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Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 12, 2013, Pages 3654-3661

Small-molecule pyrimidine inhibitors of the cdc2-like (Clk) and dual specificity tyrosine phosphorylation-regulated (Dyrk) kinases: Development of chemical probe ML315

(9) Coombs, Thomas C a Tanega, Cordelle b Shen, Min b Wang, Jenna L a Auld, Douglas S b Gerritz, Samuel W c Schoenen, Frank J a Thomas, Craig J b Aubé, Jeffrey a

a UNIVERSITY OF KANSAS (United States)

b NATIONAL INSTITUTES OF HEALTH (United States)

c BRISTOL MYERS SQUIBB (United States)

Author keywords

Clk; Dyrk; Kinase inhibitor; Pyrimidine; Splicing

Indexed keywords

CLK1 PROTEIN; CLK2 PROTEIN; CLK4 PROTEIN; DYRK1A KINASE; DYRK1B KINASE; HARMINE; KHCB 19; LEUCETTINE L; ML 315; PROTEIN KINASE INHIBITOR; PROTEIN TYROSINE KINASE; PROTEIN TYROSINE KINASE INHIBITOR; PYRIMIDINE DERIVATIVE; QUINOLINE DERIVATIVE; TG 003; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG DESIGN; DRUG INHIBITION; DRUG POTENCY; DRUG SELECTIVITY; DRUG SOLUBILITY; DRUG STABILITY; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; HUMAN; IC 50; MAXIMUM PLASMA CONCENTRATION; MOLECULAR PROBE; NONHUMAN; PROTEIN PHOSPHORYLATION; STRUCTURE ACTIVITY RELATION;

PHOSPHORYLATION; PROTEIN-SERINE-THREONINE KINASES; PROTEIN-TYROSINE KINASES; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 84878111705 PISSN: 0960894X EISSN: 14643405 Source Type: Journal
DOI: 10.1016/j.bmcl.2013.02.096 Document Type: Article

Times cited : (45)

References (48)

1
- 0030778935
- O. Nayler, S. Stamm, and A. Ullrich Biochem. J. 326 1997 693
- (1997) Biochem. J. , vol.326 , pp. 693
- Nayler, O.¹ Stamm, S.² Ullrich, A.³

2
- 0038656410
- J. Prasad, and J.L. Manley Mol. Cell. Biol. 23 2003 4139
- (2003) Mol. Cell. Biol. , vol.23 , pp. 4139
- Prasad, J.¹ Manley, J.L.²

3
- 0032526770
- P.I. Duncan, D.F. Stojdl, R.M. Marius, K.H. Scheit, and J.C. Bell Exp. Cell Res. 241 1998 300
- (1998) Exp. Cell Res. , vol.241 , pp. 300
- Duncan, P.I.¹ Stojdl, D.F.² Marius, R.M.³ Scheit, K.H.⁴ Bell, J.C.⁵

4
- 61449243728
- A.N. Bullock, S. Das, J.É. Debreczeni, P. Rellos, O. Fedorov, F.H. Niesen, K. Guo, E. Papagrigoriou, A.L. Amos, S. Cho, B.E. Turk, G. Ghosh, and S. Knapp Structure 17 2009 352
- (2009) Structure , vol.17 , pp. 352
- Bullock, A.N.¹ Das, S.² Debreczeni, J.É.³ Rellos, P.⁴ Fedorov, O.⁵ Niesen, F.H.⁶ Guo, K.⁷ Papagrigoriou, E.⁸ Amos, A.L.⁹ Cho, S.¹⁰ Turk, B.E.¹¹ Ghosh, G.¹² Knapp, S.¹³

5
- 58249093940
- J.C. Long, and J.F. Caceres Biochem. J. 417 2009 15
- (2009) Biochem. J. , vol.417 , pp. 15
- Long, J.C.¹ Caceres, J.F.²

6
- 2342450548
- M.A. Garcia-Blanco, A.P. Baraniak, and E.L. Lasda Nat. Biotechnol. 22 2004 535
- (2004) Nat. Biotechnol. , vol.22 , pp. 535
- Garcia-Blanco, M.A.¹ Baraniak, A.P.² Lasda, E.L.³

