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


Chen, Weiwei; Matsushita, Takahiko; Shcherbakov, Dimitri; Boukari, Heithem; Vasella, Andrea; Böttger, Erik C; Crich, David (2014). Synthesis, antiribosomal and antibacterial activity of 4'-O-glycopyranosyl paromomycin aminoglycoside antibiotics. MedChemComm, 5:1179-1187.

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.

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.

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3 citations in Scopus®
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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:04 Faculty of Medicine > Institute of Medical Microbiology
Dewey Decimal Classification:570 Life sciences; biology
610 Medicine & health
Language:English
Date:2014
Deposited On:24 Feb 2015 15:46
Last Modified:05 Apr 2016 19:00
Publisher:RSC Publishing
ISSN:2040-2503
Publisher DOI:https://doi.org/10.1039/C4MD00119B

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