Synthesis and functional survey of new Tacrine analogs modified with nitroxides or their precursors

European Journal of Medicinal Chemistry

Volumn 77, Issue , 2014, Pages 343-350

  Kálai, Tamás ^a   Altman, Robin ^b   Maezawa, Izumi ^c   Balog, Mária ^a   Morisseau, Christophe ^d   Petrlova, Jitka ^b   Hammock, Bruce D ^d   Jin, Lee Way ^c   Trudell, James R ^e   Voss, John C ^b   Hideg, Kálmán ^a  

^a UNIVERSITY OF PÉCS   (Hungary)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d UNIVERSITY OF CALIFORNIA   (United States)

^e STANFORD UNIVERSITY   (United States)

Author keywords

Alzheimer's disease; Antioxidants; Nitroxides; Spin trapping; Tacrine

Indexed keywords

ANTIOXIDANT; CHOLINESTERASE INHIBITOR; HYDROXYL RADICAL; NITROXIDE DERIVATIVE; PEROXY RADICAL; PIPERAZINE; TACRINE DERIVATIVE; ACETYLCHOLINESTERASE; ANTINEOPLASTIC AGENT; NITROGEN OXIDE; TACRINE;

ALZHEIMER DISEASE; ANTIOXIDANT ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG SYNTHESIS; SPIN TRAPPING; ANALOGS AND DERIVATIVES; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; DRUG SCREENING; HUMAN; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ACETYLCHOLINESTERASE; ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; CELL LINE, TUMOR; CELL PROLIFERATION; CHOLINESTERASE INHIBITORS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITROGEN OXIDES; STRUCTURE-ACTIVITY RELATIONSHIP; TACRINE;

EID: 84897902367     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.03.026     Document Type: Article

References (33)

