Site-activated chelators derived from anti-parkinson drug rasagiline as a potential safer and more effective approach to the treatment of Alzheimer's disease

Neurochemical Research

Volumn 35, Issue 12, 2010, Pages 2117-2123

  Zheng, Hailin ^a,d   Fridkin, Mati ^a   Youdim, Moussa B H ^b,c  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^b TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^c Yonsei University   (South Korea)

^d Intra Cellular Therapies Inc   (United States)

Author keywords

Amyloid aggregation; Acetylcholinesterase; Alzheimer's disease; Inhibitor; Monoamine oxidase; Oxidative stress; Prochelator; Tau hyperphosphorylation

Indexed keywords

2 METHYL 5 (3,4,5 TRIMETHOXYBENZAMIDO)DECAHYDROISOQUINOLINE; 5 (4 PROPARGYLPIPERAZIN 1 YLMETHYL) 8 HYDROXYQUINOLINE; ACETYLCHOLINESTERASE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; AMYLOID BETA PROTEIN; AMYLOID PRECURSOR PROTEIN; CHELATING AGENT; CHOLINESTERASE; COPPER ION; DONEPEZIL; FERRIC ION; HLA 20; HLA 20A; M 30D; RASAGILINE; RIVASTIGMINE; TACRINE; UNCLASSIFIED DRUG; ZINC ION;

ALZHEIMER DISEASE; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; CHOLINESTERASE INHIBITION; CONTROLLED STUDY; CYTOTOXICITY; DRUG DESIGN; DRUG EFFICACY; DRUG POTENCY; DRUG SAFETY; DRUG STRUCTURE; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; NEUROBLASTOMA CELL; NONHUMAN; OXIDATIVE STRESS; PHARMACOPHORE; PRIORITY JOURNAL; RAT;

ALZHEIMER DISEASE; CHELATING AGENTS; CHOLINESTERASE INHIBITORS; HUMANS; INDANS; NEUROPROTECTIVE AGENTS; OXIDATIVE STRESS; PHOSPHORYLATION;

PROCHELATOR;

EID: 78651312050     PISSN: 03643190     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11064-010-0293-1     Document Type: Article

References (42)

