Electrochemical and homogeneous electron transfers to the Alzheimer amyloid-β copper complex follow a preorganization mechanism

Proceedings of the National Academy of Sciences of the United States of America

Volumn 107, Issue 40, 2010, Pages 17113-17118

  Balland, Véronique ^a   Hureau, Christelle ^b   Savéant, Jean Michel ^a  

^a UNIVERSITÉ PARIS DIDEROT   (France)

^b CNRS   (France)

Author keywords

Amyloid peptide; Copper amyloid complexes; Cyclic voltammetry; Electrochemistry

Indexed keywords

AMYLOID BETA PROTEIN; COPPER COMPLEX; ELECTRON TRANSFERRING FLAVOPROTEIN; HYDROGEN PEROXIDE; OSMIUM DERIVATIVE; OXYGEN; PEPTIDE DERIVATIVE; REACTIVE OXYGEN METABOLITE;

ALZHEIMER DISEASE; ARTICLE; CHEMICAL REACTION KINETICS; CYCLIC POTENTIOMETRY; ELECTROCHEMISTRY; ENERGY; PRIORITY JOURNAL;

ALZHEIMER DISEASE; AMINO ACID SEQUENCE; AMYLOID BETA-PROTEIN; COPPER; ELECTROCHEMISTRY; ELECTRON TRANSPORT; MOLECULAR SEQUENCE DATA; PEPTIDES;

EID: 78049317224     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1011315107     Document Type: Article

References (54)

