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dc.contributor.author
Perez Fernandez, Déborah
dc.contributor.author
Shcherbakov, Dmitri
dc.contributor.author
Matt, Tanja
dc.contributor.author
Leong, Ng C.
dc.contributor.author
Kudyba, Iwona
dc.contributor.author
Duscha, Stefan
dc.contributor.author
Boukari, Heithem
dc.contributor.author
Patak, Rashmi
dc.contributor.author
Dubbaka, Srinivas R.
dc.contributor.author
Lang, Kathrin
dc.contributor.author
Meyer, Martin
dc.contributor.author
Akbergenov, Rashid
dc.contributor.author
Freihofer, Pietro
dc.contributor.author
Vaddi, Swapna
dc.contributor.author
Thommes, Pia
dc.contributor.author
Ramakrishnan, V.
dc.contributor.author
Vasella, Andrea
dc.contributor.author
Böttger, Erik C.
dc.date.accessioned
2018-09-11T15:54:45Z
dc.date.available
2017-06-11T05:06:55Z
dc.date.available
2018-09-11T15:54:45Z
dc.date.issued
2014
dc.identifier.other
10.1038/ncomms4112
en_US
dc.identifier.uri
http://hdl.handle.net/20.500.11850/80677
dc.identifier.doi
10.3929/ethz-b-000080677
dc.description.abstract
Clinical use of 2-deoxystreptamine aminoglycoside antibiotics, which target the bacterial ribosome, is compromised by adverse effects related to limited drug selectivity. Here we present a series of 4′,6′-O-acetal and 4′-O-ether modifications on glucopyranosyl ring I of aminoglycosides. Chemical modifications were guided by measuring interactions between the compounds synthesized and ribosomes harbouring single point mutations in the drug-binding site, resulting in aminoglycosides that interact poorly with the drug-binding pocket of eukaryotic mitochondrial or cytosolic ribosomes. Yet, these compounds largely retain their inhibitory activity for bacterial ribosomes and show antibacterial activity. Our data indicate that 4′-O-substituted aminoglycosides possess increased selectivity towards bacterial ribosomes and little activity for any of the human drug-binding pockets.
en_US
dc.format
application/pdf
en_US
dc.language.iso
en
en_US
dc.publisher
Nature Publishing Group
en_US
dc.rights.uri
http://creativecommons.org/licenses/by/3.0/
dc.title
4′-O-substitutions determine selectivity of aminoglycoside antibiotics
en_US
dc.type
Journal Article
dc.rights.license
Creative Commons Attribution 3.0 Unported
dc.date.published
2014-01-28
ethz.journal.title
Nature Communications
ethz.journal.volume
5
en_US
ethz.pages.start
3112
en_US
ethz.size
11 p.
en_US
ethz.version.deposit
publishedVersion
en_US
ethz.identifier.scopus
ethz.identifier.nebis
007044158
ethz.publication.place
London
en_US
ethz.publication.status
published
en_US
ethz.leitzahl
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02020 - Dep. Chemie und Angewandte Biowiss. / Dep. of Chemistry and Applied Biosc.::02514 - Laboratorium für Organische Chemie / Laboratory of Organic Chemistry::03425 - Chen, Peter / Chen, Peter
en_US
ethz.leitzahl.certified
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02020 - Dep. Chemie und Angewandte Biowiss. / Dep. of Chemistry and Applied Biosc.::02514 - Laboratorium für Organische Chemie / Laboratory of Organic Chemistry::03425 - Chen, Peter / Chen, Peter
ethz.date.deposited
2017-06-11T05:09:04Z
ethz.source
ECIT
ethz.identifier.importid
imp593651a35ec5032103
ethz.ecitpid
pub:126673
ethz.eth
yes
en_US
ethz.availability
Open access
en_US
ethz.rosetta.installDate
2017-07-13T13:37:32Z
ethz.rosetta.lastUpdated
2019-02-03T07:52:37Z
ethz.rosetta.exportRequired
true
ethz.rosetta.versionExported
true
ethz.COinS
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