Diazenedicarboxamides as inhibitors of d-alanine-d-alanine ligase (Ddl)

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 7, 2007, Pages 2047-2054

  Kovač, Andreja ^a   Majce, Vita ^a   Lenaršič, Roman ^a   Bombek, Sergeja ^a   Bostock, Julieanne M ^b   Chopra, Ian ^b   Polanc, Slovenko ^a   Gobec, Stanislav ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

Antibacterials; d Alanine ligase; Inhibitors

Indexed keywords

AMIDE; CYCLOSERINE; DEXTRO ALANINE DEXTRO ALANINE LIGASE;

ANTIBACTERIAL ACTIVITY; ARTICLE; BIOSYNTHESIS; CATALYSIS; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ADENOSINE DIPHOSPHATE; ANTI-BACTERIAL AGENTS; CARBOXYLIC ACIDS; CATALYSIS; CHEMISTRY, PHARMACEUTICAL; CRYSTALLOGRAPHY, X-RAY; CYCLOSERINE; DRUG DESIGN; ESCHERICHIA COLI; IMIDES; MODELS, CHEMICAL; MOLECULAR CONFORMATION; PEPTIDE SYNTHASES; PHOSPHORYLATION;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI;

EID: 33847775590     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.01.015     Document Type: Article

References (42)

