Rational design of a structural framework with potential use to develop chemical reagents that target and modulate multiple facets of Alzheimer's disease

Journal of the American Chemical Society

Volumn 136, Issue 1, 2014, Pages 299-310

  Lee, Sanghyun ^a,e   Zheng, Xueyun ^b   Krishnamoorthy, Janarthanan ^a   Savelieff, Masha G ^a   Park, Hyun Min ^a,c   Brender, Jeffrey R ^a   Kim, Jin Hoon ^a,c   Derrick, Jeffrey S ^a   Kochi, Akiko ^a   Lee, Hyuck Jin ^a   Kim, Cheal ^c   Ramamoorthy, Ayyalusamy ^a   Bowers, Michael T ^b   Lim, Mi Hee ^a,d  

^a UNIVERSITY OF MICHIGAN   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c Seoul National University of Science and Technology   (South Korea)

^d Ulsan National Institute of Science and Technology   (South Korea)

^e Sgs Life Science Services   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALZHEIMER'S DISEASE; ANTI-OXIDANT ACTIVITIES; CHEMICAL REAGENTS; REACTIVE OXYGEN SPECIES; STRUCTURAL COMPONENT; STRUCTURAL ELEMENTS; STRUCTURAL FRAMEWORKS; STRUCTURE-BASED DESIGNS;

CHELATION; FREE RADICALS; METAL IONS; MOLECULES; NEURODEGENERATIVE DISEASES;

METALS;

AMYLOID BETA PROTEIN; LIGAND; METAL; METHANOL DERIVATIVE; PHENOL DERIVATIVE; REACTIVE OXYGEN METABOLITE; REAGENT;

ALZHEIMER DISEASE; ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; BLOOD BRAIN BARRIER; CHELATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; HUMAN; HUMAN CELL; IN VITRO STUDY; ION MOBILITY SPECTROMETRY; MASS SPECTROMETRY; MEMBRANE PERMEABILITY; METAL BINDING; MODULATION; MOLECULE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOMERIZATION; PROTEIN AGGREGATION; PROTEIN INTERACTION; REGULATORY MECHANISM;

ALZHEIMER DISEASE; ANTIOXIDANTS; BINDING SITES; CHELATING AGENTS; COPPER; DRUG DELIVERY SYSTEMS; DRUG DESIGN; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; REACTIVE OXYGEN SPECIES; ZINC;

EID: 84892177268     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja409801p     Document Type: Article

References (75)