7
- 29144463738
- M. Hagiwara BBA-Proteins Proteom. 1754 2005 324
- (2005) BBA-Proteins Proteom. , vol.1754 , pp. 324
- Hagiwara, M.¹

8
- 66449111724
- K. Jiang, N.A. Patel, J.E. Watson, H. Apostolatos, E. Kleiman, O. Hanson, M. Hagiwara, and D.R. Cooper Endocrinology 150 2009 2087
- (2009) Endocrinology , vol.150 , pp. 2087
- Jiang, K.¹ Patel, N.A.² Watson, J.E.³ Apostolatos, H.⁴ Kleiman, E.⁵ Hanson, O.⁶ Hagiwara, M.⁷ Cooper, D.R.⁸

9
- 79958844308
- R. Wong, A. Balachandran, A.YQ Mao, W. Dobson, S. Gray-Owen, and A. Cochrane Retrovirology 8 2011 47
- (2011) Retrovirology , vol.8 , pp. 47
- Wong, R.¹ Balachandran, A.² Mao, A.Y.³ Dobson, W.⁴ Gray-Owen, S.⁵ Cochrane, A.⁶

10
- 39749151729
- J.-i. Yomoda, M. Muraki, N. Kataoka, T. Hosoya, M. Suzuki, M. Hagiwara, and H. Kimura Genes Cells 13 2008 233
- (2008) Genes Cells , vol.13 , pp. 233
- Yomoda, J.-I.¹ Muraki, M.² Kataoka, N.³ Hosoya, T.⁴ Suzuki, M.⁵ Hagiwara, M.⁶ Kimura, H.⁷

11
- 63649100364
- A. Eisenreich, V.Y. Bogdanov, A. Zakrzewicz, A. Pries, S. Antoniak, W. Poller, H.-P. Schultheiss, and U. Rauch Circ. Res. 104 2009 589
- (2009) Circ. Res. , vol.104 , pp. 589
- Eisenreich, A.¹ Bogdanov, V.Y.² Zakrzewicz, A.³ Pries, A.⁴ Antoniak, S.⁵ Poller, W.⁶ Schultheiss, H.-P.⁷ Rauch, U.⁸

12
- 72649098153
- J.T. Rodgers, W. Haas, S.P. Gygi, and P. Puigserver Cell Metab. 11 2010 23
- (2010) Cell Metab. , vol.11 , pp. 23
- Rodgers, J.T.¹ Haas, W.² Gygi, S.P.³ Puigserver, P.⁴

13
- 0033572973
- H. Menegay, F. Moeslein, and G. Landreth Exp. Cell Res. 253 1999 463
- (1999) Exp. Cell Res. , vol.253 , pp. 463
- Menegay, H.¹ Moeslein, F.² Landreth, G.³

14
- 0027939858
- M.P. Myers, M.B. Murphy, and G. Landreth Mol. Cell. Biol. 14 1994 6954
- (1994) Mol. Cell. Biol. , vol.14 , pp. 6954
- Myers, M.P.¹ Murphy, M.B.² Landreth, G.³

15
- 2342655502
- 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
- (2004) J. Biol. Chem. , vol.279 , pp. 24246
- Muraki, M.¹ Ohkawara, B.² Hosoya, T.³ Onogi, H.⁴ Koizumi, J.⁵ Koizumi, T.⁶ Sumi, K.⁷ Yomoda, J.-I.⁸ Murray, M.V.⁹ Kimura, H.¹⁰ Furuichi, K.¹¹ Shibuya, H.¹² Krainer, A.R.¹³ Suzuki, M.¹⁴ Hagiwara, M.¹⁵

16
- 84878110967
- Smith, WO 2008/014602 A1
- Hekimi, S.; McBride, K.; Hihi, A.K.; Kianicka, I.; Wang, Y.; Hayes, S. L.; Guimond, M.-P.; Sévigny, G.; Dumas, D.; Smith, WO 2008/014602 A1, 2008.
- (2008)
- Hekimi, S.¹ McBride, K.² Hihi, A.K.³ Kianicka, I.⁴ Wang, Y.⁵ Hayes, S.L.⁶ Guimond, M.-P.⁷ Sévigny, G.⁸ Dumas, D.⁹

