Curcumin derivative with the substitution at C-4 position, but not curcumin, is effective against amyloid pathology in APP/PS1 mice

Neurobiology of Aging

Volumn 36, Issue 1, 2015, Pages 201-210

  Yanagisawa, Daijiro ^a   Ibrahim, Nor Faeizah ^a   Taguchi, Hiroyasu ^a   Morikawa, Shigehiro ^a   Hirao, Koichi ^b   Shirai, Nobuaki ^b   Sogabe, Takayuki ^c   Tooyama, Ikuo ^a  

^a SHIGA UNIVERSITY OF MEDICAL SCIENCE   (Japan)

^b INDUSTRIAL RESEARCH CENTER OF SHIGA PREFECTURE   (Japan)

^c OTSUKA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Alzheimer's disease; Amyloid ; APP PS1 transgenic mice; Curcumin

Indexed keywords

1,7 BIS(4' HYDROXY 3' TRIFLUOROMETHOXYPHENYL) 4 METHOXYCARBONYLETHYL 1,6 HEPTADIENE 3,5 DIONE; AMYLOID BETA PROTEIN; AMYLOID BETA PROTEIN[1-40]; AMYLOID BETA PROTEIN[1-42]; CURCUMIN; POLYPHENOL DERIVATIVE; UNCLASSIFIED DRUG; PRESENILIN 1; PRESENILIN 1, MOUSE;

ALZHEIMER DISEASE; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CHEMOPROPHYLAXIS; COGNITIVE DEFECT; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG BLOOD LEVEL; DRUG EFFECT; DRUG STRUCTURE; FEMALE; GLIA CELL; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MALE; MEMORY DISORDER; MOUSE; NONHUMAN; PROTEIN AGGREGATION; ANALOGS AND DERIVATIVES; ANIMAL; BRAIN; C57BL MOUSE; CHEMISTRY; COGNITION; GENETICS; GLIA; METABOLISM; MOLECULARLY TARGETED THERAPY; PHYSIOLOGY; PROTEIN AGGREGATION, PATHOLOGICAL; PSYCHOLOGY; TRANSGENIC MOUSE;

ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; ANIMALS; BRAIN; COGNITION; CURCUMIN; MICE, INBRED C57BL; MICE, TRANSGENIC; MOLECULAR TARGETED THERAPY; NEUROGLIA; PRESENILIN-1; PROTEIN AGGREGATION, PATHOLOGICAL;

EID: 84920420732     PISSN: 01974580     EISSN: 15581497     Source Type: Journal    
DOI: 10.1016/j.neurobiolaging.2014.07.041     Document Type: Article

References (38)

