New class of competitive inhibitor of bacterial histidine kinases

Journal of Bacteriology

Volumn 187, Issue 23, 2005, Pages 8196-8200

  Gilmour, Raymond ^a   Foster, J Estelle ^a,c   Sheng, Qin ^a   McClain, Jonathan R ^a   Riley, Anna ^a   Sun, Pei Ming ^a   Ng, Wai Leung ^b   Yan, Dalai ^a,d   Nicas, Thalia I ^a   Henry, Kenneth ^a   Winkler, Malcolm E ^b  

^a ELI LILLY AND COMPANY   (United States)

^b INDIANA UNIVERSITY   (United States)

^c Protana Inc   (Canada)

^d INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,6 DIAMINO 5 CYANO 4 PHENYLTHIENO[2,3 B]PYRIDINE 2 CARBOXYLIC ACID (4 BROMOPHENYL) AMIDE; ANTIBIOTIC AGENT; ENZYME INHIBITOR; PROTEIN HISTIDINE KINASE; THIENO[2,3 B]PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL CELL; CONTROLLED STUDY; ENTEROCOCCUS FAECIUM; ENZYME INHIBITION; ESCHERICHIA COLI; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; NONHUMAN; PRIORITY JOURNAL; STREPTOCOCCUS PNEUMONIAE;

BACTERIAL PROTEINS; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; PROTEIN KINASES; PYRIDINES;

ANIMALIA; BACTERIA (MICROORGANISMS); ENTEROCOCCUS FAECIUM; ESCHERICHIA COLI; MAMMALIA; NEGIBACTERIA; POSIBACTERIA; STREPTOCOCCUS PNEUMONIAE;

EID: 28044469003     PISSN: 00219193     EISSN: None     Source Type: Journal    
DOI: 10.1128/JB.187.23.8196-8200.2005     Document Type: Article

References (48)

