Folded small molecule manipulation of islet amyloid polypeptide

Chemistry and Biology

Volumn 21, Issue 6, 2014, Pages 775-781

  Kumar, Sunil ^a   Brown, Mark A ^a   Nath, Abhinav ^a   Miranker, Andrew D ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA SYNUCLEIN; AMYLIN; AMYLOID; CARBOXYLIC ACID; QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CELL MEMBRANE; CONTROLLED STUDY; DIABETES MELLITUS; HUMAN; LIPID BILAYER; MOLECULAR RECOGNITION; PANCREAS ISLET BETA CELL; PHASE 2 CLINICAL TRIAL (TOPIC); PHOSPHOLIPID BILAYER; PRIORITY JOURNAL; PROTEIN ASSEMBLY; PROTEIN CONFORMATION; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; KINETICS; METABOLISM; PARTICLE SIZE; SURFACE PROPERTY;

ISLET AMYLOID POLYPEPTIDE; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PARTICLE SIZE; QUINOLINES; SURFACE PROPERTIES;

EID: 84903183482     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2014.05.007     Document Type: Article

References (31)

1. M. Apostolidou, S.A. Jayasinghe, and R. Langen Structure of α-helical membrane-bound human islet amyloid polypeptide and its implications for membrane-mediated misfolding J. Biol. Chem. 283 2008 17205 17210
2. J. Bieschke, J. Russ, R.P. Friedrich, D.E. Ehrnhoefer, H. Wobst, K. Neugebauer, and E.E. Wanker EGCG remodels mature alpha-synuclein and amyloid-β fibrils and reduces cellular toxicity Proc. Natl. Acad. Sci. U S A 107 2010 7710 7715
3. J.N. Buxbaum, and R.P. Linke A molecular history of the amyloidoses J. Mol. Biol. 421 2012 142 159
4. P. Cao, A. Abedini, H. Wang, L.H. Tu, X. Zhang, A.M. Schmidt, and D.P. Raleigh Islet amyloid polypeptide toxicity and membrane interactions Proc. Natl. Acad. Sci. U S A 110 2013 19279 19284
5. P.S. Chen, T.Y. Toribara, and H. Warner Microdetermination of phosphorus Anal. Chem. 28 1956 1756 1758
6. C.G. Cummings, and A.D. Hamilton Disrupting protein-protein interactions with non-peptidic, small molecule α-helix mimetics Curr. Opin. Chem. Biol. 14 2010 341 346
7. S.H. Gellman Foldamers: a manifesto Acc. Chem. Res. 31 1998 173 180 (Pubitemid 128474551)
8. E.R. Gillies, C. Dolain, J.-M. Léger, and I. Huc Amphipathic helices from aromatic amino acid oligomers J. Org. Chem. 71 2006 7931 7939 (Pubitemid 44571796)
9. S. Grzesiek, S.J. Stahl, P.T. Wingfield, and A. Bax The CD4 determinant for downregulation by HIV-1 Nef directly binds to Nef. Mapping of the Nef binding surface by NMR Biochemistry 35 1996 10256 10261 (Pubitemid 26277283)
10. G. Guichard, and I. Huc Synthetic foldamers Chem. Commun. (Camb.) 47 2011 5933 5941
11. T. Gurlo, S. Ryazantsev, C.J. Huang, M.W. Yeh, H.A. Reber, O.J. Hines, T.D. O'Brien, C.G. Glabe, and P.C. Butler Evidence for proteotoxicity in β cells in type 2 diabetes: toxic islet amyloid polypeptide oligomers form intracellularly in the secretory pathway Am. J. Pathol. 176 2010 861 869
12. L. Haataja, T. Gurlo, C.J. Huang, and P.C. Butler Islet amyloid in type 2 diabetes, and the toxic oligomer hypothesis Endocr. Rev. 29 2008 303 316 (Pubitemid 351679701)
13. J.A. Hebda, and A.D. Miranker The interplay of catalysis and toxicity by amyloid intermediates on lipid bilayers: insights from type II diabetes Annu. Rev. Biophys. 38 2009 125 152
14. J.A. Hebda, I. Saraogi, M. Magzoub, A.D. Hamilton, and A.D. Miranker A peptidomimetic approach to targeting pre-amyloidogenic states in type II diabetes Chem. Biol. 16 2009 943 950
15. H. Jiang, J.-M. Léger, and I. Huc Aromatic δ-peptides J. Am. Chem. Soc. 125 2003 3448 3449
