Complexation between Cu(II) and curcumin in the presence of two different segments of amyloid β

Biophysical Chemistry

Volumn 184, Issue , 2013, Pages 62-67

  Picciano, Angela L ^a   Vaden, Timothy D ^a  

^a ROWAN UNIVERSITY   (United States)

Author keywords

Amyloid metal ion binding; Chelation drug; Curcumin; Fluorescence spectroscopy; Mass spectrometry; Peptide

Indexed keywords

AMYLOID BETA PROTEIN; CUPRIC ION; CURCUMIN; METHANOL; WATER;

ARTICLE; BINDING AFFINITY; BINDING SITE; CHELATION; COMPLEX FORMATION; DISSOCIATION CONSTANT; ELECTROSPRAY MASS SPECTROMETRY; FLUORESCENCE SPECTROSCOPY; METAL BINDING; PRIORITY JOURNAL; PROTEIN DOMAIN; QUANTITATIVE ANALYSIS;

AMYLOID-METAL ION BINDING; CHELATION DRUG; CURCUMIN; FLUORESCENCE SPECTROSCOPY; MASS SPECTROMETRY; PEPTIDE;

AMYLOID BETA-PEPTIDES; COPPER; CURCUMIN; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84885078046     PISSN: 03014622     EISSN: 18734200     Source Type: Journal    
DOI: 10.1016/j.bpc.2013.09.004     Document Type: Article

References (56)

