Resolution of localized small molecule-Aβ interactions by deep-ultraviolet resonance Raman spectroscopy

Biophysical Chemistry

Volumn 158, Issue 2-3, 2011, Pages 96-103

  Wang, Mingjuan ^a,b   Jiji, Renee D ^a  

^a UNIVERSITY OF MISSOURI   (United States)

^b Rhodia (China) Co Ltd   (China)

Author keywords

Alzheimer's disease; Amyloid peptide; Circular dichroism; Myricetin; Thioflavin T; Ultraviolet resonance Raman

Indexed keywords

AMIDE; AMYLOID; AMYLOID BETA PROTEIN; AMYLOID BETA PROTEIN[1-16]; AMYLOID BETA PROTEIN[1-42]; AMYLOID BETA PROTEIN[25-35]; AMYLOID BETA PROTEIN[25-40]; MYRICETIN; THIOFLAVINE; UNCLASSIFIED DRUG;

ARTICLE; CARBOXY TERMINAL SEQUENCE; CIRCULAR DICHROISM; CONFORMATIONAL TRANSITION; FLUORESCENCE SPECTROSCOPY; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN INTERACTION; PROTEIN STRUCTURE; RAMAN SPECTROMETRY; ULTRAVIOLET RAMAN RESONANCE SPECTROSCOPY;

ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; CIRCULAR DICHROISM; FLAVONOIDS; HUMANS; PEPTIDE FRAGMENTS; PROTEIN BINDING; PROTEIN STRUCTURE, SECONDARY; SPECTRUM ANALYSIS, RAMAN; THIAZOLES;

EID: 79960740352     PISSN: 03014622     EISSN: 18734200     Source Type: Journal    
DOI: 10.1016/j.bpc.2011.05.017     Document Type: Article

References (72)

