Modulation of gamma-secretase for the treatment of alzheimer's disease

International Journal of Alzheimer's Disease

Volumn , Issue , 2012, Pages

  Tate, Barbara ^a   McKee, Timothy D ^a   Loureiro, Robyn M B ^a   Dumin, Jo Ann ^a   Xia, Weiming ^a   Pojasek, Kevin ^a   Austin, Wesley F ^a   Fuller, Nathan O ^a   Hubbs, Jed L ^a   Shen, Ruichao ^a   Jonker, Jeff ^a   Ives, Jeff ^a   Bronk, Brian S ^a  

^a Satori Pharmaceuticals Incorporated   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMYLOID BETA PROTEIN; AMYLOID BETA PROTEIN[1-42]; AVAGACESTAT; BEGACESTAT; E 2012; E 20212; GAMMA SECRETASE; GAMMA SECRETASE INHIBITOR; JNJ 40418677; MK GSM 1; N2 [2 (3,5 DIFLUOROPHENYL) 2 HYDROXYACETYL] N1 (6,7 DIHYDRO 5 METHYL 6 OXO 5H DIBENZ[B,D]AZEPIN 7 YL)ALANINAMIDE; SEMAGACESTAT; SPI 1802; SPI 1810; TARENFLURBIL; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG TARGETING; FEMALE; HUMAN; HUMAN TISSUE; IN VIVO STUDY; NONHUMAN; PRIORITY JOURNAL;

EID: 84872139600     PISSN: None     EISSN: 20900252     Source Type: Journal    
DOI: 10.1155/2012/210756     Document Type: Article

References (53)

