Rationally Designed Peptidomimetic Modulators of Aβ Toxicity in Alzheimer's Disease

Scientific Reports

Volumn 5, Issue , 2015, Pages

  Rajasekhar, K ^a   Suresh, S N ^a   Manjithaya, Ravi ^a   Govindaraju, T ^a  

^a JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMYLOID BETA PROTEIN; AMYLOID BETA-PROTEIN (1-42); GREEN FLUORESCENT PROTEIN; PEPTIDE FRAGMENT; PEPTIDOMIMETIC AGENT; PROTEIN AGGREGATE; THIAZOLE DERIVATIVE; THIOFLAVINE;

ALZHEIMER DISEASE; ANTAGONISTS AND INHIBITORS; AUTOPHAGY; BIOASSAY; BIOLOGICAL MODEL; BLOOD; CHEMISTRY; CIRCULAR DICHROISM; DRUG DESIGN; DRUG EFFECTS; FLUORESCENCE MICROSCOPY; HUMAN; KINETICS; METABOLISM; PATHOLOGY; PROTEIN DEGRADATION; SACCHAROMYCES CEREVISIAE; ULTRASTRUCTURE;

ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; AUTOPHAGY; BIOLOGICAL ASSAY; CIRCULAR DICHROISM; DRUG DESIGN; GREEN FLUORESCENT PROTEINS; HUMANS; KINETICS; MICROSCOPY, FLUORESCENCE; MODELS, BIOLOGICAL; PEPTIDE FRAGMENTS; PEPTIDOMIMETICS; PROTEIN AGGREGATES; PROTEOLYSIS; SACCHAROMYCES CEREVISIAE; THIAZOLES;

EID: 84939847883     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep08139     Document Type: Article

References (48)