1. Y Biran CL Masters KJ Barnham, et al. 2009 Pharmacotherapeutic targets in Alzheimer's disease J Cell Mol Med 13 61 86 1:CAS:528:DC%2BD1MXjsVegu7w%3D 10.1111/j.1582-4934.2008.00595.x 19040415
2. MP Mattson 2004 Pathways towards and away from Alzheimer's disease Nature 430 631 639 1:CAS:528:DC%2BD2cXmt1Gis7o%3D 10.1038/nature02621 15295589 (Pubitemid 39061671)
3. DM Barten CF Albright 2008 Therapeutic strategies for Alzheimer's disease Mol Neurobiol 37 171 186 1:CAS:528:DC%2BD1cXptFOrur0%3D 10.1007/s12035-008- 8031-2 18581273
4. MA Lovell JD Robertson WJ Teesdale, et al. 1998 Copper, iron and zinc in Alzheimer's disease senile plaques J Neurol Sci 158 47 52 1:CAS:528: DyaK1cXjsVentbo%3D 10.1016/S0022-510X(98)00092-6 9667777 (Pubitemid 28277534)
5. KJ Barnham AI Bush 2008 Metals in Alzheimer's and Parkinson's diseases Curr Opin Chem Biol 12 222 228 1:CAS:528:DC%2BD1cXlslKlsbY%3D 10.1016/j.cbpa.2008.02.019 18342639
6. S Bandyopadhyay X Huang H Cho, et al. 2006 Metal specificity of an iron-responsive element in Alzheimer's APP mRNA 5'untranslated region, tolerance of SH-SY5Y and H4 neural cells to desferrioxamine, clioquinol, VK-28, and a piperazine chelator J Neural Transm Suppl 71 237 247 1:CAS:528: DC%2BD28Xht1OltLbP 10.1007/978-3-211-33328-0-25 17447434
7. JT Rogers JD Randall CM Cahill, et al. 2002 An iron-responsive element type II in the 5′-untranslated region of the Alzheimer's amyloid precursor protein transcript J Biol Chem 277 45518 45528 1:CAS:528:DC%2BD38Xosl2ks70%3D 10.1074/jbc.M207435200 12198135 (Pubitemid 36159162)
8. LM Sayre G Perry MA Smith 2008 Oxidative stress and neurotoxicity Chem Res Toxicol 21 172 188 10.1021/tx700210j 18052107 (Pubitemid 351219718)
9. KA Price PJ Crouch AR White 2007 Therapeutic treatment of Alzheimer's disease using metal complexing agents Recent Pat CNS Drug Discov 2 180 187 1:CAS:528:DC%2BD2sXhsVaht7rM 10.2174/157488907782411774 18221229 (Pubitemid 350200290)
10. PA Adlard RA Cherny DI Finkelstein, et al. 2008 Rapid restoration of cognition in Alzheimer's transgenic mice with 8-hydroxy quinoline analogs is associated with decreased interstitial Abeta Neuron 59 43 55 1:CAS:528:DC%2BD1cXoslyjur0%3D 10.1016/j.neuron.2008.06.018 18614028 (Pubitemid 351905863)
11. DR Crapper McLachlan AJ Dalton TP Kruck, et al. 1991 Intramuscular desferrioxamine in patients with Alzheimer's disease Lancet 337 1304 1308 1:STN:280:DyaK3M3jt1aruw%3D%3D 10.1016/0140-6736(91)92978-B 1674295
12. D Kaur F Yantiri S Rajagopalan, et al. 2003 Genetic or pharmacological iron chelation prevents MPTP-induced neurotoxicity in vivo: a novel therapy for Parkinson's disease Neuron 37 899 909 1:CAS:528:DC%2BD3sXivFWkurg%3D 10.1016/S0896-6273(03)00126-0 12670420 (Pubitemid 36398297)
13. K Arasaki T Nakanishi 1989 Selective neurotoxicity of clioquinol on the function of the posterior column nuclei Neurosci Lett 107 85 88 1:CAS:528:DyaK3cXmvFClug%3D%3D 10.1016/0304-3940(89)90795-7 2533335 (Pubitemid 20013253)
14. JB Porter ER Huehns 1989 The toxic effects of desferrioxamine Baillieres Clin Haematol 2 459 474 1:STN:280:DyaL1M3oslGjtA%3D%3D 10.1016/S0950-3536(89) 80027-7 2660937 (Pubitemid 19128435)
15. H Zheng MB Youdim M Fridkin 2009 Site-activated multifunctional chelator with acetylcholinesterase and neuroprotective-neurorestorative moieties for Alzheimer's therapy J Med Chem 52 4095 4098 1:CAS:528:DC%2BD1MXms1entLg%3D 10.1021/jm900504c 19485411
