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An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants
An azide-functionalised analogue of the oxazolidinone antibiotic linezolid was synthesised and shown to retain antimicrobial activity. Using facile ‘click’ chemistry, this versatile intermediate can be further functionalised to explore antimicrobial structure–activity relationships or conjugated to...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Elsevier Science
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4141890/ https://www.ncbi.nlm.nih.gov/pubmed/25023540 http://dx.doi.org/10.1016/j.bmc.2014.05.054 |
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author | Phetsang, Wanida Blaskovich, Mark A.T. Butler, Mark S. Huang, Johnny X. Zuegg, Johannes Mamidyala, Sreeman K. Ramu, Soumya Kavanagh, Angela M. Cooper, Matthew A. |
author_facet | Phetsang, Wanida Blaskovich, Mark A.T. Butler, Mark S. Huang, Johnny X. Zuegg, Johannes Mamidyala, Sreeman K. Ramu, Soumya Kavanagh, Angela M. Cooper, Matthew A. |
author_sort | Phetsang, Wanida |
collection | PubMed |
description | An azide-functionalised analogue of the oxazolidinone antibiotic linezolid was synthesised and shown to retain antimicrobial activity. Using facile ‘click’ chemistry, this versatile intermediate can be further functionalised to explore antimicrobial structure–activity relationships or conjugated to fluorophores to generate fluorescent probes. Such probes can report bacteria and their location in a sample in real time. Modelling of the structures bound to the cognate 50S ribosome target demonstrates binding to the same site as linezolid is possible. The fluorescent probes were successfully used to image Gram-positive bacteria using confocal microscopy. |
format | Online Article Text |
id | pubmed-4141890 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | Elsevier Science |
record_format | MEDLINE/PubMed |
spelling | pubmed-41418902014-08-26 An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants Phetsang, Wanida Blaskovich, Mark A.T. Butler, Mark S. Huang, Johnny X. Zuegg, Johannes Mamidyala, Sreeman K. Ramu, Soumya Kavanagh, Angela M. Cooper, Matthew A. Bioorg Med Chem Article An azide-functionalised analogue of the oxazolidinone antibiotic linezolid was synthesised and shown to retain antimicrobial activity. Using facile ‘click’ chemistry, this versatile intermediate can be further functionalised to explore antimicrobial structure–activity relationships or conjugated to fluorophores to generate fluorescent probes. Such probes can report bacteria and their location in a sample in real time. Modelling of the structures bound to the cognate 50S ribosome target demonstrates binding to the same site as linezolid is possible. The fluorescent probes were successfully used to image Gram-positive bacteria using confocal microscopy. Elsevier Science 2014-08-15 /pmc/articles/PMC4141890/ /pubmed/25023540 http://dx.doi.org/10.1016/j.bmc.2014.05.054 Text en © 2014 The Authors https://creativecommons.org/licenses/by/3.0/This work is licensed under a Creative Commons Attribution 3.0 Unported License (https://creativecommons.org/licenses/by/3.0/) . |
spellingShingle | Article Phetsang, Wanida Blaskovich, Mark A.T. Butler, