Identification of peptide substrate and small molecule inhibitors of Testis-Specific Serine/Threonine Kinase1 (TSSK1) by the developed assays

Journal of Medicinal Chemistry

Volumn 52, Issue 14, 2009, Pages 4419-4428

  Zhang, Leilei ^a   Yan, Yu ^a   Liu, Zijie ^a   Abliz, Zeper ^a   Liu, Gang ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

PROTEIN SERINE THREONINE KINASE; PROTEIN SERINE THREONINE KINASE INHIBITOR;

ARTICLE; ENZYME ANALYSIS; ENZYME ASSAY; ENZYME INHIBITION; ENZYME PHOSPHORYLATION; ENZYME SUBSTRATE; LIQUID CHROMATOGRAPHY; LUMINESCENCE; MASS SPECTROMETRY;

AMINO ACID SEQUENCE; ANIMALS; BIPHENYL COMPOUNDS; CATTLE; CHROMATOGRAPHY, LIQUID; DRUG DISCOVERY; DRUG EVALUATION, PRECLINICAL; LUMINESCENT MEASUREMENTS; MASS SPECTROMETRY; MOLECULAR SEQUENCE DATA; PEPTIDES; PROTEIN KINASE INHIBITORS; PROTEIN-SERINE-THREONINE KINASES; QUINOXALINES; REPRODUCIBILITY OF RESULTS; SMALL MOLECULE LIBRARIES;

EID: 67650756925     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9002846     Document Type: Article

References (44)

