Curcumin Binding to Beta Amyloid: A Computational Study

Chemical Biology and Drug Design

Volumn 86, Issue 4, 2015, Pages 813-820

  Rao, Praveen P N ^a   Mohamed, Tarek ^a   Teckwani, Karan ^a   Tin, Gary ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

Alzheimer's disease; amyloid fibril; binding energy; curcumin; hexapeptide; keto enol; molecular docking; molecular dynamics

Indexed keywords

AMYLOID; AMYLOID BETA PROTEIN; AMYLOID BETA PROTEIN[1-40]; AROMATIC AMINO ACID; CURCUMIN; HEXAPEPTIDE; ANTINEOPLASTIC AGENT; NONSTEROID ANTIINFLAMMATORY AGENT; PEPTIDE FRAGMENT; PROTEIN BINDING;

ARTICLE; BETA SHEET; CRYSTAL STRUCTURE; DRUG PROTEIN BINDING; HYDROGEN BOND; MOLECULAR DOCKING; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTEIN ASSEMBLY; ALZHEIMER DISEASE; AMINO ACID SEQUENCE; CHEMISTRY; CURCUMA; HUMAN; METABOLISM;

ALZHEIMER DISEASE; AMINO ACID SEQUENCE; AMYLOID BETA-PEPTIDES; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTINEOPLASTIC AGENTS; CURCUMA; CURCUMIN; HUMANS; MOLECULAR DOCKING SIMULATION; MOLECULAR DYNAMICS SIMULATION; PEPTIDE FRAGMENTS; PROTEIN BINDING;

EID: 84942553590     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12552     Document Type: Article

References (26)

