Synthesis and activity of fibrillogenesis peptide inhibitors related to the 17-21 β-amyloid sequence

European Journal of Medicinal Chemistry

Volumn 44, Issue 1, 2009, Pages 179-189

  Giordano, Cesare ^a   Masi, Annalisa ^a   Pizzini, Aldo ^a   Sansone, Anna ^a   Consalvi, Valerio ^a   Chiaraluce, Roberta ^a   Lucente, Gino ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Amyloid; Aggregation inhibitor; Alzheimer's disease; Fibrillogenesis; Fluorescence assay; Scanning electron microscopy

Indexed keywords

ACETYLLEUCYLPROLYLPHENYLALANYLPHENYLALANYLASPARTAMIDE; ACETYLLEUCYLPROLYLPHENYLALANYLPHENYLALANYLASPARTAMIDE DERIVATIVE; AMYLOID BETA PROTEIN; PENTAPEPTIDE; PEPTIDE DERIVATIVE; PROTEIN INHIBITOR; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; DRUG ACTIVITY; DRUG CONFORMATION; DRUG DESIGN; DRUG POTENCY; DRUG STABILITY; DRUG SYNTHESIS; SPECTROSCOPY;

AMINO ACID SEQUENCE; AMYLOID; AMYLOID BETA-PROTEIN; DRUG DESIGN; DRUG STABILITY; HUMANS; MOLECULAR CONFORMATION; PEPTIDE FRAGMENTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 57949105540     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.03.036     Document Type: Article

References (45)