1. Manning, G.; Whyte, D. B.; Martinez, R.; Hunter, T.; Sudarsanam, S. The protein kinase complement of the human genome. Science 2002, 298, 1912-1934.
2. Cohen, P. Protein kinases - the major drug targets of the twenty-first century?. Nat. Rev. Drug Discovery 2002, 1, 309-315.
3. Bielke, W.; Blaschke, R. J.; Miescher, G. C.; Zurcher, G.; Andres, A. C.; Ziemiecki, A. Characterization of a novel murine testis-specific serine/threonine kinase. Gene 1994, 139, 235-239.
4. Kueng, P.; Nikolova, Z.; Djonov, V.; Hemphill, A.; Rohrbach, V.; Boehlen, D.; Zuercher, G.; Andres, A. C.; Ziemiecki, A. A Novel Family of Serine/Threonine Kinases Participating in Spermiogenesis. J. Cell Biol. 1997, 139, 1851-1859.
5. Zuercher, G.; Rohrbach, V.; Andres, A. C.; Ziemiecki, A. A novel member of the testis specific serine kinase family, tssk-3, expressed in the Leydig cells of sexually mature mice. Mech. Dev. 2000, 93, 175-177.
6. Visconti, P. E.; Hao, Z.; Purdon, M. A.; Stein, P.; Balsara, B. R.; Testa, J. R.; Herr, J. C.; Moss, S. B.; Kopf, G. S. Cloning and chromosomal localization of a gene encoding a novel serine/threonine kinase belonging to the subfamily of testis-specific kinases. Genomics 2001, 77, 163-170.
7. Bucko-Justyna, M.; Lipinski, L.; Burgering, B. M.; Trzeciak, L. Characterization of testis-specific serine-threonine kinase 3 and its activation by phosphoinositide-dependent kinase-1-dependent signalling. FEBS J. 2005, 272, 6310-6323.
8. Chen, X.; Lin, G.; Wei, Y.; Hexige, S.; Niu, Y.; Liu, L.; Yang, C.; Yu, L. TSSK5, a novel member of the testis-specific serine/threonine kinase family, phosphorylates CREB at Ser-133, and stimulates the CRE/CREB responsive pathway. Biochem. Biophys. Res. Commun. 2005, 333, 742-749.
9. Hao, Z.; Jha, K. N.; Kim, Y. H.; Vemuganti, S.; Westbrook, V. A.; Chertihin, O.; Markgraf, K.; Flickinger, C. J.; Coppola, M.; Herr, J. C.; Visconti, P. E. Expression analysis of the human testis-specific serine/threonine kinase (TSSK) homologues. A TSSK member is present in the equatorial segment of human sperm. Mol. Hum. Reprod. 2004, 10, 433-444.
10. Spiridonov, N. A.; Wong, L.; Zerfas, P. M.; Starost, M. F.; Pack, S. D.; Paweletz, C. P.; Johnson, G. R. Identification and characterization of SSTK, a serine/threonine protein kinase essential for male fertility. Mol. Cell. Biol. 2005, 25, 4250-4256.
11. Xu, B.; Hao, Z.; Jha, K. N.; Digilio, L.; Urekar, C.; Kim, Y. H.; Pulido, S.; Flickinger, C. J.; Herr, J. C. Validation of a testis specific serine/threonine kinase [TSSK] family and the substrate of TSSK1 & 2, TSKS, as contraceptive targets. Soc. Reprod. Fertil. Suppl. 2007, 63, 87-101.
12. Herr, J. C.; Xu, B.; Hao, Z. Validation of TSSK family members and TSKS as male contraceptive targets. U.S. Patent US 2008/0274117 A1, 2008.
13. Xu, B.; Hao, Z.; Jha, K. N.; Zhang, Z.; Urekar, C.; Digilio, L.; Pulido, S.; Strauss, J. F.; Flickinger, C. J.; Herr, J. C. Targeted deletion of Tssk1 and 2 causes male infertility due to haploinsufficiency. Dev. Biol. 2008, 319, 211-222.
14. AnaSpec; www.anaspec.com, accessed October 6, 2005.
15. Cell Signaling Technology; www.cellsignal.com, accessed October 6, 2005.
16. Hu, H.; Li, L.; Kao, R. Y.; Kou, B.; Wang, Z.; Zhang, L.; Zhang, H.; Hao, Z.; Tsui, W. H.; Ni, A.; Cui, L.; Fan, B.; Guo, F.; Rao, S.; Jiang, C.; Li, Q.; Sun, M.; He, W.; Liu, G. Screening and identification of linear B-cell epitopes and entry-blocking peptide of severe acute respiratory syndrome (SARS)-associated coronavirus using synthetic overlapping peptide library. J. Comb. Chem. 2005, 7, 648-656.
17. Promega; www.promega.com, accessed September 18, 2007.
18. Zhao, H. Y.; Liu, G. Solution-phase parallel synthesis of diverse 1,5-benzodiazepin-2-ones. J. Comb. Chem. 2007, 9, 1164-1176.
19. 6-benzo[1, 4]thiazin-3-one. J. Comb. Chem. 2007, 9, 959-972.
20. Zhao, H. Y.; Liu, G. Solution-phase parallel synthesis of 2,3-dihydro-1,5-benzothiazepin-4(5H)-ones. J. Comb. Chem. 2007, 9, 756-772.
21. 6-benzo[1,4]thiazin-3-one derivatives from 1,5-difluoro-2,4-dinitrobenzene. J. Comb. Chem. 2007, 9, 652-660.
