NSAID-derived γ-secretase modulation requires an acidic moiety on the carbazole scaffold

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 16, 2011, Pages 4903-4909

  Zall, Andrea ^a   Kieser, Daniel ^a   Höttecke, Nicole ^a   Naumann, Eva C ^a   Thomaszewski, Binia ^a   Schneider, Katrin ^a   Steinbacher, Dirk T ^a   Schubenel, Robert ^b   Masur, Stefan ^b   Baumann, Karlheinz ^b   Schmidt, Boris ^a  

^a DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

^b F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

Secretase modulation; Alzheimer's disease; Carboxylic acid isosteres; Carprofen

Indexed keywords

2 (2 BROMOETHOXY) 9 OCTYL 9H CARBAZOLE; 2 (9 OCTYL 9H CARBAZOL 2 YLOXY)ETHANESULFONIC ACID; 2 HYDROXY N OCTYLCARBAZOLE; 2 SULFONYLATED CARBAZOLYLOXYACETIC ACID DERIVATIVE; AMYLOID; AMYLOID BETA PROTEIN; AMYLOID BETA PROTEIN[1-40]; AMYLOID BETA PROTEIN[1-42]; BSC 3041; CARPROFEN; GAMMA SECRETASE; GAMMA SECRETASE INHIBITOR; LYSINE; N ALKYLATED CARBAZOLYLOXYACETIC ACID DERIVATIVE; N ALKYLATED CARPROFEN DERIVATIVE; NONSTEROID ANTIINFLAMMATORY AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; CELL ASSAY; CELL SECRETION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG BLOOD LEVEL; DRUG BRAIN LEVEL; DRUG PENETRATION; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; LIPOPHILICITY; MOLECULAR INTERACTION; MOUSE; NONHUMAN; PROTEIN SECRETION; STRUCTURE ACTIVITY RELATION;

ACIDS; ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; AMYLOID BETA-PROTEIN PRECURSOR; AMYLOID PRECURSOR PROTEIN SECRETASES; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CARBAZOLES; CARBOXYLIC ACIDS; CELL LINE; CELL PROLIFERATION; FENOFIBRATE; HUMANS; MICE; MOLECULAR TARGETED THERAPY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79961173070     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.06.062     Document Type: Article

References (23)

1. D. Beher, J.D. Wrigley, A.P. Owens, and M.S. Shearman J. Neurochem. 82 2002 563
2. M.S. Wolfe Biochemistry 45 2006 7931
3. C. Kaether, C. Haass, and H. Steiner Neurodegener. Dis. 3 2006 275
4. A.L. Brunkan, and A.M. Goate J. Neurochem. 93 2005 769
5. W.T. Kimberly, W. Xia, T. Rahmati, M.S. Wolfe, and D.J. Selkoe J. Biol. Chem. 275 2000 3173
6. H. Steiner, R. Fluhrer, and C. Haass J. Biol. Chem. 283 2008 29627
7. B. Schmidt, S. Baumann, H.A. Braun, and G. Larbig Curr. Top. Med. Chem. 6 2006 377
8. M.S. Brown, J. Ye, R.B. Rawson, and J.L. Goldstein Cell 100 2000 391
9. S. Weggen, J.L. Eriksen, P. Das, S.A. Sagi, R. Wang, C.U. Pietrzik, K.A. Findlay, T.E. Smith, M.P. Murphy, T. Bulter, D.E. Kang, N. Marquez-Sterling, T.E. Golde, and E.H. Koo Nature 414 2001 212
10. T.L. Kukar, T.B. Ladd, M.A. Bann, P.C. Fraering, R. Narlawar, G.M. Maharvi, B. Healy, R. Chapman, A.T. Welzel, R.W. Price, B. Moore, V. Rangachari, B. Cusack, J. Eriksen, K. Jansen-West, C. Verbeeck, D. Yager, C. Eckman, W. Ye, S. Sagi, B.A. Cottrell, J. Torpey, T.L. Rosenberry, A. Fauq, M.S. Wolfe, B. Schmidt, D.M. Walsh, E.H. Koo, and T.E. Golde Nature 453 2008 925
11. L.M. Munter, P. Voigt, A. Harmeier, D. Kaden, K.E. Gottschalk, C. Weise, R. Pipkorn, M. Schaefer, D. Langosch, and G. Multhaup EMBO J. 26 2007 1702
12. S. Baumann, N. Hoettecke, R. Schubenel, K. Baumann, and B. Schmidt Bioorg. Med. Chem. Lett. 19 2009 6986
13. R. Narlawar, B.I. Perez Revuelta, K. Baumann, R. Schubenel, C. Haass, H. Steiner, and B. Schmidt Bioorg. Med. Chem. Lett. 17 2007 176
14. R. Narlawar, B.I. Perez Revuelta, C. Haass, H. Steiner, B. Schmidt, and K. Baumann J. Med. Chem. 49 2006 7588
15. E. Czirr, S. Leuchtenberger, C. Dorner-Ciossek, A. Schneider, M. Jucker, E.H. Koo, C.U. Pietrzik, K. Baumann, and S. Weggen J. Biol. Chem. 282 2007 24504
16. R.M. Page, K. Baumann, M. Tomioka, B.I. Perez-Revuelta, A. Fukumori, H. Jacobsen, A. Flohr, T. Luebbers, L. Ozmen, H. Steiner, and C. Haass J. Biol. Chem. 283 2008 677
17. D. Oehlrich, D.J.C. Berthelot, and H.J.M. Gijsen J. Med. Chem. 54 2011 669
18. L. Richter, L.-M. Munter, J. Ness, P.W. Hildebrand, M. Dasari, S. Unterreitmeier, B. Bulic, M. Beyermann, R. Gust, B. Reif, S. Weggen, D. Langosch, and G. Multhaup Proc. Nat. Acad. Sci. 107 2010 14597
19. K. Uemura, K. Farner, N. Nasser-Ghodsi, P. Jones, and O. Berezovska Mol. Neurodegeneration 6 2011 15
20. F. Péhourcq, M. Matoga, and B. Bannwarth Fundam. Clin. Pharmacol. 18 2004 65
21. S. Hahn, T. Bruening, J. Ness, E. Czirr, S. Baches, H. Gijsen, C. Korth, C.U. Pietrzik, B. Bulic, and S. Weggen J. Neurochem. 116 2011 385
22. B. Kretner, A. Fukumori, A. Gutsmiedl, R.M. Page, T. Luebbers, G. Galley, K. Baumann, C. Haass, and H. Steiner J. Biol. Chem. 286 2011 15240
23. O. Chiry, L. Pellerin, F. Monnet-Tschudi, W.N. Fishbein, N. Merezhinskaya, P.J. Magistretti, and S. Clarke Brain Res. 1070 2006 65