17
- 79251579303
- 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
- (2011) Chem. Biol. , vol.18 , pp. 67
- Fedorov, O.¹ Huber, K.² Eisenreich, A.³ Filippakopoulos, P.⁴ King, O.⁵ Bullock, A.N.⁶ Szklarczyk, D.⁷ Jensen, L.J.⁸ Fabbro, D.⁹ Trappe, J.¹⁰ Rauch, U.¹¹ Bracher, F.¹² Knapp, S.¹³

18
- 79959406830
- M. Debdab, F. Carreaux, S. Renault, M. Soundararajan, O. Fedorov, P. Filippakopoulos, O. Lozach, L. Babault, T. Tahtouh, B. Baratte, Y. Ogawa, M. Hagiwara, A. Eisenreich, U. Rauch, S. Knapp, L. Meijer, and J.-P. Bazureau J. Med. Chem. 54 2011 4172
- (2011) J. Med. Chem. , vol.54 , pp. 4172
- Debdab, M.¹ Carreaux, F.² Renault, S.³ Soundararajan, M.⁴ Fedorov, O.⁵ Filippakopoulos, P.⁶ Lozach, O.⁷ Babault, L.⁸ Tahtouh, T.⁹ Baratte, B.¹⁰ Ogawa, Y.¹¹ Hagiwara, M.¹² Eisenreich, A.¹³ Rauch, U.¹⁴ Knapp, S.¹⁵ Meijer, L.¹⁶ Bazureau, J.-P.¹⁷

19
- 79551647919
- S. Aranda, A. Laguna, and S. de la Luna FASEB J. 25 2011 449
- (2011) FASEB J. , vol.25 , pp. 449
- Aranda, S.¹ Laguna, A.² De La Luna, S.³

20
- 0032475973
- W. Becker, Y. Weber, K. Wetzel, K. Eirmbter, F.J. Tejedor, and H.-G. Joost J. Biol. Chem. 273 1998 25893
- (1998) J. Biol. Chem. , vol.273 , pp. 25893
- Becker, W.¹ Weber, Y.² Wetzel, K.³ Eirmbter, K.⁴ Tejedor, F.J.⁵ Joost, H.-G.⁶

21
- 78651070244
- W. Becker, and W. Sippl FEBS J. 278 2011 246
- (2011) FEBS J. , vol.278 , pp. 246
- Becker, W.¹ Sippl, W.²

22
- 70349947061
- N. Göckler, G. Jofre, C. Papadopoulos, U. Soppa, F.J. Tejedor, and W. Becker FEBS J. 276 2009 6324
- (2009) FEBS J. , vol.276 , pp. 6324
- Göckler, N.¹ Jofre, G.² Papadopoulos, C.³ Soppa, U.⁴ Tejedor, F.J.⁵ Becker, W.⁶

23
- 78651062069
- F.J. Tejedor, and B. Hämmerle FEBS J. 278 2011 223
- (2011) FEBS J. , vol.278 , pp. 223
- Tejedor, F.J.¹ Hämmerle, B.²

24
- 0033135902
- J. Guimera, C. Casas, X. Estivill, and M. Pritchard Genomics 57 1999 407
- (1999) Genomics , vol.57 , pp. 407
- Guimera, J.¹ Casas, C.² Estivill, X.³ Pritchard, M.⁴

25
- 77949678789
- O. Yabut, J. Domogauer, and G. D'Arcangelo J. Neurosci. 30 2010 4004
- (2010) J. Neurosci. , vol.30 , pp. 4004
- Yabut, O.¹ Domogauer, J.² D'Arcangelo, G.³

26
- 70350512022
- J. Park, W.-J. Song, and K.C. Chung Cell. Mol. Life Sci. 66 2009 3235
- (2009) Cell. Mol. Life Sci. , vol.66 , pp. 3235
- Park, J.¹ Song, W.-J.² Chung, K.C.³

27
- 26944433068
- I. Ferrer, M. Barrachina, B. Puig, M. Martínez de Lagrán, E. Martí, J. Avila, and M. Dierssen Neurobiol. Dis. 20 2005 392
- (2005) Neurobiol. Dis. , vol.20 , pp. 392
- Ferrer, I.¹ Barrachina, M.² Puig, B.³ Martínez De Lagrán, M.⁴ Martí, E.⁵ Avila, J.⁶ Dierssen, M.⁷