1. Courvalin P., and Davies J. Curr. Opin. Microbiol. 6 (2003) 425
2. Labischinski H., and Maidhof H. In: Ghuysen J.-M., and Hakenbeck R. (Eds). Bacterial Cell Wall (1994), Elsevier Science B.V., Amsterdam 23
3. van Heijenoort J. Nat. Prod. Rep. 18 (2001) 503
4. Zawadzke L.E., Bugg T.D.H., and Walsh C.T. Biochemistry 30 (1991) 1673
5. Fan C., Moews P.C., Walsh C.T., and Knox J.R. Science 266 (1994) 439
6. Fan C., Park I.-S., Walsh C.T., and Knox J.R. Biochemistry 36 (1997) 2531
7. Walsh C.T. J. Biol. Chem. 164 (1989) 2393
8. Shi Y., and Walsh C.T. Biochemistry 34 (1995) 2768
9. Arthur M., Reynolds P., and Courvalin P. Trends Microbiol. 4 (1996) 401
10. Liu S., Chang J.S., Herberg J.T., Horng M.-M., Tomich P.K., Lin A.H., and Marotti K.R. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 15178
11. Neuhaus F.C., and Lynch J.L. Biochemistry 3 (1964) 471
12. Strominger J.L., Ito E., and Threnn R.H. J. Am. Chem. Soc. 82 (1960) 998
13. Parsons W.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
14. Chakravarty P.K., Greenlee W.J., Parsons W.H., Patchett A.A., Combs P., Roth A., Busch R.D., and Mellin T.N. J. Med. Chem. 32 (1989) 1886
15. Lacoste A.M., Chollet-Gravey A.M., Vo Quang L., Vo Quang Y., and Le Goffic F. Eur. J. Med. Chem. 26 (1991) 255
16. Ellsworth B.A., Tom N.J., and Bartlett P.A. Chem. Biol. 3 (1996) 37
17. Besong G.E., Bostock J.M., Stubbings W., Chopra I., Roper D.I., Lloyd A.J., Fishwick C.W.G., and Johnson A.P. Angew. Chem. Int. Ed. 44 (2005) 2
18. Lee J.H., Na Y., Song H.-E., Kim D., Park B.-H., Rho S.-H., Im Y.J., Kim M.-K., Kang G.B., Lee D.-S., and Eom S.H. Proteins 64 (2006) 1078
19. Štrancar K., Blanot D., and Gobec S. Bioorg. Med. Chem. Lett. 16 (2006) 343
20. Humljan J., Kotnik M., Boniface A., Šolmajer T., Urleb U., Blanot D., and Gobec S. Tetrahedron 67 (2006) 10980
21. 3 (241.22): C, 49.79; H, 5.01; N, 17.42. Found: C, 49.72; H, 4.99; N 17.69.
22. 3 (235.67): C, 40.77; H, 5.99; N, 17.83. Found: C, 40.78; H, 6.09; N 17.64.
23. Košmrlj J., Kočevar M., and Polanc S. J. Chem. Soc., Perkin Trans. 1 (1998) 3917
24. 2 (317.73): C, 52.92; H, 3.81; N, 22.04. Found: C, 53.14; H, 3.88; N, 21.72.
25. 2.frac(1, 4)MeOH: C, 52.22; H, 4.61; N, 21.37. Found: C, 52.15; H, 4.61; N, 21.50.
26. Bombek S., Požgan F., Kočevar M., and Polanc S. J. Org. Chem. 69 (2004) 2224
27. Bombek S., Požgan F., Kočevar M., and Polanc S. New J. Chem. 29 (2005) 948
28. Zinner G., and Deucker W. Arch. Pharm. 249 (1961) 370
29. Strickler J.C., and Pirkle W.H. J. Org. Chem. 31 (1966) 3444
30. Bollbuck G., Stroh H.H., and Barnikow G. J. Prakt. Chem. 313 (1971) 773
31. Knight G.T., Loadman M.J.R., Saville B., and Wildgoose J. J. Chem. Soc., Chem. Commun. (1974) 193
32. Pieters L., Košmrlj J., Lenaršič R., Kočevar M., and Polanc S. ARKIVOC (2001) 42 (Part V)
33. Lenaršič R., Kočevar M., and Polanc S. J. Org. Chem. 64 (1999) 2558
34. Kraebel C.M., and Davis S.M. J. Chem. Eng. Data 14 (1969) 133
35. ® reagent was added. After 5 min, absorbance was read at 650 nm. Residual activity was calculated with respect to a similar assay without inhibitor. To exclude possible non-specific (promiscuous) inhibitors, representative compounds 3c, 4c, 6aD, 6bD, 6cC, 6cD, 6eD, 6fD, 6iA, and 6jD were tested also in the presence of Tween (0.003%), Triton X-114 (0.005%), and SDS (420 μM), as described by McGovern, S. L. et al. J. Med. Chem. 2003, 46, 4265, and Ryan, A. J. et al. J. Med. Chem. 2003, 46, 3448. No significant differences were found when compared to measurements without detergents.
36. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A.J. J. Comp. Chem. 19 (1998) 1639
37. 6 cells per mL for S. aureus. The antimicrobial agents were prepared in a 2-fold dilution series in 50% dimethyl sulfoxide (Sigma-Aldrich, Dorset, UK). Microwell plates with 96 wells (Nunc, Fisher Scientific, Loughborough, UK) containing the antimicrobial agent and bacterial suspension were incubated for 16 h at 37 °C in a Spectramax 384 plus microwell plate reader (Molecular Devices, Abingdon, UK), running SOFTmax PRO 3.1.1 software. Optical density readings (600 nm) were taken at 10 min intervals. Plates were shaken for 30 s before each reading. The MIC was taken as the lowest concentration of antimicrobial agent that prevented growth.
38. Miller K., O'Neill A.J., and Chopra I. J. Antimicrob. Chemother. 49 (2002) 925
39. O'Neill A.J., Bostock J.M., Morais Moita A., and Chopra I. J. Antimicrob. Chemother. 50 (2002) 839
40. Sulavik M.C., Houseweart C., Cramer C., Jiwani N., Murgolo N., Greene J., DiDomenico B., Shaw K.J., Miller G.H., Hare R., and Shimer G. Antimicrob. Agents Chemother. 45 (2001) 1126
41. Xiong L.Q., Kloss P., Douthwaite S., Andersen N.M., Swaney S., Shinabarger D.L., and Mankin A.S. J. Bacteriol. 182 (2000) 5325
42. Novick R. Virology 33 (1967) 155