Kinetic studies of inhibition of the amyloid beta (1–42) aggregation using a ferrocene-tagged β-sheet breaker peptide

Prusiner, 1997, Prion diseases and the BSE crisis, Science, 278, 245, 10.1126/science.278.5336.245 Cobb, 2009, Prion diseases and their biochemical mechanisms, Biochemistry, 48, 2574, 10.1021/bi900108v Brandner, 2003, CNS pathogenesis of prion diseases, Br. Med. Bull., 66, 131, 10.1093/bmb/66.1.131 Spillantini, 1998, α-Synuclein in filamentous inclusions of Lewy bodies from Parkinson’s disease and dementia with Lewy bodies, Proc. Natl. Acad. Sci. USA, 95, 6469, 10.1073/pnas.95.11.6469 Selkoe, 2002, Alzheimer’s disease is a synaptic failure, Science, 298, 789, 10.1126/science.1074069 Hardy, 2002, The amyloid hypothesis of Alzheimer’s disease: progress and problems on the road to therapeutics, Science, 297, 353, 10.1126/science.1072994 Jarrett, 1993, The carboxy terminus of the β-amyloid protein is critical for the seeding of amyloid formation: implications for the pathogenesis of Alzheimer’s disease, Biochemistry, 32, 4693, 10.1021/bi00069a001 Jiang, 2012, Aggregation pathways of the amyloid beta (1–42) peptide depend on its colloidal stability and ordered β-sheet stacking, Langmuir, 28, 12711, 10.1021/la3021436 Kotarek, 2008, Quartz crystal microbalance analysis of growth kinetics for aggregation intermediates of the amyloid-beta protein, Anal. Biochem., 378, 15, 10.1016/j.ab.2008.03.022 Kang, 1987, The precursor of Alzheimer’s disease amyloid A4 protein resembles a cell-surface receptor, Nature, 325, 733, 10.1038/325733a0 Cannon, 2004, Kinetic analysis of β-amyloid fibril elongation, Anal. Biochem., 328, 67, 10.1016/j.ab.2004.01.014 Liang, 2010, Direct observation of nucleation and growth in amyloid self-assembly, J. Am. Chem. Soc., 132, 6306, 10.1021/ja910964c Estrada, 2006, Inhibition of protein misfolding and aggregation by small rationally-designed peptides, Curr. Pharm. Des., 12, 2557, 10.2174/138161206777698792 Watanabe, 2002, Inhibitors of fibril formation and cytotoxicity of β-amyloid peptide composed of KLVFF recognition element and flexible hydrophilic disrupting element, Biochem. Biophys. Res. Commun., 290, 121, 10.1006/bbrc.2001.6191 Watanabe, 2001, Identification of the molecular interaction site of amyloid beta peptide by using a fluorescence assay, J. Pept. Res., 58, 342, 10.1034/j.1399-3011.2001.00920.x Doig, 2006, N-methylated peptide inhibitors of β-amyloid aggregation and toxicity: optimization of the inhibitor structure, Biochemistry, 45, 9906, 10.1021/bi060837s Bett, 2010, Structure–activity relationships in peptide modulators of β-amyloid protein aggregation: variation in α,α-disubstitution results in altered aggregate size and morphology, ACS Chem. Neurosci., 1, 608, 10.1021/cn100045q Adessi, 2002, β-Sheet breaker strategy for the treatment of Alzheimer’s disease, Drug Dev. Res., 56, 184, 10.1002/ddr.10074 El-Agnaf, 2004, A strategy for designing inhibitors of α-synuclein aggregation and toxicity as a novel treatment for Parkinson’s disease and related disorders, FASEB J., 18, 1315, 10.1096/fj.03-1346fje Bodles, 2004, Inhibition of fibril formation and toxicity of a fragment of α-synuclein by an N-methylated peptide analogue, Neurosci. Lett., 359, 89, 10.1016/j.neulet.2003.12.077 Jensen, 2012, Inhibition of Cu–amyloid-beta by using bifunctional peptides with β-sheet breaker and chelator moieties, Chem. Eur. J., 18, 4836, 10.1002/chem.201103546 Castelletto, 2011, Amyloid peptides incorporating a core sequence from the amyloid beta peptide and gamma amino acids: relating bioactivity to self-assembly, Chem. Commun., 47, 12470, 10.1039/c1cc15493a Tjernberg, 1996, Arrest of β-amyloid fibril formation by a pentapeptide ligand, J. Biol. Chem., 271, 8545, 10.1074/jbc.271.15.8545 Soto, 1996, Inhibition of Alzheimer’s amyloidosis by peptides that prevent β-sheet conformation, Biochem. Biophys. Res. Commun., 226, 672, 10.1006/bbrc.1996.1413 Pallitto, 1999, Recognition sequence design for peptidyl modulators of β-amyloid aggregation and toxicity, Biochemistry, 38, 3570, 10.1021/bi982119e Kim, 2004, Mechanism of accelerated assembly of β-amyloid filaments into fibrils by KLVFFK6, Biophys. J., 86, 3194, 10.1016/S0006-3495(04)74367-2 Klunk, 1999, Quantifying amyloid beta-peptide (Aβ) aggregation using the Congo red A beta (CR-Aβ) spectrophotometric assay, Anal. Biochem., 266, 66, 10.1006/abio.1998.2933 Matsumura, 