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- Title
Tobramycin and Nebramine as Pseudo-oligosaccharide Scaffolds for the Development of Antimicrobial Cationic Amphiphiles.
- Authors
Berkov ‐ Zrihen, Yifat; Herzog, Ido M.; Benhamou, Raphael I.; Feldman, Mark; Steinbuch, Kfir B.; Shaul, Pazit; Lerer, Shachar; Eldar, Avigdor; Fridman, Micha
- Abstract
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.
- Subjects
TOBRAMYCIN; ANTIBIOTICS; AMPHIPHILES; BACTERIAL cell walls; GLYCOSIDE synthesis
- Publication
Chemistry - A European Journal, 2015, Vol 21, Issue 11, p4340
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201406404