1. Arendash G.W., King D.L., Gordon M.N., Morgan D., Hatcher J.M., Hope C.E., Diamond D.M. Progressive, age-related behavioral impairments in transgenic mice carrying both mutant amyloid precursor protein and presenilin-1 transgenes. Brain Res. 2001, 891:42-53.
2. Balasubramanian K. Molecular orbital basis for yellow curry spice curcumin's prevention of Alzheimer's disease. J.Agric. Food Chem. 2009, 54:3512-3520.
3. Begum A.N., Jones M.R., Lim G.P., Morihara T., Kim P., Heath D.D., Rock C.L., Pruitt M.A., Yang F., Hudspeth B., Hu S., Faull K.F., Teter B., Cole G.M., Frautschy S.A. Curcumin structure-function, bioavailability, and efficacy in models of neuroinflammation and Alzheimer's disease. J.Pharmacol. Exp. Ther. 2008, 326:196-208.
4. Benilova I., Karran E., De Strooper B. The toxic Aβ oligomer and Alzheimer's disease: an emperor in need of clothes. Nat. Neurosci. 2012, 15:349-357.
5. Caesar I., Jonson M., Nilsson K.P., Thor S., Hammarström P. Curcumin promotes A-beta fibrillation and reduces neurotoxicity in transgenic Drosophila. PLoS One 2012, e31424.
6. Citron M. Alzheimer's disease: strategies for disease modification. Nat. Rev. Drug Discov. 2010, 9:387-398.
7. Garcia-Alloza M., Borrelli L.A., Rozkalne A., Hyman B.T., Bacskai B.J. Curcumin labels amyloid pathology invivo, disrupts existing plaques, and partially restores distorted neurites in an Alzheimer mouse model. J.Neurochem. 2007, 102:1095-1104.
8. Garcia-Alloza M., Robbins E.M., Zhang-Nunes S.X., Purcell S.M., Betensky R.A., Raju S., Prada C., Greenberg S.M., Bacskai B.J., Frosch M.P. Characterization of amyloid deposition in the APPswe/PS1dE9 mouse model of Alzheimer disease. Neurobiol. Dis. 2006, 24:516-524.
9. Goel A., Kunnumakkara A.B., Aggarwal B.B. Curcumin as "Curecumin": from kitchen to clinic. Biochem. Pharmacol. 2008, 75:787-809.
10. Haass C., Selkoe D.J. Soluble protein oligomers in neurodegeneration: lessons from the Alzheimer's amyloid β-peptide. Nat. Rev. Mol. Null. Biol 2007, 8:101-112.
11. Hatcher H., Planalp R., Cho J., Torti F.M., Torti S.V. Curcumin: from ancient medicine to current clinical trials. Cell. Mol. Life Sci 2008, 65:1631-1652.
12. Hamaguchi T., Ono K., Murase A., Yamada M. Phenolic compounds prevent Alzheimer's pathology through different effects on the amyloid-beta aggregation pathway. Am. J. Pathol. 2009, 75:2557-2565.
13. Hamaguchi T., Ono K., Yamada M. Review: curcumin and Alzheimer's disease. CNS Neurosci. Ther. 2010, 16:285-297.
14. Hardy J., Selkoe D.J. The amyloid hypothesis of Alzheimer's disease: progress and problems on the road to therapeutics. Science 2002, 297:353-356.
15. Heath D.D., Pruitt M.A., Brenner D.E., Rock C.L. Curcumin in plasma and urine: quantitation by high-performance liquid chromatography. J.Chromatogr. B Analyt. Technol. Biomed. Life Sci. 2003, 783:287-295.
16. Jack C.R., Knopman D.S., Jagust W.J., Shaw L.M., Aisen P.S., Weiner M.W., Petersen R.C., Trojanowski J.Q. Hypothetical model of dynamic biomarkers of the Alzheimer's pathological cascade. Lancet Neurol. 2010, 9:119-128.
17. Jankowsky J.L., Fadale D.J., Anderson J., Xu G.M., Gonzales V., Jenkins N.A., Copeland N.G., Lee M.K., Younkin L.H., Wagner S.L., Younkin S.G., Borchelt D.R. Mutant presenilins specifically elevate the levels of the 42 residue beta-amyloid peptide invivo: evidence for augmentation of a 42-specific gamma secretase. Hum. Mol. Genet. 2004, 13:159-170.
18. Kawarabayashi T., Younkin L.H., Saido T.C., Shoji M., Ashe K.H., Younkin S.G. Age-dependent changes in brain, CSF, and plasma amyloid (beta) protein in the Tg2576 transgenic mouse model of Alzheimer's disease. J.Neurosci. 2001, 21:372-381.
19. Lim G.P., Chu T., Yang F., Beech W., Frautschy S.A., Cole G.M. The curry spice curcumin reduces oxidative damage and amyloid pathology in an Alzheimer transgenic mouse. J.Neurosci. 2001, 21:8370-8377.