1. M. Jucker, L.C. Walker, Pathogenic protein seeding in Alzheimer disease and other degenerative disorders, Annals of Neurology 70 (2011) 532-540.
2. R. Sultana, D.A. Butterfield, Role of oxidative stress in the progression of Alzheimer's disease, Journal of Alzheimer's Disease 19 (2010) 341-353.
3. M.S. Rafii, P.S. Aisen, Recent developments in Alzeimer's disease therapeutics, BMC Medicine 7 (2009) 7.
4. H.F. Kung, The β-Amyloid hypothesis in Alzeimer's disease: seeing is believing, Medicinal Chemistry Letters 3 (2012) 265-267.
5. G. Xiong, P.M. Doraiwsamy, Combination drug therapy for Alzheimer's disease: what is evidence -based, and what is not? Geriatrics 60 (2005) 22-26. (Pubitemid 40840357)
6. M. Dumont, M.F. Beal, Neuroprotective strategies involving ROS in Alzheimer disease, Free Radical Biology & Medicine 51 (2011) 1014-1026.
7. M. Rosini, E. Simoni, M. Bartolini, A. Cavalli, L. Ceccarini, N. Pascu, D.W. McClymont, A. Tarozzi, M.L. Bolognesi, A. Minarin, V. Tumiatti, V. Andrisano, I.R. Mellor, C. Melchiorre, Inhibition of acetylcholinesterase, b-amiloid aggregation, and MNDA receptors in Alzheimer's disease: a promising direction for the multi-target-directed gold rush, Journal of Medicinal Chemistry 51 (2008) 4381-4384.
8. M.I. Rodríguez-Franco, M.I. Fernández-Bachiller, C. Pérez, B. Hernández-Ledesma, B. Bartolomé, Novel tacrine-melatonine hybrids as dual-actingdrugs for Alzheimer disease, with improved acetylcholinesterase inhibitory and antioxidant properties, Journal of Medicinal Chemistry 49 (2009) 459-462. (Pubitemid 43157478)
9. L. Fanga, B. Krausc, J. Lehmanna, J. Heilmannc, Y. Zhangb, M. Decker, Design and synthesis of tacrine-ferulic acid hybrids as multi-potent anti-Alzheimer drug candidates, Bioorganic & Medicinal Chemistry Letters 18 (2008) 2905-2909. (Pubitemid 351608873)
10. T. Kálai, J. Petrlova, M. Balog, H.H. Aung, J.C. Voss, K. Hideg, Synthesis and study of 2-amino-7-bromofluorenes modified with nitroxides and their precursors as dual anti-amyloid and antioxidant active compounds, European Journal of Medicinal Chemistry 46 (2011) 1348-1355.
11. I.K. Mohan, M. Kahn, S. Wisel, K. Selvendiran, A. Sridhar, C.A. Carnes, B. Bognár, T. Kálai, K. Hideg, P. Kuppusamy, Cardioprotection by HO-4038, a novel verapamil derivative, targeted against ischemia and reperfusion-mediated acute myocardial infarction, Heart and Circulatory Physiology - American Journal of Physiology 296 (2009) 140-151.
12. T. Kálai, M. Balog, A. Szabó, G. Gulyás, J. Jeko{combining double acute accent}, B. Sümegi, K. Hideg, New poly(ADP-ribose) polymerase-1 inhibitors with antioxidant activity based on 4-Car-boxamidobenzimidazole-2-ylpyrroline and -tetrahydropyridine nitroxides and their precursors, Journal of Medicinal Chemistry 52 (2009) 1619-1629.
13. T. Kálai, G. Mugesh, G. Roy, H. Sies, Z. Berente, K. Hideg, Combining benzo[d] isoselenazol-3-ones with sterically hindered alicyclic amines and nitroxides: enhanced activity as glutathione peroxidase mimics, Organic & Biomolecular Chemistry 3 (2005) 3564-3569. (Pubitemid 41497564)
14. D. Thomae, G. Kirsch, P. Seck, Synthesis of selenophene analogues of the tacrine series: comparison of classical route and microwave irradiation, Synthesis 40 (2008) 1600-1606. (Pubitemid 351817127)
15. K. Hideg, H.O. Hankovszky, L. Lex, Gy. Kulcsár, Nitroxyls; VI. Synthesis and reactions of 3-Hydroxymethyl-2,2,5,5-tetramethyl-2,5- dihydropyrrole-1-oxyl and 3-formyl derivatives, Synthesis 12 (1980) 911-914.
16. J. Cseko{combining double acute accent}, H.O. Hankovszky, K. Hideg, Synthesis of novel, highly reactive 1-oxyl-2,2,6,6-tetramethyl-1,2,5,6- tetrahydropyridine derivatives, Canadian Journal of Chemistry 63 (1985) 940-943.
17. P.W. Elsinhorst, C.M.G. Tanarro, M. Gütschow, Novel heterobivalent tacrine derivatives as cholinesterase inhibitors with notable selectivity toward butyrylcholinesterase, Journal of Medicinal Chemistry 49 (2006) 7540-7544. (Pubitemid 44913413)