1. Kakuda N., Funamoto S., Yagishita S., Takami M., Osawa S., Dohmae N., Ihara Y., Equimolar production of amyloid β -protein and amyloid precursor protein intracellular domain from β -carboxyl-terminal fragment by γ -secretase. Journal of Biological Chemistry 2006 281 21 14776 14786 2-s2.0-33744957163 10.1074/jbc.M513453200 (Pubitemid 43855183)
2. Sato T., Dohmae N., Qi Y., Kakuda N., Misonou H., Mitsumori R., Maruyama H., Koo E. H., Haass C., Takio K., Morishima-Kawashima M., Ishiura S., Ihara Y., Potential link between amyloid β -protein 42 and C-terminal fragment γ 49-99 of β -amyloid precursor protein. Journal of Biological Chemistry 2003 278 27 24294 20301 2-s2.0-0041589353 10.1074/jbc.M211161200 (Pubitemid 37548579)
3. Qi-Takahara Y., Morishima-Kawashima M., Tanimura Y., Dolios G., Hirotani N., Horikoshi Y., Kametani F., Maeda M., Saido T. C., Wang R., Ihara Y., Longer forms of amyloid β protein: implications for the mechanism of intramembrane cleavage by γ -secretase. Journal of Neuroscience 2005 25 2 436 445 2-s2.0-19944430034 10.1523/JNEUROSCI.1575-04.2005 (Pubitemid 40105614)
4. Takami M., Nagashima Y., Sano Y., Ishihara S., Morishima-Kawashima M., Funamoto S., Ihara Y., γ -Secretase: successive tripeptide and tetrapeptide release from the transmembrane domain of β -carboxyl terminal fragment. Journal of Neuroscience 2009 29 41 13042 13052 2-s2.0-70350451482 10.1523/JNEUROSCI.2362-09.2009
5. Golde T. E., Ran Y., Felsenstein K. M., Shifting a complex debate on γ -secretase cleavage and Alzheimer's disease. The EMBO Journal 2012 31 10 2237 2239 10.1038/emboj.2012.111
6. Suzuki N., Cheung T. T., Cai X. D., Odaka A., Otvos L., Eckman C., Golde T. E., Younkin S. G., An increased percentage of long amyloid β protein secreted by familial amyloid β protein precursor (β APP717) mutants. Science 1994 264 5163 1336 1340 2-s2.0-0028322017
7. Saito T., Suemoto T., Brouwers N., Sleegers K., Funamoto S., Mihira N., Matsuba Y., Yamada K., Nilsson P., Takano J., Nishimura M., Iwata N., Van Broeckhoven C., Ihara Y., Saido T. C., Potent amyloidogenicity and pathogenicity of A β 243. Nature Neuroscience 2011 14 8 1023 1032 10.1038/nn.2858
8. Jarrett J. T., Berger E. P., Lansbury P. T. Jr., The carboxy terminus of the β amyloid protein is critical for the seeding of amyloid formation: Implications for the pathogenesis of Alzheimer's disease. Biochemistry 1993 32 18 4693 4697 2-s2.0-0027258525 (Pubitemid 23162022)
9. Milano J., McKay J., Dagenais C., Foster-Brown L., Pognan F., Gadient R., Jacobs R. T., Zacco A., Greenberg B., Ciaccio P. J., Modulation of Notch processing by γ -secretase inhibitors causes intestinal goblet cell metaplasia and induction of genes known to specify gut secretory lineage differentiation. Toxicological Sciences 2004 82 1 341 358 2-s2.0-8444247084 10.1093/toxsci/kfh254 (Pubitemid 39485346)
10. Searfoss G. H., Jordan W. H., Calligaro D. O., Galbreath E. J., Schirtzinger L. M., Berridge B. R., Gao H., Higgins M. A., May P. C., Ryan T. P., Adipsin, a biomarker of gastrointestinal toxicity mediated by a functional γ -secretase inhibitor. Journal of Biological Chemistry 2003 278 46 46107 46116 2-s2.0-0242412482 10.1074/jbc.M307757200 (Pubitemid 37432761)
11. Wong G. T., Manfra D., Poulet F. M., Zhang Q., Josien H., Bara T., Engstrom L., Pinzon-Ortiz M., Fine J. S., Lee H. J. J., Zhang L., Higgins G. A., Parker E. M., Chronic treatment with the γ -secretase inhibitor LY-411,575 inhibits γ -amyloid peptide production and alters lymphopoiesis and intestinal cell differentiation. Journal of Biological Chemistry 2004 279 13 12876 12882 2-s2.0-11144355129 10.1074/jbc.M311652200 (Pubitemid 38445862)
12. Lilly E., Lilly Halts Development of Semagacestat for Alzheimer's Disease Based on Preliminary Results of Phase III Clinical Trials. 2010, http://newsroom.lilly.com/releasedetail.cfm?releaseid=499794
13. Selkoe D. J., Resolving controversies on the path to Alzheimer's therapeutics. Nature Medicine 2011 17 9 1060 1065
14. Imbimbo B. P., Panza F., Frisardi V., Solfrizzi V., D'Onofrio G., Logroscino G., Seripa D., Pilotto A., Therapeutic intervention for Alzheimer's disease with γ -secretase inhibitors: still a viable option? Expert Opinion on Investigational Drugs 2011 20 3 325 341 2-s2.0-79951617234 10.1517/13543784.2011.550572
15. Weggen S., Eriksen J. L., Das P., Sagi S. A., Wang R., Pietrzik C. U., Findlay K. A., Smith T. E., Murphy M. P., Bulter T., Kang D. E., Marquez-Sterling N., Golde T. E., Koo E. H., A subset of NSAIDs lower amyloidogenic A β 42 independently of cyclooxygenase activity. Nature 2001 414 6860 212 216 2-s2.0-0035829592 10.1038/35102591 (Pubitemid 33051236)
