Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 11, Pages 4340-4349Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201406404
Keywords
cationic amphiphiles; antibiotic resistance; antibiotics; bacterial membranes; glycosides
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Funding
- Israel Science Foundation [6-14]
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Antimicrobial cationic amphiphiles derived from aminoglycoside pseudo-oligosaccharide antibiotics interfere with the structure and function of bacterial membranes and offer a promising direction for the development of novel antibiotics. Herein, we report the design and synthesis of cationic amphiphiles derived from the pseudo-trisaccharide aminoglycoside tobramycin and its pseudo-disaccharide segment nebramine. Antimicrobial activity, membrane selectivity, mode of action, and structure-activity relationships were studied. Several cationic amphiphiles showed marked antimicrobial activity, and one amphiphilic nebramine derivative proved effective against all of the tested strains of bacteria; furthermore, against several of the tested strains, this compound was well over an order of magnitude more potent than the parent antibiotic tobramycin, the membrane-targeting antimicrobial peptide mixture gramicidin D, and the cationic lipopeptide polymyxin B, which are in clinical use.
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