Tacrine-6-ferulic acid, a novel multifunctional dimer, inhibits amyloid-β-mediated Alzheimer's disease-associated pathogenesis in vitro and in vivo

PLoS ONE

Volumn 7, Issue 2, 2012, Pages

  Pi, Rongbiao ^a   Mao, Xuexuan ^a,d   Chao, Xiaojuan ^a   Cheng, Zhiyi ^a   Liu, Mengfei ^a   Duan, Xiaolu ^a   Ye, Mingzhong ^a   Chen, Xiaohong ^a   Mei, Zhengrong ^a   Liu, Peiqing ^a   Li, Wenming ^b,c   Han, Yifan ^b  

^a SUN YAT SEN UNIVERSITY   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

^c EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d Tsinghua University   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCHOLINESTERASE; AMYLOID BETA PROTEIN[1-40]; CHOLINE ACETYLTRANSFERASE; CHOLINESTERASE INHIBITOR; MALONALDEHYDE; REACTIVE OXYGEN METABOLITE; SUPEROXIDE DISMUTASE; TACRINE 6 FERULIC ACID; UNCLASSIFIED DRUG; AMYLOID BETA PROTEIN; COUMARIC ACID; DRUG DERIVATIVE; FERULIC ACID; PEPTIDE; TACRINE; TACRINE-6-FERULIC ACID;

ALZHEIMER DISEASE; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; APOPTOSIS; ARTICLE; CELL STRAIN; CELL VIABILITY; COGNITIVE DEFECT; CONTROLLED STUDY; ENZYME ACTIVITY; IN VITRO STUDY; IN VIVO STUDY; MAZE TEST; MOUSE; NONHUMAN; PATHOGENESIS; PHARMACOLOGICAL BLOCKING; ANIMAL; C57BL MOUSE; CELL SURVIVAL; CHEMICAL MODEL; CHEMISTRY; DIMERIZATION; DISEASE MODEL; HUMAN; MALE; METABOLISM; METHODOLOGY; TRANSMISSION ELECTRON MICROSCOPY;

ACETYLCHOLINESTERASE; ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; ANIMALS; CELL SURVIVAL; COUMARIC ACIDS; DIMERIZATION; DISEASE MODELS, ANIMAL; HUMANS; MALE; MICE; MICE, INBRED C57BL; MICROSCOPY, ELECTRON, TRANSMISSION; MODELS, CHEMICAL; PC12 CELLS; PEPTIDES; REACTIVE OXYGEN SPECIES; SUPEROXIDE DISMUTASE; TACRINE;

EID: 84863144997     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0031921     Document Type: Article

References (42)

