Structural optimization of a CXCR2-directed antagonist that indirectly inhibits γ-secretase and reduces Aβ

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 23, 2009, Pages 8102-8112

  Bakshi, Pancham ^a   Jin, Chao ^a   Broutin, Pierre ^a   Berhane, Beniam ^a   Reed, Jon ^a   Mullan, Michael ^a  

^a ROSKAMP INSTITUTE   (United States)

Author keywords

Alzheimer's disease; Amyloid beta; CXCR2; Secretase

Indexed keywords

1 (2 BROMOPHENYL) 3 (2 HYDROXY 4 NITROPHENYL)UREA; AMYLOID BETA PROTEIN; AMYLOID BETA PROTEIN[1-40]; AMYLOID PRECURSOR PROTEIN; CHEMOKINE RECEPTOR ANTAGONIST; CHEMOKINE RECEPTOR CXCR2; G PROTEIN COUPLED RECEPTOR; GAMMA SECRETASE; GAMMA SECRETASE INHIBITOR;

ALZHEIMER DISEASE; ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ALZHEIMER DISEASE; AMYLOID BETA-PROTEIN; AMYLOID PRECURSOR PROTEIN SECRETASES; ANIMALS; CHO CELLS; CRICETINAE; CRICETULUS; ENZYME INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; PHENYLUREA COMPOUNDS; RECEPTORS, INTERLEUKIN-8B; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 71849088630     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.09.051     Document Type: Article

References (44)