1. C.L. Masters, R. Cappai, K.J. Barnham, and V.L. Villemagne Molecular mechanisms for Alzheimer's disease: implications for neuroimaging and therapeutics J. Neurochem. 97 2006 1700 1725 (Pubitemid 43873662)
2. L.-F. Lue, Y.-M. Kuo, A.E. Roher, L. Brachova, Y. Shen, L. Sue, T. Beach, J.H. Kurth, R.E. Rydel, and J. Rogers Soluble amyloid β peptide concentration as a predictor of synaptic change in Alzheimer's disease Am. J. Pathol. 155 1999 853 862 (Pubitemid 29426831)
3. C.A. McLean, R.A. Cherny, F.W. Fraser, S.J. Fuller, M.J. Smith, K. Beyreuther, A.I. Bush, and C.L. Masters Soluble pool of Aβ amyloid as a determinant of severity of neurodegeneration in Alzheimer's disease Ann. Neurol. 46 1999 860 866
4. M.M. Husain, K. Trevino, H. Siddique, and S.M. McClintock Present and prospective clinical therapeutic regimens for Alzheimer's disease Neuropsychiatr. Dis. Treat. 4 2008 765 777
5. N.C. Inestrosa, M.C. Dinamarca, and A. Alvarez Amyloid-cholinesterase interactions. Implications for Alzheimer's disease FEBS J. 275 2008 625 632 (Pubitemid 351160969)
6. T. Heinen-Kammerer, H. Rulhoff, S. Nelles, and R. Rychlik Added therapeutic value of memantine in the treatment of moderate to severe Alzheimer's disease Clin. Drug Investig. 26 2006 303 314 (Pubitemid 43876564)
7. M. Asai, C. Hattori, N. Iwata, T.C. Saido, N. Sasagawa, B. Szabo, Y. Hashimoto, K. Maruyama, S. Tanuma, Y. Kiso, and S. Ishiura The novel β-secretase inhibitor KMI-429 reduces amyloid beta peptide production in amyloid precursor protein transgenic and wild-type mice J. Neurochem. 96 2006 533 540
8. G.K. Wilcock, S.E. Black, S.B. Hendrix, K.H. Zavitz, E.A. Swabb, and M.A. Laughlin Efficacy and safety of tarenflurbil in mild to moderate Alzheimer's disease: a randomised phase II trial Lancet neurology 7 2008 483 493
9. J. Walter, C. Kaether, H. Steiner, and C. Haass The cell biology of Alzheimer's disease: uncovering the secrets of secretases Curr. Opin. Neurobiol. 11 2001 585 590 (Pubitemid 32938290)
10. D. Schenk, R. Barbour, W. Dunn, G. Gordon, H. Grajeda, T. Guido, K. Hu, J. Huang, K. Johnson-Wood, K. Khan, D. Kholodenko, M. Lee, Z. Liao, I. Lieberburg, R. Motter, L. Mutter, F. Soriano, G. Shopp, N. Vasquez, C. Vandevert, S. Walker, M. Wogulis, T. Yednock, D. Games, and P. Seubert Immunization with amyloid-β attenuates Alzheimer-disease-like pathology in the PDAPP mouse Nature 400 1999 173 177 (Pubitemid 29327547)
11. J.-M. Orgogozo, S. Gilman, J.-F. Dartigues, B. Laurent, M. Puel, L.C. Kirby, P. Jouanny, B. Dubois, L. Eisner, S. Flitman, B.F. Michel, M. Boada, A. Frank, and C. Hock Subacute meningoencephalitis in a subset of patients with AD after Aβ42 immunization Neurology 61 2003 46 54 (Pubitemid 36818745)
12. K. Samson, 'Passive' Alzheimer vaccine gets accelerated phase 3 start, Neurology Today 7 (2007) 15-16.
13. J.O. Rinne, D.J. Brooks, M.N. Rossor, N.C. Fox, R. Bullock, W.E. Klunk, C.A. Mathis, K. Blennow, J. Barakos, A.A. Okello, S.R.M. de Liano, E. Liu, M. Koller, K.M. Gregg, D. Schenk, R. Black, and M. Grundman 11C-PiB PET assessment of change in fibrillar amyloid-β load in patients with Alzheimer's disease treated with bapineuzumab: a phase 2, double-blind, placebo-controlled, ascending-dose study Lancet Neurol. 9 2010 363 372
14. T.E. Golde Disease modifying therapy for AD? J. Neurochem. 99 2006 689 707 (Pubitemid 44583429)
15. C. Féart, C. Samieri, and P. Barberger-Gateau Mediterranean diet and cognitive function in older adults Curr. Opin. Clin. Nutr. 13 2010 14 18
16. S. Bastianetto, and R. Quirion Natural extracts as possible protective agents of brain aging Neurobiol. Aging 23 2002 891 897 (Pubitemid 35217714)
17. G.P. Lim, T. Chu, F. Yang, W. Beech, S.A. Frautschy, and G.M. Cole The curry spice curcumin reduces oxidative damage and amyloid pathology in an Alzheimer transgenic mouse J. Neurosci. 21 2001 8370 8377 (Pubitemid 33051435)