1. Ballard C, Gauthier S, Corbett A, Brayne C, Aarsland D, et al. (2011) Alzheimer's disease. Lancet 377: 1019-1031.
2. Singh M, Nam DT, Arseneault M, Ramassamy C, (2010) Role of by-products of lipid oxidation in Alzheimer's disease brain: a focus on acrolein. J Alzheimers Dis 21: 741-756.
3. Sultana R, Butterfield DA, (2010) Role of oxidative stress in the progression of Alzheimer's disease. J Alzheimers Dis 19: 341-353.
4. Terry AV Jr, Buccafusco JJ, (2003) The cholinergic hypothesis of age and Alzheimer's disease-related cognitive deficits: recent challenges and their implications for novel drug development. J Pharmacol Exp Ther 306: 821-827.
5. Nitsch RM, Hock C, (2008) Targeting beta-amyloid pathology in Alzheimer's disease with Abeta immunotherapy. Neurotherapeutics 5: 415-420.
6. Chopra K, Misra S, Kuhad A, (2011) Current perspectives on pharmacotherapy of Alzheimer's disease. Expert Opin Pharmacother 12: 335-350.
7. Hiramatsu M, Takiguchi O, Nishiyama A, Mori H, (2010) Cilostazol prevents amyloid beta peptide(25-35)-induced memory impairment and oxidative stress in mice. Br J Pharmacol 161: 1899-1912.
8. Jesudason EP, Masilamoni JG, Ashok BS, Baben B, Arul V, et al. (2008) Inhibitory effects of short-term administration of DL-alpha-lipoic acid on oxidative vulnerability induced by Abeta amyloid fibrils (25-35) in mice. Mol Cell Biochem 311: 145-156.
9. Tumiatti V, Minarini A, Bolognesi ML, Milelli A, Rosini M, et al. (2010) Tacrine derivatives and Alzheimer's disease. Curr Med Chem 17: 1825-1838.
10. Van Der Schyf CJ, Geldenhuys WJ, Youdim MB, (2006) Multifunctional drugs with different CNS targets for neuropsychiatric disorders. J Neurochem 99: 1033-1048.
11. Ye MZ, Pi RB, (2008) Development of the multi-target-directed acetylcholinesterase inhibitors based on tacrine. Chin Pharmacol Bull 24: 421-426.
12. Ou SY, Kwok KC, (2004) Ferulic acid: pharmaceutical functions, preparation and applications in foods. Journal of the Science of Food and Agriculture 84: 1261-1269.
13. Durairajan SS, Yuan Q, Xie L, Chan WS, Kum WF, et al. (2008) Salvianolic acid B inhibits Abeta fibril formation and disaggregates preformed fibrils and protects against Abeta-induced cytotoxicty. Neurochem Int 52: 741-750.
14. Ono K, Hirohata M, Yamada M, (2005) Ferulic acid destabilizes preformed beta-amyloid fibrils in vitro. Biochem Biophys Res Commun 336: 444-449.
15. Yan JJ, Cho JY, Kim HS, Kim KL, Jung JS, et al. (2001) Protection against beta-amyloid peptide toxicity in vivo with long-term administration of ferulic acid. Br J Pharmacol 133: 89-96.
16. Srinivasan M, Rukkumani R, Ram Sudheer A, Menon VP, (2005) Ferulic acid, a natural protector against carbon tetrachloride-induced toxicity. Fundam Clin Pharmacol 19: 491-496.
17. Ye M, (2009) Novel tacrine-farulic acid hybrids as multiple targeted drug candidates against Alzheimer's disease Sun Yat-Sen University, Guangzhou.
18. Fang L, Kraus B, Lehmann J, Heilmann J, Zhang Y, et al. (2008) Design and synthesis of tacrine-ferulic acid hybrids as multi-potent anti-Alzheimer drug candidates. Bioorg Med Chem Lett 18: 2905-2909.
19. Pi RYM, Cheng Z, Liu P, (2008) Univ Zhongshan (UZHO-C). New tacrine-ferulic acid compound for medicine composition for preventing and treating acetylcholinesterase mediated disease including Alzheimer's disease. CN101284812-A.
20. Fleck C, Appenroth D, Fang L, Schott Y, Lehmann J, et al. (2010) Investigation into the in vivo effects of five novel tacrine/ferulic acid and beta-carboline derivatives on scopolamine-induced cognitive impairment in rats using radial maze paradigm. Arzneimittel-Forschung-Drug Research 60: 299-306.
21. Lupp A, Appenroth D, Fang L, Decker M, Lehmann J, et al. (2010) Tacrine-NO donor and tacrine-ferulic acid hybrid molecules as new anti-Alzheimer agents: hepatotoxicity and influence on the cytochrome P450 system in comparison to tacrine. Arzneimittel-Forschung-Drug Research 60: 229-237.
22. Byeon SR, Jin YJ, Lim SJ, Lee JH, Yoo KH, et al. (2007) Ferulic acid and benzothiazole dimer derivatives with high binding affinity to beta-amyloid fibrils. Bioorg Med Chem Lett 17: 4022-4025.