1. Hardy J., and Selkoe D.J. Science 297 (2002) 353
2. Wilquet V., and De Strooper B. Curr. Opin. Neurobiol. 14 (2004) 582
3. Esler W.P., and Wolfe M.S. Science 293 (2001) 1449
4. Dominguez D.I., and De Strooper B. Trends Pharmacol. Sci. 23 (2002) 324
5. Jakob-Roetne R., and Jacobsen H. Angew. Chem., Int. Ed. 48 (2009) 3030
6. Yan R., Bienkowski M.J., Shuck M.E., Miao H., Tory M.C., Pauley A.M., Brashier J.R., Stratman N.C., Mathews W.R., Buhl A.E., Carter D.B., Tomasselli A.G., Parodi L.A., Heinrikson R.L., and Gurney M.E. Nature 402 (1999) 533
7. Hussain I., Powell D., Howlett D.R., Tew D.G., Meek T.D., Chapman C., Gloger I.S., Murphy K.E., Southan C.D., Ryan D.M., Smith T.S., Simmons D.L., Walsh F.S., Dingwall C., and Christie G. Mol. Cell Neurosci. 14 (1999) 419
8. Vassar R., Bennett B.D., Babu-Khan S., Kahn S., Mendiaz E.A., Denis P., Teplow D.B., Ross S., Amarante P., Loeloff R., Luo Y., Fisher S., Fuller J., Edenson S., Lile J., Jarosinski M.A., Biere A.L., Curran E., Burgess T., Louis J.C., Collins F., Treanor J., Rogers G., and Citron M. Science 286 (1999) 735
9. Sinha S., Anderson J.P., Barbour R., Basi G.S., Caccavello R., Davis D., Doan M., Dovey H.F., Frigon N., Hong J., Jacobson-Croak K., Jewett N., Keim P., Knops J., Lieberburg I., Power M., Tan H., Tatsuno G., Tung J., Schenk D., Seubert P., Suomensaari S.M., Wang S., Walker D., and John V. Nature 402 (1999) 537
10. Guo T., and Hobbs D.W. Curr. Med. Chem. 13 (2006) 1811
11. Dominguez D., Tournoy J., Hartmann D., Huth T., Cryns K., Deforce S., Serneels L., Camacho I.E., Marjaux E., Craessaerts K., Roebroek A.J., Schwake M., D'Hooge R., Bach P., Kalinke U., Moechars D., Alzheimer C., Reiss K., Saftig P., and De Strooper B. J. Biol. Chem. 280 (2005) 30797
12. Ghosh A.K., Kumaragurubaran N., Hong L., Koelsh G., and Tang J. Curr. Alzheimer Res. 5 (2008) 121
13. Evin G., and Kenche V.B. Recent Pat. CNS Drug Disc. 2 (2007) 188
14. Hills I.D., and Vacca J.P. Curr. Opin. Drug Discovery Dev. 10 (2007) 383
15. Wolfe M.S. Biochemistry 45 (2006) 7931
16. Edbauer D., Winkler E., Regula J.T., Pesold B., Steiner H., and Haass C. Nat. Cell Biol. 5 (2003) 486
17. Kimberly W.T., LaVoie M.J., Ostaszewski B.L., Ye W., Wolfe M.S., and Selkoe D.J. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 6382
18. Takasugi N., Tomita T., Hayashi I., Tsuruoka M., Niimura M., Takahashi Y., Thinakaran G., and Iwatsubo T. Nature 422 (2003) 438
19. Li H., Wolfe M.S., and Selkoe D.J. Structure 17 (2009) 326
20. Osenkowski P., Li H., Ye W., Li D., Aeschbach L., Fraering P.C., Wolfe M.S., Selkoe D.J., and Li H. J. Mol. Biol. 385 (2009) 642
21. Wolfe M.S. Neurotherapeutics 5 (2008) 391
22. Esler W.P., Das C., and Wolfe M.S. Bioorg. Med. Chem. Lett. 14 (2004) 1935
23. Esler W.P., Kimberly W.T., Ostaszewski B.L., Ye W., Diehl T.S., Selkoe D.J., and Wolfe M.S. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 2720
24. Wolfe M.S. Curr. Alzheimer Res. 5 (2008) 158
25. Kornilova A.Y., Bihel F., Das C., and Wolfe M.S. Proc. Natl. Acad. Sci. U.S.A. 102 (2005) 3230
26. Bakshi P., and Wolfe M.S. J. Med. Chem. 47 (2004) 6485
27. Wolfe M.S.B.M.C. Neuroscience 9 (2008) S4
28. Bateman R.J., Siemers E.R., Mawuenyega K.G., Wen G., Browning K.R., Sigurdson W.C., Yarasheski K.E., Friedrich S.W., Demattos R.B., May P.C., Paul S.M., and Holtzman D.M. Ann. Neurol. (2009)
29. Fleisher A.S., Raman R., Siemers E.R., Becerra L., Clark C.M., Dean R.A., Farlow M.R., Galvin J.E., Peskind E.R., Quinn J.F., Sherzai A., Sowell B.B., Aisen P.S., and Thal L.J. Arch. Neurol. 65 (2008) 1031
30. Kukar T.L., Ladd T.B., Bann M.A., Fraering P.C., Narlawar R., Maharvi G.M., Healy B., Chapman R., Welzel A.T., Price R.W., Moore B., Rangachari V., Cusack B., Eriksen J., Jansen-West K., Verbeeck C., Yager D., Eckman C., Ye W., Sagi S., Cottrell B.A., Torpey J., Rosenberry T.L., Fauq A., Wolfe M.S., Schmidt B., Walsh D.M., Koo E.H., and Golde T.E. Nature 453 (2008) 925
31. Bakshi P., Margenthaler E., Laporte V., Crawford F., and Mullan M. ACS Chem. Biol. 3 (2008) 777
32. Ni Y., Zhao X., Bao G., Zou L., Teng L., Wang Z., Song M., Xiong J., Bai Y., and Pei G. Nat. Med. 12 (2006) 1390
33. Thathiah A., Spittaels K., Hoffmann M., Staes M., Cohen A., Horre K., Vanbrabant M., Coun F., Baekelandt V., Delacourte A., Fischer D.F., Pollet D., De Strooper B., and Merchiers P. Science 323 (2009) 946
34. Kuo L.H., Hu M.K., Hsu W.M., Tung Y.T., Wang B.J., Tsai W.W., Yen C.T., and Liao Y.F. Mol. Biol. Cell (2008)
35. White J.R., Lee J.M., Young P.R., Hertzberg R.P., Jurewicz A.J., Chaikin M.A., Widdowson K., Foley J.J., Martin L.D., Griswold D.E., and Sarau H.M. J. Biol. Chem. 273 (1998) 10095
36. Jin Q., Nie H., McCleland B.W., Widdowson K.L., Palovich M.R., Elliott J.D., Goodman R.M., Burman M., Sarau H.M., Ward K.W., Nord M., Orr B.M., Gorycki P.D., and Busch-Petersen J. Bioorg. Med. Chem. Lett. 14 (2004) 4375
37. Widdowson K.L., Elliott J.D., Veber D.F., Nie H., Rutledge M.C., McCleland B.W., Xiang J.N., Jurewicz A.J., Hertzberg R.P., Foley J.J., Griswold D.E., Martin L., Lee J.M., White J.R., and Sarau H.M. J. Med. Chem. 47 (2004) 1319
38. McCleland B.W., Davis R.S., Palovich M.R., Widdowson K.L., Werner M.L., Burman M., Foley J.J., Schmidt D.B., Sarau H.M., Rogers M., Salyers K.L., Gorycki P.D., Roethke T.J., Stelman G.J., Azzarano L.M., Ward K.W., and Busch-Petersen J. Bioorg. Med. Chem. Lett. 17 (2007) 1713
39. Koo E.H., and Squazzo S.L. J. Biol. Chem. 269 (1994) 17386
40. Liao Y.F., Wang B.J., Cheng H.T., Kuo L.H., and Wolfe M.S. J. Biol. Chem. 279 (2004) 49523
41. Kuo L.H., Hu M.K., Hsu W.M., Tung Y.T., Wang B.J., Tsai W.W., Yen C.T., and Liao Y.F. Mol. Biol. Cell 19 (2008) 4201
42. Lee S., and Das H.K. Brain Res. 1207 (2008) 19
43. Campbell W.A., Iskandar M.K., Reed M.L., and Xia W. Biochemistry 41 (2002) 3372
44. Baxter A., Bennion C., Bent J., Boden K., Brough S., Cooper A., Kinchin E., Kindon N., McInally T., Mortimore M., Roberts B., and Unitt J. Bioorg. Med. Chem. Lett. 13 (2003) 2625