16. S. Kumar, and A.D. Miranker A foldamer approach to targeting membrane bound helical states of islet amyloid polypeptide Chem. Commun. (Camb.) 49 2013 4749 4751
17. M. Levy, Y. Porat, E. Bacharach, D.E. Shalev, and E. Gazit Phenolsulfonphthalein, but not phenolphthalein, inhibits amyloid fibril formation: implications for the modulation of amyloid self-assembly Biochemistry 47 2008 5896 5904 (Pubitemid 351770020)
18. M. Magzoub, and A.D. Miranker Concentration-dependent transitions govern the subcellular localization of islet amyloid polypeptide FASEB J. 26 2012 1228 1238
19. F. Meng, A. Abedini, A. Plesner, C.T. Middleton, K.J. Potter, M.T. Zanni, C.B. Verchere, and D.P. Raleigh The sulfated triphenyl methane derivative acid fuchsin is a potent inhibitor of amyloid formation by human islet amyloid polypeptide and protects against the toxic effects of amyloid formation J. Mol. Biol. 400 2010 555 566
20. F. Meng, A. Abedini, A. Plesner, C.B. Verchere, and D.P. Raleigh The flavanol (-)-epigallocatechin 3-gallate inhibits amyloid formation by islet amyloid polypeptide, disaggregates amyloid fibrils, and protects cultured cells against IAPP-induced toxicity Biochemistry 49 2010 8127 8133
21. R. Mishra, D. Sellin, D. Radovan, A. Gohlke, and R. Winter Inhibiting islet amyloid polypeptide fibril formation by the red wine compound resveratrol ChemBioChem 10 2009 445 449
22. A. Nath, A.J. Trexler, P. Koo, A.D. Miranker, W.M. Atkins, and E. Rhoades Single-molecule fluorescence spectroscopy using phospholipid bilayer nanodiscs Methods Enzymol. 472 2010 89 117
23. T. Qi, V. Maurizot, H. Noguchi, T. Charoenraks, B. Kauffmann, M. Takafuji, H. Ihara, and I. Huc Solvent dependence of helix stability in aromatic oligoamide foldamers Chem. Commun. (Camb.) 48 2012 6337 6339
24. A.M. Ruschak, and A.D. Miranker Fiber-dependent amyloid formation as catalysis of an existing reaction pathway Proc. Natl. Acad. Sci. U S A 104 2007 12341 12346 (Pubitemid 47206139)
25. A.M. Ruschak, and A.D. Miranker The role of prefibrillar structures in the assembly of a peptide amyloid J. Mol. Biol. 393 2009 214 226
26. D.M. Walsh, I. Klyubin, J.V. Fadeeva, W.K. Cullen, R. Anwyl, M.S. Wolfe, M.J. Rowan, and D.J. Selkoe Naturally secreted oligomers of amyloid beta protein potently inhibit hippocampal long-term potentiation in vivo Nature 416 2002 535 539 (Pubitemid 34288854)
27. J.A. Williamson, and A.D. Miranker Direct detection of transient α-helical states in islet amyloid polypeptide Protein Sci. 16 2007 110 117 (Pubitemid 46036503)
28. J.A. Williamson, J.P. Loria, and A.D. Miranker Helix stabilization precedes aqueous and bilayer-catalyzed fiber formation in islet amyloid polypeptide J. Mol. Biol. 393 2009 383 396
29. B. Winner, R. Jappelli, S.K. Maji, P.A. Desplats, L. Boyer, S. Aigner, C. Hetzer, T. Loher, M. Vilar, and S. Campioni et al. In vivo demonstration that alpha-synuclein oligomers are toxic Proc. Natl. Acad. Sci. U S A 108 2011 4194 4199
30. L.S. Wolfe, M.F. Calabrese, A. Nath, D.V. Blaho, A.D. Miranker, and Y. Xiong Protein-induced photophysical changes to the amyloid indicator dye thioflavin T Proc. Natl. Acad. Sci. U S A 107 2010 16863 16868
31. L.M. Yan, M. Tatarek-Nossol, A. Velkova, A. Kazantzis, and A. Kapurniotu Design of a mimic of nonamyloidogenic and bioactive human islet amyloid polypeptide (IAPP) as nanomolar affinity inhibitor of IAPP cytotoxic fibrillogenesis Proc. Natl. Acad. Sci. U S A 103 2006 2046 2051 (Pubitemid 43271620)