1. Thies, W.; Bleiler, L.; Alzheimer's Association Alzheimer's Dementia 2013, 9, 208-245
2. Corbett, A.; Pickett, J.; Burns, A.; Corcoran, J.; Dunnett, S. B.; Edison, P.; Hagan, J. J.; Holmes, C.; Jones, E.; Katona, C.; Kearns, I.; Kehoe, P.; Mudher, A.; Passmore, A.; Shepherd, N.; Walsh, F.; Ballard, C. Nat. Rev. Drug Discov. 2012, 11, 833-846
3. Jakob-Roetne, R.; Jacobsen, H. Angew. Chem. Int. Ed. 2009, 48, 3030-3059
4. Hamley, I. W. Chem. Rev. 2012, 112, 5147-5192
5. Kepp, K. P. Chem. Rev. 2012, 112, 5193-5239
6. Savelieff, M. G.; Lee, S.; Liu, Y.; Lim, M. H. ACS Chem. Biol. 2013, 8, 856-865
7. Duce, J. A.; Bush, A. I. Prog. Neurobiol. 2010, 92, 1-18
8. DeToma, A. S.; Salamekh, S.; Ramamoorthy, A.; Lim, M. H. Chem. Soc. Rev. 2012, 41, 608-621
9. Scott, L. E.; Orvig, C. Chem. Rev. 2009, 109, 4885-4910
10. Que, E. L.; Domaille, D. W.; Chang, C. J. Chem. Rev. 2008, 108, 1517-1549
11. Zatta, P.; Drago, D.; Bolognin, S.; Sensi, S. L. Trends Pharmacol. Sci. 2009, 30, 346-355
12. Pithadia, A. S.; Lim, M. H. Curr. Opin. Chem. Biol. 2012, 16, 67-73
13. Miller, Y.; Ma, B.; Nussinov, R. Chem. Rev. 2010, 110, 4820-4838
14. Haass, C.; Selkoe, D. J. Nat. Rev. Mol. Cell Biol. 2007, 8, 101-112
15. Shankar, G. M.; Li, S.; Mehta, T. H.; Garcia-Munoz, A.; Shepardson, N. E.; Smith, I.; Brett, F. M.; Farreel, M. A.; Rowan, M. J.; Lemere, C. A.; Regan, C. M.; Walsh, D. M.; Sabatini, B. L.; Selkoe, D. J. Nat. Med. 2008, 14, 837-842
16. Faller, P.; Hureau, C. Dalton Trans. 2009, 1080-1094
17. Faller, P. ChemBioChem 2009, 10, 2837-2845
18. Telpoukhovskaia, M.; Orvig, C. Chem. Soc. Rev. 2013, 42, 1836-1846
19. Rodríguez-Rodríguez, C.; Telpoukhovskaia, M.; Orvig, C. Coord. Chem. Rev. 2012, 256, 2308-2332
20. Braymer, J. J.; DeToma, A. S.; Choi, J.-S.; Ko, K. S.; Lim, M. H. Int. J. Alzheimer's Dis. 2011, 2011:623051
21. Hindo, S. S.; Mancino, A. M.; Braymer, J. J.; Liu, Y.; Vivekanandan, S.; Ramamoorthy, A.; Lim, M. H. J. Am. Chem. Soc. 2009, 131, 16663-16665
22. Choi, J.-S.; Braymer, J. J.; Nanga, R. P. R.; Ramamoorthy, A.; Lim, M. H. Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 21990-21995
23. Braymer, J. J.; Choi, J.-S.; DeToma, A. S.; Wang, C.; Nam, K.; Kampf, J. W.; Ramamoorthy, A.; Lim, M. H. Inorg. Chem. 2011, 50, 10724-10734
24. Choi, J.-S.; Braymer, J. J.; Park, S. K.; Mustafa, S.; Chae, J.; Lim, M. H. Metallomics 2011, 3, 284-291
25. Pithadia, A. S.; Kochi, A.; Soper, M. T.; Beck, M. W.; Liu, Y.; Lee, S.; DeToma, A. S.; Ruotolo, B. T.; Lim, M. H. Inorg. Chem. 2012, 51, 12959-12967
26. Liu, Y.; Kochi, A.; Pithadia, A. S.; Lee, S.; Nam, Y.; Beck, M. W.; He, X.; Lee, D.; Lim, M. H. Inorg. Chem. 2013, 52, 8121-8130
27. Hyung, S. J.; DeToma, A. S.; Brender, J. R.; Lee, S.; Vivekanandan, S.; Kochi, A.; Choi, J. S.; Ramamoorthy, A.; Ruotolo, B. T.; Lim, M. H. Proc. Natl. Acad. Sci. U. S. A. 2013, 110, 3743-3748
28. DeToma, A. S.; Choi, J.-S.; Braymer, J. J.; Lim, M. H. ChemBioChem 2011, 12, 1198-1201
29. Kung, H. F.; Lee, C.-W.; Zhuang, Z.-P.; Kung, M.-P.; Hou, C.; Plössl, K. J. Am. Chem. Soc. 2001, 123, 12740-12741
30. Lim, M. H.; Wong, B. A.; Pitcock, W. H.; Mokshagundam, D.; Baik, M.-H.; Lippard, S. J. J. Am. Chem. Soc. 2006, 128, 14364-14373
31. Orhan Puskullu, M.; Tekiner, B.; Suzen, S. Mini Rev. Med. Chem. 2013, 13, 365-372
32. Havsteen, B. H. Pharmacol. Ther. 2002, 96, 67-202
33. Rice-Evans, C. A.; Miller, N. J.; Paganga, G. Free Radical Biol. Med. 1996, 20, 933-956
34. Di, L.; Kerns, E. H.; Fan, K.; McConnell, O. J.; Carter, G. T. Eur. J. Med. Chem. 2003, 38, 223-232
35. Avdeef, A.; Bendels, S.; Di, L.; Faller, B.; Kansy, M.; Sugano, K.; Yamauchi, Y. J. Pharm. Sci. 2007, 96, 2893-2909
36. Vivekanandan, S.; Brender, J. R.; Lee, S. Y.; Ramamoorthy, A. Biochem. Biophys. Res. Commun. 2011, 411, 312-316
37. Hou, L.; Shao, H.; Zhang, Y.; Li, H.; Menon, N. K.; Neuhaus, E. B.; Brewer, J. M.; Byeon, I.-J. L.; Ray, D. G.; Vitek, M. P.; Iwashita, T.; Makula, R. A.; Przybyla, A. B.; Zagorski, M. G. J. Am. Chem. Soc. 2004, 126, 1992-2005