1. Serpell L.C. Biochim. Biophys. Acta 1502 (2000) 16-30
2. Adessi C., and Soto C. Drug Dev. Res. 56 (2002) 184-193
3. Soto C., Castano M.E., Frangione B., and Inestrosa N.C. J. Biol. Chem. 270 (1995) 3063-3067
4. Ghanta J., Shen C.L., Kiessling L.L., and Murphy R.M. J. Biol. Chem. 271 (1996) 29525-29528
5. Soto C., Kindi M.S., Baumann M., and Frangione B. Biochem. Biophys. Res. Commun. 226 (1996) 672-680
6. Gordon D., and Meredith S.C. Biochemistry 42 (2003) 475-485
7. Chalifour R.J., McLaughlin R.W., Lavoie L., Morissette C., Tremblay N., Boulé M., Sarazin P., Stéa D., Lacombe D., Tremblay P., and Gervais F. J. Biol. Chem. 278 (2003) 34874-34881
8. Yang F., Lim G.P., Begum A.N., Ubeda O.J., Simmons M.R., Ambegaokar S.S., Chen P.P., Kayed R., Glabe C.G., Frautschy S.A., and Cole G.M. J. Biol. Chem. 280 (2005) 5892-5901
9. Cohen T., Frydman-Marom A., Rechter M., and Gazit E. Biochemistry 45 (2006) 4727-4735
10. Kokkoni N., Stott K., Amijee H., Mason J.M., and Doig A.J. Biochemistry 45 (2006) 9906-9918
11. Sato T., Kienlen-Campard P., Ahmed M., Liu W., Li H., Elliott J.I., Aimoto S., Constantinescu S.N., Octave J.-N., and Smith S.O. Biochemistry 45 (2006) 5503-5516
12. Torok M., Abid M., Mhadgut S.C., and Torok B. Biochemistry 45 (2006) 5377-5383
13. Soto C. Mol. Med. Today 5 (1999) 343-350
14. Hilbich C., Kister-Woike B., Reed J., Masters C.L., and Beyreuther K. J. Mol. Biol. 228 (1992) 460-473
15. Adessi C., Frossard M.J., Boissard C., Fraga S., Bieler S., Ruckle T., Vilbois F., Robinson S.M., Mutters M., Banks W.A., and Soto C. J. Biol. Chem. 278 (2003) 13905-13911
16. Permanne B., Adessi C., Saborio G.P., Fraga S., Frossard M.J., Van Dorpe J., Dewachter I., Banks W.A., Van Leuven F., and Soto C. FASEB J. 16 (2002) 860-862
17. Soto C., Sigurdsson E.M., Morelli L., Kumar R.A., Castano E.M., and Frangione B. Nat. Med. 4 (1998) 822-826
18. Wood S.J., Wetzel R., Martin J.D., and Hurle M.R. Biochemistry 34 (1995) 724-730
19. Couty F., Evano G., Vargas-Sanchez M., and Bouzas G. J. Org. Chem. 70 (2005) 9028-9031
20. Abele S., Vogali K., and Seebach D. Helv. Chim. Acta 82 (1999) 1539-1558
21. Liskamp R.M.J., and Kruijtzer J.A.W. Mol. Divers. 8 (2004) 79-87
22. Giordano C., Lucente G., Mollica A., Nalli M., Pagani Zecchini G., Paglialunga Paradisi M., Gavuzzo E., Mazza F., and Spisani S. J. Pept. Sci. 10 (2004) 510-523
23. Nelsen S.F., and Weisman G.R. Tetrahedron Lett. 26 (1973) 2321-2324
24. Couty F., Evano G., and Ribasso N. Tetrahedron: Asymmetry 14 (2003) 2407-2412
25. Braghiroli D., Avallone R., and Di Bella M. Tetrahedron: Asymmetry 8 (1997) 2209-2213
26. Brouwer A.J., Monnee C.F., and Liskamp R.M.J. Synthesis (2000) 1579-1584
27. Atherton E., and Sheppard R.C. Solid Phase Synthesis - A Practical Approach (1989), IRL Press, Oxford
28. LeVine H. Protein Sci. 2 (1993) 404-410
29. Fezoui Y., Hartley D.M., Harper J.D., Khurana R., Walsh D.M., Condron M.M., Selkoe D.J., Lansbury Jr. P.T., Fink A.L., and Teplow D.B. Amyloid 7 (2000) 166-178
30. Goldsbury C., Frey P., Olivieri V., Aebi U., and Müller S.A. J. Mol. Biol. 352 (2005) 282-298
31. Moore R.A., Hayes S.F., Fischer E.R., and Priola S.A. Biochemistry 46 (2007) 7079-7087
32. Ma K., Kann L., and Wang K. Biochemistry 40 (2001) 3427-3438
33. Perczel A., and Hollosi M. In: Fasman G.D. (Ed). Circular Dichroism and the Conformational Analysis of Biomolecules (1996), Plenum Press, New York 285-380
34. Woody R.W., and Dunker A.K. In: Fasman G.D. (Ed). Circular Dichroism and the Conformational Analysis of Biomolecules (1996), Plenum Press, New York 109-157
35. Bochicchio B., Pepe A., and Tamburro A.M. Chirality 17 (2005) 364-372
36. Vuilleumier S., Sancho J., Loewenthal R., and Fersht A.R. Biochemistry 32 (1993) 10303-10313
37. Jackson M., and Mantsch H.H. Crit. Rev. Biochem. Mol. Biol. 30 (1995) 95-120
38. Barth A. Prog. Biophys. Mol. Biol. 74 (2000) 141-173
39. Barth A., and Zscherp C.Q. Rev. Biophys. 35 (2002) 369-430
40. Pilpel Y., Bogin O., Brumfeld V., and Reich Z. Biochemistry 42 (2003) 3519-3526
41. Rivière C., Richard T., Quentin L., Krisa S., Mérillon J.M., and Monti J.P. Bioorg. Med. Chem. 15 (2007) 1160-1167
42. Selkoe D.J. Nature 399 (1999) A23-A31
43. Zagari A., Nemethy G., and Scheraga H.A. Biopolymers 30 (1990) 951-959
44. Elgersma R.C., Meijneke T., de Jong R., Brouwer A.J., Postuma G., Dirk T.S., Rijkers D.T., and Liskamp R.M. J. Org. Biomol. Chem. 4 (2006) 3587-3597
45. Cussac D., Vidal M., Leprince C., Liu W., Cornille F., Tiraboschi G., Roques B.P., and Garbay C. FASEB J. 13 (1999) 31-38