D-Ala-D-Lac binding is not required for the high activity of vancomycin dimers against vancomycin resistant enterococci

Journal of the American Chemical Society

Volumn 125, Issue 29, 2003, Pages 8740-8741

  Jain, Rishi K ^a   Trias, Joaquim ^b   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Versicor Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIMER; VANCOMYCIN; VANCOMYCIN DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; DRUG STRUCTURE; ENTEROCOCCUS; ENTEROCOCCUS FAECIUM; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STRUCTURE ANALYSIS;

ALANINE; ANTI-BACTERIAL AGENTS; BINDING SITES; DIMERIZATION; ENTEROCOCCUS FAECALIS; KINETICS; OLIGOPEPTIDES; SPECTROMETRY, FLUORESCENCE; VANCOMYCIN; VANCOMYCIN RESISTANCE;

EID: 0037622609     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0359761     Document Type: Article

References (38)

1. (a) Neu, H. C. Science 1992, 257, 1064-1073.
2. (b) Walsh, C. T. Nature 2000, 406, 775-781.
3. For reviews, see: (a) Malabarba, A.; Nicas, T. I.; Thompson, R. C. Med. Res. Rev. 1997, 17, 69-137.
4. (b) Zhu, J. P. Expert Opin. Ther. Pat. 1999, 9, 1005-1019.
5. (c) Nicolaou, K. C.; Boddy, C. N. C.; Brase, S.; Winssinger, N. Angew. Chem., Int. Ed. 1999, 38, 2096-2152.
6. (d) Sussmuth, R. D. ChemBioChem 2002, 3, 295-298.
7. Vancomycin dimers and oligomers: (a) Sundram, U. N.; Griffin, J. H.; Nicas, T. I. J. Am. Chem. Soc. 1996, 118, 13107-13108.
8. (b) Stack, D. R.; Thompson, R. G. EP0801075 Al, 1997.
9. (c) Rao, J.; Whitesides, G. M. J. Am. Chem. Soc. 1997, 119, 10286-10290.
10. (d) Staroske, T.; Williams, D. H. Tetrahedron Lett. 1998, 39, 4917-4920.
11. (e) Rao, J.; Yan, L.; Xu, B.; Whitesides, G. M. J. Am. Chem. Soc. 1999, 121, 2629-2630.
12. (f) Rao, J.; Yan, L.; Lahiri, J.; Whitesides, G. M.; Weis, R. M.; Warren, H. S. Chem. Biol. 1999, 6, 353-359.
13. (g) Adamczyk, M.; Moore, J. A.; Rege, S. D.; Yu, Z. Bioorg. Med. Chem. Lett. 1999, 9, 2437-2440.
14. (h) Arimoto, H.; Nishimura, K.; Kinumi, T.; Hayakawa, I.; Uemura, D. Chem. Commun. 1999, 1361-1362.
15. (i) Nicolaou, K. C.; Hughes, R.; Cho, S. Y.; Winssinger, N.; Smethurst, C.; Labischinski, H.; Endermann, R. Angew. Chem., Int. Ed. 2000, 39, 3823-3828.
16. (j) Nicolaou, K. C.; Hughes, R.; Cho, S. Y.; Winssinger, N.; Labischinski, H.; Endermann, R. Chem.-Eur. J. 2001, 7, 3824-3843.
17. (k) Arimoto, H.; Oishi, T.; Nishijima, M.; Kinumi, T. Tetrahedron Lett. 2001, 42, 3347-3350.
18. (l) Griffin, J. H.; et al. J. Am. Chem. Soc. 2003, 125, 6517-6531.
19. (a) Ge, M.; Chen, Z.; Onishi, H. R.; Kohler, J.; Silver, L. L.; Kern, R.; Fukuzawa, S.; Thompson, C.; Kahne, D. Science 1999, 284, 507-511.
20. (b) Roy, R. S.; et al. Chem. Biol. 2001, 8, 1095-1106.
21. (c) Printsevskaya, S. S.; et al. J. Med. Chem. 2002, 45, 1340-1347.
22. (d) Printsevskaya, S. S.; Pavlov, A. Y.; Olsufyeva, E. N.; Mirchink, E. P.; Preobrazhenskaya, M. N. J. Med. Chem. 2003, 46, 1204-1209.
23. Barne, J. C. J.; Williams, D. H. Annu. Rev. Microbiol. 1984, 38, 339.
24. (a) Walsh, C. T.; Fisher, S. L.; Park, I. S.; Prahalad, M.; Wu, Z. Chem. Biol. 1996, 3, 21-28.
25. (b) Arthur, M.; Courvalin, P. Antimicrob. Agents Chemother. 1993, 37, 1563-1571.
26. Mammen, M.; Choi, S. K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2755-2794.
27. Williams, D. H.; Maguire, A. J.; Tsuzuki, W.; Westwell, M. S. Science 1998, 280, 711-714.
28. (a) Xu, R.; Greiveldinger, G.; Marenus, L. E.; Cooper, A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 4898-4899.
29. (b) Ahrendt, K. A.; Olsen, J. A.; Wakao, M.; Trias, J.; Ellman, J. A. Bioorg. Med. Chem. Lett. 2003, 13, 1683-1686.
30. (a) Nagarajan, R. J. Antibiot. 1993, 46, 1181-1195.
31. (b) Cristofaro, M.; Beauregard, D. A.; Yan, H.; Osborn, N. J.; Williams, D. H. J. Antibiot. 1995, 48, 805-810.
32. See Supporting Information.
33. Compounds were tested according to NCCLS protocols. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, Approved Standard, 5th ed.; NCCLS Document M7-A5; National Committee for Clinical Laboratory Standards: Wayne, PA, 2000.
34. Popielniek, P. H.; Pratt, R. F. Anal. Biochem. 1987, 165, 108-113.
35. Cooper, M. A.; Williams, D. H.; Cho, Y. R. Chem. Commun. 1997, 1625-1626.
36. d under these conditions.
37. Soluble carboxymethyl-dextran (0.5 mg/mL) was added to suppress nonspecific adsorption, allowing the measurement of specific binding of 4 to chip surfaces at higher concentrations. Even under these conditions, only modest binding was detected for 4 (25 μM) to Ac-Lys-D-Ala-D-Ala surfaces, and no binding was observed for 4 (25 μM) to Ac-Lys-D-Ala-D-Lac surfaces (see Supporting Information).
38. Alternatively, aggregation of vancomycin-based dimers could potentially result in antibacterial activity through complex mechanisms: McGovern, S. L.; Caselli, E.; Grigorieff, N.; Shoichet, B. K. J. Med. Chem. 2002, 45, 1712-1722.