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Semiquantitation of Cooperativity in Binding of Vancomycin-Group Antibiotics to Vancomycin-Susceptible and -Resistant Organisms

Semiquantitation of Cooperativity in Binding of Vancomycin-Group Antibiotics to Vancomycin-Susceptible and -Resistant Organisms

D A Beauregard, A J Maguire, D H Williams, P E Reynolds

Antimicrob Agents Chemother. 1997 Nov;41(11):2418-23.

PMID: 9371343

Abstract:

The association of vancomycin group antibiotics with the growing bacterial cell wall was investigated by using the cell wall precursor analog di-N-acetyl-Lys-D-Ala-D-Ala in competition binding experiments. The affinities of the antibiotics for the -D-Ala-D-Ala-containing cell wall precursors of Bacillus subtilis ATCC 6633 (a model for vancomycin-susceptible gram-positive bacteria) and for the -D-Ala-D-Lac-containing cell wall precursors of Leuconostoc mesenteroides (a model for vancomycin-resistant strains of Enterococcus faecium and Enterococcus faecalis) were determined by a whole-cell assay. The binding of strongly dimerizing antibiotics such as eremomycin to the bacterial surface was thus shown to be enhanced by up to 2 orders of magnitude (relative to the binding in free solution) by the chelate effect, whereas weakly dimerizing antibiotics like vancomycin and antibiotics carrying lipid tails (teicoplanin) benefited less (ca. 1 order of magnitude). The affinity measured in this way correlates well with the MIC of the antibiotic, and a consequence of this is that future design of semisynthetic vancomycin-group antibiotics should attempt to incorporate chelate effect-enhancing structural features.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP28845978	Acetyl-Lys-D-Ala-D-Ala		28845-97-8	Price

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