16. Golde T. E., Schneider L. S., Koo E. H., Anti-A β therapeutics in alzheimer's disease: the need for a paradigm shift. Neuron 2011 69 2 203 213 2-s2.0-78751692575 10.1016/j.neuron.2011.01.002
17. Imbimbo B. P., Why did tarenflurbil fail in alzheimer's disease? Journal of Alzheimer's Disease 2009 17 4 757 760 2-s2.0-68049148021 10.3233/JAD-2009- 1092
18. Green R. C., Schneider L. S., Amato D. A., Beelen A. P., Wilcock G., Swabb E. A., Zavitz K. H., Effect of tarenflurbil on cognitive decline and activities of daily living in patients with mild Alzheimer disease: a randomized controlled trial. Journal of the American Medical Association 2009 302 23 2557 2564 2-s2.0-72549105935 10.1001/jama.2009.1866
19. Bulic B., Ness J., Hahn S., Rennhack A., Jumpertz T., Weggen S., Chemical biology, molecular mechanism and clinical perspective of γ -secretase modulators in Alzheimer's disease. Current Neuropharmacology 2011 9 4 598 622
20. Hubbs J. L., Fuller N. O., Austin W. F., Shen R., Creaser S. P., McKee T. D., Loureiro R. M. B., Tate B., Xia W., Ives J., Bronk B. S., Optimization of a natural product-based class of gamma-secretase modulators. Journal of Medicinal Chemistry 2012 55 21 9270 9282 10.1021/jm300976b
21. Koo E. H. M., Golde T. E., Galasko D. R., Nonsteroidal antiinflammatory drug (NSAID) and NSAID derivative amyloid A β 42 polypeptide-lowering agents for the treatment of Alzheimer's disease, and screening methods. pp. 73, Mayo Foundation for Medical Education and Research, USA, 2001
22. Raveglia L., Peretto I., Radaelli S., Imbimbo B. P., Rizzi A., Villetti G., Preparation of 1-phenylalkanecarboxylic acid derivatives for the treatment of neurodegenerative diseases. pp. 91, Chiesi Farmaceutici S.p.A., Italy, 2004
23. Blurton P., Arylacetic acids and related compounds and their preparation, pharmaceutical compositions and their use for treatment of diseases associated with the deposition of β -amyloid peptides in the brain such as Alzheimer's disease. pp. 58, Merck Sharp & Dohme Limited, UK, 2006
24. Ho C. Y., Preparation of Biphenyl Derivatives as γ -secretAse Modulators 2009 Belg, Germany Janssen Pharmaceutica
25. Wilson F., Reid A., Reader V., Preparation of biphenylacetic acids as γ -secretase modulators for the treatment of Alzheimer's disease. pp. 57, Cellzome, Germany, 2006
26. Shapiro G., Chesworth R., 1,3,4-Trisubstituted benzenes as γ -secretase inhibitors and their preparation and use in the treatment of neurodegenerative diseases. pp. 165, Envivo Pharmaceuticals, USA, 2009
27. Kulagowski J. J., Madin A., Ridgill P. M., Seward M. E., Preparation of piperidines and related compounds for treatment of Alzheimer's disease. pp. 178, Merck Sharp & Dohme Limited, UK, 2006
28. Hall A., Elliott R. L., Giblin G. M. P., Hussain I., Musgrave J., Sasse R., Smith B., Piperidine-derived γ -secretase modulators. Bioorganic and Medicinal Chemistry Letters 2010 20 3 1306 1311 10.1016/j.bmcl.2009.08.072
29. Am E. C. W., Aminocyclohexanes and aminotetrahydropyrans as γ -secretase modulators and their preparation and use for thetreatment of neurological and psychiatric diseases. pp. 91, Pfizer, USA, 2011
30. Cheng S., Comer D. D., Mao L., Balow G. P., Pleynet D., Aryl compounds and uses in modulating amyloid β pp. 178, Neurogenetics, USA 2004
31. Baumann K., Preparation of thiazolyl-substituted imidazolylphenylamine derivatives and related compounds as modulators of amyloid beta. pp. 32, Hoffmann-La Roche, USA, 2008
32. Marcin L. R., Preparation of bicyclic compounds, especially bicyclic triazoles, for the reduction of beta-amyloid protein production. pp. 242, Bristol-Myers Squibb Company, USA, 2010
33. Forsblom R., Paulsen K., Waldman M., Rotticci D., Santangelo E., Preparation of 2-aminopyrimidines as amyloid beta modulators. pp. 227, AstraZeneca AB, Sweden, 2010
34. Biswas K., Chen J. J., Falsey J. R., Preparation of urea compounds as gamma secretase modulators. pp. 116, Amgen, USA, 2009
35. Gijsen H. J. M., Velter A. I., MacDonald G. J., Novel substituted bicyclic heterocyclic compounds as gamma secretase modulators and their preparation and use in the treatment of diseases. pp. 164, Ortho-Mcneil-Janssen Pharmaceuticals, USA, 2010
36. Blurton P., Preparation of heteroarylpiperazine derivatives for use in treatment of Alzheimer's disease. pp.68, Merck & Co., Merck Sharp & Dohme Limited, USA, 2008
37. Findeis M. A., Schroeder F., McKee T. D., Yager D., Fraering P. C., Creaser S. P., Austin W. F., Clardy J., Wang R., Selkoe D., Eckman C. B., Discovery of a novel pharmacological and structural class of gamma secretase modulators derived from the extract of actaea racemosa. ACS Chemical Neuroscience 2012 3 11 941 951 10.1021/cn3000857