1. Gaggelli E, Kozlowski H, Valensin D, Valensin G (2006) Copper homeostasis and neurodegenerative disorders (Alzheimer's, Prion, and Parkinson's diseases and amyotrophic lateral sclerosis). Chem Rev 106:1995-2044.
2. Roychaudhuri R, Yang M, Hoshi MM, Teplow DB (2009) Amyloid beta-protein assembly and Alzheimer disease. J Biol Chem 284:4749-4753.
3. Barnham KJ, Bush AI (2008) Metals in Alzheimer's and Parkinson's diseases. Curr Opin Chem Biol 12:222-228.
4. Smith DG, Cappai R, Barnham KJ (2007) The redox chemistry of the Alzheimer's disease amyloid b peptide. Biochim Biophys Acta Biomembr 1768:1976-1990. (Pubitemid 47125850)
5. Hureau C, Faller P (2009) Aβ-mediated ROS production by the Cu ions: Structural insights, mechanisms and relevance to Alzheimer's disease. Biochimie 91:1212-1217.
6. Sarell CJ, Syme CD, Rigby SEJ, Viles JH (2009) Copper(II) binding to amyloid-b fibrils of Alzheimer's disease reveals a picomolar affinity: Stoichiometry and coordination geometry are independent of Ab oligomeric form. Biochemistry 48:4388-4402.
7. Faller P, Hureau C (2009) Bioinorganic chemistry of copper and zinc ions coordinated to amyloid-b peptide. Dalton Trans 1080-1094.
8. Shearer J, Szalai VA (2008) The amyloid-β peptide of Alzheimer's disease binds CuI in a linear bis-his coordination environment: Insight into a possible neuroprotective mechanism for the amyloid-β peptide. J Am Chem Soc 130:17826-17835.
9. Minicozzi V, et al. (2008) Identifying the minimal copper- and zinc-binding site sequence in amyloid-b peptides. J Biol Chem 283:10784-10792.
10. Karr JW, Szalai VA (2008) Cu(II) binding to monomeric, oligomeric, and fibrillar forms of the Alzheimer's disease amyloid-b peptide. Biochemistry 47:5006-5016.
11. Syme CD, Nadal RC, Rigby SEJ, Viles JH (2004) Copper binding to the amyloid-b (Ab) peptide associated with Alzheimer's disease: Folding, coordination geometry, Ph dependence, stoichiometry, and affinity of A-(1-28): Insights from a range of complementary spectroscopic techniques. J Biol Chem 279:18169-18177.
12. Hureau C, et al. (2009) Deprotonation of the Asp1-Ala2 peptide bond induces modification of the dynamic copper(II) environment in the amyloid-b peptide near physiological pH. Angew Chem Int Edit 48:9522-9525.
13. Dorlet P, Gambarelli S, Faller P, Hureau C (2009) Pulse EPR spectroscopy reveals the coordination sphere of copper(II) ions in the 1-16 amyloid-b peptide: A key role of the first two N-terminus residues. Angew Chem Int Edit 48:9273-9276.
14. Shin B-k, Saxena S (2008) Direct evidence that all three histidine residues coordinate to Cu(II) in amyloid-b1-16. Biochemistry 47:9117-9123.
15. Drew SC, Noble CJ, Masters CL, Hanson GR, Barnham KJ (2009) Pleomorphic copper coordination by Alzheimer's disease amyloid-beta peptide. J Am Chem Soc 131:1195-1207.
16. 2+ coordination of Alzheimer's disease amyloid-b peptide - Relevance to N-terminally truncated forms. J Am Chem Soc 131:8760-8761.
17. Himes RA, Park GY, Siluvai GS, Blackburn NJ, Karlin KD (2008) Structural studies of copper(I) complexes of amyloid-beta peptide fragments: Formation of two-coordinate bis(histidine) complexes. Angew Chem Int Edit 47:9084-9087.
18. Hureau C, et al. (2009) Importance of dynamical processes in the coordination chemistry and redox conversion of copper amyloid-β complexes. J Biol Inorg Chem 14:995-1000.
19. Jiang D, et al. (2007) Redox reactions of copper complexes formed with different b-amyloid peptides and their neuropathalogical relevance. Biochemistry 46:9270-9282.
20. Brzyska M, Trzesniewska K, Wieckowska A, Szczepankiewicz A, Elbaum D (2009) Electrochemical and conformational consequences of copper (CuI and CuII) binding to b-amyloid(1-40). ChemBioChem 10:1045-1055.
21. Sorrell TN, Jameson DL (1983) Synthesis, structure, and reactivity of monomeric two-coordinate copper(I) complexes. J Am Chem Soc 105:6013-6018.
22. Sanyal I, Karlin KD, Strange RW, Blackburn NJ (1993) Chemistry and structural studies on the dioxygen-binding copper-1,2-dimethylimidazole system. J Am Chem Soc 115:11259-11270.
23. Le Clainche L, Giorgi M, Reinaud O (2000) Synthesis and characterization of a novel calix[4]arene-based two-coordinate copper(I) complex that is unusually resistant to dioxygen. Eur J Inorg Chem 2000:1931-1933.
24. Himes RA, Park GY, Barry AN, Blackburn NJ, Karlin KD (2007) Synthesis and X-ray absorption spectroscopy structural studies of Cu(I) complexes of histidyl histidine peptides: The predominance of linear 2-coordinate geometry. J Am Chem Soc 129:5352-5353.