18. H.O. Hankovszky, K. Hideg, L. Lex, Nitroxyls VII. Synthesis and reactions of highly reactive 1-Oxyl-2,2,5,5-tetramethyl-2,5-dihydropyrrole-3-ylmethyl sulfonates, Synthesis 12 (1980) 914-916.
19. K. Hideg, H.O. Hankovszky, J. Tigyi, Nitroxides, I. Sulfonic esters of 4-hydroxy-2,2,6,6-tetramethyl-piperidine-1-oxyl and their reaction with nucleophilic reactants, Acta Chimica Academiae Scientiarum Hungaricae 92 (1977) 85-87.
20. T. Kálai, W.L. Hubbell, K. Hideg, Click reactions with nitroxides, Synthesis 41 (2009) 1336-1341.
21. T. Kálai, M. Khan, M. Balog, K.V. Kutala, P. Kuppusamy, K. Hideg, Structure-activity studies on the protection of trimetazidine derivatives modified with nitroxides and their precursor from myocardial ischemia-reperfusion injury, Bioorganic & Medicinal Chemistry 14 (2006) 5510-5516. (Pubitemid 43994478)
22. C. Rios, J. Ega, J. Marco-Contelles, R. León, A. Samadi, I. Iriepa, I. Moraleda, E. Gálvez, A.G. Garcia, M.G. López, M. Villaroya, A. Romero, Synthesis inhibitory activity of cholinesterases, and neuroprotective profile of novel 1,8-naphthyridine derivative, Journal of Medicinal Chemistry 53 (2010) 5129-5143.
23. R.M. Dupreye, A. Rassat, P. Rey, Nitroxides. XVIII. Pyrrolidine free radicals, Bulletin de la Societe Chimque de France (1965) 3643-3644.
24. M.C. Krishna, W. Degraff, H.O. Hankovszky, P.C. Sár, T. Kálai, J. Jeko{combining double acute accent}, A. Russo, J.B. Mitchell, K. Hideg, Studies of structure-activity relationship of nitroxide free radicals and their precursors as modifiers against oxidative damage, Journal of Medicinal Chemistry 41 (1998) 3477-3492. (Pubitemid 28406556)
25. H. Zhao, J. Joseph, H. Zhang, H. Karoui, B. Kalyanaraman, Synthesis and biochemical applications of a solid cyclic nitrone spin trap: a relatively superior trap for detecting superoxide anions and glutathiyl radicals, Free Radical Biology & Medicine 31 (2001) 599-606. (Pubitemid 32777860)
26. C. Guarnieri, C. Muscari, Anti oxy-radical properties of trimetazidine, Research Communications in Chemical Pathology and Pharmacology 64 (1989) 215-225. (Pubitemid 19143877)
27. J.P. Blinco, J.L. Hodgson, B.J. Morrow, J.R. Walker, G.D. Will, M.L. Coote, S.E. Bottle, Experimental and theoretical studies of the redox potentials of cyclic nitroxides, Journal of Organic Chemistry 73 (2008) 6763-6771.
28. V. Kadlcik, C. Sicard-Roselli, T.A. Mattioli, M. Kodicek, C. Houée-Levin, One-electron oxidation of b-amyloid peptide: sequence modulation of reactivity, Free Radical Biology & Medicine 37 (2004) 881-891. (Pubitemid 39078557)
29. S. Dhitavat, D. Ortiz, E. Rogers, E. Rivera, T.B. Shea, Folate, vitamin E and acetyl-L-carnitine provide synergistyc protection against oxidative stress resulting from exposure of human neuroblastoma cells to amyloid-beta, Brain Research 1061 (2005) 114-117. (Pubitemid 41587919)
30. R. Sultana, A. Ravgna, H. Mohammad-Abdul, V. Calabrese, D.A. Butterfield, Ferrulic acid ethyl ester protects neurons against amyloid beta-peptide(1-42)- induced oxidative stress and neurotoxicity: relationship to antioxidant activity, Journal of Neurochemistry 92 (2005) 749-758. (Pubitemid 40229546)
31. I. Maezawa, H.S. Hong, R. Liu, C.Y. Wu, R.H. Cheng, M.P. Kung, H.F. Kung, K.S. Lam, S. Oddo, F.M. Laferla, L.W. Jin, Congo red and thioflavin-T analogs detect Abeta oligomers, Journal of Neurochemsitry 104 (2008) 457-468. (Pubitemid 350293869)
32. J. Petrlova, T. Kálai, I. Maezawa, R. Altman, G. Harishchandra, H.S. Hong, D.A. Bricarello, A.N. Parikh, G.A. Lorigan, L.W. Jin, K. Hideg, J.C. Voss, The influence of spin-labeled fluorene compounds on the assembly and toxicity of the aβ peptide, PLoS One 7 (2012) e35443.
33. B.W. Wilson, J.D. Henderson, Determination of cholinesterase in blood and tissue, Current Protocols in Toxicology 34 (2007) 12.13.1-12.13.16.