1. Prince, M. et al. The global prevalence of dementia: A systematic review and metaanalysis. Alzheimer's & Dementia 9, 63-75 (2013).
2. Selkoe, D. J. Folding proteins in fatal ways. Nature 426, 900-904 (2003).
3. Ross, C. A. & Poirier, M. A. Protein aggregation and neurodegenerative disease. Nat. Med. 10, S10-S17 (2004).
4. Hamley, I. W. The amyloid beta peptide: a chemist's perspective. Role in Alzheimer's and fibrillization. Chem. Rev. 112, 5147-5192 (2012).
5. DeToma, A. S., Salamekh, S., Ramamoorthy, A. & Lim,M. H.Misfolded proteins in Alzheimer's disease and type II diabetes. Chem. Soc. Rev. 41, 608-621 (2012).
6. Savelieff, M. G., Lee, S., Liu, Y. & Lim, M. H. Untangling Amyloid-b, Tau, and Metals in Alzheimer's Disease. ACS Chem. Biol. 8, 856-865 (2013).
7. Rauk, A. The chemistry of Alzheimer's disease. Chem. Soc. Rev. 38, 2698-2715 (2009).
8. Nie, Q., Du, X. G. & Geng, M. Y. Small molecule inhibitors of amyloid b peptide aggregation as a potential therapeutic strategy for Alzheimer's disease. ActaPharmacol. Sin. 32, 545-551 (2011).
9. Takahashi, T. & Mihara, H. Peptide and protein mimetics inhibiting amyloid b peptide aggregation. Acc. Chem. Res. 41, 1309-1318 (2008).
10. Acerra, N. et al. Retro-inversal of intracellular selected b-amyloid-interacting peptides: implications for a novel Alzheimer's disease treatment. Biochemistry 53, 2101-2111 (2014).
11. Castelletto, V., Hamley, I. W., Lim, T., De Tullio, M. B. & Castano, E. M. Abamino acid modified heptapeptide containing a designed recognition element disrupts fibrillization of the amyloid b-peptide. J. Pept. Sci. 16, 443-450 (2010).
12. Ouberai, M.,Dumy, P., Chierici, S. &Garcia, J. Synthesis and biological evaluation of clicked curcumin and clicked KLVFFA conjugates as inhibitors of b amyloid fibril formation. Bioconjugate Chem. 20, 2123-2132 (2009).
13. Soto, C., Kindy, M. S., Baumann, M. & Frangione, B. Inhibition of Alzheimer's amyloidosis by peptides that prevent b-sheet conformation. Biochem. Biophys. Res. Commun. 226, 672-680 (1996).
14. Ghanta, J., Shen, C. L., Kiessling, L. L. & Murphy, R. M. A strategy for designing inhibitors of b2amyloid toxicity. J. Biol. Chem. 271, 29525-29528 (1996).
15. Mishra, R. et al. Small-molecule inhibitors of islet amyloid polypeptide fibril formation. Angew. Chem. Int. Ed. 47, 4679-4682 (2008).
16. Serpell, C. L. Alzheimer's amyloid fibrils: Structure and assembly. Biochim. Biophys. Acta. 1502, 16-30 (2000).
17. Tjernberg, L. O. et al. Arrest of amyloid fibril formation by a pentapeptide ligand. J. Biol. Chem. 271, 8545-8548 (1996).
18. Soto, C. et al. b-Sheet breaker peptide inhibits fibrogenesis in a rat brain model of amyloidosis: Implications in Alzheimer's therapy. Nat. Med. 4, 822-826 (1998).
19. Pallitto, M. M., Ghanta, J., Heinzelman, P., Kiessling, L. L. & Murphy, R. M. Recognition sequence design for peptidyl modulators of b-amyloid aggregation and toxicity. Biochemistry 38, 3570-3578 (1999).
20. Lowe, T. L., Strzelec, A., Kiessling, L. L. & Murphy, R. M. Structure-function relationships for inhibitors of b-amyloid toxicity containing the recognition sequence KLVFF. Biochemistry 40, 7882-7889 (2001).
21. Gibson, T. J. & Murphy, R. M. Design of peptidyl compounds that affect bamyloid aggregation: importance of surface tension and context. Biochemistry 44, 8898-8907 (2005).
22. Chafekar, S. M. et al. Branched KLVFF tetramers strongly potentiate inhibition of b-amyloid aggregation. ChemBioChem 8, 1857-1864 (2007).
23. Findeis, M. A. et al. Modified-peptide inhibitors of amyloid b-peptide polymerization. Biochemistry 38, 6791-6800 (1999).
24. Wei, C. W. et al. Synthesis and evaluation of ferrocenoylpentapeptide (Fc-KLVFF). Bioorg. Med. Chem. Lett. 21, 5818-5821 (2011).
25. Gordon, D. J., Tappe, R. & Meredith, S. C. Design and characterization of a membrane permeable N-methyl amino acid-containing peptide that inhibits Ab1-40 fibrillogenesis. J. Peptide Res. 60, 37-55 (2002).