1. A. Serrano-Pozo, M.P. Frosch, E. Masliah, and B.T. Hyman Neuropathological alterations in Alzheimer Disease Cold Spring Harb. Perspect. Med. 1 2011 a006189
2. F. Chiti, and C.M. Dobson Protein misfolding, functional amyloid, and human disease Annu. Rev. Biochem. 75 2006 333 366 (Pubitemid 44118036)
3. O.S. Makin, and L.C. Serpell Structures for amyloid fibrils FEBS J. 272 2005 5950 5961 (Pubitemid 41713687)
4. K.E. Marshall, K.L. Morris, D. Charlton, O.R. Nicola, L. Lewis, H. Walden, and L.C. Serpell Hydrophobic, aromatic, and electrostatic interactions play a central role in amyloid fibril formation and stability Biochemistry 50 2011 2061 2071
5. Y. Miller, B. Ma, and R. Nussinov Polymorphism in Alzheimer a-beta amyloid organization reflects conformational selection in a rugged energy landscape Chem. Rev. 110 2010 4820 4838
6. R. Nelson, M.R. Sawaya, M. Balbirnie, A.∅. Madsen, C. Riekel, R. Grothe, and D. Eisenberg Structure of the cross-beta spine of amyloid-like fibrils Nature 435 2005 773 778 (Pubitemid 40839722)
7. A. Perczel, P. Hudaky, and V.K. Palfi Dead-end street of protein folding: thermodynamic rationale of amyloid fibril formation J. Am. Chem. Soc. 129 2007 14959 14965 (Pubitemid 350230718)
8. D.B. Teplow, N.L. Lazo, G. Bitan, S. Bernstein, T. Wyttenbach, M.T. Bowers, A. Baumketner, J.-E. Shea, B. Urbanc, L. Cruz, J. Borreguero, and H.E. Stanley Elucidating amyloid beta-protein folding and assembly: a multidisciplinary approach Acc. Chem. Res. 39 2006 635 645
9. R. Tycko Molecular structure of amyloid fibrils: insights from solid-state NMR Q. Rev. Biophys. 39 2006 1 55 (Pubitemid 44566373)
10. J. Reifert, D. Hartung-Cranston, and S.C. Feinstein Amyloid beta-mediated cell death of cultured hippocampal neurons reveals extensive tau fragmentation without increased full-length tau phosphorylation J. Biol. Chem. 286 2011 20797 20811
11. A.S. DeToma, S. Salamekh, A. Ramamoorthy, and M.H. Lim Misfolded proteins in Alzheimer's disease and type II diabetes Chem. Soc. Rev. 41 2012 608 621
12. L. Haataja, T. Gurlo, C.J. Huang, and P.C. Butler Islet amyloid in type 2 diabetes, and the toxic oligomer hypothesis Endocr. Rev. 29 2008 303 316 (Pubitemid 351679701)
13. H.R. Kalhor, M. Kamizi, J. Akbari, and A. Heydari Inhibition of amyloid formation by ionic liquids: ionic liquids affecting intermediate oligomers Biomacromolecules 10 2009 2468 2475
14. W.L. Klein, G.A. Krafft, and C.E. Finch Targeting small Aβ oligomers: the solution to an Alzheimer's disease conundrum? Trends Neurosci. 24 2001 219 224 (Pubitemid 32204378)
15. Y. Miller, B. Ma, and R. Nussinov Metal binding sites in amyloid oligomers: complexes and mechanisms Coord. Chem. Rev. 256 2012 2245 2252
16. F.X. Zhou, H.J. Merianos, A.T. Brunger, and D.M. Engelman Polar residues drive association of polyleucine transmembrane helices Proc. Natl. Acad. Sci. U. S. A. 98 2001 2250 2255 (Pubitemid 32209468)
17. S. Lesné, M.T. Koh, L. Kotilinek, R. Kayed, C.G. Glabe, A. Yang, M. Gallagher, and K.H. Ashe A specific amyloid-β protein assembly in the brain impairs memory Nature 440 2006 352 357
18. E.A. Stern, B.J. Bacskai, G.A. Hickey, F.J. Attenello, J.A. Lombardo, and B.T. Hyman Cortical synaptic integration in vivo is disrupted by amyloid-β plaques J. Neurosci. 24 2004 4535 4540 (Pubitemid 38656609)
19. A. Esteras-Chopo, M.T. Pastor, L. Serrano, and M. Lopez de la Paz New strategy for the generation of specific D-peptide amyloid inhibitors J. Mol. Biol. 377 2008 1372 1381
20. S.S. Hindo, A.M. Mancino, J.J. Braymer, Y. Liu, A. Ramamoorthy, Vivekanandan, and M.H. Lim Small molecule modulators of copper-induced Abeta aggregation J. Am. Chem. Soc. 131 2009 16663 16665
21. Y.S. Kim, J.H. Lee, J. Ryu, and D.J. Kim Multivalent and multifunctional ligands to beta-amyloid Curr. Pharm. Des. 15 2009 637 658
22. A. Opar Mixed results for disease-modification strategies for Alzheimer's disease Nat. Rev. 7 2008 717 718
