Structure-Activity Relationships of Organofluorine Inhibitors of β-Amyloid Self-Assembly

ChemMedChem

Volumn 7, Issue 5, 2012, Pages 910-919

  Török, Béla ^a   Sood, Abha ^a   Bag, Seema ^a   Kulkarni, Aditya ^a   Borkin, Dmitry ^a   Lawler, Elizabeth ^a   Dasgupta, Sujaya ^a   Landge, Shainaz ^a   Abid, Mohammed ^a   Zhou, Weihong ^a   Foster, Michelle ^a   Levine, Harry ^b   Török, Marianna ^a  

^a UNIVERSITY OF MASSACHUSETTS BOSTON   (United States)

^b UNIVERSITY OF KENTUCKY   (United States)

Author keywords

amyloid; Alzheimer's disease; Chiral inhibitors; Heterocycles; Organofluorine compounds

Indexed keywords

1 (1H INDOL 1 YL) 2,2,2 TRIFLUOROETHANOL DERIVATIVE; 1 (5 BROMO 1H INDOL 3 YL) 2,2,2, TRIFLUOROETHANOL; 1,1,1,3,3,3 HEXAFLUORO 2 (1H PYRROL 2 YL)PROPAN 2 OL DERIVATIVE; 1,1,1,3,3,3 HEXAFLUORO 2 (INDOL 3 YL)PROPAN 2 OL DERIVATIVE; 1,1,1,3,3,3 HEXAFLUORO 2 PHENYLPROPAN 2 OL DERIVATIVE; 1,3 PHENYLENE BIS(METHYLENE)BIS[3 (ETHOXY 1,1,1 TRIFLUORO 2 HYDROXY 3 OXO PROPAN 2 YL) 1H INDOLE 5 CARBOXYLATE; 1,4 PHENYLENE BIS(METHYLENE)BIS[3 (ETHOXY 1,1,1 TRIFLUORO 2 HYDROXY 3 OXO PROPAN 2 YL) 1H INDOLE 5 CARBOXYLATE; 3,3,3 TRIFLUORO 2 HYDROXY 2 (1H PYRROL 2 YL)PROPANOATE DERIVATIVE; 3,3,3 TRIFLUORO 2 HYDROXY 2 (INDOL 3 YL)PROPIONIC ACID ETHYL ESTER DERIVATIVE; AMYLOID BETA PROTEIN ANTIBODY; AMYLOID BETA PROTEIN[1-40]; AMYLOID BETA PROTEIN[1-42]; ETHYL 2 AMINO 3,3,3 TRIFLUORO 2 (1H INDOL 3 YL)PROPANOATE DERIVATIVE; ETHYL 3,3,3 TRIFLUORO 2 HYDROXY 2 PHENYLPROPANOATE DERIVATIVE; ETHYL 4,4,4 TRIFLUORO 3 HYDROXY 3 (1H INDOL 3 YL)BUTANOATE DERIVATIVE; ETHYL 4,4,4 TRIFLUORO 3 HYDROXY 3 (1H PYRROL 2 YL)BUTANOATE DERIVATIVE; OLIGOMER; ORGANOFLUORINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC FORCE MICROSCOPY; DRUG STRUCTURE; DRUG SYNTHESIS; FIBER; FLUORESCENCE SPECTROSCOPY; PRIORITY JOURNAL; PROTEIN ASSEMBLY; STRUCTURE ACTIVITY RELATION;

AMYLOID BETA-PEPTIDES; MICROSCOPY, ATOMIC FORCE; PEPTIDE FRAGMENTS; PROTEIN FOLDING; PROTEIN MULTIMERIZATION; SMALL MOLECULE LIBRARIES; STRUCTURE-ACTIVITY RELATIONSHIP; TRIFLUOROETHANOL;

EID: 84860321639     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201100569     Document Type: Article

References (37)

