Abstract
The antibacterial activities of the series of novel N′-(α-aminoacyl)- and N′-α-(N-akylamino)acyl derivatives of eremomycin and vancomycin containing hydrophobic moieties have been investigated. The N′-(N-alkylglycyl) derivatives of vancomycin are more active against vancomycin-susceptible staphylococci and enterococci and glycopeptide intermediate-resistant Staphylococcus aureus (GISA) than the corresponding eremomycin derivatives, but except for N′-[N-(p-octyloxybenzyl)glycyl-vancomycin] (28) and N′-[N-(p-octyloxybenzyl)-L-alanyl-vancomycin (33)—they are less active against glycopeptide-resistant enterococci (GRE). Derivatives 28 and 33 are the most active compounds (MIC's for glycopeptide-sensitive staphylococci and enterococci are 0.25~1 μg/ml, for GISA 1~2 μg/ml, for GRE 2~6 μg/ml). In in vivo studies, derivative 28 was active against S. aureus infections in mice with ED50 1 mg/kg versus 2 mg/kg for vancomycin (iv). In general N′-(N-alkylglycyl)-derivatives of vancomycin and eremomycin were more active than the corresponding N′-aminoacylated derivatives of these antibiotics containing other than glycin amino acids (L-Lys, L-Met, L-Orn, L- and D-Ala) and also L- and D-Phe or benzyl-O-L-Tyr.
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Plattner, J., Chu, D., Mirchink, E. et al. N′-(α-Aminoacyl)- and N′-α-(N-Alkylamino)acyl Derivatives of Vancomycin and Eremomycin. J Antibiot 60, 245–250 (2007). https://doi.org/10.1038/ja.2007.29
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DOI: https://doi.org/10.1038/ja.2007.29