38. Mayer, M.; Meyer, B. J. Am. Chem. Soc. 2001, 123, 6108-6117
39. Wyttenbach, T.; Bowers, M. T. Modern Mass Spectrometry, Topics in Current Chemistry; Christoph, A Schalley, Ed.; Springer: Berlin, 2003; 225, 207-232.
40. Bernstein, S. L.; Wyttenbach, T.; Baumketner, A.; Shea, J.-E.; Bitan, G.; Teplow, D. B.; Bowers, M. T. J. Am. Chem. Soc. 2005, 127, 2075-2084
41. Bernstein, S. L.; Dupuis, N. F.; Lazo, N. D.; Wyttenbach, T.; Condron, M. M.; Bitan, G.; Teplow, D. B.; Shea, J.-E.; Ruotolo, B. T.; Robinson, C. V.; Bowers, M. T. Nat. Chem. 2009, 1, 326-331
42. Gessel, M. M.; Wu, C.; Li, H.; Bitan, G.; Shea, J.-E.; Bowers, M. T. Biochemistry 2012, 51, 108-117
43. Zheng, X.; Gessel, M. M.; Wisniewski, M. L.; Viswanathan, K.; Wright, D. L.; Bahr, B. A.; Bowers, M. T. J. Biol. Chem. 2012, 287, 6084-6088
44. Lesné, S.; Koh, M. T.; Kotilinek, L.; Kayed, R.; Glabe, C. G.; Yang, A.; Gallagher, M.; Ash, K. H. Nature 2006, 440, 352-357
45. Thinakaran, G.; Teplow, D. B.; Siman, R.; Greenberg, B.; Sisodia, S. S. J. Biol. Chem. 1996, 271, 9390-9397
46. Charkoudian, L. K.; Pham, D. M.; Franz, K. J. J. Am. Chem. Soc. 2006, 128, 12424-12425
47. Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Free Radical Biol. Med. 1999, 26, 1231-1237
48. Schugar, H.; Green, D. E.; Bowen, M. L.; Scott, L. E.; Storr, T.; Böhmerle, K.; Thomas, F.; Allen, D. D.; Lockman, P. R.; Merkel, M.; Thompson, K. H.; Orvig, C. Angew. Chem., Int. Ed. 2007, 46, 1716-1718
49. BBB Protocol and Test Compounds; pION Inc.: Woburn, MA, 2009.
50. Roth, R.; Erlenmeyer, H. Helv. Chim. Acta 1954, 37, 1064-1068
51. Waibel, M.; Hasserodt, J. Tetrahedron Lett. 2009, 50, 2767-2769
52. Pringle, S. D.; Giles, K.; Wildgoose, J. L.; Williams, J. P.; Slade, S. E.; Thalassinos, K.; Bateman, R. H.; Bowers, M. T.; Scrivens, J. H. Int. J. Mass Spectrom. 2007, 261, 1-12
53. Wyttenbach, T.; Kemper, P. R.; Bowers, M. T. Int. J. Mass Spectrom. 2001, 212, 13-23
54. Gidden, J.; Baker, E. S.; Ferzoco, A.; Bowers, M. T. Int. J. Mass Spectrom. 2005, 240, 183-193
55. Mason, E. A.; McDaniel, E. W. Transport Properties of Ions in Gases; Wiley: New York, 1988.
56. Schanda, P.; Brutscher, B. J. Am. Chem. Soc. 2005, 127, 8014-8015
57. Glasoe, P. K.; Long, F. A. J. Phys. Chem. 1960, 64, 188-190
58. Yoo, S. I.; Yang, M.; Brender, J. R.; Vivekanandan, S.; Sun, K.; Joo, N. E.; Jeong, S.-H.; Ramamoorthy, A.; Kotov, N. A. Angew. Chem., Int. Ed. 2011, 50, 5110-5115
59. Fawzi, N. L.; Ying, J.; Torchia, D. A.; Clore, G. M. J. Am. Chem. Soc. 2010, 132, 9948-9951
60. Soong, R.; Brender, J. R.; Macdonald, P. M.; Ramamoorthy, A. J. Am. Chem. Soc. 2009, 131, 7079-7085
61. Huang, R.; Vivekanandan, S.; Brender, J. R.; Abe, Y.; Naito, A.; Ramamoorthy, A. J. Mol. Biol. 2012, 416, 108-120
62. Narayanan, S.; Reif, B. Biochemistry 2005, 44, 1444-1452
63. Airoldi, C.; Sironi, E.; Dias, C.; Marcelo, F.; Martins, A.; Rauter, A. P.; Nicotra, F.; Jimenez-Barbero, J. Chem. Asian J. 2013, 8, 596-602
64. Laurents, D. V.; Gorman, P. M.; Guo, M.; Rico, M.; Chakrabartty, A.; Bruix, M. J. Biol. Chem. 2005, 280, 3675-3685
65. Morris, G. M.; Huey, R.; Lindstrom, W.; Sanner, M. F.; Belew, R. K.; Goodsell, D. S.; Olson, A. J. J. Comput. Chem. 2009, 30, 2785-2791
66. Petkova, A. T.; Yau, W.-M.; Tycko, R. Biochemistry 2006, 45, 498-512
67. Schüttelkopf, A. W.; van Aalten, D. M. F. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 1355-1363
68. Singh, U. C.; Kollman, P. A. J. Comput. Chem. 1984, 5, 129-145
69. Gasteiger, J.; Marsili, M. Tetrahedron 1980, 36, 3219-3228
70. Gasteiger, J.; Marsili, M. Tetrahedron Lett. 1978, 19, 3181-3184
71. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. J. Comput. Chem. 1998, 19, 1639-1662
72. Gans, P.; Sabatini, A.; Vacca, A. Ann. Chim. 1999, 89, 45-49
73. Alderighi, L.; Gans, P.; Ienco, A.; Peters, D.; Sabatini, A.; Vacca, A. Coord. Chem. Rev. 1999, 184, 311-318
74. Mancino, A. M.; Hindo, S. S.; Kochi, A.; Lim, M. H. Inorg. Chem. 2009, 48, 9596-9598
75. Spencer, V. A.; Sun, J.-M.; Li, L.; Davie, J. R. Methods 2003, 31, 67-75