28
- 78651061790
- J. Wegiel, C.-X. Gong, and Y.-W. Hwang FEBS J. 278 2011 236
- (2011) FEBS J. , vol.278 , pp. 236
- Wegiel, J.¹ Gong, C.-X.² Hwang, Y.-W.³

29
- 33645531727
- K. de Graaf, H. Czajkowska, S. Rottmann, L.C. Packman, R. Lilischkis, B. Luscher, and W. Becker BMC Biochem. 7 2006 7
- (2006) BMC Biochem. , vol.7 , pp. 7
- De Graaf, K.¹ Czajkowska, H.² Rottmann, S.³ Packman, L.C.⁴ Lilischkis, R.⁵ Luscher, B.⁶ Becker, W.⁷

30
- 0036724569
- V. Fotaki, M. Dierssen, S. Alcántara, S. Martínez, E. Martí, C. Casas, J. Visa, E. Soriano, X. Estivill, and M.L. Arbonés Mol. Cell. Biol. 22 2002 6636
- (2002) Mol. Cell. Biol. , vol.22 , pp. 6636
- Fotaki, V.¹ Dierssen, M.² Alcántara, S.³ Martínez, S.⁴ Martí, E.⁵ Casas, C.⁶ Visa, J.⁷ Soriano, E.⁸ Estivill, X.⁹ Arbonés, M.L.¹⁰

31
- 43049162678
- R.S. Møller, S. Kübart, M. Hoeltzenbein, B. Heye, I. Vogel, C.P. Hansen, C. Menzel, R. Ullmann, N. Tommerup, H.-H. Ropers, Z. Tümer, and V.M. Kalscheuer Am. J. Hum. Gen. 82 2008 1165
- (2008) Am. J. Hum. Gen. , vol.82 , pp. 1165
- Møller, R.S.¹ Kübart, S.² Hoeltzenbein, M.³ Heye, B.⁴ Vogel, I.⁵ Hansen, C.P.⁶ Menzel, C.⁷ Ullmann, R.⁸ Tommerup, N.⁹ Ropers, H.-H.¹⁰ Tümer, Z.¹¹ Kalscheuer, V.M.¹²

32
- 55949091108
- K. Yoshida Biochem. Pharmacol. 76 2008 1389
- (2008) Biochem. Pharmacol. , vol.76 , pp. 1389
- Yoshida, K.¹

33
- 77951225449
- X. Guo, J.G. Williams, T.T. Schug, and X. Li J. Biol. Chem. 285 2010 13223
- (2010) J. Biol. Chem. , vol.285 , pp. 13223
- Guo, X.¹ Williams, J.G.² Schug, T.T.³ Li, X.⁴

34
- 0033582339
- S. Leder, Y. Weber, X. Altafaj, X. Estivill, H.-G. Joost, and W. Becker Biochem. Biophys. Res. Commun. 254 1999 474
- (1999) Biochem. Biophys. Res. Commun. , vol.254 , pp. 474
- Leder, S.¹ Weber, Y.² Altafaj, X.³ Estivill, X.⁴ Joost, H.-G.⁵ Becker, W.⁶

35
- 77953284901
- M. Lauth, A. Bergstrom, T. Shimokawa, U. Tostar, Q. Jin, V. Fendrich, C. Guerra, M. Barbacid, and R. Toftgard Nat. Struct. Mol. Biol. 17 2010 718
- (2010) Nat. Struct. Mol. Biol. , vol.17 , pp. 718
- Lauth, M.¹ Bergstrom, A.² Shimokawa, T.³ Tostar, U.⁴ Jin, Q.⁵ Fendrich, V.⁶ Guerra, C.⁷ Barbacid, M.⁸ Toftgard, R.⁹

36
- 34948848556
- E. Friedman J. Cell. Biochem. 102 2007 274
- (2007) J. Cell. Biochem. , vol.102 , pp. 274
- Friedman, E.¹

37
- 33746457418
- S.E. Mercer, and E. Friedman Cell Biochem. Biophys. 45 2006 303
- (2006) Cell Biochem. Biophys. , vol.45 , pp. 303
- Mercer, S.E.¹ Friedman, E.²