1. The Alzheimer's Association, (accessed October 2011).
2. C. Ballard, S. Gauthier, A. Corbett, C. Brayne, D. Aarsland, E. Jones, Lancet 2011, 377, 1019-1031.
3. F. Chiti, C. M. Dobson, Nat. Chem. Biol. 2009, 5, 15-22.
4. L. D. Estrada, C. Soto, Curr. Top. Med. Chem. 2007, 7, 115-126.
5. C. Stains, K. Mondal, I. Ghosh, ChemMedChem 2007, 2, 1674-1692.
6. D. M. Walsh, D. J. Selkoe, J. Neurochem. 2007, 101, 1172-1184.
7. M. Necula, R. Kayed, S. Milton, C. G. Glabe, J. Biol. Chem. 2007, 282, 10311-10324.
8. C. G. Glabe, J. Biol. Chem. 2008, 283, 29639-29643.
9. C. Nerelius, J. Johansson, A. Sandegren, Front. Biosci. 2009, 14, 1716-1729.
10. H. LeVine III, Amyloid 2007, 14, 185-197.
11. B. Török, S. Dasgupta, M. Török, Curr. Bioact. Comp. 2008, 4, 159-174.
12. S. L. Adamski-Werner, S. K. Palaninathan, J. C. Sacchettini, J. W. Kelly, J. Med. Chem. 2004, 47, 355-374.
13. M. Török, M. Abid, S. C. Mhadgut, B. Török, Biochemistry 2006, 45, 5377-5383.
14. A. Sood, M. Abid, C. Sauer, S. Hailemichael, M. Foster, B. Török, M. Török, Bioorg. Med. Chem. Lett. 2011, 21, 2044-2047.
15. A. Sood, M. Abid, S. Hailemichael, M. Foster, B. Török, M. Török, Bioorg. Med. Chem. Lett. 2009, 19, 6931-6934.
16. M. Abid, B. Török, Adv. Synth. Catal. 2005, 347, 1797-1803.
17. S. M. Landge, D. A. Borkin, B. Török, Tetrahedron Lett. 2007, 48, 6372-6376.
18. D. Borkin, S. M. Landge, B. Török, Chirality 2011, 23, 612-616.
19. M. Sridhar, C. Narsaiah, B. C. Ramanaiah, V. M. Ankathi, R. B. Pawar, S. N. Asthana, Tetrahedron Lett. 2009, 50, 1777-1779.
20. B. Török, M. Abid, G. London, J. Esquibel, M. Török, S. C. Mhadgut, P. Yan, G. K. S. Prakash, Angew. Chem. 2005, 117, 3146-3149; Angew. Chem. Int. Ed. 2005, 44, 3086-3089.
21. M. Abid, L. Teixeira, B. Török, Org. Lett. 2008, 10, 933-935.
22. H. S. Ban, H. Minegishi, K. Shimizu, M. Maruyama, Y. Yasui, H. Nakamura, ChemMedChem 2010, 5, 1236-1241.
23. H. Naiki, K. Higuchi, M. Hosokawa, T. Takeda, Anal. Biochem. 1989, 177, 244-249.
24. H. LeVine III, Protein Sci. 1993, 2, 404-410.
25. M. R. Nilsson, Methods 2004, 34, 151-160.
26. H. LeVine III, Anal. Biochem. 2006, 356, 265-272.
27. H. LeVine III, Q. Ding, J. A. Walker, R. S. Voss, C. E. Augelli-Szafran, Neurosci. Lett. 2009, 465, 99-103.
28. K. L. Sciaretta, D. J. Gordon, S. C. Meredith, Methods Enzymol. 2006, 413, 273-312.
29. T. Takahashi, H. Mihara, Acc. Chem. Res. 2008, 41, 1309-1318.
30. A. H. Armstrong, J. Chen, A. F. McKoy, M. H. Hecht, Biochemistry 2011, 50, 4058-4067.
31. S. A. Moore, T. N. Huckerby, G. L. Gibson, N. J. Fullwood, S. T. Turnbull, B. J. Tabner, O. M. A. El-Agnaf, D. Allsop, Biochemistry 2004, 43, 819-826.
32. R. J. Chalifour, R. W. McLaughlin, L. Lavoie, C. Morisette, N. Tremblay, M. Boule, P. Sarazin, D. Stea, P. Tremblay, J. Biol. Chem. 2003, 278, 34874-34881.
33. M. Bartolini, M. Pistolozzi, V. Andrisano, J. Egea, M. G. Lopez, I. Iriepa, I. Moraleda, E. Galvez, J. Marco-Contelles, A. Samadi, ChemMedChem 2011, 6, 1990-1997.
34. Y. Fezoui, D. M. Hartley, J. D. Harper, R. Khurana, D. M. Walsh, M. M. Condron, D. J. Selkoe, P. T. Lansbury, A. L. Fink, D. B. Teplow, Amyloid 2000, 7, 166-78.
35. M. Bourhim, M. Kruzel, T. Srikrishnan, T. Nicotera, J. Neurosci. Methods 2007, 160, 264-268.
36. T. T. Ding, J. D. Harper, Methods Enzymol. 1999, 309, 510-25.
37. O. N. Antzutkin, Magn. Reson. Chem. 2004, 42, 231-246.