26. Kapurniotu, A., Schmauder, A. & Tenidis, K. Structure-based design and study of non-amyloidogenic, double N-methylated IAPP amyloid core sequences as inhibitors of IAPP amyloid formation and cytotoxicity. J. Mol. Biol. 315, 339-350 (2002).
27. Amijee, H. et al. The N-methylated peptide SEN304 powerfully inhibits Ab(1242) toxicity by perturbing oligomer formation. Biochemistry 51, 8338-8352 (2010).
28. Kokkoni, N., Stott, K., Amijee, H., Mason, J. M. & Doig, A. J. N-Methylated peptide inhibitors of b-amyloid aggregation and toxicity. Optimization of the inhibitor structure. Biochemistry 45, 9906-9918 (2006).
29. Gordon, D. J., Sciarretta, K. L. & Meredith, S. C. Inhibition of b-amyloid(40) fibrillogenesis and disassembly of b-amyloid (40) fibrils by short b-amyloid congeners containing N-methyl amino acids at alternate residues. Biochemistry 40, 8237-8245 (2001).
30. Turner, J. P. et al. Rationally designed peptoids modulate aggregation of amyloidbeta 40. ACS Chem. Neurosci. 5, 552-558 (2014).
31. Manjithaya, R. & Subramani, S. Autophagy: A broad role in unconventional protein secretion? Trends Cell Biol. 21, 67-73 (2011).
32. Rajasekhar, K. et al. Synthesis of hybrid cyclic peptoids and identification of autophagy enhancer. ChemPlusChem. 79, 25-30 (2014).
33. Matlack, K. E. S. et al. Clioquinol promotes the degradation of metal-dependent amyloid-b (Ab) oligomers to restore endocytosis and ameliorate Ab toxicity. Proc. Natl. Acad. Sci. USA 111, 4013-4018 (2014).
34. Smith,M. G.&Snyder, M. Yeast as aModel for HumanDisease. Current Protocols in Human Genetics. (John Wiley & Sons, Inc. 2006).
35. Khurana, V. & Lindquist, S. Modelling neurodegeneration in Saccharomyces cerevisiae: why cook with baker's yeast? Nat. Rev. Neurosci. 11, 436-449 (2010).
36. Treusch, S. et al. Functional links between Abtoxicity, endocytic trafficking, and Alzheimer's disease risk factors in Yeast. Science 334, 1241-1245 (2011).
37. Gilead, S. & Gazit, E. Inhibition of amyloid fibril formation by peptide analogues modified with alpha-aminoisobutyric acid. Angew. Chem. Int. Ed. 43, 4041-4044 (2004).
38. Hochdrffer, K. et al. Rational design of b-sheet ligands against Ab42-induced toxicity. J. Am. Chem. Soc. 133, 4348-4358 (2011).
39. De Bona, P. et al. Design and synthesis of new trehalose-conjugated pentapeptides as inhibitors of Ab(1-42) fibrillogenesis and toxicity. J. Pept. Sci. 15, 220-228 (2009).
40. Etienne, M. A., Aucoin, J. P., Fu, Y., McCarley, R. L. & Hammer, R. P. Stoichiometric Inhibition of Amyloid b-Protein Aggregation with Peptides Containing Alternating a,a-Disubstituted Amino Acids. J. Am. Chem. Soc. 128, 3522-3523 (2006).
41. Hong, H. S. et al. Inbibition of Alzheimer's amyloid toxicity with a tricyclic pyrone molecule in vitro and in vivo. J. Neurochem. 108, 1097-1108 (2009).
42. Hung, S. Y., Huang, W. P., Liou, H. C. & Fu, W. M. Autophagy protects neuron from Ab-induced cytotoxicity. Autophagy 5, 502-510 (2009).
43. Overbye, A., Brinchmann,M. F. & Seglen, P.O. Proteomic analysis of membraneassociated proteins from rat liver autophagosomes. Autophagy 3, 300-322 (2007).
44. Jan, A., Hartley, D. M. & Lashuel, H. A. Preparation and characterization of toxic Abaggregates for structural and functional studies in Alzheimer's disease research. Nat. Protoc. 5, 1186-1209 (2010).
45. Halai, R. et al. Effects of cyclization on stability, structure, and activity of aconotoxinrgia at the a9a10 nicotinic acetylcholine receptor and GABAB receptor. J. Med. Chem. 54, 6984-6992 (2011).
46. Lovelace, E. S. et al. Cyclic MrIA: Astable and potent cyclic conotoxin with a novel topological fold that targets the norepinephrine transporter. J. Med. Chem. 49, 6561-6568 (2006).
47. Dominik, M., Rolf, M. & Martin, F. Yeast vectors for controlled expression of heterologous proteins in different genetic backgrounds. Gene 156, 119-122 (1995).
48. Caine, J. et al. Alzheimer's Ab fused to green fuorescent protein induces growth stress and a heat shock response. FEMS Yeast Res. 7, 1230-1236 (2007).