Semiquantitation of cooperativity in binding of vancomycin-group antibiotics to vancomycin-susceptible and -resistant organisms

Antimicrobial Agents and Chemotherapy

Volumn 41, Issue 11, 1997, Pages 2418-2423

  Beauregard, Daniel A ^a,b   Maguire, Alison J ^a,c   Williams, Dudley H ^a   Reynolds, Peter E ^b  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b Department of Biochemistry ^*  (United Kingdom)

^c ADDENBROOKE S HOSPITAL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROORIENTICIN A; DECAPLANIN; EREMOMYCIN; GLYCOPEPTIDE; RISTOCETIN; TEICOPLANIN; VANCOMYCIN DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ANTIBIOTIC SENSITIVITY; ARTICLE; BACILLUS SUBTILIS; BACTERIAL CELL WALL; CONTROLLED STUDY; DIMERIZATION; DRUG BINDING; DRUG DESIGN; ENTEROCOCCUS FAECALIS; LEUCONOSTOC; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL;

EID: 0030717475     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.41.11.2418     Document Type: Article

References (28)

1. Allen N. E., J. N. Hobbs, Jr., and T. I. Nicas. 1996. Inhibition of peptidoglycan biosynthesis in vancomycin-susceptible and -resistant bacteria by a semisynthetic glycopeptide antibiotic. Antimicrob. Agents Chemother. 40:2356-2362.
2. Allen, N. E., D. L. LeTourneau, and J. N. Hobbs, Jr. 1997. Molecular interactions of a semisynthetic glycopeptide antibiotic with D-alanyl-D-alanine and D-alanyl-D-lactate residues. Antimicrob. Agents Chemother. 41:66-71.
3. Arthur, M., F. Depardieu, P. E. Reynolds, and P. Courvalin. 1996. Quantitative analysis of the metabolism of soluble cytoplasmic peptidoglycan precursors of glycopeptide-resistant enterococci. Mol. Microbiol. 21:33-44.
4. Beauregard, D. A., D. H. Williams, M. N. Gwynn, and D. J. C. Knowles. 1995. Dimerization and membrane achors in extracellular targeting of vancomycin group antibiotics. Antimicrob. Agents Chemother. 39:781-785.
5. Billot-Klein, D., L. Gutmann, S. Sablé, E. Guittet, and J. van Heijinoort. 1994. Modification of peptidoglycan precursors is a common feature of the low-level vancomycin-resistant species Lactobacillus casei, Pediococcus pentosaceus, Leuconostoc mesenteroides, and Enterococcus gallinarum. J. Bacteriol. 176:2398-2405.
6. Bugg, T. D. H., G. D. Wright, S. Dutka-Malen, M. Arthur, P. Courvalin, and C. T. Walsh. 1991. Molecular basis for vancomycin resistance in Enterococcus faecium BM4147: biosynthesis of a depsipeptide peptidoglycan precursor by vancomycin resistance proteins VanH and VanA. Biochemistry 30:10408-10415.
7. Cavelleri, B., and F. Parenti. 1992. Glycopeptides (dalbaheptides), p. 995-1018. In R. E. Kirk and D. F. Othmer (ed.), Encyclopedia of chemical technology, vol. 2, 4th ed. John Wiley & Sons, Inc., New York, N.Y.
8. Cooper, R. D. G., D. L. Mullen, T. F. Butler, Y. Lin, N. J. Synder, M. J. Zweifel, S. C. Wilkie, T. I. Nicas, M. J. Rodriguez, D. A. Preston, and R. C. Thompson. 1995. Discovery of new semisynthetic glycopeptides active against vancomycin-resistant enterococci, abstr. F242, p. 155. In Program and abstracts of the 35th Interscience Conference on Antimicrobial Agents and Chemotherapy. American Society for Microbiology, Washington, D.C.
9. Dancer, R. J., A. C. Try, G. J. Sharman, and D. H. Williams. 1996. Binding of a vancomycin group antibiotic to a cell wall analogue from vancomycin-resistant bacteria. J. Chem. Soc. Chem. Commun. 12:1445-1446.
10. Good, V. M., M. N. Gwynn, and D. J. C. Knowles. 1990. MM 45289, a potent glycopeptide antibiotic which interacts weakly with diacetyl-L-lysyl-D-alanyl-D-alanine. J. Antibiot. 43:550-555.