1. Aggarwal B.B., Sundaram C., Malini N., Ichikawa H., (2007) Curcumin: the Indian solid gold. Adv Exp Med Biol; 595: 1-75.
2. Aggarwal B.B., Sung B., (2009) Pharmacological basis for the role of curcumin in chronic diseases: an age-old spice with modern targets. Trends Pharmacol Sci; 30: 85-94.
3. Wilken R., Veena M.S., Wang M.B., Srivatsan E.S., (2011) Curcumin: a review of anti-cancer properties and therapeutic activity in head and neck squamous cell carcinoma. Mol Cancer; 10: 12.
4. Rodwell C., (2012) Curcumin curries favor. Nat Rev Cancer; 12: 376.
5. Miklossy G., Hilliard T.S., Turkson J., (2013) Therapeutic modulators of STAT signalling for human diseases. Nat Rev Drug Discov; 12: 611-629.
6. Zorofchian Moghadamtousi S., Abdul Kadir H., Hassandarvish P., Tajik H., Abubakar S., Zandi K., (2014) A review of antibacterial, antiviral and antifungal activity of curcumin. Bio Med Res Int; 2014: 186864.
7. Hamaguchi T., Ono K., Yamada M., (2010) Review: curcumin and Alzheimer's disease. CNS Neurosci Ther; 16: 285-297.
8. Potter P.E., (2013) Curcumin: a natural substance with potential efficacy in Alzheimer's disease. J Exp Pharmacol; 5: 23-31.
9. Yang F., Lim G.P., Begum A.N., Ubeda O.J., Simmon M.R., Ambegaokar S.S., Chen P.P., Kayed R., Glabe C.G., Frautschy S.A., Cole G.M., (2005) Curcumin inhibits formation of amyloid beta oligomers and fibrils, binds plaques and reduced amyloid in vivo. J Biol Chem; 280: 5892-5901.
10. 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., (2013) Curcumin suppresses soluble tau dimers and corrects molecular chaperone, synaptic, and behavioral deficits in aged human tau transgenic mice. J Biol Chem; 288: 4056-4065.
11. Reinke A.A., Gestwicki J.E., (2007) Structure activity relationships of amyloid beta-aggregation inhibitors based on curcumin: influence of chain length and flexibility. Chem Biol Drug Des; 70: 207-215.
12. Zhao L.N., Chiu S.W., Benoit J., Chew L.Y., Mu Y., (2012) The effect of curcumin on the stability of Aβ dimers. J Phys Chem B; 116: 7428-7435.
13. Yanagisawa D., Shirai N., Amatsubo T., Taguchi H., Hirao K., Urushitani M., Morikawa S., et al., (2010) Relationship between the tautomeric structures of curcumin derivatives and their abeta-binding activities in the context of therapies for Alzheimer's disease. Biomaterials; 31: 4179-4185.
14. Landau M., Sawaya M.R., Faull K.F., Laganowsky A., Jiang L., Sievers S.A., Liu J., Barrio J.R., Eisenberg D., (2011) Towards a pharmacophore for amyloid. PLoS Biol; 9: e1001080.
15. Sievers S.A., Karanicolas J., Chang H.W., Zhao A., Jiang L., Zirafi O., Stevens J.T., Munch J., Baker D., Eisenberg D., (2011) Structure-based design of non-natural amino acid inhibitors of amyloid fibrils formation. Nature; 475: 96-100.
16. Jiang L., Liu C., Leibly D., Landau M., Zhao M., Huges M.P., Eisenberg D., (2013) Structure-based discovery of fiber-binding compounds that reduce the cytotoxicity of amyloid beta. Elife; 2: e00857.
17. Zheng J., Baghkhanian A.M., Nowick J.S., (2013) A hydrophobic surface is essential to inhibit the aggregation of a tau-protein-derived hexapeptide. J Am Chem Soc; 135: 6846-6852.
18. Liu R., McAllister C., Lyubchenko Y., Sierks M.R., (2004) Residues 17-20 and 30-35 of beta-amyloid play critical roles in aggregation. J Neurosci Res; 75: 162-171.
19. Petkova A.T., Yau W.M., Tycko R., (2006) Experimental constraints on quaternary structure in Alzheimer's beta-amyloid fibrils. Biochemistry; 45: 498-512.
20. Bieschke J., Herbst M., Wiglenda T., Friedrich R.P., Boeddrich A., Schiele F., Kleckers D., et al., (2011) Small-molecule conversion of toxic oligomers to nontoxic β-sheet-rich amyloid fibrils. Nat Chem Biol; 8: 93-101.
21. Gazit E., (2002) A possible role for pi-stacking in the self assembly of amyloid fibrils. FASEB J; 16: 77-83.
22. Smith D.G., Ciccotosto G.D., Tew D.J., Perez K., Curtain C.C., Boas J.F., Masters C.L., Cappai R., Barnham K.J., (2010) Histidine 14 modulates membrane binding and neurotoxicity of the Alzheimer's disease amyloid-beta peptide. J Alzheimers Dis; 19: 1387-1400.
23. Kotler S.A., Walsh P., Brender J.R., Ramamoorthy A., (2014) Differences between amyloid-β aggregation in solution and on the membrane: insights into elucidation of the mechanistic details of Alzheimer's disease. Chem Soc Rev; 43: 6692-6700.
24. Sandberg A., Luheshi L.M., Sollvander S., Pereira de Barros T., Macao B., Knowles T.P., Biverstal H., Lendel C., Ekholm-Petterson F., Dubnovitsky A., Lannfelt L., Dobson C.M., Hard T., (2010) Stabilization of neurotoxic Alzheimers amyloid-beta oligomers by protein engineering. Proc Natl Acad Sci USA; 107: 15595-15600.
25. Stroud J.C., Liu C., Teng P.K., Eisenberg D., (2012) Toxic fibrillar oligomers of amyloid-β have cross-β structure. Proc Natl Acad Sci USA; 109: 7717-7722.
26. Liu C., Zhao M., Jiang L., Cheng P.N., Park J., Sawaya M.R., Pensalfini A., Gou D., Berk A.J., Glabe C.G., Nowick J., Eisenberg D., (2012) Out-of-register β-sheets suggest a pathway to toxic amyloid aggregates. Proc Natl Acad Sci USA; 109: 20913-20918.