Efficient access to highly pure β-amyloid peptide by optimized solid-phase synthesis

References

• Alzheimer A. A contribution concerning the pathological anatomy of mental disturbances in old age, 1899. Alzheimer Dis Assoc Disord 1991;5:69–70.
   PubMedGoogle Scholar
• Hardy JA, Higgins GA. Alzheimer’s disease: the amyloid cascade hypothesis. Science 1992;256:184–185.
   PubMed Web of Science ®Google Scholar
• Bitan G, Kirkitadze MD, Lomakin A, Vollers SS, Benedek GB, Teplow DB. Amyloid β -protein (Aβ) assembly: Aβ 40 and A β 42 oligomerize through distinct pathways. Proc Natl Acad Sci USA 2003;100:330–335.
   PubMed Web of Science ®Google Scholar
• Kim Y, Lee JH, Ryu J, Kim DJ. Multivalent & multifunctional ligands to β-amyloid. Curr Pharm Des 2009;15:637–658.
   PubMedGoogle Scholar
• Mehta PD, Pirttila T, Patrick BA, Barshatzky M, Mehta SP. Amyloid β protein 1-40 and 1-42 levels in matched cerebrospinal fluid and plasma from patients with Alzheimer disease. Neurosci Lett 2001;304:102–106.
   PubMed Web of Science ®Google Scholar
• Apelt J, Ach K, Schliebs R. Aging-related down-regulation of neprilysin, a putative β-amyloid-degrading enzyme, in transgenic Tg2576 Alzheimer-like mouse brain is accompanied by an astroglial upregulation in the vicinity of β-amyloid plaques. Neurosci Lett 2003;339:183–186.
   PubMed Web of Science ®Google Scholar
• Barrow CJ, Zagorski MG. Solution structures of β peptide and its constituent fragments: relation to amyloid deposition. Science 1991;253:179–182.
   PubMed Web of Science ®Google Scholar
• Soto C, Martin Z. Therapeutic strategies against protein misfolding in neurodegenerative diseases. Expert Opin Drug Discov 2009;4:71–84.
   PubMed Web of Science ®Google Scholar
• Lazo ND, Grant MA, Condron MC, Rigby AC, Teplow DB. On the nucleation of amyloid β-protein monomer folding. Protein Sci 2005;14:1581–1596.
   PubMed Web of Science ®Google Scholar
• Xu Y, Shen J, Luo X, Zhu W, Chen K, Ma J, Jiang H. Conformational transition of amyloid β-peptide. Proc Natl Acad Sci USA 2005;102:5403–5407.
   PubMed Web of Science ®Google Scholar
• Anderson JP, Esch FS, Keim PS, Sambamurti K, Lieberburg I, Robakis NK. Exact cleavage site of Alzheimer amyloid precursor in neuronal PC-12 cells. Neurosci Lett 1991;128:126–128.
   PubMed Web of Science ®Google Scholar
• Rojo LE, Gaspar PA, Maccioni RB. Molecular targets in the rational design of AD specific PET tracers: tau or amyloid aggregates? Curr Alzheimer Res 2011;8:652–658.
   PubMedGoogle Scholar
• Tarozzi A, Morroni F, Merlicco A, Bolondi C, Teti G, Falconi M, Cantelli-Forti G, Hrelia P. Neuroprotective effects of cyanidin 3-O-glucopyranoside on amyloid β(25-35) oligomer-induced toxicity. Neurosci Lett 2010;473:72–76.
   PubMed Web of Science ®Google Scholar
• Yun SH, Gamkrelidze G, Stine WB, Sullivan PM, Pasternak JF, Ladu MJ, Trommer BL. Amyloid-β1-42 reduces neuronal excitability in mouse dentate gyrus. Neurosci Lett 2006;403:162–165.
   PubMedGoogle Scholar
• Manczak M, Mao P, Calkins MJ, Cornea A, Reddy AP, Murphy MP, Szeto HH, et al. Mitochondria-targeted antioxidants protect against amyloid-β toxicity in Alzheimer’s disease neurons. J Alzheimers Dis 2010;20 Suppl 2:S609–S631.
   Google Scholar
• Kim YS, Moss JA, Janda KD. Biological tuning of synthetic tactics in solid-phase synthesis: application to A β(1-42). J Org Chem 2004;69:7776–7778.
   PubMedGoogle Scholar
• Fukuda H, Shimizu T, Nakajima M, Mori H, Shirasawa T. Synthesis, aggregation, and neurotoxicity of the Alzheimer’s Aβ1-42 amyloid peptide and its isoaspartyl isomers. Bioorg Med Chem Lett 1999;9:953–956.