16. JJ Chen DM Swope K Dashtipour 2007 Comprehensive review of rasagiline, a second-generation monoamine oxidase inhibitor, for the treatment of Parkinson's disease Clin Ther 29 1825 1849 1:CAS:528:DC%2BD2sXhtlakt7rE 10.1016/j.clinthera. 2007.09.021 18035186 (Pubitemid 350212811)
17. D Munoz-Torrero 2008 Acetylcholinesterase inhibitors as disease-modifying therapies for Alzheimer's disease Curr Med Chem 15 2433 2455 1:CAS:528:DC%2BD1cXhtFCqsLbI 10.2174/092986708785909067 18855672
18. HY Zhang H Yan XC Tang 2008 Non-cholinergic effects of huperzine A: beyond inhibition of acetylcholinesterase Cell Mol Neurobiol 28 173 183 10.1007/s10571-007-9163-z 17657601 (Pubitemid 351253069)
19. T Amit Y Avramovich-Tirosh MB Youdim, et al. 2008 Targeting multiple Alzheimer's disease etiologies with multimodal neuroprotective and neurorestorative iron chelators FASEB J 22 1296 1305 1:CAS:528: DC%2BD1cXltlWlu7s%3D 10.1096/fj.07-8627rev 18048580 (Pubitemid 351656771)
20. H Zheng S Gal LM Weiner, et al. 2005 Novel multifunctional neuroprotective iron chelator-monoamine oxidase inhibitor drugs for neurodegenerative diseases: in vitro studies on antioxidant activity, prevention of lipid peroxide formation and monoamine oxidase inhibition J Neurochem 95 68 78 1:CAS:528:DC%2BD2MXhtVygs7bE 10.1111/j.1471-4159.2005.03340.x 16181413 (Pubitemid 41384426)
21. H Zheng LM Weiner O Bar-Am, et al. 2005 Design, synthesis, and evaluation of novel bifunctional iron-chelators as potential agents for neuroprotection in Alzheimer's, Parkinson's, and other neurodegenerative diseases Bioorg Med Chem 13 773 783 1:CAS:528:DC%2BD2MXksVamtw%3D%3D 10.1016/j.bmc.2004.10.037 15653345 (Pubitemid 40093620)
22. MB Youdim D Edmondson KF Tipton 2006 The therapeutic potential of monoamine oxidase inhibitors Nat Rev Neurosci 7 295 309 1:CAS:528: DC%2BD28Xis1Gksrs%3D 10.1038/nrn1883 16552415
23. J Saura JM Luque AM Cesura, et al. 1994 Increased monoamine oxidase B activity in plaque-associated astrocytes of Alzheimer brains revealed by quantitative enzyme radioautography Neuroscience 62 15 30 1:STN:280: DyaK2M7hsFylug%3D%3D 10.1016/0306-4522(94)90311-5 7816197 (Pubitemid 24287342)
24. KJ Reinikainen H Soininen PJ Riekkinen 1990 Neurotransmitter changes in Alzheimer's disease: implications to diagnostics and therapy J Neurosci Res 27 576 586 1:CAS:528:DyaK3MXnvFGqtg%3D%3D 10.1002/jnr.490270419 1981917
25. M Yogev-Falach O Bar-Am T Amit, et al. 2006 A multifunctional, neuroprotective drug, ladostigil (TV3326), regulates holo-APP translation and processing FASEB J 20 2177 2179 1:CAS:528:DC%2BD28XhtVyrurvJ 10.1096/fj.05-4910fje 16935943 (Pubitemid 44953892)
26. H Zheng MB Youdim M Fridkin 2010 Site-activated chelators targeting acetylcholinesterase and monoamine oxidase for Alzheimer's therapy ACS Chem Biol 5 603 610 1:CAS:528:DC%2BC3cXmt1Krur4%3D 10.1021/cb900264w 20455574
27. E Groner Y Ashani D Schorer-Apelbaum, et al. 2007 The kinetics of inhibition of human acetylcholinesterase and butyrylcholinesterase by two series of novel carbamates Mol Pharmacol 71 1610 1617 1:CAS:528:DC%2BD2sXmt1Wqtb4%3D 10.1124/mol.107.033928 17347320 (Pubitemid 47010914)
28. T Maurer HL Fung 2000 Comparison of methods for analyzing kinetic data from mechanism-based enzyme inactivation: application to nitric oxide synthase AAPS PharmSci 2 E8 1:STN:280:DC%2BD3MjgtVKqtw%3D%3D 10.1208/ps020211 11741224
29. R Kitz IB Wilson 1962 Esters of methanesulfonic acid as irreversible inhibitors of acetylcholinesterase J Biol Chem 237 3245 3249 1:CAS:528:DyaF38Xks1Cmsrg%3D 14033211
