currently studied for the treatment of Alzheimer's disease. Chem. Biol. Interact. 1997, 105, 199-228. [CrossRef]
29. Iqbal, J.; Zaib, S.; Saeed, A.; Muddassar, M. Biological Evaluation of Halogenated Thioureas as Cholinesterases Inhibitors against Alzheimer's Disease & Molecular Modeling Studies. Lett. Drug Des. Discov. 2015, 12, 488-494.
30. Paula Lima, A.C.; Arriagada, C.; Toro, R.; Cárdenas, A.M.; Caviedes, R.; Ferreira, S.T.; Caviedes, P. Small-molecule aggregation inhibitors reduce excess amyloid in a trisomy 16 mouse cortical cell line. Biol. Res. 2008, 41, 129-136.[PubMed]
31. Munch, H.; Hansen, J.S.; Pittelkow, M.; Christensen, J.B.; Boas, U. A new efficient synthesis of isothiocyanates from amines using di-tert-butyl dicarbonate. Tetrahedron Lett. 2008, 49, 3117-3119. [CrossRef]
32. 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. [CrossRef]
33. Pohanka, M.; Karasova, J.Z.; Kuca, K.; Pikula, J.; Holas, O.; Korabecny, J.; Cabal, J. Colorimetric dipstick for assay of organophosphate pesticides and nerve agents represented by paraoxon, sarin and VX. Talanta 2010, 81, 621-624. [CrossRef][PubMed]
34. Geula, C.; Mesulam, M.M. Cholinesterases and the pathology of Alzheimer disease. Alzheimer Dis. Assoc. Disord. 1995, 9 (Suppl. 2), 23-28. [CrossRef][PubMed]
35. Darvesh, S.; Hopkins, D.A.; Geula, C. Neurobiology of butyrylcholinesterase. Nat. Rev. Neurosci. 2003, 4, 131-138. [CrossRef][PubMed]
36. Wilkinson, D.G. The pharmacology of donepezil: A new treatment of Alzheimer's disease. Expert Opin. Pharmacother. 1999, 1, 121-135. [CrossRef][PubMed]
37. Inestrosa, N.C.; Dinamarca, M.C.; Alvarez, A. Amyloid-cholinesterase interactions. FEBS J. 2008, 275, 625-632. [CrossRef][PubMed]
38. Trott, O.; Olson, A.J. AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J. Comput. Chem. 2010, 31, 455-461. [CrossRef][PubMed]
39. Nachon, F.; Carletti, E.; Ronco, C.; Trovaslet, M.; Nicolet, Y.; Jean, L.; Renard, P. Crystal Structures of Human Cholinesterases in Complex with Huprine W and Tacrine: Elements of Specificity for Anti-Alzheimer'S Drugs Targeting Acetyl- and Butyrylcholinesterase. Biochem. J. 2012, 453, 393-399. [CrossRef][PubMed]
40. Cheung, J.; Rudolph, M.J.; Burshteyn, F.; Cassidy, M.S.; Gary, E.N.; Love, J.; Franklin, M.C.; Height, J.J. Structures of human acetylcholinesterase in complex with pharmacologically important ligands. J. Med. Chem. 2012, 55, 10282-10286. [CrossRef][PubMed]
41. Dolezal, R.; Sobeslav, V.; Hornig, O.; Balik, L.; Korabecny, J.; Kuca, K. HPC Cloud Technologies for Virtual Screening in Drug Discovery. In Intelligent Information and Database Systems; Nguyen, N.T., Trawiński, B., Kosala, R., Eds.; Lecture Notes in Computer Science; Springer International Publishing: Cham, Switzerland, 2015; pp. 440-449.
42. Dolezal, R.; Korabecny, J.; Malinak, D.; Honegr, J.; Musilek, K.; Kuca, K. Ligand-based 3D QSAR analysis of reactivation potency of mono- and bis-pyridinium aldoximes toward VX-inhibited rat acetylcholinesterase. J. Mol. Graph. Model. 2015, 56, 113-129. [CrossRef][PubMed]
43. PoseView. Available online: http://poseview.zbh.uni-hamburg.de/poseview/wizard (accessed on 16 July 2012).
44. Nepovimova, E.; Korabecny, J.; Dolezal, R.; Babkova, K.; Ondrejicek, A.; Jun, D.; Sepsova, V.; Horova, A.; Hrabinova, M.; Soukup, O.; et al. Tacrine-Trolox Hybrids: A Novel Class of Centrally Active, Non-Hepatotoxic Multi-Target-Directed Ligands Exerting Anticholinesterase and Antioxidant Activities with Low in Vivo Toxicity. J. Med. Chem. 2015, 58, 8985-9003. [CrossRef][PubMed]
45. Liu, B.; Wang, L.; Jin, Y.-H. An effective PSO-based memetic algorithm for flow shop scheduling. IEEE Trans. Syst. Man Cybern. B Cybern. Cybern. 2007, 37, 18-27. [CrossRef]
46. Korábecný, J.; Hrubá, E.; Soukup, O.; Zemek, F.; Musílek, K.; Nepovímová, E.; Spilovská, K.; Opletalová, V.; Kuca, K. Intended pharmacotherapeutical approaches of Alzheimer's disease therapy. Ceská Slov. Farm. Cas. Ceské Farm. Spolecnosti Slov. Farm. Spolecnosti 2012, 61, 4-10.
47. Cavalli, A.; Bolognesi, M.L.; Minarini, A.; Rosini, M.; Tumiatti, V.; Recanatini, M.; Melchiorre, C. Multi-target-directed ligands to combat neurodegenerative diseases. J. Med. Chem. 2008, 51, 347-372. [CrossRef][PubMed]
48. León, R.; Garcia, A.G.; Marco-Contelles, J. Recent advances in the multitarget-directed ligands approach for the treatment of Alzheimer's disease. Med. Res. Rev. 2013, 33, 139-189. [CrossRef][PubMed]