38. Haugabook S. J., Yager D. M., Eckman E. A., Golde T. E., Younkin S. G., Eckman C. B., High throughput screens for the identification of compounds that alter the accumulation of the Alzheimer's amyloid β peptide (A β). Journal of Neuroscience Methods 2001 108 2 171 179 2-s2.0-0035974232 10.1016/S0165-0270(01)00388-0 (Pubitemid 32674401)
39. Murphy M. P., Uljon S. N., Fraser P. E., Fauq A., Lookingbill H. A., Findlay K. A., Smith T. E., Lewis P. A., Chris McLendon D., Wang R., Golde T. E., Presenilin 1 regulates pharmacologically distinct γ -secretase activities: implications for the role of presenilin in γ -secretase cleavage. Journal of Biological Chemistry 2000 275 34 26277 26284 2-s2.0-0034714316 10.1074/jbc.M002812200
40. Lanz T. A., Karmilowicz M. J., Wood K. M., Pozdnyakov N., Du P., Piotrowski M. A., Brown T. M., Nolan C. E., Richter K. E. G., Finley J. E., Fei Q., Ebbinghaus C. F., Chen Y. L., Spracklin D. K., Tate B., Geoghegan K. F., Lau L.-F., Auperin D. D., Schachter J. B., Concentration-dependent modulation of amyloid- β in vivo and in vitro using the γ -secretase inhibitor, LY-450139. Journal of Pharmacology and Experimental Therapeutics 2006 319 2 924 933 10.1124/jpet.106.110700
41. Rogers K., Optimization of a natural product-based class of gamma secretase modulators. International Conference on Alzheimer's Disease 2009 Vienna, Austria
42. Burton C. R., Meredith J. E., Barten D. M., Goldstein M. E., Krause C. M., Kieras C. J., Sisk L., Iben L. G., Polson C., Thompson M. W., Lin X.-A., Corsa J., Fiedler T., Pierdomenico M., Cao Y., Roach A. H., Cantone J. L., Ford M. J., Drexler D. M., Olson R. E., Yang M. G., Bergstrom C. P., McElhone K. E., Bronson J. J., Macor J. E., Blat Y., Grafstrom R. H., Stern A. M., Seiffert D. A., Zaczek R., Albright C. F., Toyn J. H., The amyloid- β rise and γ -secretase inhibitor potency depend on the level of substrate expression. Journal of Biological Chemistry 2008 283 34 22992 23003 10.1074/jbc.M804175200
43. Hughes J. D., Blagg J., Price D. A., Bailey S., DeCrescenzo G. A., Devraj R. V., Ellsworth E., Fobian Y. M., Gibbs M. E., Gilles R. W., Greene N., Huang E., Krieger-Burke T., Loesel J., Wager T., Whiteley L., Zhang Y., Physiochemical drug properties associated with in vivo toxicological outcomes. Bioorganic and Medicinal Chemistry Letters 2008 18 17 4872 4875 10.1016/j.bmcl.2008.07.071
44. Wager T. T., Hou X., Verhoest P. R., Villalobos A., Moving beyond rules: the development of a central nervous system multiparameter optimization (CNS MPO) approach to enable alignment of druglike properties. ACS Chemical Neuroscience 2010 1 6 435 449 2-s2.0-77953675980 10.1021/cn100008c
45. Wager T. T., Chandrasekaran R. Y., Hou X., Troutman M. D., Verhoest P. R., Villalobos A., Will Y., Defining desirable central nervous system drug space through the alignment of molecular properties, in vitro ADME, and safety attributes. ACS Chemical Neuroscience 2010 1 6 420 434 2-s2.0-77953680038 10.1021/cn100007x
46. Lovering F., Bikker J., Humblet C., Escape from flatland: increasing saturation as an approach to improving clinical success. Journal of Medicinal Chemistry 2009 52 21 6752 6756 2-s2.0-71049126548 10.1021/jm901241e
47. Ritchie T. J., Macdonald S. J. F., The impact of aromatic ring count on compound developability-are too many aromatic rings a liability in drug design? Drug Discovery Today 2009 14 21-22 1011 1020 2-s2.0-70350409235 10.1016/j.drudis.2009.07.014
48. Kimura T., Kawano K., Doi E., Preparation of cinnamide, 3-benzylidenepiperidin-2-one, phenylpropynamide compounds as amyloid β production inhibitors. pp. 679, Eisai, Japan, 2005
49. Ebke A., Luebbers T., Fukumori A., Shirotani K., Haass C., Baumann K., Steiner H., Novel γ -secretase enzyme modulators directly target presenilin protein. Journal of Biological Chemistry 2011 286 37181 37186
50. Wolfe M. S., gamma-Secretase inhibitors and modulators for Alzheimer's disease. Journal of Neurochemistry 2012 120 supplement 1 89 98
51. Ohki Y., Higo T., Uemura K., Shimada N., Osawa S., Berezovska O., Yokoshima S., Fukuyama T., Tomita T., Iwatsubo T., Phenylpiperidine-type γ -secretase modulators target the transmembrane domain 1 of presenilin 1. The EMBO Journal 2011 30 23 4815 4824 10.1038/emboj.2011.372
52. Weggen S., Beher D., Molecular consequences of amyloid precursor protein and presenilin mutations causing autosomal-dominant Alzheimer's disease. Alzheimer's Research and Therapy 2012 4 2 9 10.1186/alzrt107
53. Takeo K., Watanabe N., Tomita T., Iwatsubo T., Contribution of the γ -secretase subunits to the formation of catalytic pore of presenilin 1 protein. Journal of Biological Chemistry 2012 287 31 25834 25843 10.1074/jbc.M111.336347