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

doi:https://doi.org/10.1002/anie.201200761

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

Tel Aviv University

Research output: Contribution to journal › Article › peer-review

Abstract

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 language	English
Pages (from-to)	5652-5656
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	23
DOIs	https://doi.org/10.1002/anie.201200761
State	Published - 4 Jun 2012

Keywords

aminoglycoside-modifying enzymes
amphiphiles
antibiotics
glycosides
hemolysis

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis

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https://doi.org/10.1002/anie.201200761

Cite this

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title = "6″-thioether tobramycin analogues: Towards selective targeting of bacterial membranes",

abstract = "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.",

keywords = "aminoglycoside-modifying enzymes, amphiphiles, antibiotics, glycosides, hemolysis",

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doi = "https://doi.org/10.1002/anie.201200761",

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TY - JOUR

T1 - 6″-thioether tobramycin analogues

T2 - Towards selective targeting of bacterial membranes

AU - Herzog, Ido M.

AU - Green, Keith D.

AU - Berkov-Zrihen, Yifat

AU - Feldman, Mark

AU - Vidavski, Roee R.

AU - Eldar-Boock, Anat

AU - Satchi-Fainaro, Ronit

AU - Eldar, Avigdor

AU - Garneau-Tsodikova, Sylvie

AU - Fridman, Micha

PY - 2012/6/4

Y1 - 2012/6/4

N2 - 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.

AB - 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.

KW - aminoglycoside-modifying enzymes

KW - amphiphiles

KW - antibiotics

KW - glycosides

KW - hemolysis

UR - http://www.scopus.com/inward/record.url?scp=84861636746&partnerID=8YFLogxK

U2 - https://doi.org/10.1002/anie.201200761

DO - https://doi.org/10.1002/anie.201200761

M3 - مقالة

C2 - 22499286

SN - 1433-7851

VL - 51

SP - 5652

EP - 5656

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 23

ER -

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

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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