1. Barrett, J. F., and J. A. Hoch. 1998. Two-component signal transduction as a target for microbial anti-infective therapy. Antimicrob. Agents Chemother. 42:1529-1536.
2. Besant, P. G., M. V. Lasker, C. D. Bui, and C. W. Turck. 2002. Inhibition of branched-chain alpha-keto acid dehydrogenase kinasc and Sln1 yeast histidine kinase by the antifungal antibiotic radicicol. Mol. Pharmacol. 62:289-296.
3. Bijlsma, J. J., and E. A. Groisman. 2003. Making informed decisions: regulatory interactions between two-component systems. Trends Microbiol. 11:359-366.
4. Cherry, M., and D. H. Williams. 2004. Recent kinase and kinase inhibitor X-ray structures: mechanisms of inhibition and selectivity insights. Curr. Med. Chem. 11:663-673.
5. Dubrac, S., and T. Msadek. 2004. Identification of genes controlled by the essential YycG/YycF two-component system of Staphylococcus aureus. J. Bacteriol. 186:1175-1181.
6. Dutta, R., and M. Inouye. 2000. GHKL, an emergent ATPase/kinase superfamily. Trends Biochem. Sci. 25:24-28.
7. Dutta, R., L. Qin, and M. Inouye. 1999. Histidine kinases: diversity of domain organization. Mol. Microbiol. 34:633-640.
8. Dutta, R., T. Yoshida, and M. Inouye. 2000. The critical role of the conserved Thr247 residue in the functioning of the osmosensor EnvZ, a histidine kinase/phosphatase, in Escherichia coli. J. Biol. Chem. 275:38645-38653.
9. Echenique, J. R., and M. C. Trombe. 2001. Competence repression under oxygen limitation through the two-component MicAB signal-transducing system in Streptococcus pneumoniae and involvement of the PAS domain of MicB. J. Bacteriol. 183:4599-4608.
10. Fabret, C., and J. A. Hoch. 1998. A two-component signal transduction system essential for growth of Bacillus subtilis: implications for anti-infective therapy. J. Bacteriol. 180:6375-6383.
11. Fischer, P. M. 2004. The design of drug candidate molecules as selective inhibitors of therapeutically relevant protein kinases. Curr. Med. Chem. 11:1563-1583.
12. Foster, J. E., Q. Sheng, J. R. McClain, M. Bures, T. I. Nicas, K. Henry, M. E. Winkler, and R. Gilmour. 2004. Kinetic and mechanistic analyses of new classes of inhibitors of two-component signal transduction systems using a coupled assay containing HpkA-DrrA from Thermotoga maritima. Microbiology 150:885-896.
13. Furuta, E., K. Yamamoto, D. Tatebe, K. Watabe, T. Kitayama, and R. Utsumi. 2005. Targeting protein homodimerization: a novel drug discovery system. FEES Lett. 579:2065-2070.
14. Grissom-Arnold, J., W. E. Alborn, Jr., T. I. Nicas, and S. R. Jaskunas. 1997. Induction of VanA vancomycin resistance genes in Enterococcus faecalis: use of a promoter fusion to evaluate glycopeptide and nonglycopeptide induction signals. Microb. Drug Resist. 3:53-64.
15. Hancock, L., and M. Perego. 2002. Two-component signal transduction in Enterococcus faecalis. J. Bacteriol. 184:5819-5825.
16. Hancock, L. E., and M. Perego. 2004. Systematic inactivation and phenotypic characterization of two-component signal transduction systems of Enterococ-cus faecalis V583. J. Bacteriol. 186:7951-7958.
17. Milliard, J. J., R. M. Goldschmidt, L. Licata, E. Z. Baum, and K. Bush. 1999. Multiple mechanisms of action for inhibitors of histidine protein kinases from bacterial two-component systems. Antimicrob. Agents Chemother. 43:1693-1699.
18. Hoch, J. A., and T. J. Silhavy (ed.). 1995. Two-component signal transduction. ASM Press, Washington, D.C.
19. Hoch, J. A., and K. I. Varughese. 2001. Keeping signals straight in phosphorelay signal transduction. J. Bacteriol. 183:4941-4949.
20. Howell, A., S. Dubrac, K. K. Andersen, D. Noone, J. Fert, T. Msadek, and K. Devine. 2003. Genes controlled by the essential YycG/YycF two-component system of Bacillus subtilis revealed through a novel hybrid regulator approach. Mol. Microbiol. 49:1639-1655.
21. Hubbard, J., M. K. Burnham, and J. P. Throup. 2003. Pathogenicity and histidine kinases: approaches toward the development of a new generation of antibiotics, p. 459-481. In M. Inouye and R. Dutta (ed.), Histidine kinases in signal transduction. Academic Press, San Diego, Calif.
22. Inouye, M., and R. Dutta (ed.), 2003. Histidine kinases in signal transduction. Academic Press, San Diego, Calif.
23. Kallipolitis, B. H., and H. Ingmer. 2001. Listeria monocytogenes response regulators important for stress tolerance and pathogenesis. FEMS Microbiol. Lett. 204:111-115.
24. Kitayama, T., R. Iwabuchi, S. Minagawa, F. Shiomi, J. Cappiello, S. Sawada, R. Utsumi, and T. Okamoto. 2004. Unprecedented olefin-dependent histidine-kinase inhibitory of zerumbone ring-opening material. Bioorg. Med. Chem. Lett. 14:5943-5946.