18. Q. Wang, A. Simonyi, W.L. Li, B.A. Sisk, R.L. Miller, R.S. MacDonald, D.E. Lubahn, G.Y. Sun, and A.Y. Sun Dietary grape supplement ameliorates cerebral ischemia-induced neuronal death in gerbils Mol. Nutr. Food Res. 49 2005 443 451 (Pubitemid 40780391)
19. Q. Wang, A.Y. Sun, A. Simonyi, M.D. Jensen, P.B. Shelat, G.E. Rottinghaus, R.S. MacDonald, D.K. Miller, D.E. Lubahn, G.A. Weisman, and G.Y. Sun Neuroprotective mechanisms of curcumin against cerebral ischemia-induced neuronal apoptosis and behavioral deficits J. Neurosci. Res. 82 2005 138 148 (Pubitemid 41604805)
20. M. Necula, R. Kayed, S. Milton, and C.G. Glabe Small molecule inhibitors of aggregation indicate that amyloid β oligomerization and fibrillization pathways are independent and distinct J. Biol. Chem. 282 2007 10311 10324 (Pubitemid 47093410)
21. H. Levine III Small molecule inhibitors of Aβ assembly Amyloid 14 2007 185 197
22. T. Bandiera, J. Lansen, C. Post, and M. Varasi Inhibitors of Aβ peptide aggregation as potential anti-Alzheimer agents Curr. Med. Chem. 4 1997 159 170 (Pubitemid 27334340)
23. F.S. Yang, G.P. Lim, A.N. Begum, O.J. Ubeda, M.R. Simmons, S.S. Ambegaokar, P.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)
24. M. Pappolla, P. Bozner, C. Soto, H.Y. Shao, N.K. Robakis, M. Zagorski, B. Frangione, and J. Ghiso Inhibition of Alzheimer β-fibrillogenesis by melatonin J. Biol. Chem. 273 1998 7185 7188
25. T. Tomiyama, S. Asano, Y. Suwa, T. Morita, K. Kataoka, H. Mori, and N. Endo Rifampicin prevents the aggregation and neurotoxicity of amyloid-β protein in-vitro Biochem. Biophys. Res. Commun. 204 1994 76 83 (Pubitemid 24335264)
26. J. McLaurin, R. Golomb, A. Jurewicz, J.P. Antel, and P.E. Fraser Inositol stereoisomers stabilize an oligomeric aggregate of Alzheimer amyloid β peptide and inhibit Aβ-induced toxicity J. Biol. Chem. 275 2000 18495 18502 (Pubitemid 30414810)
27. P. Marambaud, H. Zhao, and P. Davies Resveratrol promotes clearance of Alzheimer's disease amyloid-β peptides J. Biol. Chem. 280 2005 37377 37382 (Pubitemid 41642343)
28. J.B. Hoppe, R.L. Frozza, A.P. Horn, R.A. Comiran, A. Bernardi, M.M. Campos, A.M.O. Battastini, and C. Salbego Amyloid-β neurotoxicity in organotypic culture is attenuated by melatonin: involvement of GSK-3β, tau and neuroinflammation J. Pineal Res. 48 2010 230 238
29. T. Tomiyama, H. Kaneko, K. Kataoka, S. Asano, and N. Endo Rifampicin inhibits the toxicity of pre-aggregated amyloid peptides by binding to peptide fibrils and preventing amyloid-cell interaction Biochem. J. 322 1997 859 865 (Pubitemid 27135636)
30. K. Ono, Y. Yoshiike, A. Takashima, K. Hasegawa, H. Naiki, and M. Yamada Potent anti-amyloidogenic and fibril-destabilizing effects of polyphenols in vitro: implications for the prevention and therapeutics of Alzheimer's disease J. Neurochem. 87 2003 172 181 (Pubitemid 37210651)
31. H. Kim, B.S. Park, K.G. Lee, C.Y. Choi, S.S. Jang, Y.H. Kim, and S.E. Lee Effects of naturally occurring compounds on fibril formation and oxidative stress of β-amyloid J. Agric. Food Chem. 53 2005 8537 8541 (Pubitemid 41608910)
32. H. Onozuka, A. Nakajima, K. Matsuzaki, R.W. Shin, K. Ogino, D. Saigusa, N. Tetsu, A. Yokosuka, Y. Sashida, Y. Mimaki, T. Yamakuni, and Y. Ohizumi Nobiletin, a citrus flavonoid, improves memory impairment and Aβ pathology in a transgenic mouse model of Alzheimer's disease J. Pharmacol. Exp. Ther. 326 2008 739 744
33. A.M. Haque, M. Hashimoto, M. Katakura, Y. Hara, and O. Shido Green tea catechins prevent cognitive deficits caused by Aβ1-40 in rats J. Nutr. Biochem. 19 2008 619 626
34. S. Burda, and W. Oleszek Antioxidant and antiradical activities of flavonoids J. Agric. Food Chem. 49 2001 2774 2779 (Pubitemid 32826067)