23. Lee KH, Shin BH, Shin KJ, Kim DJ, Yu J, (2005) A hybrid molecule that prohibits amyloid fibrils and alleviates neuronal toxicity induced by beta-amyloid (1-42). Biochemical and Biophysical Research Communications 328: 816-823.
24. Bartolini M, Bertucci C, Cavrini V, Andrisano V, (2003) beta-Amyloid aggregation induced by human acetylcholinesterase: inhibition studies. Biochem Pharmacol 65: 407-416.
25. Petkova AT, Leapman RD, Guo Z, Yau WM, Mattson MP, et al. (2005) Self-propagating, molecular-level polymorphism in Alzheimer's beta-amyloid fibrils. Science 307: 262-265.
26. Kane MD, Schwarz RD, St Pierre L, Watson MD, Emmerling MR, et al. (1999) Inhibitors of V-type ATPases, bafilomycin A1 and concanamycin A, protect against beta-amyloid-mediated effects on 3-(4,5-dimethylthiazol-2-yl)-2,5- diphenyltetrazolium bromide (MTT) reduction. J Neurochem 72: 1939-1947.
27. Lebel CP, Ali SF, McKee M, Bondy SC, (1990) Organometal-Induced Increases in Oxygen Reactive Species- the Potential of 2′,7′-Dichlorofluorescin Diacetate as an Index of Neurotoxic Damage. Toxicology and Applied Pharmacology 104: 17-24.
28. Prediger RD, Medeiros R, Pandolfo P, Duarte FS, Passos GF, et al. (2008) Genetic deletion or antagonism of kinin B(1) and B(2) receptors improves cognitive deficits in a mouse model of Alzheimer's disease. Neuroscience 151: 631-643.
29. Chen XH, Lin ZZ, Liu AM, Ye JT, Luo Y, et al. (2010) The orally combined neuroprotective effects of sodium ferulate and borneol against transient global ischaemia in C57 BL/6J mice. J Pharm Pharmacol 62: 915-923.
30. Xue LB, Yu QH, Zhang HX, Liu YL, Wang CJ, et al. (2008) Effect of large dose hyperbaric oxygenation therapy on prognosis and oxidative stress of acute permanent cerebral ischemic stroke in rats. Neurological Research 30: 389-393.
31. Castro A, Martinez A, (2006) Targeting beta-amyloid pathogenesis through acetylcholinesterase inhibitors. Current Pharmaceutical Design 12: 4377-4387.
32. Hardy J, Selkoe DJ, (2002) The amyloid hypothesis of Alzheimer's disease: progress and problems on the road to therapeutics. Science 297: 353-356.
33. Inestrosa NC, Alvarez A, Dinamarca MC, Perez-Acle T, Colombres M, (2005) Acetylcholinesterase-amyloid-beta-peptide interaction: effect of Congo Red and the role of the Wnt pathway. Curr Alzheimer Res 2: 301-306.
34. Inestrosa NC, Sagal JP, Colombres M, (2005) Acetylcholinesterase interaction with Alzheimer amyloid beta. Subcell Biochem 38: 299-317.
35. Colombres M, Sagal JP, Inestrosa NC, (2004) An overview of the current and novel drugs for Alzheimer's disease with particular reference to anti-cholinesterase compounds. Curr Pharm Des 10: 3121-3130.
36. Munoz-Ruiz P, Rubio L, Garcia-Palomero E, Dorronsoro I, Del Monte-Millan M, et al. (2005) Design, synthesis, and biological evaluation of dual binding site acetylcholinesterase inhibitors: new disease-modifying agents for Alzheimer's disease. Journal of Medicinal Chemistry 48: 7223-7233.
37. Butterfield DA, Drake J, Pocernich C, Castegna A, (2001) Evidence of oxidative damage in Alzheimer's disease brain: central role for amyloid beta-peptide. Trends in Molecular Medicine 7: 548-554.
38. Brandwilliams W, Cuvelier ME, Berset C, (1995) Use of a Free-Radical Method to Evaluate Antioxidant Activity. Food Science and Technology-Lebensmittel-Wissenschaft & Technologie 28: 25-30.
39. Kawabata J, Okamoto Y, Kodama A, Makimoto T, Kasai T, (2002) Oxidative dimers produced from protocatechuic and gallic esters in the DPPH radical scavenging reaction. J Agric Food Chem 50: 5468-5471.
40. Takeda S, Sato N, Niisato K, Takeuchi D, Kurinami H, et al. (2009) Validation of A beta 1-40 administration into mouse cerebroventricles as an animal model for Alzheimer disease. Brain Research 1280: 137-147.
41. Lahiri DK, Farlow MR, Sambamurti K, (1998) The secretion of amyloid beta-peptides is inhibited in the tacrine-treated human neuroblastoma cells. Brain Res Mol Brain Research 62: 131-40.
42. Bailey JA, Ray B, Greig NH, Lahiri DK, (2011) Rivastigmine lowers Aβ and increases sAPPα levels, which parallel elevated synaptic markers and metabolic activity in degenerating primary rat neurons. PLoS One 6: e21954.