23. S. Alavez, M. Vantipalli, D.S. Zucker, I.M. Klang, and G.J. Lithgow Amyloid-binding compounds maintain protein homeostasis during ageing and extend lifespan Nature 472 2011 226 229
24. A. Kurz, and R. Perneczky Amyloid clearance as a treatment target against Alzheimer's disease J. Alzheimer's Dis. 24 2011 61 73
25. S.C. Drew, and K.J. Barnham The heterogeneous nature of Cu2 + interactions with Alzheimer's amyloid-β peptide Acc. Chem. Res. 44 11 2011 1146 1155
26. M. Kawahara, and M. Kato-Negishi Link between aluminum and the pathogenesis of Alzheimer's disease: the integration of the aluminum and amyloid cascade hypotheses Int. J. Alzheimer's Dis. 2011 2011 276393
27. S. Matsumura, S. Uemura, and H. Mihara Metal-triggered nanofiber formation of His-containing beta-sheet peptides Supramol. Chem. 18 2006 397 403 (Pubitemid 44174384)
28. M.A. Lovell, J.D. Robertson, W.J. Teesdale, J.L. Campbell, and W.R. Markesbery Copper, iron and zinc in Alzheimer's disease senile plaques J. Neurol. Sci. 158 1998 47 52 (Pubitemid 28277534)
29. D. Jiang, L. Zhang, G.P.G. Grant, C.G. Dudzik, S. Chen, S. Patel, Y. Hao, G.L. Millhauser, and F. Zhou The elevated copper binding strength of amyloid-β aggregates allows the sequestration of copper from albumin: a pathway to accumulation of copper in senile plaques Biochemistry 52 2013 547 556
30. A. Binolfi, G.R. Lamberto, R. Duran, L. Quintanar, C.W. Bertoncini, J.M. Souza, C. Cervenansky, M. Zweckstetter, C. Griesinger, and C.O. Fernandez Site-specific interactions of Cu(II) with alpha and beta-synuclein: bridging the molecular gap between metal binding and aggregation J. Am. Chem. Soc. 130 2008 11801 11812
31. J. Dong, C.S. Atwood, V.E. Anderson, S.L. Siedlak, M.A. Smith, G. Perry, and P.R. Carey Metal binding and oxidation of amyloid-beta within isolated senile plaque cores: raman microscopic evidence Biochemistry 42 2003 2768 2773 (Pubitemid 36331519)
32. S.-T. Liu, G. Howlett, and C.J. Barrow Histidine-13 is a crucial residue in the zinc ion-induced aggregation of the Abeta peptide of Alzheimer's disease Biochemistry 38 1999 9373 9378
33. L.M. Miller, Q. Wang, T.P. Telivala, R.J. Smith, A. Lanzirotti, and J. Miklossy Synchrotron-based infrared and X-ray imaging shows focalized accumulation of Cu and Zn co-localized with b-amyloid deposits in Alzheimer's disease J. Struct. Biol. 155 2006 30 37 (Pubitemid 43867313)
34. C. Talmard, R.L. Yona, and P. Faller Mechanism of zinc(II)-promoted amyloid formation: zinc(II) binding facilitates the transition from the partially a-helical conformer to aggregates of amyloid b protein (1-28) J. Biol. Inorg. Chem. 14 2009 449 455
35. W.-h Wu, P. Lei, Q. Liu, J. Hu, A.P. Gunn, M.-s Chen, Y.-f. Rui, X.-y. Su, Z.-p. Xie, Y.-F. Zhao, A.I. Bush, and Y.-m. Li Sequestration of copper from beta-amyloid promotes selective lysis by cyclen-hybrid cleavage agents J. Biol. Chem. 283 2008 31657 31664
36. T. Hayashi, N. Shishido, K. Nakayama, A. Nunomura, M.A. Smith, G. Perry, and M. Nakamura Lipid peroxidation and 4-hydroxy-2-nonenal formation by copper ion bound to amyloid-β peptide Free Radic. Biol. Med. 43 2007 1552 1559 (Pubitemid 47615399)
37. X. Huang, C.S. Atwood, M.A. Hartshorn, G. Multhaup, L.E. Goldstein, R.C. Scarpa, M.P. Cuajungco, D.N. Gray, J. Lim, R.D. Moir, R.E. Tanzi, and A.I. Bush The Aβ peptide of Alzheimer's disease directly produces hydrogen peroxide through metal ion reduction Biochemistry 38 1999 7609 7616 (Pubitemid 29289332)
38. A. Nunomura, G. Perry, G. Aliev, K. Hirai, A. Takeda, E.K. Balraj, P.K. Jones, H. Ghanbari, T. Wataya, S. Shimomama, S. Chiba, C.S. Atwood, R.B. Petersen, and M.A. Smith Oxidative damage is the earliest event in Alzheimer disease J. Neuropathol. Exp. Neurol. 60 2001 759 767 (Pubitemid 32678256)