35. H.A. Scheidt, A. Pampel, L. Nissler, R. Gebhardt, and D. Huster Investigation of the membrane localization and distribution of flavonoids by high-resolution magic angle spinning NMR spectroscopy Biochim. Biophys. Acta 1663 2004 97 107 (Pubitemid 38625584)
36. T. Hamaguchi, K. Ono, A. Murase, and M. Yamada Phenolic compounds prevent Alzheimer's pathology through different effects on the amyloid-β aggregation pathway Am. J. Pathol. 175 2009 2557 2565
37. M. Hirohata, K. Hasegawa, S. Tsutsumi-Yasuhara, Y. Ohhashi, T. Ookoshi, K. Ono, M. Yamada, and H. Naiki The anti-amyloidogenic effect is exerted against Alzheimer's β-amyloid fibrils in vitro by preferential and reversible binding of flavonoids to the amyloid fibril structure Biochemistry 46 2007 1888 1899
38. Y. Shimmyo, T. Kihara, A. Akaike, T. Niidome, and H. Sugimoto Multifunction of myricetin on Aβ: neuroprotection via a conformational change of Aβ and reduction of Aβ via the interference of secretases J. Neurosci. Res. 86 2008 368 377 (Pubitemid 351196742)
39. T. Richard, X. Vitrac, J.M. Merillon, and J.P. Monti Role of peptide primary sequence in polyphenol-protein recognition: an example with neurotensin Biochim. Biophys. Acta-Gen. Subj. 1726 2005 238 243 (Pubitemid 41668531)
40. 1H-NMR spectroscopy Eur. J. Biochem. 219 1994 923 935 (Pubitemid 24050962)
41. D.B. Teplow Preparation of amyloid beta-protein for structural and functional studies Methods Enzymol. 413 2006 20 33 (Pubitemid 44528683)
42. L.J. Saidel, A.R. Goldfarb, and S. Waldman The absorption spectra of amino acids in the region two hundred to two hundred and thirty millimicrons J. Biol. Chem. 197 1952 285 291
43. M.L. Tiffany, and S. Krimm Circular dichroism of poly-L-proline in an unordered conformation Biopolymers 6 1968 1767 1770
44. M.L. Tiffany, and S. Krimm Extended conformations of polypeptides and proteins in urea and guanidine hydrochloride Biopolymers 12 1973 575 587
45. M.L. Tiffany, and S. Krimm New chain conformations of poly(glutamic acid) and polylysine Biopolymers 6 1968 1379 1382
46. B.W. Chellgren, and T.P. Creamer Short sequences of non-proline residues can adopt the polyproline II helical conformation Biochemistry 43 2004 5864 5869 (Pubitemid 38623619)
47. M.L. Tiffany, and S. Krimm Circular dichroism of random polypeptide chain Biopolymers 8 1969 347 359
48. 1-helix, β-strand and random coil secondary structures FEBS J. 272 2005 3938 3949 (Pubitemid 41117225)
49. E. Peggion, A. Cosani, M. Terbojev, and L. Romaninj Random coil-β-form transition of poly-L-lysine - Evidence for formation of α-helical structure during transition J. Chem. Soc.-Chem. Commun. 1974 314 316
50. A. Chakrabartty, T. Kortemme, S. Padmanabhan, and R.L. Baldwin Aromatic side-chain contribution to far-ultraviolet circular dichroism of helical peptides and its effect on measurement of helix propensities Biochemistry 32 1993 5560 5565 (Pubitemid 23178520)
51. Z. Chi, X.G. Chen, J.S.W. Holtz, and S.A. Asher UV resonance Raman-selective amide vibrational enhancement: quantitative methodology for determining protein secondary structure Biochemistry 37 1998 2854 2864 (Pubitemid 28145738)
52. R.A. Copeland, and T.G. Spiro Secondary structure determination in proteins from deep (192-223 nm) ultraviolet Raman-spectroscopy Biochemistry 26 1987 2134 2139
53. R.D. JiJi, G. Balakrishnan, Y. Hu, and T.G. Spiro Intermediacy of poly(L-proline) II and β-strand conformations in poly(L-lysine) β-sheet formation probed by temperature-jump/UV resonance Raman spectroscopy Biochemistry 45 2006 34 41 (Pubitemid 43054080)
54. Y. Wang, R. Purrello, S. Georgiou, and T.G. Spiro UVRR spectroscopy of the peptide-bond. 2. Carbonyl H-bond effects on the ground-state and excited-state structures of N-methylacetamide J. Am. Chem. Soc. 113 1991 6368 6377
