ATP competitive inhibitors of d-alanine-d-alanine ligase based on protein kinase inhibitor scaffolds

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 3, 2009, Pages 1079-1087

  Triola, Gemma ^a,b   Wetzel, Stefan ^a,b   Ellinger, Bernhard ^a,b   Koch, Marcus A ^a,b   Hübel, Katja ^a,b   Rauh, Daniel ^a,c   Waldmann, Herbert ^a,b  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^b TU DORTMUND UNIVERSITY   (Germany)

^c CHEMICAL GENOMICS CENTRE OF THE MAX PLANCK SOCIETY   (Germany)

Author keywords

Antibiotics; d Ala d ala ligase; Kinase inhibitor

Indexed keywords

ADENOSINE TRIPHOSPHATE; BACTERIAL ENZYME; BRUTON TYROSINE KINASE; DEXTRO ALANINE DEXTRO ALANINE LIGASE; LFM A13; MALONONITRILAMIDE; N [(2 CHLORO 6 METHYL)PHENYL] 2 CYANO 3 HYDROXYBUTYL 2 ENAMIDE; N [2,5 BIS(TRIFLUOROMETHYL)PHENYL] 2 CYANO 3 HYDROXYBUTYL 2 ENAMIDE; SALICYLAMIDE DERIVATIVE; TERIFLUNOMIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING COMPETITION; BINDING SITE; COMPETITIVE INHIBITION; DRUG MECHANISM; DRUG STRUCTURE; DRUG TARGETING; NONHUMAN; PROTEIN FUNCTION;

ADENOSINE TRIPHOSPHATE; AMIDES; ANTI-BACTERIAL AGENTS; BINDING SITES; ISOXAZOLES; NITRILES; PEPTIDE SYNTHASES; PROTEIN KINASE INHIBITORS; SALICYLIC ACIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

BACTERIA (MICROORGANISMS);

EID: 58949090837     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.02.046     Document Type: Article

References (50)