30. S Gal ZA Abassi MB Youdim 2010 Limited potentiation of blood pressure in response to oral tyramine by the Anti-Parkinson Brain Selective Multifunctional Monoamine Oxidase-AB Inhibitor, M30 Neurotox Res 18 2 143 150 1:CAS:528:DC%2BC3cXpsVGgsb0%3D 10.1007/s12640-009-9128-8 19894083
31. S Gal H Zheng M Fridkin, et al. 2005 Novel multifunctional neuroprotective iron chelator-monoamine oxidase inhibitor drugs for neurodegenerative diseases. In vivo selective brain monoamine oxidase inhibition and prevention of MPTP-induced striatal dopamine depletion J Neurochem 95 79 88 1:CAS:528:DC%2BD2MXhtVygs7bF 10.1111/j.1471-4159.2005.03341.x 16181414 (Pubitemid 41384427)
32. Y Avramovich-Tirosh T Amit O Bar-Am, et al. 2007 Therapeutic targets and potential of the novel brain- permeable multifunctional iron chelator-monoamine oxidase inhibitor drug, M-30, for the treatment of Alzheimer's disease J Neurochem 100 490 502 1:CAS:528:DC%2BD2sXhsFaksLo%3D 10.1111/j.1471-4159.2006. 04258.x 17144902 (Pubitemid 46016026)
33. Y Avramovich-Tirosh L Reznichenko T Mit, et al. 2007 Neurorescue activity, APP regulation and amyloid-beta peptide reduction by novel multi-functional brain permeable iron- chelating- antioxidants, M-30 and green tea polyphenol, EGCG Curr Alzheimer Res 4 403 411 1:CAS:528:DC%2BD2sXhtlSitL%2FN 10.2174/156720507781788927 17908043 (Pubitemid 47416633)
34. AI Bush 2008 Drug development based on the metals hypothesis of Alzheimer's disease J Alzheimers Dis 15 223 240 1:CAS:528:DC%2BD1cXht1Cmtr3J 18953111
35. A Cavalli ML Bolognesi A Minarini, et al. 2008 Multi-target-directed ligands to combat neurodegenerative diseases J Med Chem 51 347 372 1:CAS:528:DC%2BD1cXhsl2qsbk%3D 10.1021/jm7009364 18181565 (Pubitemid 351252260)
36. H Schugar DE Green ML Bowen, et al. 2007 Combating Alzheimer's disease with multifunctional molecules designed for metal passivation Angew Chem Int Ed Engl 46 1716 1718 1:CAS:528:DC%2BD2sXjvFWisbs%3D 10.1002/anie.200603866 17397084 (Pubitemid 46991786)
37. G Liu P Men W Kudo, et al. 2009 Nanoparticle-chelator conjugates as inhibitors of amyloid-beta aggregation and neurotoxicity: a novel therapeutic approach for Alzheimer disease Neurosci Lett 455 187 190 1:CAS:528: DC%2BD1MXksVeit78%3D 10.1016/j.neulet.2009.03.064 19429118
38. LK Charkoudian DM Pham KJ Franz 2006 A pro-chelator triggered by hydrogen peroxide inhibits iron-promoted hydroxyl radical formation J Am Chem Soc 128 12424 12425 1:CAS:528:DC%2BD28XptVymtLk%3D 10.1021/ja064806w 16984186 (Pubitemid 44476626)
39. DS Folk KJ Franz 2010 A prochelator activated by beta-secretase inhibits Abeta aggregation and suppresses copper-induced reactive oxygen species formation J Am Chem Soc 132 4994 4995 1:CAS:528:DC%2BC3cXjsFSlsb8%3D 10.1021/ja100943r 20297791
40. A Di Stefano P Sozio A Cocco, et al. 2006 L-dopa- and dopamine-(R)-alpha-lipoic acid conjugates as multifunctional codrugs with antioxidant properties J Med Chem 49 1486 1493 1:CAS:528:DC%2BD28XoslKjsw%3D%3D 10.1021/jm051145p 16480285 (Pubitemid 43271901)
41. C Rodriguez-Rodriguez N Sanchez de Groot A Rimola, et al. 2009 Design, selection, and characterization of thioflavin-based intercalation compounds with metal chelating properties for application in Alzheimer's disease J Am Chem Soc 131 1436 1451 1:CAS:528:DC%2BD1MXktVyntA%3D%3D 10.1021/ja806062g 19133767
42. SS Hindo AM Mancino JJ Braymer, et al. 2009 Small molecule modulators of copper-induced Abeta aggregation J Am Chem Soc 131 16663 16665 1:CAS:528:DC%2BD1MXhtlChur7K 10.1021/ja907045h 19877631