Methylations of tryptophan-modified naphthoquinone affect its inhibitory potential toward aβ aggregation

Journal of Physical Chemistry B

Volumn 117, Issue 6, 2013, Pages 1780-1789

  Scherzer Attali, Roni ^a   Convertino, Marino ^b   Pellarin, Riccardo ^b   Gazit, Ehud ^a   Segal, Daniel ^a   Caflisch, Amedeo ^b  

^a TEL AVIV UNIVERSITY   (Israel)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CARBOXYLIC ACIDS; FUNCTIONAL GROUPS; HYDROGEN BONDS; KETONES; MOLECULES; OLIGOMERIZATION; OLIGOMERS;

ALZHEIMER'S DISEASE; AMYLOID BETAS; AROMATIC RINGS; D-ISOMERS; IN-SILICO; IN-VITRO; INHIBITORY ACTIVITY; MODE OF ACTION; NAPHTHOQUINONE; SMALL MOLECULES; SMALL-MOLECULE INHIBITORS; STRUCTURE-ACTIVITY;

AMINO ACIDS;

EID: 84873894264     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp309066p     Document Type: Article

References (43)

1. Brookmeyer, R.; Johnson, E.; Ziegler-Graham, K.; Arrighi, H. M Alzheimer's Dementia 2007, 3, 186-191
2. Bharadwaj, P. R.; Dubey, A. K.; Masters, C. L.; Martins, R. N.; Macreadie, I. G. J. Cell. Mol. Med. 2009, 13, 412-421
3. Bertram, L.; Lill, C. M.; Tanzi, R. E. Neuron 2010, 68, 270-281
4. Selkoe, D. J. Neuro 1991, 487-498
5. Terry, R. Prog. Brain Res. 1994, 383-390
6. Kirkitadze, M. D.; Bitan, G.; Teplow, D. B. J. Neurosci. Res. 2002, 567-577
7. Lashuel, H. A.; Hartley, D.; Petre, B. M.; Walz, T.; Lansbury, P. T. J. Nature 2002, 291
8. Kayed, R.; Head, E.; Thompson, J. I.; MeIntire, T. M.; Milton, S. C.; Cotman, V. W.; Glabe, C. G. Science 2003, 300, 486-489
9. Gazit, E. Drugs Future 2004, 29, 613-619
10. Barghorn, S.; Nimmrich, V.; Striebinger, A.; Krantz, C.; Keller, P. B. J.; Bahr, M.; Schmidt, M.; Bitner, R. S.; Harlan, J.; Barlow, E.; Ebert, U.; Hillen, H. J. Neurochem. 2005, 95, 834-847
11. Azriel, R.; Gazit, E. J. Biol. Chem. 2001, 276, 34156-34161
12. Gazit, E. FASEB J. 2002, 16, 77-83
13. Gazit, E. Bioinformatics 2002, 880-883
14. Jacobsen, J. S.; Wu, C. C.; Redwine, J. M.; Comery, T. A.; Arias, R.; Bowlby, M.; Martone, R.; Morrison, J. H.; Pangalos, M. N.; Reinhart, P. H.; Bloom, F. E. Proc. Natl. Acad. Sci. U.S.A. 2006, 5161-5166
15. Porat, Y.; Kolusheva, S.; Jelinek, R.; Gazit, E. Biochemistry 2003, 10971-10977
16. Mazor, Y.; Gilead, S.; Benhar, I.; Gazit, E. J. Mol. Biol. 2002, 1013-1024
17. Reches, M.; Gazit, E. Science 2003, 625-627
18. Reches, M.; Gazit, E. Amyloid 2004, 81-89
19. Cohen, T.; Frydman-Marom, A.; Rechter, M.; Gazit, E. Biochemistry 2006, 45, 4727-4735
20. Makin, O. S.; Atkins, E.; Sikorski, P.; Johansson, J.; Serpell, L. C. M. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 315-320
21. Porat, Y.; Abramowitz, A.; Gazit, E. Chem. Biol. Drug Des. 2006, 27-37