11. Groves, P. D., M. S. Searle, J. P. Mackay, and D. H. Williams. 1994. The structure of an asymmetric dimer relevant to the mode of action of the glycopeptide antibiotics. Structure 2:747-754.
12. Gwynn, M. N. Unpublished data.
13. Handwerger, S., M. J. Pucci, K. J. Volk, J. Liu, and M. S. Lee. 1994. Vancomycin-resistant Leuconostoc mesenteroides and Lactobacillus casei synthesize cytoplasmic peptidoglycan precursors that terminate in lactate. J. Bacteriol. 176:260-264.
14. Herrin, T. R., A. M. Thomas, T. J. Perun, J. C. Mao, and S. W. Fesik. 1985. Preparation of biologically active ristocetin derivatives: replacements of the 1′-amino group. J. Med. Chem. 28:1371-1375.
15. Kalman, J. R., and D. H. Williams. 1980. An NMR study of the interaction between the antibiotic ristocetin A and a cell wall peptide analogue. Negative nuclear Overhauser effects in the investigation of drug binding sites. J. Am. Chem. Soc. 102:906-912.
16. Mackay, J. P., U. Gerhard, D. A. Beauregard, R. A. Maplestone, and D. H. Williams. 1994. Dissection of the contributions toward dimerization of glycopeptide antibiotics. J. Am. Chem. Soc. 116:4573-4580.
17. Mackay, J. P., U. Gerhard, D. A. Beauregard, M. S. Westwell, M. S. Searle, and D. H. Williams. 1994. Glycopeptide antibiotic activity and the possible role of dimerization: a model for biological signaling. J. Am. Chem. Soc. 116:4581-4590.
18. Malabarba, A., A. Trani, G. Tarzia, P. Ferrari, R. Pallanza, and M. Berti. 1989. Synthesis and biological evaluation of de(acetylglucosaminyl)didehydrodeoxy derivatives of teicoplanin antibiotics. J. Med. Chem. 32:783-788.
19. Nicas, T. I., D. L. Mullen, J. E. Flokowitsch, D. A. Preston, N. J. Snyder, M. J. Zweifel, S. C. Wilkie, M. J. Rodriguez, R. C. Thompson, and R. D. G. Cooper. 1996. Semisynthetic glycopeptide antibiotics derived from LY264826 active against vancomycin-resistant enterococci. Antimicrob. Agents Chemother. 40:2194-2199.
20. Nieto, M., and H. R. Perkins. 1971. Modifications of the acyl-D-alanyl-D-alanine terminus affecting complex-formation with vancomycin. Biochem. J. 123:789-803.
21. Nieto, M., and H. R. Perkins. 1971. Physicochemical properties of vancomycin and iodovancomycin and their complexes with diacetyl-L-lysyl-D-alanyl-D-alanine. Biochem. J. 123:773-787.
22. Noble, W. C., Z. Virani, and R. G. A. Cree. 1992. Co-transfer of vancomycin and other resistance genes from Enterococcus faecalis NCTC 12201 to Staphylococcus aureus. FEMS Microbiol. Lett. 93:195-198.
23. Prowse, W. G., A. D. Kline, M. A. Skelton, and R. J. Loncharich. 1995. Conformation of A82846B, a glycopeptide antibiotic, complexed with its cell wall fragment: an asymmetric homodimer determined using NMR spectroscopy. Biochemistry 34:9632-9644.
24. Rake, J. B., R. Gerber, R. J. Mehta, D. J. Newman, Y. K. Oh, C. Phelen, M. C. Shearer, R. D. Sitrin, and L. J. Nisbet. 1986. Glycopeptide antibiotics: a mechanism-based screen employing a bacterial cell wall receptor mimetic. J. Antibiot. 39:58-67.
25. Reynolds, P. E. 1989. Structure, biochemistry and mechanism of action of glycopeptide antibiotics. Eur. J. Clin. Microbiol. Infect. Dis. 8:943-950.
26. Sharman, G. J., A. C. Try, R. J. Dancer, M. Cooper, A. J. Maguire, B. Bardsley, and D. H. Williams. The role of membrane anchoring and dimerization in activity against vancomycin-resistant bacteria. J. Am. Chem. Soc., in press.
27. Sheldrick, G. M., P. G. Jones, O. Kennard, D. H. Williams, and G. A. Smith. 1978. Structure of vancomycin and its complex with acetyl-D-alanyl-D-alanine. Nature 271:223-225.
28. Sheldrick, G. M., E. Paulus, L. Vértesy, and F. Hahn. 1995. Structure of ureidobalhimycin. Acta Crystallogr. B 51:89-98.