39. C. Rodriguez-Rodriguez, N. Sanchez de Groot, A. Rimola, A. Alvarez-Larena, V. Lloveras, J. Vidal-Gancedo, S. Ventura, J. Vendrell, M. Sodupe, and P. Gonzalez-Duarte Design, selection, and characterization of thioflavin-based intercalation compounds with metal chelating properties for application in Alzheimer's disease J. Am. Chem. Soc. 131 2009 1436 1451
40. N.J.M. Sanghamitra, N. Varghese, and C.N.R. Rao Effect of curcumin and Cu2 +/Zn2 + ions on the fibrillar aggregates formed by the amyloid peptide and other peptides at the organic-aqueous interface Chem. Phys. Lett. 496 2010 104 108
41. T. Storr, M. Merkel, G.X. Song-Zhao, L.E. Scott, D.E. Green, M.L. Bowen, K.H. Thompson, B.O. Patrick, H.J. Schugar, and C. Orvig Synthesis, characterization, and metal coordinating ability of multifunctional carbohydrate-containing compounds for Alzheimer's therapy J. Am. Chem. Soc. 129 2007 7453 7463 (Pubitemid 46991735)
42. D. Yanagisawa, H. Taguchi, A. Yamamoto, N. Shirai, K. Hirao, and I. Tooyama Curcuminoid binds to amyloid-beta1-24 oligomer and fibril J. Alzheimer's Dis. 24 2011 33 42
43. X.-Z. Zhao, T. Jiang, L. Wang, H. Yang, S. Zhang, and P. Zhou Interaction of curcumin with Zn(II) and Cu(II) ions based on experiment and theoretical calculation J. Mol. Struct. 984 2010 316 325
44. B. Zebib, Z. Mouloungui, and V. Noirot Stabilization of curcumin by complexation with divalent cations in glycerol/water system Bioinorg. Chem. Appl. 2010 2010 292760
45. F. Yang, G.P. Lim, A.N. Begum, O.J. Ubeda, M.R. Simmons, S.S. Ambegaokar, P. Chen, R. Kayed, C.G. Glabe, S.A. Frautschy, and G.M. Cole Curcumin inhibits formation of amyloid beta oligomers and fibrils, binds plaques, and reduces amyloid in vivo J. Biol. Chem. 280 2005 5892 5901 (Pubitemid 40280072)
46. L.N. Zhao, S.-W. Chiu, J. Benoit, L.Y. Chew, and Y. Mu The effect of curcumin on the stability of Aβ dimers J. Phys. Chem. B 116 2012 7428 7435
47. H. Hatcher, R. Planalp, J. Cho, F.M. Torti, and S.V. Torti Curcumin: from ancient medicine to current clinical trials Cell. Mol. Life Sci. 65 2008 1631 1652
48. M.L. Hegde, P. Bharathi, A. Suram, C. Venugopal, R. Jagannathan, P. Poddar, P. Srinivas, K. Sambamurti, K.J. Rao, J. Scancar, L. Messori, L. Zecca, and P. Zatta Challenges associated with metal chelation therapy in Alzheimer's disease J. Alzheimer's Dis. 17 2009 457 468
49. A.C. Badrick, and C.E. Jones Reorganizing metals: the use of chelating compounds as potential therapies for metal-related neurodegenerative disease Curr. Top. Med. Chem. 11 2011 543 552
50. N.C. Maiti, D. Jiang, A.J. Wain, S. Patel, K.L. Dinh, and F. Zhou Mechanistic studies of Cu(II) binding to amyloid-beta peptides and the fluorescence and redox behaviors of the resulting complexes J. Phys. Chem. B 112 2008 8406 8411
51. C.C. Curtain, F. Ali, I. Volitakis, R.A. Cherny, R.S. Norton, K. Beyreuther, C.J. Barrow, C.L. Masters, A.I. Bush, and K.J. Barnham Alzheimer's disease amyloid-β binds copper and zinc to generate an allosterically ordered membrane-penetrating structure containing superoxide dismutase-like subunits J. Biol. Chem. 276 2001 20466 20473
52. J. Lindgren, P. Segerfeldt, S.B. Sholts, A. Graeslund, A.E. Karlstroem, and S.K.T.S. Waermlaender Engineered non-fluorescent affibody molecules facilitate studies of the amyloid-beta (Aβ) peptide in monomeric form: low pH was found to reduce Aβ/Cu(II) binding affinity J. Inorg. Biochem. 122 2013
53. P. Kumaraswamy, S. Sethuraman, and U.M. Krishnan Mechanistic insights of curcumin interactions with the core-recognition motif of β-amyloid peptide J. Agric. Food Chem. 61 2013 3278 3285
54. S.T. Ngo, and M.S. Li Curcumin binds to Aβ1-40 peptides and fibrils stronger than ibuprofen and naproxen J. Phys. Chem. B 116 2012 10165 10175
55. J. Lakowicz Principles of fluorescence spectroscopy 2nd ed. 1999 (New York)
56. L. Hong, and J.D. Simon Insights into the thermodynamics of copper association with amyloid-b, a-synuclein and prion proteins Metallomics 3 2011 262 266