25. 2+/+ couple. Inorg Chem 38:12-19.
26. Rorabacher DB (2004) Electron transfer by copper centers. Chem Rev 104:651-698.
27. Robandt PV, Schroeder RR, Rorabacher DB (1993) Cyclic voltammetric characterization of rate constants for conformational change in an electron-transfer square scheme involving a copper(II)/(I) macrocyclic tetrathiaether complex. Inorg Chem 32:3957-3963.
28. Le Poul N, et al. (2005) Electrochemical behavior of the Tris(pyridine)-Cu funnel complexes: An overall induced-fit process involving an entatic state through a supramolecular stress. J Am Chem Soc 127:5280-5281.
29. Le Poul N, et al. (2007) Monocopper center embedded in a biomimetic cavity: From supramolecular control of copper coordination to redox regulation. J Am Chem Soc 129:8801-8810.
30. Savéant J-M (2006) Elements of Molecular and Biomolecular Electrochemistry (Wiley-Interscience, New York), Chap. 2, pp 80-96.
31. Savéant J-M (2006) Elements of Molecular and Biomolecular Electrochemistry (Wiley-Interscience, New York), Chap. 1.
32. Levich VG (1955) Present state of the theory of oxidation-reduction in solution (bulk and electrode reactions). Advances in Electrochemistry and Electrochemical Engineering, eds P Delahay and CW Tobias (Wiley, New York), pp 250-371.
33. Hale JM (1968) The potential-dependence and the upper limits of electrochemical rate constants. J Electroanal Chem 19:315-318.
34. Gosavi S, Marcus RA (2000) Nonadiabatic electron transfer at metal surfaces. J Phys Chem B 104:2067-2072.
35. Chidsey CED (1991) Free energy and temperature dependence of electron transfer at the metal-electrolyte interface. Science 251:919-922.
36. Costentin C, Robert M, Savéant J-M (2006) Electron transfer and bond breaking: Recent advances. Chem Phys 324:40-56.
37. Costentin C, Robert M, Savéant J-M (2010) Concerted proton-electron transfers: electrochemical and related approaches. Acc Chem Res 43:1019-1029.
38. He L, Niemeyer B (2003) A novel correlation for protein diffusion coefficients based on molecular weight and radius of gyration. Biotechnol Progr 19:544-548.
39. Lide DR (2002) CRC Handbook of Chemistry and Physics, ed DR Lide (CRC Press, Boca Raton, FL), 82nd Ed, p 6-3.
40. Talmard C, Guilloreau L, Coppel Y, Mazarguil H, Faller P (2007) Amyloid-beta peptide forms monomeric complexes with CuII and ZnII prior to aggregation. ChemBioChem 8:163-165.
41. Smalley JF, et al. (2003) Heterogeneous electron-transfer kinetics for ruthenium and ferrocene redox moieties through alkanethiol monolayers on gold. J Am Chem Soc 125:2004-2013.
42. Moser CC, Keske JM, Warncke K, Farid RS, Dutton PL (1992) Nature of biological electron transfer. Nature 355:796-802.
43. Savéan J-M (2006) Elements of Molecular and Biomolecular Electrochemistry (Wiley-Interscience, New York), Chap. 2, pp 106-119.
44. Andrieux CP, Blocman C, Dumas-Bouchiat JM, M'Halla F, Savéant JM (1980) Determination of the lifetimes of unstable ion radicals by homogeneous redox catalysis of electrochemical reactions. Application to the reduction of aromatic halides. J Am Chem Soc 102:3806-3813.
45. Marcus RA (1964) Chemical and electrochemical electron-transfer theory. Annu Rev Phys Chem 15:155-196.
46. Williams RJP (1995) Energised (entatic) states of groups and of secondary structures in proteins and metalloproteins. Eur J Biochem 234:363-381.
47. Williams RJP (1971) Catalysis by metallo-enzymes: The entatic state. Inorg Chim Acta Rev 5:137-155.
48. Vallee BL, Williams RJ (1968) Metalloenzymes: The entatic nature of their active sites. Proc Natl Acad Sci USA 59:498-505.
49. Gray HB, Malmstrom BG, Williams RJP (2000) Copper coordination in blue proteins. J Biol Inorg Chem 5:551-559.
50. Chaka G, et al. (2007) A definitive example of a geometric "entatic state" effect: Electron-transfer kinetics for a copper(II/I) complex involving a quinquedentate macrocyclic trithiaether-bipyridine ligand. J Am Chem Soc 129:5217-5227.
51. Comba P (2000) Coordination compounds in the entatic state. Coord Chem Rev 200:217-245.
52. Comba P, Schiek W (2003) Fit and misfit between ligands and metal ions. Coord Chem Rev 238:21-29.
53. 2+/+ redox couple. Inorg Chem 40:3606-3614.
54. Rudolph M (2003) Digital simulations on unequally spaced grids.: Part 2. Using the box method by discretisation on a transformed equally spaced grid. J Electroanal Chem 543:23-39.