1. Waxman D.J. Annu. Rev. Biochem. 52 (1983) 825
2. Gale, E.F.; Cundliffe, E.; Reynolds, P.E.; Richmond, M.H.; Waring, M.J. In The Molecular Basis of Antibiotic Action 2nd Ed.; Sons, J.W.A., Ed.: London, 1981, p. 646.
3. Howe R., Monk A., Wootton M., Walsh T.R., and Enright M.C. Emerg. Infect. Dis. 10 (2004) 855
4. Ellsworth. Chem. Biol. 3 (1996) 37
5. Zawadzke L.E., Bugg T.D.H., and Walsh C.T. Biochemistry 30 (1991) 1673
6. Neuhaus F.C., and Lynch J.L. Biochemistry 3 (1964) 471
7. Strominger J.L., Ito E., and Threnn R.H. J. Am. Chem. Soc. 82 (1960) 998
8. Stammer, C.H.; McKinney, J.D. 1965, 30, 3436.
9. Fan C., Moews P.C., Walsh C.T., and Knox J.R. Science 266 (1994) 439
10. Vo-Quang Y., Carniato D., Vo-Quang L., Lacoste A., Neuzi E., and Le Goffic F. J. Med. Chem. 29 (1986) 579
11. Parsons H., Patchett A.A., Bull H.G., Schoen W.R., Taub D., Davidson J., Combs P.L., Springer J.P., Gadebusch H., Weissberger B., Valiant M.E., Mellin T.N., and Busch R.D. J. Med. Chem. 31 (1988) 1772
12. Besong G.E., Bostock J.M., Stubbings W., Chopra I., Roper D.I., Lloyd A.J., Fishwick C.W., and Johnson A.P. Angew. Chem. Int. Ed. (2005) 6403
13. Liu S., Chang J.S., Herberg J.T., Horng M., Tomich P.K., Lin A.H., and Marotti K.R. Proc Natl Acad Sci U.S.A. 103 (2006) 15178
14. Kovac A., Majce V., Lenarsic R., Bombek S., Bostock J.M., Chopra I., Polanc S., and Gobec S. Bioorg. Med. Chem. Lett. (2007)
15. Koch M.A., Wittenberg L.O., Basu S., Jeyaraj D.A., Gourzoulidou E., Reinecke K., Odermatt A., and Waldmann H. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 16721
16. Charette B.D., Macdonald R.G., Wetzel S., Berkowitz D.B., and Waldmann H. Angew. Chem. Int. Ed. 45 (2006) 7766
17. Wetzel S., Schuffenhauer A., Silvio R., Ertl P., and Waldmann H. Chimia 61 (2007) 355
18. Kobayashi N., and Go N. Eur. Biophys. J. 26 (1997) 135
19. Grishin N.V. J. Mol. Biol. 291 (1999) 239
20. Denessiouk K.A., and Johnson M.P. Proteins: Structure, Function and Genetics 38 (2000) 310
21. Bridges A.I. Chem. Rev. 101 (2001) 2541
22. Toledo L.M., Lydon N.B., and Elbaum D. Curr. Med. Chem. 9 (1999) 775
23. Traxler P.M. Exp. Opin. Ther. Patents 8 (1998) 1599
24. Lawrence D.S., and Niu J. Pharmacol. Ther. 77 (1998) 81
25. Lindsley C.W., Barnett S.F., Yaroschak M., Bilodeau M.T., and Layton M.E. Curr. Top. Med. Chem. 7 (2007) 1349
26. Kissau L., Stahl P., Mazitschek R., Giannis A., and Waldmann H. J. Med. Chem. 46 (2003) 2917
27. Stahl P., Kissau L., Mazitschek R., Giannis A., and Waldmann H. Angew. Chem. Int. Ed. 41 (2002) 1174
28. Stahl P., Kissau L., Mazitschek R., Huwe A., Furet P., Giannis A., and Waldmann H. J. Am. Chem. Soc. 123 (2001) 11586
29. Rosenbaum C., Baumhof P., Mazitschek R., Müller O., Giannis A., and Waldmann H. Angew.Chem. Int. Ed. 43 (2004) 224
30. Gazit A., Yaish P., Gilon C., and Levitzki A. J. Med. Chem. 32 (1989) 2344
31. Levitzki A. Biochem. Pharmacol. 40 (1990) 913
32. Yaish P., Gazit A., Gilon C., and Levitzki A. Science 242 (1988) 933
33. Posner I., Engel M., Gazit A., and Levitzki A. Mol. Pharmacol. 45 (1994) 673
34. Mahajan S., Ghosh S., Sudbeck E.A., Zheng Y., Down S., Hupke M., and Uckun F. J. Biol. Chem. 274 (1999) 9587
35. Ghosh S., Zheng Y., jun X., Mahajan S., Mao C., Sudbeck E.A., and Uckun F. Clin. Cancer Res. 5 (1999) 4264
36. Xu X., Williams J.W., Bremer E.G., Finnegan A., and Chong A.S.F. J. Biol. Chem. 270 (1995) 12398
37. Mattar T., Kochhar K., Barlett R., Bremer E.G., and Finnegan A. FEBS Letts. 334 (1993) 161
38. Elder R.T., Xu X., Williams J.W., Gong H., Finnegan A., and Chong A.S. J. Immunol. 159 (1997) 22
39. Van den. Akker E., van Dijk T.B., Schmidt U., Felida L., Beug H., Löwenberg B., and von Lindern M. Biol. Chem. 385 (2004) 409
40. Fernandes M.J., Lachance G., Paré G., Rollet-Labelle E., and Naccache P.H. J. Leukoc. Biol. 78 (2005) 524
41. Uckun F., Tibbles H., Venkataraman K., DuMez D., and Erbeck D. Bioorg. Med. Chem. 15 (2007) 800
42. Silva H.T., and MOrris R.E. Exp. Opin. Invest. Drugs 6 (1997) 51
43. Bertolini G., Aquino M., Biffi M., d'Atri G., di Pierro F., Ferrario F., Mascagni P., Somenzi F., Zaliani A., and Leoni F. J. Med. Chem. 40 (1997) 2011
44. Bradford M.M. Anal. Biochem. 72 (1976) 248
45. Lanzetta P.A., Alvarez P.S., Reinach P.S., and Candia O.A. Biochemistry 18 (1979) 95
46. Sicheri F., Moarefi I., and Kuriyn J. Nature 385 (1997) 602
47. Walker E.H., Pacold M.E., Perisic O., Stephens L., Hawkins P.T., Wymann M.P., and Williams R.L. Mol. Cell. 6 (2000) 909
48. Holm L., and Park J. Bioinformatics 16 (2000) 566
49. Davies S.P., Reddy H., Caivano M., and Cohen P. Biochem. J. 351 (2000) 95
50. Bain, J.; Plater, L.; Elliott, M.; Shpiro, N.; Hastie, J.; McLauchlan, H.; Klevernic, I.; Arthur, S.; Alessi, D.; Cohen, P. Biochem. J. 2007, Sep 13, Epub ahead of print.