25. Kulanthaivel, P., A. J. Kreuzman, M. A. Strege, M. D. Belvo, T. A. Smitka, M. Clemens, J. R. Swartling, K. L. Minton, F. Zheng, E. L. Angleton, D. Mullen, L. N. Jungheim, V. J. Klimkowski, T. I. Nicas, R. C. Thompson, and S. B. Peng. 2004. Novel lipoglycopeptides as inhibitors of bacterial signal peptidase I. J. Biol. Chem. 279:36250-36258.
26. Le Breton, Y., G. Boel, A. Benachour, H. Prevost, Y. Auffray, and A. Rince. 2003. Molecular characterization of Enterococcus faecalis two-component signal transduction pathways related to environmental stresses. Environ. Microbiol. 5:329-337.
27. Lyon, G. J., P. Mayville, T. W. Muir, and R. P. Novick. 2000. Rational design of a global inhibitor of the virulence response in Staphylococcus aureus, based in part on localization of the site of inhibition to the receptor-histidine kinase, AgrC. Proc. Natl. Acad. Sci. USA 97:13330-13335.
28. Madoff, S. (ed.). 1986. The bacterial L-forms. Marcel Dekker, Inc., New York, N.Y.
29. Martin, P. K., T. Li, D. Sun, D. P. Biek, and M. B. Schmid. 1999. Role in cell permeability of an essential two-component system in Staphylococcus aureus. J. Bacteriol. 181:3666-3673.
30. Matsushita, M., and K. D. Janda. 2002. Histidine kinases as targets for new antimicrobial agents. Bioorg. Med. Chem. 10:855-867.
31. Ng, W. L., G. T. Robertson, K. M. Kazmierczak, J. Zhao, R. Gilmour, and M. E. Winkler. 2003. Constitutive expression of PcsB suppresses the requirement for the essential VicR (YycF) response regulator in Streptococcus pneumoniae R6. Mol. Microbiol. 50:1647-1663.
32. Pratt, D. J., J. A. Endicott, and M. E. Noble. 2004. The role of structure in kinase-targeted inhibitor design. Curr. Opin. Drug Discov. Dev. 7:428-436.
33. Ramstrom, H., M. Bourotte, C. Philippe, M. Schmitt, J. Haiech, and J. J. Bourguignon. 2004. Heterocyclic bis-cations as starting hits for design of inhibitors of the bifunctional enzyme histidine-containing protein kinase/phosphatase from Bacillus subtilis. J. Med. Chem. 47:2264-2275.
34. Robinson, V. L., D. R. Buckler, and A. M. Stock. 2000. A tale of two components: a novel kinase and a regulatory switch. Nat. Struct. Biol. 7:626-633.
35. Roychoudhury, S., N. A. Zielinski, A. J. Ninfa, N. E. Allen, L, N. Jungheim, T. I. Nicas, and A. M. Chakrabarty. 1993. Inhibitors of two-component signal transduction systems: inhibition of alginate gene activation in Pseudomonas aeruginosa. Proc. Natl. Acad. Sci. USA 90:965-969.
36. Sawyers, C. L. 2003. Opportunities and challenges in the development of kinase inhibitor therapy for cancer. Genes Dev. 17:2998-3010.
37. Schär, J., A. Sickmann, and D. Beier. 2005. Phosphorylation- independent activity of atypical response regulators of Helicobacter pylon. J. Bacteriol. 187:3100-3109.
38. Scudiero, D. A., R. H. Shoemaker, K. D. Paull, A. Monks, S. Tierney, T. H. Nofziger, M. J. Currens, D. Seniff, and M. R. Boyd. 1988. Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines. Cancer Res. 48:4827-4833.
39. Stephenson, K., and J. A. Hoch. 2004. Developing inhibitors to selectively target two-component and phosphorelay signal transduction systems of pathogenic microorganisms. Curr. Med. Chem. 11:765-773.
40. Stephenson, K., and J. A. Hoch. 2002. Two-component and phosphorelay signal-transduction systems as therapeutic targets. Curr. Opin. Pharmacol. 2:507-512.
41. Stephenson, K., Y. Yamaguchi, and J. A. Hoch. 2000. The mechanism of action of inhibitors of bacterial two-component signal transduction systems. J. Biol. Chem. 275:38900-38904.
42. Stock, A. M., V. L. Robinson, and P. N. Goudreau. 2000. Two-component signal transduction. Annu. Rev. Biochem. 69:183-215.
43. Throup, J. P., K. K. Koretke, A. P. Bryant, K. A. Ingraham, A. F. Chalker, Y. Ge, A. Marra, N. G. Wallis, J. R. Brown, D. J. Holmes, M. Rosenberg, and M. K. Burnham. 2000. A genomic analysis of two-component signal transduction in Streptococcus pneumoniae. Mol. Microbiol. 35:566-576.
44. Watanabe. T., Y. Hashimoto, Y. Umemoto, D. Tatebe, E. Furuta, T. Fukamizo, K. Yamamoto, and R. Utsumi. 2003. Molecular characterization of the essential response regulator protein YycF in Bacillus subtilis. 3. Mol. Microbiol. Biotechnol. 6:155-163.
45. West, A. H., and A. M. Stock. 2001. Histidine kinases and response regulator proteins in two-component signaling systems. Trends Biochem. Sci. 26:369-376.
46. Wolanin. P. M., P. A. Thomason, and J. B. Stock. 2002. Histidine protein kinases: key signal transducers outside the animal kingdom. Genome Biol. 3:REV1EWS3013.
47. Wright, G. D., T. R. Holman, and C. T. Walsh. 1993. Purification and characterization of VanR and the cytosolic domain of VanS: a two-component regulatory system required for vancomycin resistance in Enterococcus faecium BM4147. Biochemistry 32:5057-5063.
48. Yang, W. 2003. Histidine kinases: extended relationship with GHL ATPases, p. 219-236. In M. lnouye and R. Dutta (ed.), Histidine kinases in signal transduction. Academic Press, San Diego, Calif.