55. C.J. Barrow, A. Yasuda, P.T.M. Kenny, and M.G. Zagorski Solution conformations and aggregational properties of synthetic amyloid β-peptides of Alzheimers-disease-analysis of circular-dichroism spectra J. Mol. Biol. 225 1992 1075 1093
56. L.A. Popova, R. Kodali, R. Wetzel, and I.K. Lednev Structural variations in the cross-beta core of amyloid beta fibrils revealed by deep UV resonance Raman spectroscopy J. Am. Chem. Soc. 132 2010 6324 6328
57. Z. Ye, K.C. French, L.A. Popova, I.K. Lednev, M.M. Lopez, and G.I. Makhatadze Mechanism of fibril formation by a 39-residue peptide (PAPf39) from human prostatic acidic phosphatase Biochemistry 48 2009 11582 11591
58. M. Xu, V.V. Ermolenkov, V.N. Uversky, and I.K. Lednev Hen egg white lysozyme fibrillation: a deep-UV resonance Raman spectroscopic study J. Biophotonics 1 2008 215 229
59. M. Xu, V.A. Shashilov, V.V. Ermolenkov, L. Fredriksen, D. Zagorevski, and I.K. Lednev The first step of hen egg white lysozyme fibrillation, irreversible partial unfolding, is a two-state transition Protein Sci. 16 2007 815 832 (Pubitemid 46683187)
60. M. Xu, V.V. Ermolenkov, W. He, V.N. Uversky, L. Fredriksen, and I.K. Lednev Lysozyme fibrillation: deep UV Raman spectroscopic characterization of protein structural transformation Biopolymers 79 2005 58 61 (Pubitemid 41445307)
61. Y. Wang, S. Petty, A. Trojanowski, K. Knee, D. Goulet, I. Mukerji, and J. King Formation of amyloid fibrils in vitro from partially unfolded intermediates of human gammaC-crystallin Invest. Ophth. Vis. Sci. 51 2010 672 678
62. S.H. Song, and S.A. Asher UV resonance Raman studies of peptide conformation in poly(L-lysine), poly(L-glutamic acid), and model complexes-the basis for protein secondary structure determinations J. Am. Chem. Soc. 111 1989 4295 4305 (Pubitemid 19156932)
63. Y. Wang, R. Purrello, T. Jordan, and T.G. Spiro UVRR spectroscopy of the peptide bond. 1. Amide S, a nonhelical structure marker, is a CαH bending mode J. Am. Chem. Soc. 113 1991 6359 6368
64. C.Y. Huang, G. Balakrishnan, and T.G. Spiro Protein secondary structure from deep-UV resonance Raman spectroscopy J. Raman Spectrosc. 37 2006 277 282
65. 1-helix, and β-sheet psi angle energy landscape in poly-L-lysine and poly-L-glutamic acid J. Am. Chem. Soc. 127 2005 7712 7720 (Pubitemid 40745960)
66. A.V. Mikhonin, S.V. Bykov, N.S. Myshakina, and S.A. Asher Peptide secondary structure folding reaction coordinate: correlation between UV Raman amide III frequency, Psi Ramachandran angle, and hydrogen bonding J. Phys. Chem. B 110 2006 1928 1943 (Pubitemid 43235795)
67. S.A. Asher, A. Ianoul, G. Mix, M.N. Boyden, A. Karnoup, M. Diem, and R. Schweitzer-Stenner Dihedral psi angle dependence of the amide III vibration: a uniquely sensitive UV resonance Raman secondary structural probe J. Am. Chem. Soc. 123 2001 11775 11781 (Pubitemid 33121797)
68. R.P. Rava, and T.G. Spiro Ultraviolet resonance Raman spectra of insulin and alpha-lactalbumin with 218- and 200-nm laser excitation Biochemistry 24 1985 1861 1865 (Pubitemid 15019778)
69. J.C. Austin, T. Jordan, and T.G. Spiro Ultraviolet resonance Raman studies of proteins and related model compounds R.J.H. Clark, R.E. Hester, Biomolecular Spectroscopy 1993 Wiley & Sons Ltd. New York 55 127
70. G. Socrates Infrared and Raman Characteristic Group Frequencies Third ed. 2001 John Wiley & Sons, Ltd. Chichester
71. G.J. Smith, and K.R. Markham Tautomerism of flavonol glucosides: relevance to plant UV protection and flower colour J. Photochem. Photobiol. A Chem. 118 1998 99 105 (Pubitemid 128346936)
72. T. Richard, D. Lefeuvre, A. Descendit, S. Quideau, and J.P. Monti Recognition characters in peptide-polyphenol complex formation Biochim. Biophys. Acta-Gen. Subj. 1760 2006 951 958 (Pubitemid 43833263)