Jump to main content
Jump to site search

Issue 8, 2014
Previous Article Next Article

Synthesis, antiribosomal and antibacterial activity of 4′-O-glycopyranosyl paromomycin aminoglycoside antibiotics

Author affiliations

Abstract

A series of 4′-O-glycopyranosyl paromomycin analogs and a 4′-O-(glucosyloxymethyl) analog were synthesized and evaluated for their ribosomal activity to determine the influence of the glycosyl moiety on drug activity and selectivity. Antibacterial activity against clinical strains of Escherichia coli and Staphylococcus aureus was also investigated. While all compounds were less active than paromomycin itself, differences in activity were seen between the gluco-, manno-, and galactopyranosyl series and between individual anomers. These differences in activity, which are discussed in terms of variations in affinity for the ribosomal decoding A site, may prove useful in the design of subsequent generations of improved aminoglycoside antibiotics with reduced toxicity.

Graphical abstract: Synthesis, antiribosomal and antibacterial activity of 4′-O-glycopyranosyl paromomycin aminoglycoside antibiotics

Back to tab navigation

Supplementary files

Publication details

The article was received on 14 Mar 2014, accepted on 05 Apr 2014 and first published on 07 Apr 2014


Article type: Concise Article
DOI: 10.1039/C4MD00119B
Author version available: Download Author version (PDF)
Citation: Med. Chem. Commun., 2014,5, 1179-1187
  •   Request permissions

    Synthesis, antiribosomal and antibacterial activity of 4′-O-glycopyranosyl paromomycin aminoglycoside antibiotics

    W. Chen, T. Matsushita, D. Shcherbakov, H. Boukari, A. Vasella, E. C. Böttger and D. Crich, Med. Chem. Commun., 2014, 5, 1179
    DOI: 10.1039/C4MD00119B

Search articles by author

Spotlight

Advertisements