Assessing the target differentiation potential of imidazole-based protein kinase inhibitors

Journal of Medicinal Chemistry

Volumn 55, Issue 24, 2012, Pages 11067-11071

  Dimova, Dilyana ^a   Iyer, Preeti ^a   Vogt, Martin ^a   Totzke, Frank ^c   Kubbutat, Michael H G ^c   Schächtele, Christoph ^c   Laufer, Stefan ^b   Bajorath, Jürgen ^a  

^a UNIVERSITY OF BONN   (Germany)

^b UNIVERSITY OF TÜBINGEN   (Germany)

^c PROQINASE GMBH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE DERIVATIVE; PROTEIN KINASE; PROTEIN KINASE INHIBITOR;

ARTICLE; DRUG RESEARCH; DRUG SCREENING; DRUG STRUCTURE; DRUG TARGETING; ENZYME INHIBITION;

ENZYME ASSAYS; IMIDAZOLES; NEOPLASMS; PROTEIN KINASE INHIBITORS; PROTEIN KINASES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84871644568     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3014508     Document Type: Article

References (25)

1. Rix, U.; Superti-Furga, G. Target Profiling of Small Molecules by Chemical Proteomics Nat. Chem. Biol. 2009, 5, 616-624
2. Bajorath, J. Computational Analysis of Ligand Relationships within Target Families Curr. Opin. Chem. Biol. 2008, 12, 352-358
3. Kenakin, T. Functional Selectivity in GPCR Modulator Screening Comb. Chem. High Throughput Screening 2008, 11, 337-343 (Pubitemid 351830304)
4. Allen, J. A.; Roth, B. L. Strategies To Discover Unexpected Targets for Drugs Active at G Protein-Coupled Receptors Annu. Rev. Pharmacol. Toxicol. 2011, 51, 117-144
5. Goldstein, D. M.; Gray, N. S.; Zarrinkar, P. P. High-Throughput Kinase Profiling as a Platform for Drug Discovery Nat. Rev. Drug Discovery 2008, 6, 391-397 (Pubitemid 351619111)
6. Bi, K.; Lebakken, C. S.; Vogel, K. W. Transformation of in Vitro Tools for Kinase Profiling: Keeping an Eye over the Off-Target Liabilities Expert Opin. Drug Discovery 2011, 6, 701-712
7. Fabian, M. A.; Biggs, W. H., 3rd; Treiber, D. K.; Atteridge, C. E.; Azimioara, M. D.; Benedetti, M. G.; Carter, T. A.; Ciceri, P.; Edeen, P. T.; Floyd, M.; Ford, J. M.; Galvin, M.; Gerlach, J. L.; Grotzfeld, R. M.; Herrgard, S.; Insko, D. E.; Insko, M. A.; Lai, A. G.; Lélias, J. M.; Mehta, S. A.; Milanov, Z. V.; Velasco, A. M.; Wodicka, L. M.; Patel, H. K.; Zarrinkar, P. P.; Lockhart, D. J. A Small Molecule-Kinase Interaction Map for Clinical Kinase Inhibitors Nat. Biotechnol. 2005, 23, 329-336 (Pubitemid 41094421)
8. Metz, J. T.; Johnson, E. F.; Soni, N. B.; Merta, P. J.; Kifle, L.; Hajduk, P. J. Navigating the Kinome Nat. Chem. Biol. 2011, 7, 200-202
9. Milletti, F.; Hermann, J. C. Targeted Kinase Selectivity from Kinase Profiling Data ACS Med. Chem. Lett. 2012, 3, 383-386
10. Martin, E.; Mukherjee, P. Kinase-Kernel Models: Accurate in Silico Screening of 4 Million Compounds across the Entire Human Kinome J. Chem. Inf. Model. 2012, 52, 156-170
11. Niijima, S.; Shiraishi, A.; Okuno, Y. Dissecting Kinase Profile Data To Predict Activity and Understand Cross-Reactivity of Kinase Inhibitors J. Chem. Inf. Model. 2012, 52, 901-912
12. Laufer, S. A.; Wagner, G. K. From Imidazoles to Pyrimidines: New Inhibitors of Cytokine Release J. Med. Chem. 2002, 45, 2733-2740 (Pubitemid 34627645)
13. Laufer, S. A.; Kotschenreuther, D.; Wagner, G. K. Ones, Thiones and N -Oxides: An Exercise in Imidazole Chemistry Angew. Chem., Int. Ed. 2002, 41, 2290-2293 (Pubitemid 34778546)
14. Laufer, S. A.; Striegel, H.-G.; Wagner, G. K. Imidazole Inhibitors of Cytokine Release: Probing Substituents in the 2 Position J. Med. Chem. 2002, 45, 4695-4705
15. Laufer, S. A.; Kotschenreuther, D. A.; Wagner, G. K.; Albrecht, W. Novel Substituted Pyridinyl Imidazoles as Potent Anti-Cytokine Agents with Low Cytochrome P450 Activity J. Med. Chem. 2003, 46, 3230-3244 (Pubitemid 36849601)
16. 1H-NMR J. Org. Chem. 2003, 68, 4527-4530 (Pubitemid 36622746)
17. Laufer, S. A.; Striegel, H.-G.; Zimmermann, W.; Ruff, K. J. Tetrasubstituted Imidazole Inhibitors of Cytokine Release: Probing Substituents in the N-1 Position J. Med. Chem. 2004, 47, 6311-6325 (Pubitemid 39587255)
18. ProQinase Free Choice Biochemical Kinase Assays. http://www.proqinase. com/ (accessed September 3, 2012).
19. Dimova, D.; Bajorath, J. Computational Chemical Biology: Identification of Small Molecular Probes that Discriminate between Members of Target Protein Families Chem. Biol. Drug Des. 2012, 79, 369-375
20. Willett, P.; Barnard, J. M.; Downs, G. M. Chemical Similarity Searching J. Chem. Inf. Comput. Sci. 1998, 38, 983-996 (Pubitemid 128591261)
21. MACCS Structural Keys; Symyx Software: San Ramon, CA, U.S., 2005.
22. Wagner, G.; Laufer, S. Small Molecular Anti-Cykotine Agents Med. Res. Rev. 2006, 26, 1-62
23. Tong, L.; Pav, S.; White, D. M.; Rogers, S.; Crane, K. M.; Cywin, C. L.; Brown, M. L.; Pargellis, C. A. A Highly Specific Inhibitor of Human p38 MAP Kinase Binds in the ATP Pocket Nat. Struct. Biol. 1997, 4, 311-316 (Pubitemid 27157204)
24. Karaman, M. W.; Herrgard, S.; Treiber, D. K.; Gallant, P.; Atteridge, C. E.; Campbell, B. T.; Chan, K. W.; Ciceri, P.; Davis, M. I.; Edeen, P. T.; Faraoni, R.; Floyd, M.; Hunt, J. P.; Lockhart, D. J.; Milanov, Z. V.; Morrison, M. J.; Pallares, G.; Patel, H. K.; Pritchard, S.; Wodicka, L. M.; Zarrinkar, P. P. A Quantitative Analysis of Kinase Inhibitor Selectivity Nat. Biotechnol. 2008, 26, 127-132
25. Cheng, A. C.; John Eksterowicz, J.; Geuns-Meyer, S.; Sun, Y. Analysis of Kinase Inhibitor Selectivity Using a Thermodynamics-Based Partition Index J. Med. Chem. 2010, 53, 4502-4510