Potent and selective small molecule inhibitors of specific isoforms of Cdc2-like kinases (Clk) and dual specificity tyrosine-phosphorylation-regulated kinases (Dyrk)

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 10, 2011, Pages 3152-3158

  Rosenthal, Andrew S ^a   Tanega, Cordelle ^a   Shen, Min ^a   Mott, Bryan T ^a   Bougie, James M ^a   Nguyen, Dac Trung ^a   Misteli, Tom ^b   Auld, Douglas S ^a   Maloney, David J ^a   Thomas, Craig J ^a  

^a NATIONAL HUMAN GENOME RESEARCH INSTITUTE   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

Clk1; Clk2; Clk3; Clk4; Dyrk1A; Dyrk1B; Kinase inhibition; Pre mRNA splicing; Quinazoline

Indexed keywords

CYCLIN DEPENDENT KINASE; CYCLIN DEPENDENT KINASE 1; CYCLIN DEPENDENT KINASE 2; CYCLIN DEPENDENT KINASE 3; CYCLIN DEPENDENT KINASE 4; CYCLIN DEPENDENT KINASE INHIBITOR; DUAL SPECIFICITY TYROSINE PHOSPHORYLATION REGULATED KINASE 1A; DUAL SPECIFICITY TYROSINE PHOSPHORYLATION REGULATED KINASE 1B; ML 195; ML 196; ML 197; PHOSPHOTRANSFERASE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; PROTEIN PHOSPHORYLATION; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; SUZUKI REACTION;

ENZYME ACTIVATION; ENZYME INHIBITORS; INHIBITORY CONCENTRATION 50; ISOENZYMES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOSPHORYLATION; PROTEIN-SERINE-THREONINE KINASES; PROTEIN-TYROSINE KINASES; QUINAZOLINES; SMALL MOLECULE LIBRARIES; SUBSTRATE SPECIFICITY; THIAZOLES;

EID: 79955567813     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.02.114     Document Type: Article

References (44)