22. Hamaguchi, T.; Ono, K.; Yamada, M. Cell. Mol. Life Sci. 2006, 1538-1552
23. Lorenzo, A.; Yankner, B. A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 12243-12247
24. Lee, V. M. Neurobiol. Aging 2002, 23, 1039-1042
25. Poli, G.; Ponti, W.; Carcassola, G.; Ceciliani, F.; Colombo, L.; Dall'Ara, P.; Gervasoni, M.; Giannino, M. L.; Martino, P. A.; Pollera, C.; Villa, S.; Salmona, M. Arzneimittelforschung 2003, 53, 875-888
26. Scherzer-Attali, R.; Shaltiel-Karyo, R.; Adalist, Y. H.; Segal, D.; Gazit, E. Proteins 2012, 80, 1962-1973
27. Scherzer-Attali, R.; Pellarin, R.; Convertino, M.; Frydman-Marom, A.; Egoz-Matia, N.; Peled, S.; Levy-Sakin, M.; Shalev, D. E.; Caflisch, A.; Gazit, E.; Segal, D. PLoS One 2010, 5, e11101
28. Chebaro, Y.; Jiang, P.; Zang, T.; Mu, Y.; Nguyen, P. H.; Mousseau, N.; Derreumaux, P. J. Phys. Chem. B 2012, 116, 8412-8422
29. Convertino, M.; Vitalis, A.; Caflisch, A. J. Biol. Chem. 2011, 286, 41578-41588
30. Straub, J. E.; Guevara, J.; Huo, S.; Lee, J. P. Acc. Chem. Res. 2002, 35, 473-481
31. Zhang, S.; Casey, N.; Lee, J. P. Fold. Des. 1998, 3, 413-422
32. Tjernberg, L. O.; Naslund, J.; Lindqvist, F.; Johansson, J.; Karlstrom, A. R.; Thyberg, J.; Terenius, L.; Nordstedt, C. J. Biol. Chem. 1996, 271, 8545-8548
33. Williams, A. D.; Portelius, E.; Kheterpal, I.; Guo, J. T.; Cook, K. D.; Xu, Y.; Wetzel, R. J. Mol. Biol. 2004, 335, 833-842
34. Vitalis, A.; Caflisch, A. J. Mol. Biol. 2010, 403, 148-165
35. Convertino, M.; Pellarin, R.; Catto, M.; Carotti, A.; Caflisch, A. Protein Sci. 2009, 18, 792-800
36. Pellarin, R.; Caflisch, A. J. Mol. Biol. 2006, 360, 882-892
37. Wurth, C.; Guimard, N. K.; Hecht, M. H. J. Mol. Biol. 2002, 319, 1279-1290
38. Kolb, P.; Caflisch, A. J. Med. Chem. 2006, 49, 7384-7392
39. Shrestha-Dawadi, P. B.; Prativa, B.; Bittner, S.; Fridkin, M.; Rahimipour, S. Synthesis 1996, 1468-1472
40. Bassindale, A. R.; Parker, D. J.; Patel, P.; Taylor, P. G. Tetrahedron Lett. 2000, 41, 4933-4936
41. Brooks, B. R.; Brooks, C. L.; Mackerell, A. D.; Nilsson, L.; Petrella, R. J.; Roux, B.; Won, Y.; Archontis, G.; Bartels, C.; Boresch, S.; Caflisch, A.; Caves, L.; Cui, Q.; Dinner, A. R.; Feig, M.; Fischer, S.; Gao, J.; Hodoscek, M.; Im, W.; Kuczera, K.; Lazaridis, T.; Ma, J.; Ovchinnikov, V.; Paci, E.; Pastor, R. W.; Post, C. B.; Pu, J. Z.; Schaefer, M.; Tidor, B.; Venable, R. M.; Woodcock, H. L.; Wu, X.; Yang, W.; York, D. M.; Karplus, M. J. Comput. Chem. 2009, 30, 1545-1614
42. Ferrara, P.; Apostolakis, J.; Caflisch, A. Proteins Struct. Funct. Bioinf. 2002, 46, 24-33
43. Kim, W.; Kim, Y.; Min, J.; Kim, D. J.; Chang, Y. T.; Hecht, M. H. ACS Chem. Biol. 2006, 1, 461-469