22. Yuan, Y. Y.; Liu, G.; Li, L.; Wang, Z. G.; Wang, L. Synthesis of diverse benzo[1,4]oxazin-3-one-based compounds using 1,5-difluoro-2,4-dinitrobenzene. J. Comb. Chem. 2007, 9, 158-170.
23. Yang, T. M.; Liu, G. Solution-phase parallel synthesis of 3,5,6-substituted indolin-2-ones. J. Comb. Chem. 2007, 9, 86-95.
24. Liu, G.; Li, L.; Kou, B. B.; Zhang, S. D.; Zhang, L.; Yuan, Y. Y.; Ma, T.; Shang, Y.; Li, Y. C. Benzofused tricycles based on 2-quinoxalinol. J. Comb. Chem. 2007, 9, 70-78.
25. Kou, B. B.; Zhang, F.; Yang, T. M.; Liu, G. Simultaneous solid-phase synthesis of quinoxalinone and benzimidazole scaffold libraries. J. Comb. Chem. 2006, 8, 841-847.
26. Zhang, J.; Zhang, L.; Zhang, S. D.; Liu, G. Solution-phase parallel synthesis of a 1,2,7-trialkyl-1H-imidazo[4,5-g]quinoxalin-6-ol library scaffold. J. Comb. Chem. 2005, 7, 657-664.
27. Li, L.; Liu, G. Multistep parallel synthesis of substituted 5-amino-benzimidazoles in solution phase. J. Comb. Chem. 2004, 6, 811-821.
28. Zhang, L.; Liu, G. Parallel approach for solution-phase synthesis of 2-quinoxalinol analogues and their inhibition of LPS-induced TNF-α release on mouse macrophages in vitro. J. Comb. Chem. 2004, 6, 431-436.
29. Wu, X. H.; Liu, G. Solution-phase reductive cyclization of 2-quinoxalinol analogs: systematic study of parallel synthesis.. Mol. Diversity 2004, 8, 165-174.
30. Jia, Y.; Quinn, C. M.; Gagnon, A. I.; Talanian, R. Homogeneous time-resolved fluorescence and its applications for kinase assays in drug discovery. Anal. Biochem. 2006, 356, 273-281.
31. Seethala, R.; Menzel, R. A homogeneous, fluorescence polarization assay for src-family tyrosine kinases. Anal. Biochem. 1997, 253, 210-218.
32. Seethala, R.; Menzel, R. A fluorescence polarization competition immunoassay for tyrosine kinases. Anal. Biochem. 1998, 255, 257-262.
33. Kupcho, K.; Somberg, R.; Bulleit, B.; Goueli, S. A homogeneous, nonradioactive high-throughput fluorogenic protein kinase assay. Anal. Biochem. 2003, 317, 210-217.
34. Tritsch, D.; Hemmerlin, A.; Rohmer, M.; Bach, T. J. A sensitive radiometric assay to measure D-xylulose kinase activity. J. Biochem. Biophys. Methods 2004, 58, 75-83.
35. Park, Y. W.; Cummings, R. T.; Wu, L.; Zheng, S.; Cameron, P. M.; Woods, A.; Zaller, D. M.; Marcy, A. I.; Hermes, J. D. Homogeneous proximity tyrosine kinase assays: scintillation proximity assay versus homogeneous time-resolved fluorescence. Anal. Biochem. 1999, 269, 94-104.
36. Tagliati, F.; Bottoni, A.; Bosetti, A.; Zatelli, M. C.; degli Uberti, E. C. Utilization of luminescent technology to develop a kinase assay: Cdk4 as a model system. J. Pharm. Biomed. Anal. 2005, 39, 811-814.
37. Baki, A.; Bielik, A.; Molnar, L.; Szendrei, G.; Keseru, G. M. A High throughput luminescent assay for glycogen synthase kinase-3β inhibitors. Assay Drug Dev. Technol. 2007, 5, 75-83.
38. Chapman, E.; Wong, C. H. A pH sensitive colorometric assay for the high-throughput screening of enzyme inhibitors and substrates: a case study using kinase. Bioorg. Med. Chem. 2002, 10, 551-555.
39. Wang, Z.; Lévy, R.; Fernig, D. G.; Brust, M. Kinase-catalyzed modification of gold nanoparticles: a new approach to colorimetric kinase activity screening. J. Am. Chem. Soc. 2006, 128, 2214-2215.
40. Greis, K. D. Mass spectrometry for enzyme assays and inhibitor screening: an emerging application in pharmaceutical research. Mass Spectrom. Rev. 2007, 26, 324-339.
41. de Boer, A. R.; Lingeman, H.; Niessen, W. M. A.; Irth, H. Mass spectrometry-based biochemical assays for enzyme inhibitor screening. Trends Anal. Chem 2007, 26, 867-883.
42. Ge, X.; Sirich, T. L.; Beyer, M. K.; Desaire, H.; Leary, J. A. A strategy for the determination of enzyme kinetics using electrospray ionization with an ion trap mass spectrometer. Anal. Chem. 2001, 73, 5078-5082.
43. Wu, Y. L.; Wang, L.; Jiang, X. J.; Huang, L. Studies on the antiviral compounds III. The synthesis of aromatic α-glyoxals. Acta Pharm. Sin. 1965, 12, 254-266.
44. Liu, G.; Lam, K. S. "One-bead one-compound" combinatorial library method. In Combinatorial Chemistry, Practical Approach; Fenniri, H., Ed.; Oxford University Press: New York, 2000; pp 33-49.