1. J. Prasad, and J.L. Manley Mol. Cell. Biol. 23 2003 4139
2. D.L. Black Annu. Rev. Biochem. 72 2003 291
3. Z. Wang, and C.B. Burge RNA 14 2008 802
4. N.A. Faustino, and T.A. Cooper Genes Dev. 17 2003 419
5. C. He, F. Zhou, Z. Zuo, H. Cheng, and R. Zhou PLoS ONE 4 2009 e4732
6. A.J. Matlin, F. Clark, and C.W.J. Smith Nature 6 2005 386
7. K. Jiang, N.A. Patel, J.E. Watson, H. Apostolatos, E. Kleiman, O. Hanson, M. Hagiwara, and D.R. Cooper Endocrinology 150 2009 2087
8. H. Schwertz, N.D. Tolley, J.M. Foulks, M.M. Denis, B.W. Risenmay, M. Buerke, R.E. Tilley, M.T. Rondina, E.M. Harris, L.W. Kraiss, N. Mackman, G.A. Zimmerman, and A.S. Weyrich J. Exp. Med. 203 2006 2433
9. M. Muraki, B. Ohkawara, T. Hosoya, H. Onogi, J. Koizumi, T. Koizumi, K. Sumi, J.-i. Yomoda, M.V. Murray, H. Kimura, K. Furuichi, H. Shibuya, A.R. Krainer, M. Suzuki, and M. Hagiwara J. Biol. Chem. 279 2004 24246
10. J.-i. Yomoda, M. Muraki, N. Kataoka, T. Hosoya, M. Suzuki, M. Hagiwara, and H. Kimura Genes Cells 13 2008 233
11. A.M. Hartmann, D. Rujescu, T. Giannakouros, E. Nikolakaki, M. Goedert, E.-M. Mandelkow, Q.S. Gao, A. Andreadis, and S. Stamm Mol. Cell. Neurosci. 18 2001 80
12. Perni, R. B.; Bemis, J.; Nunes, J. J.; Szczepankiewicz, B. G. Inhibitors of the CDC2-like Kinases and Methods of Use Therof. WO 2009/085226 A2, 9 July 2009.
13. Hekimi, S.; McBride, K.; Hihi, A. K.; Kianjcka, I.; Wang, Y.; Hayes, S. L.; Guimond, M.-P.; Sevigny, G.; Dumas, D.; Smith, J. New Quinoline Derivatives. 60/832937, 25 July 2006.
14. O. Fedorov, K. Huber, A. Eisenreich, P. Filippakopoulos, O. King, A.N. Bullock, D. Szklarczyk, L.J. Jensen, D. Fabbro, J. Trappe, U. Rauch, F. Bracher, and S. Knapp Chem. Biol. 18 2011 67
15. B.T. Mott, C. Tanega, M. Shen, D.J. Maloney, P. Shinn, W. Leister, J.J. Marugan, J. Inglese, C.P. Austin, T. Mistelli, D.S. Auld, and C.J. Thomas Bioorg. Med. Chem. Lett. 19 2009 6700
16. W. Becker, Y. Weber, K. Wetzel, K. Eirmbter, F.J. Tejedor, and H.-G. Joost J. Biol. Chem. 273 1998 25893
17. M. Alvarez, X. Estivill, and S.d.l. Luna J. Cell Sci. 116 2003 3099
18. K. de Graaf, H. Czajkowska, S. Rottmann, L. Packman, R. Lilischkis, B. Luscher, and W. Becker BMC Biochemistry 7 2006 7
19. J. Park, W.-J. Song, and K.C. Chung Cell. Mol. Life Sci. 66 2009 3235
20. K. Yoshida Biochem. Pharmacol. 76 2008 1389
21. N.D. Kim, J. Yoon, J.H. Kim, J.T. Lee, Y.S. Chon, M.-K. Hwang, I. Hac, and W.-J. Songc Bioorg. Med. Chem. Lett. 16 2006 3772
22. A. Seifert, L.A. Allan, and P.R. Clarke FEBS J. 275 2008 6268
23. J. Guimera, C. Casas, X. Estivill, and M. Pritchard Genomics 57 1999 407
24. F.J. Tejedor, and B. Hammerle FEBS J. 278 2011 223
25. J. Wegiel, C.-X. Gong, and Y.-W. Hwang FEBS J. 278 2011 236
26. D. Toiber, G. Azkona, S. Ben-Ari, N. Toran, H. Soreq, and M. Dierssen Neurobiol. Dis. 40 2010 348
27. X. Guo, J.G. Williams, T.T. Schug, and X. Li J. Biol. Chem. 285 2010 13223
28. O. Yabut, J. Domogauer, and G. D'Arcangelo J. Neurosci. 30 2010 4004
29. J.R. Arron, M.M. Winslow, A. Polleri, C.-P. Chang, H. Wu, X. Gao, J.R. Neilson, L. Chen, J.J. Heit, S.K. Kim, N. Yamasaki, T. Miyakawa, U. Francke, I.A. Graef, and G.R. Crabtree Nature 441 2006 595
30. S.E. Mercer, and E. Friedman Cell Biochem. Biophys. 45 2006 303
31. K. Lee, X. Deng, and E. Friedman Cancer Res. 60 2000 3631
32. E. Friedman Cancers 2 2010 1492
33. K. Jin, S. Park, D.Z. Ewton, and E. Friedman Cancer Res. 67 2007 7247
34. E. Friedman J. Cell Biol. 102 2007 274
35. K. Jin, D.Z. Ewton, S. Park, J. Hu, and E. Friedman J. Biol. Chem. 284 2009 22916
36. J. Gao, Z. Zheng, B. Rawal, M.J. Schell, G. Bepler, and E.B. Haura Cancer Biol. Ther. 8 2009 1671
37. J. Bain, L. Plater, M. Elliott, N. Shpiro, C.J. Hastie, H. McLauchlan, I. Klevernic, J.S.C. Arthur, D.R. Alessi, and P. Cohen Biochem. J. 408 2007 297
38. N. Gockler, G. Jofre, C. Papadopoulos, U. Soppa, F.J. Tejedor, and W. Becker FEBS J. 276 2009 6324
39. W. Becker, and W. Sippl FEBS J. 278 2011 246
40. < www.tarceva.com >.
41. P.B. Mehta, B.L. Jenkins, L. McCarthy, L. Thilak, C.N. Robson, D.E. Neal, and H.Y. Leung Oncogene 22 2003 1381
42. D. Makoto, S. Hidenori, O. Toshihide, T. Sayumi, S. Takafumi, K. Shigeru, J. Yumi, W. Kiriko, K. Wataru, S. Shinji, Y. Hiroshi, E. Mitsuru, M. Masaaki, K. Isao, K. Sumio, and T. Kato Biochem. Biophys. Res. Commun. 365 2008 466
43. MOE Molecular Operating EnVironment, 2008.10; Chemical Computing Group Inc.: Montreal, Canada, 2008.
44. FRED, OpenEye Scientific Software, Inc.: Santa Fe, NM, 2010. < http://www.eyesopen.com/ >.