20. Ma Q.L., Yang F., Rosario E.R., Ubeda O.J., Beech W., Gant D.J., Chen P.P., Hudspeth B., Chen C., Zhao Y., Vinters H.V., Frautschy S.A., Cole G.M. Beta-amyloid oligomers induce phosphorylation of tau and inactivation of insulin receptor substrate via c-Jun N-terminal kinase signaling: suppression by omega-3 fatty acids and curcumin. J.Neurosci. 2009, 29:9078-9089.
21. Ma Q.L., Zuo X., Yang F., Ubeda O.J., Gant D.J., Alaverdyan M., Teng E., Hu S., Chen P.P., Maiti P., Teter B., Cole G.M., Frautschy S.A. Curcumin suppresses soluble tau dimers and corrects molecular chaperone, synaptic, and behavioral deficits in aged human tau transgenic mice. J.Biol. Chem. 2014, 288:4056-4065.
22. Necula M., Kayed R., Milton S., Glabe C.G. Small molecule inhibitors of aggregation indicate that amyloid beta oligomerization and fibrillization pathways are independent and distinct. J.Biol. Chem. 2007, 282:10311-10324.
23. Payton F., Sandusky P., Alworth W.L. NMR study of the solution structure of curcumin. J.Nat. Prod. 2007, 70:143-146.
24. Ono K., Hasegawa K., Naiki H., Yamada M. Curcumin has potent anti-amyloidogenic effects for Alzheimer's beta-amyloid fibrils invitro. J.Neurosci. Res. 2004, 75:742-750.
25. Orlando R.A., Gonzales A.M., Royer R.E., Deck L.M., Vander Jagt D.L. Achemical analog of curcumin as an improved inhibitor of amyloid Aβ oligomerization. PLoS One 2012, 7:e31869.
26. Querfurth H.W., LaFerla F.M. Alzheimer's disease. N.Engl. J. Med. 2010, 362:329-344.
27. Rajasekar N., Dwivedi S., Tota S.K., Kamat P.K., Hanif K., Nath C., Shukla R. Neuroprotective effect of curcumin on okadaic acid induced memory impairment in mice. Eur. J. Pharmacol. 2013, 715:381-394.
28. Reinke A.A., Gestwicki J.E. Structure-activity relationships of amyloid beta-aggregation inhibitors based on curcumin: influence of linker length and flexibility. Chem. Biol. Drug Des. 2007, 70:206-215.
29. Roychaudhuri R., Yang M., Hoshi M.M., Teplow D.B. Amyloid β-protein assembly and Alzheimer disease. J.Biol. Chem. 2009, 284:4749-4753.
30. Savonenko A., Xu G.M., Melnikova T., Morton J.L., Gonzales V., Wong M.P., Price D.L., Tang F., Markowska A.L., Borchelt D.R. Episodic-like memory deficits in the APPswe/PS1dE9 mouse model of Alzheimer's disease: relationships to beta-amyloid deposition and neurotransmitter abnormalities. Neurobiol. Dis. 2005, 18:602-617.
31. Stine W.B., Dahlgren K.N., Krafft G.A., LaDu M.J. Invitro characterization of conditions for amyloid-beta peptide oligomerization and fibrillogenesis. J.Biol. Chem. 2003, 278:11612-11622.
32. Tempier A., He J., Zhu S., Zhang R., Kong L., Tan Q., Luo H., Kong J., Li X.M. Quetiapine modulates conditioned anxiety and alternation behavior in Alzheimer's transgenic mice. Curr. Alzheimer Res. 2010, 10:199-206.
33. Wang K., Qiu F. Curcuminoid metabolism and its contribution to the pharmacological effects. Curr. Drug Metab. 2013, 14:791-806.
34. 19F-containing curcumin derivative in a mouse model of Alzheimer's disease. Neuroscience 2011, 184:120-127.
35. Yanagisawa D., Shirai N., Amatsubo T., Taguchi H., Hirao K., Urushitani M., Morikawa S., Inubushi T., Kato M., Kato F., Morino K., Kimura H., Nakano I., Yoshida C., Okada T., Sano M., Wada Y., Wada K.N., Yamamoto A., Tooyama I. Relationship between the tautomeric structures of curcumin derivatives and their Aβ-binding activities in the context of therapies for Alzheimer's disease. Biomaterials 2010, 31:4179-4185.
36. Yanagisawa D., Taguchi H., Yamamoto A., Shirai N., Hirao K., Tooyama I. Curcuminoid binds to amyloid-β 1-42 oligomer and fibril. J.Alzheimers Dis. 2011, 24(Suppl 2):33-42.
37. Yang F., Lim G.P., Begum A.N., Ubeda O.J., Simmons M.R., Ambegaokar S.S., Chen P.P., Kayed R., Glabe C.G., Frautschy S.A., Cole G.M. Curcumin inhibits formation of amyloid beta oligomers and fibrils, binds plaques, and reduces amyloid invivo. J.Biol. Chem. 2004, 280:5892-5901.
38. Yu S.Y., Zhang M., Luo J., Zhang L., Shao Y., Li G. Curcumin ameliorates memory deficits via neuronal nitric oxide synthase in aged mice. Prog. Neuropsychopharmacol. Biol. Psychiatry 2013, 45:47-53.