2011, Two distinct amyloid beta-protein (Aβ) assembly pathways leading to oligomers and fibrils identified by combined fluorescence correlation spectroscopy, morphology, and toxicity analyses, J. Biol. Chem., 286, 11555, 10.1074/jbc.M110.181313 Vestergaard, 2005, A rapid label-free electrochemical detection and kinetic study of Alzheimer’s amyloid beta aggregation, J. Am. Chem. Soc., 127, 11892, 10.1021/ja052522q Kheterpal, 2001, Structural features of the Aβ amyloid fibril elucidated by limited proteolysis, Biochemistry, 40, 11757, 10.1021/bi010805z Geng, 2008, Rapid label-free detection of metal-induced Alzheimer’s amyloid beta peptide aggregation by electrochemical method, Electrochem. Commun., 10, 1797, 10.1016/j.elecom.2008.09.020 Martic, 2012, Electrochemical screening of the indole/quinolone derivatives as potential protein kinase CK2 inhibitors, Anal. Biochem., 421, 617, 10.1016/j.ab.2011.11.017 Takenaka, 2000, DNA sensing on a DNA probe-modified electrode using ferrocenylnaphthalene diimide as the electrochemically active ligand, Anal. Chem., 72, 1334, 10.1021/ac991031j Metzler-Nolte, 2004, Bioorganometallic chemistry of ferrocene, Chem. Rev., 104, 5931, 10.1021/cr0101510 Zhao, 2010, Electrochemical assay of active prostate-specific antigen (PSA) using ferrocene-functionalized peptide probes, Electrochem. Commun., 12, 471, 10.1016/j.elecom.2010.01.022 Long, 2003, A comparison of electron-transfer rates of ferrocenoyl-linked DNA, J. Am. Chem. Soc., 125, 8724, 10.1021/ja034684x Wei, 2011, Synthesis and evaluation of ferrocenoyl pentapeptide (Fc-KLVFF) as an inhibitor of Alzheimer’s Aβ(1–42) fibril formation in vitro, Bioorg. Med. Chem. Lett., 21, 5818, 10.1016/j.bmcl.2011.07.111 Krysmann, 2008, Self-assembly and hydrogelation of an amyloid peptide fragment, Biochemistry, 47, 4597, 10.1021/bi8000616 Hamley, 2012, The amyloid beta peptide: a chemist’s perspective—role in Alzheimer’s and fibrillization, Chem. Rev., 112, 5147, 10.1021/cr3000994 Tougu, 2008, Binding of zinc(II) and copper(II) to the full-length Alzheimer’s amyloid-beta peptide, J. Neurochem., 104, 1249, 10.1111/j.1471-4159.2007.05061.x Chromy, 2003, Self-assembly of Aβ(1–42) into globular neurotoxins, Biochemistry, 42, 12749, 10.1021/bi030029q Stine, 2003, In vitro characterization of conditions for amyloid-beta peptide oligomerization and fibrillogenesis, J. Biol. Chem., 278, 11612, 10.1074/jbc.M210207200 Jiang, 2007, Redox reactions of copper complexes formed with different β-amyloid peptides and their neuropathological relevance, Biochemistry, 46, 9270, 10.1021/bi700508n Wang, 2010, Redox reactions of the α-synuclein–Cu2+ complex and their effects on neuronal cell viability, Biochemistry, 49, 8134, 10.1021/bi1010909 Olivieri, 2001, N-Acetyl-l-cysteine protects SHSY5Y neuroblastoma cells from oxidative stress and cell cytotoxicity: effects on β-amyloid secretion and tau phosphorylation, J. Neurochem., 76, 224, 10.1046/j.1471-4159.2001.00090.x Lowe, 2001, Structure–function relationships for inhibitors of β-amyloid toxicity containing the recognition sequence KLVFF, Biochemistry, 40, 7882, 10.1021/bi002734u Jiang, 2009, Ternary complexes of iron, amyloid-beta, and nitrilotriacetic acid: binding affinities, redox properties, and relevance to iron-induced oxidative stress in Alzheimer’s disease, Biochemistry, 48, 7939, 10.1021/bi900907a Bard, 2001 Bard, 2009, Scanning electrochemical microscopy of HeLa cells: effects of ferrocene methanol and silver ion, J. Electroanal. Chem., 628, 35, 10.1016/j.jelechem.2009.01.002 Sabella, 2004, Capillary electrophoresis studies on the aggregation process of β-amyloid 1–42 and 1–40 peptides, Electrophoresis, 25, 3186, 10.1002/elps.200406062 Cernescu, 2012, Laser-induced liquid bead ion desorption mass spectrometry: an approach to precisely monitor the oligomerization of the β-amyloid peptide, Anal. Chem., 84, 5276, 10.1021/ac300258m Teplow, 2003, Amyloid beta-protein (Aβ) assembly: Aβ40 and Aβ42 oligomerize through distinct pathways, Proc. Natl. Acad. Sci. USA, 100, 330, 10.1073/pnas.222681699 Lambert, 1998, Diffusible, nonfibrillar ligands derived from Aβ(1–42) are potent central nervous system neurotoxins, Proc. Natl. Acad. Sci. USA, 95, 6448, 10.1073/pnas.95.11.6448 Dukes, 2008, Monitoring the earliest amyloid-β oligomers via quantized photobleaching of dye-labeled peptides, Anal. Biochem., 382, 29, 10.1016/j.ab.2008.07.011