Design, synthesis, and biological evaluation of glycine-based molecular tongs as inhibitors of Aβ1-40 aggregation in vitro

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 9, 2008, Pages 4810-4822

  Cellamare, Saverio ^a   Stefanachi, Angela ^a   Stolfa, Diana A ^a   Basile, Teodora ^a   Catto, Marco ^a   Campagna, Francesco ^a   Sotelo, Eddy ^a   Acquafredda, Pasquale ^a   Carotti, Angelo ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

Amyloid aggregation; A 1 40; Glycine based molecular tongs; Polyphenolic amides inhibitors

Indexed keywords

AMIDE; AMYLOID; AMYLOID BETA PROTEIN[1-40]; BENZAMIDE DERIVATIVE; DIAMINE DERIVATIVE; GLYCINE; HYDROGEN;

ARTICLE; BIOLOGY; EVALUATION; HYDROGEN BOND; IC 50; IN VITRO STUDY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMYLOID BETA-PROTEIN; ANILINE COMPOUNDS; BENZAMIDES; CAFFEIC ACIDS; DRUG DESIGN; GLYCINE; MOLECULAR STRUCTURE; PEPTIDE FRAGMENTS; PEPTIDES; PHENYL ETHERS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TIME FACTORS; XYLENES;

EID: 43049088115     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.03.052     Document Type: Article

References (68)

