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6′′‐Thioether Tobramycin Analogues: Towards Selective Targeting of Bacterial Membranes
Author(s) -
Herzog Ido M.,
Green Keith D.,
BerkovZrihen Yifat,
Feldman Mark,
Vidavski Roee R.,
EldarBoock Anat,
SatchiFainaro Ronit,
Eldar Avigdor,
GarneauTsodikova Sylvie,
Fridman Micha
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201200761
Subject(s) - tobramycin , aminoglycoside , bacteria , membrane , chemistry , thioether , combinatorial chemistry , biochemistry , gentamicin , antibiotics , biology , stereochemistry , genetics
Amphiphilic tobramycin analogues with potent antibacterial activity against tobramycin‐resistant bacteria were synthesized. Most analogues were found to be less prone to deactivation by aminoglycoside‐modifying enzymes than tobramycin. These compounds target the bacterial membrane rather than the ribosome (see picture). The lipophilic residue of these analogues is key to their antibacterial potency and selectivity towards bacterial membranes.