   PubMedGoogle Scholar
• Bacsa B, Bosze S, Kappe CO. Direct solid-phase synthesis of the β-amyloid (1-42) peptide using controlled microwave heating. J Org Chem 2010;75:2103–2106.
   PubMed Web of Science ®Google Scholar
• Kok WM, Scanlon DB, Karas JA, Miles LA, Tew DJ, Parker MW, Barnham KJ, Hutton CA. Solid-phase synthesis of homodimeric peptides: preparation of covalently-linked dimers of amyloid β peptide. Chem Commun (Camb) 2009:6228–6230.
   Google Scholar
• Sohma Y, Hayashi Y, Kimura M, Chiyomori Y, Taniguchi A, Sasaki M, Kimura T, Kiso Y. The ‘O-acyl isopeptide method’ for the synthesis of difficult sequence-containing peptides: application to the synthesis of Alzheimer’s disease-related amyloid β peptide (Aβ) 1-42. J Pept Sci 2005;11:441–451.
   PubMedGoogle Scholar
• Fukuda H, Shimizu T, Nakajima M, Mori H, Shirasawa T. Synthesis, aggregation, and neurotoxicity of the Alzheimer’s A β 1-42 amyloid peptide and its isoaspartyl isomers. Bioorg Med Chem Lett 1999;9:953–956.
   PubMedGoogle Scholar
• Tam JP, Heath WF, Merrifield RB. Sn2 Deprotection of Synthetic Peptides with a Low Concentration of Hf in Dimethyl Sulfide - Evidence and Application in Peptide-Synthesis. J Am Chem Soc 1983;105:6442–6455.
   Web of Science ®Google Scholar
• Kim HY, Kim Y, Han G, Kim DJ. Regulation of in vitro Aß1-40 aggregation mediated by small molecules. J Alzheimers Dis 2010;22:73–85.
   PubMedGoogle Scholar
• Fancy DA, Kodadek T. Chemistry for the analysis of protein-protein interactions: rapid and efficient cross-linking triggered by long wavelength light. Proc Natl Acad Sci USA 1999;96:6020–6024.
   PubMed Web of Science ®Google Scholar
• Bitan G, Lomakin A, Teplow DB. Amyloid β-protein oligomerization: prenucleation interactions revealed by photo-induced cross-linking of unmodified proteins. J Biol Chem 2001;276:35176–35184.
   PubMed Web of Science ®Google Scholar
• Bitan G, Teplow DB. Rapid photochemical cross-linking–a new tool for studies of metastable, amyloidogenic protein assemblies. Acc Chem Res 2004;37:357–364.
   PubMedGoogle Scholar
• Rahimi F, Maiti P, Bitan G. Photo-induced cross-linking of unmodified proteins (PICUP) applied to amyloidogenic peptides. J Vis Exp 2009;23:e1071.
   Google Scholar
• Schnölzer M, Alewood P, Jones A, Alewood D, Kent SB. In situ neutralization in Boc-chemistry solid phase peptide synthesis. Rapid, high yield assembly of difficult sequences. Int J Pept Protein Res 1992;40:180–193.
   PubMedGoogle Scholar
• Schöneich C, Pogocki D, Hug GL, Bobrowski K. Free radical reactions of methionine in peptides: mechanisms relevant to β-amyloid oxidation and Alzheimer’s disease. J Am Chem Soc 2003;125:13700–13713.
   PubMed Web of Science ®Google Scholar
• Tam JP. Synthesis of biologically active transforming growth factor α. Int J Pept Protein Res 1987;29:421–431.
   PubMedGoogle Scholar
• Tam JP, Heath WF, Merrifield RB. SN 1 and SN 2 mechanisms for the deprotection of synthetic peptides by hydrogen fluoride. Studies to minimize the tyrosine alkylation side reaction. Int J Pept Protein Res 1983;21:57–65.
   PubMedGoogle Scholar
• Hyde C, Johnson T, Sheppard RC. Internal Aggregation during Solid-Phase Peptide-Synthesis - Dimethyl-Sulfoxide as a Powerful Dissociating Solvent. J Am Chem Soc 1992;1573–1575.
   Google Scholar
• Miranda LP, Alewood PF. Accelerated chemical synthesis of peptides and small proteins. Proc Natl Acad Sci USA 1999;96:1181–1186.
   PubMedGoogle Scholar