1. Selkoe D.J. Neuron 6 (1991) 487
2. Rochet J.C., and Lansbury P.T. Curr. Opin. Struct. Biol. 10 (2000) 60
3. Chiti F., and Dobson C.M. Annu. Rev. Biochem. 75 (2006)
4. Walsh D.M., and Selkoe D.J. Neuron 44 (2004) 181
5. Hardy J.D., and Selkoe D.J. Science 297 (2002) 353
6. Harper J.D., Wong S.S., Lieber C.M., and Lansbury P.T. Chem. Biol. 4 (1997) 119
7. Walsh D.M., Lomakin A., Benedek G.B., Condron M.M., and Teplow D.B. J. Biol. Chem. 272 (1997) 22364
8. Lashuel H.A., Hartley D., Petre B.M., Walz T., and Lansbury P.T. Nature 418 (2002) 291
9. Caughey B., and Lansbury P.T. Annu. Rev. Neurosci. 26 (2003) 267
10. Gong Y., Chang L., Viola K.L., Lacor P.N., Lambert M.P., Finch C.E., Krafft G.A., and Klein W.L. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 10417
11. Tsai J., Grutzendler J., Duff K., and Gan W.B. Nat. Neurosci. 7 (2004) 1181
12. Sabella S., Quaglia M., Lanni C., Racchi M., Covoni S., Caccialanza G., Calligaro A., Bellotti V., and De Lorenzi E. Electrophoresis 25 (2004) 3186
13. Baglioni S., Casamenti F., Bucciantini M., Luheshi L.M., Taddei N., Chiti F., Dobson C.M., and Stefani M. J. Neurosci. 26 (2006) 8160
14. Haass C. EMBO J. 23 (2004) 483
15. Estrada L.D., and Soto C. Curr. Topics Med. Chem. 7 (2007) 115
16. Walsh D.M., Klyubin I., Fadeeva J.V., Cullen W.K., Anwy R., Wolfe M.S., Rowan M.J., and Selkoe D.J. Nature 416 (2002) 535
17. Tsai M., Hattori C., Iwata N., Saido T.C., Sasagawa N., Haschimoto Y., Maruyama K., Tanuma S., Kiso Y., and Ishiura S. J. Neurochem. 96 (2006) 533
18. Wetzel R., Shivaprasad S., and Williams A.D. Biochemistry 46 (2007) 1
19. Mandal P.K., Pettergrew J.W., McKeag D., and Mandal D. Neurochem. Res. 31 (2006) 883
20. Tycko R. Protein Pept. Lett. 13 (2006) 229
21. Gnanakaran S., Nussinov R., and Garcia A.E. J. Am. Chem. Soc. 128 (2006) 2158
22. Tjernberg L.O., Naslund J., Lindqvist F., Johansson J., Karlstrom A.R., Thyberg J., Terenius L., and Nordstedt C. J. Biol. Chem. 271 (1996) 8545
23. Chalifour R.J., McLaughlin R.W., Lavoie L., Morissette C., Tremblay N., Boule M., Sarazin P., Stea D., Lacombe D., Tremblay P., and Gervais F. J. Biol. Chem. 278 (2003) 34874
24. Gibson T.J., and Murphy R.M. Biochemistry 44 (2005) 8898
25. Findeis M.A., Lee J.J., Kelley M., Wakefield J.D., Zhang M.H., Chin J., Kubasek W., and Molineaux S.M. Amyloid 8 (2001) 231
26. Hughes E., Burke R.M., and Doig A.J. J. Biol. Chem. 275 (2000) 25109
27. Gordon D.J., Tappe R., and Meredith S.C. J. Pept. Res. 60 (2002) 37
28. Blanchard B.J., Konopka G., Russell M., and Ingram V.M. Brain Res. 776 (1997) 40
29. Blanchard B.J., Hiniker A.E., Lu C.C., Margolin Y., Yu A.S., and Ingram V.M. J. Alzheimers Dis. 2 (2000) 137
30. 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
31. Liu W., Crocker E., Zhang W., Elliott J.I., Luy B., Li H., Aimoto S., and Smith S.O. Biochemistry 44 (2005) 3591
32. Wang L., Oconnell T., Tropsha A., and Hermans J. J. Mol. Biol. 262 (1996) 283
33. Hegde R.S., Mastrianni J.A., Scott M.R., DeFea K.A., Tremblay P., Torchia M., DeArmond S.J., Prusiner S.B., and Lingappa V.R. Science 279 (1998) 827
34. Kessler J.C., Rochet J.C., and Lansbury P.T. Biochemistry 42 (2003) 672
35. Parrini C., Taddei N., Ramazzotti M., Degl'Innocenti D., Ramponi G., Dobson C.M., and Chiti F. Structure 13 (2005) 1143
36. Lührs T., Ritter C., Adrian M., Riek-Loher D., Bohrmann B., Döbeli H., Schubert D., and Riek R. Proc. Natl. Acad. Sci. U.S.A. 102 (2005) 17342
37. Meijer J.T., Roeters M., Viola V., Löwik D.W.P.M., Vriend G., and van Hest J.C.M. Langmuir 23 (2007) 2058
38. Hunter C.A., Lawson K.R., Perkins J., and Urch C.J. J. Chem. Soc. Perkin Trans. 2 (2001) 651
39. Waters M.L. Curr. Opin. Chem. Biol. 6 (2002) 736
40. Porat Y., Abramowitz A., and Gazit E. Chem. Biol. Drug. Res. 67 (2006) 23
41. Porat Y., Mazor Y., Efrat S., and Gazit E. Biochemistry 43 (2004) 14454
42. Bemporad F., Taddei N., Stefani S., and Chiti F. Protein Sci. 15 (2006) 862
43. Marek P., Abedini A., Song B., Kanungo M., Johnson M.E., Gupta R., Zaman W., Wong S.S., and Raleigh D.P. Biochemistry 46 (2007) 3255
44. Ono K., Yoshiike Y., Takashima A., Hasegawa K., Naiki H., and Yamada M. J. Neurochem. 87 (2003) 172
45. Ono K., Hasegawa K., Naiki H., and Yamada M. Biochim. Biophys. Acta 1690 (2004) 193
46. Ono K., Hasegawa K., Naiki H., and Yamada M. J. Neurosci. Res. 75 (2004) 742
47. Rivière C., Tristan R., Quentin L., Krisa S., Mérillon J.-M., and Monti J.-P. Bioorg. Med. Chem. 17 (2007) 1160
48. Cockrof S.L., Hunter C.A., Lawson K.R., Perkins J., and Urch C.J. J. Am. Chem. Soc. 127 (2005) 8594
49. Cockrof S.L., Perkins J., Zonta C., Adams H., Spey S.E., Low C.M.R., Vinter J.G., Lawson K., Urch C.J., and Hunter C.A. Org. Biomol. Chem. 5 (2007) 1062
50. May B.C.H., Fafarman A.T., Hong S.B., Rogers M., Deady L.V., Prusiner S.B., and Cohen F.E. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 3416
51. Saunders B.C. J. Chem. Soc. (1938) 1397
52. Pirkle W.H., and Hyun M.H. J. Org. Chem. 49 (1984) 3043
53. Acheson R.M., Booth D.A., Brettle R., and Harris A.M. J. Chem. Soc. (1960) 3457
54. Elmore D.T., and Ogle J.R. J. Chem. Soc. (1958) 1141
55. Offermans, H.; Posselt, K. DE Patent 2338172, 1974.
56. Spilburg C.A., Bethune J.L., and Vallee B.L. Biochemistry 16 (1977) 1142
57. Compound 2a. Ruggli P., Leupin E., and Dahn H. Helv. Chim. Acta 30 (1947) 1845
58. Compounds 2b and 2c: Aurora Screening Library, 2007, Registry Nos. 609797-93-5 (2b) and 415692-45-4 (2c).
59. OH: Takashi, T.; Tsuneji, S.; Katsutoshi, T.; Toshiyuki S. JP Patent 2004035483, 2004.
60. Sciarretta K.L., Gordon D.J., and Meredith S.C. In: Kheterpal I., and Wetzel R. (Eds). Methods in Enzimology Vol. 13 (2006), Elsevier Academic Press, San Diego 273-312
61. Catto, M.; Cellamare, S.; Chiti, F.; Carotti, A. Proceedings of the EMBO-FEBS Workshop on Amyloid Formation Firenze, Italy March 25-28, 2006; poster #054.
62. Vieira E.P., Hermel H., and Mohwald H. Biochim. Biophys. Acta 6 (2003) 1645
63. Nichols M.R., Moss M.A., Reed D.K., Cratic-McDaniel S., Hoh J.H., and Rosenberry T.L. J. Biol. Chem. 280 (2005) 2471
64. Howlett D.R., George A.R., Owen D.E., Ward R.V., and Markwell R.E. Biochem. J. 343 (1999) 419
65. Ono K., Hirohata M., and Yamada M. Biochem. Biophys. Res. Commun. 336 (2005) 444
66. Taniguchi S., Suzuki N., Masuda M., Hisanaga S., Iwatsubo T., Goedert M., and Hasegawa M. J. Biol. Chem. 280 (2005) 7614
67. LeVine III H. Prot. Sci. 2 (1993) 404
68. Liu R., Yuan B., Emadi S., Zameer A., Schulz P., McAllister C., Lyubchenko Y., Goud G., and Sierks M.R. Biochemistry 43 (2004) 6959