6″-thioether tobramycin analogues: Towards selective targeting of bacterial membranes

Ido M. Herzog, Keith D. Green, Yifat Berkov-Zrihen, Mark Feldman, Roee R. Vidavski, Anat Eldar-Boock, Ronit Satchi-Fainaro, Avigdor Eldar, Sylvie Garneau-Tsodikova*, Micha Fridman

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

77 Scopus citations


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.

Original languageEnglish
Pages (from-to)5652-5656
Number of pages5
JournalAngewandte Chemie - International Edition
Issue number23
StatePublished - 4 Jun 2012


FundersFunder number
National Institute of Allergy and Infectious DiseasesR01AI090048
Seventh Framework Programme246673


    • aminoglycoside-modifying enzymes
    • amphiphiles
    • antibiotics
    • glycosides
    • hemolysis


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