38
- 79951946396
- T. Adayev, J. Wegiel, and Y.-W. Hwang Arch. Biochem. Biophys. 507 2011 212
- (2011) Arch. Biochem. Biophys. , vol.507 , pp. 212
- Adayev, T.¹ Wegiel, J.² Hwang, Y.-W.³

39
- 71749110422
- B.T. Mott, C. Tanega, M. Shen, D.J. Maloney, P. Shinn, W. Leister, J.J. Marugan, J. Inglese, C.P. Austin, T. Misteli, D.S. Auld, and C.J. Thomas Bioorg. Med. Chem. Lett. 19 2009 6700
- (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 6700
- Mott, B.T.¹ Tanega, C.² Shen, M.³ Maloney, D.J.⁴ Shinn, P.⁵ Leister, W.⁶ Marugan, J.J.⁷ Inglese, J.⁸ Austin, C.P.⁹ Misteli, T.¹⁰ Auld, D.S.¹¹ Thomas, C.J.¹²

40
- 84878109002
- WO 2005/042525 A1
- Wang, S.; Wood, G.; Duncan, K.W.; Meades, C.; Gibson, D.; McLachlan, J.C.; Perry, A.; Blake, D.; Zheleva, D.I.; Fischer, P.M. WO 2005/042525 A1, 2005.
- (2005)
- Wang, S.¹ Wood, G.² Duncan, K.W.³ Meades, C.⁴ Gibson, D.⁵ McLachlan, J.C.⁶ Perry, A.⁷ Blake, D.⁸ Zheleva, D.I.⁹ Fischer, P.M.¹⁰

41
- 84878112288
- http://www.reactionbiology.com/pages/kinase.htm
- http://www.reactionbiology.com/pages/kinase.htm.

42
- 76449108493
- C. Tanega, M. Shen, B.T. Mott, C.J. Thomas, R. MacArthur, J. Inglese, and D.S. Auld Assay Drug Dev. Technol. 7 2009 606
- (2009) Assay Drug Dev. Technol. , vol.7 , pp. 606
- Tanega, C.¹ Shen, M.² Mott, B.T.³ Thomas, C.J.⁴ Macarthur, R.⁵ Inglese, J.⁶ Auld, D.S.⁷

43
- 79955567813
- A.S. Rosenthal, C. Tanega, M. Shen, B.T. Mott, J.M. Bougie, D.-T. Nguyen, T. Misteli, D.S. Auld, D.J. Maloney, and C.J. Thomas Bioorg. Med. Chem. Lett. 21 2011 3152
- (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 3152
- Rosenthal, A.S.¹ Tanega, C.² Shen, M.³ Mott, B.T.⁴ Bougie, J.M.⁵ Nguyen, D.-T.⁶ Misteli, T.⁷ Auld, D.S.⁸ Maloney, D.J.⁹ Thomas, C.J.¹⁰

44
- 84878109536
- An MLPCN probe report describing ML315 will soon be published on the NCBI bookshelf
- An MLPCN probe report describing ML315 will soon be published on the NCBI bookshelf: http://www.ncbi.nlm.nih.gov/books/NBK47352/.

45
- 84876675322
- J.G. Topliss J. Med. Chem. 1006 1972 15
- (1972) J. Med. Chem. , vol.1006 , pp. 15
- Topliss, J.G.¹

46
- 84899255665
- J. Garner, T. Hill, L. Odell, P. Keller, J. Morgan, and A. McCluskey Aust. J. Chem. 1079 2004 57
- (2004) Aust. J. Chem. , vol.1079 , pp. 57
- Garner, J.¹ Hill, T.² Odell, L.³ Keller, P.⁴ Morgan, J.⁵ McCluskey, A.⁶

47
- 17844384784
- C.D. Gutierrez, V. Bavetsias, and E. McDonald Tetrahedron Lett. 46 2005 3595
- (2005) Tetrahedron Lett. , vol.46 , pp. 3595
- Gutierrez, C.D.¹ Bavetsias, V.² McDonald, E.³

48
- 84878108553
- SYBYL 8.0; Tripos Associates:, St. Louis, MO, 2010
- SYBYL 8.0; Tripos Associates:, St. Louis, MO, 2010.

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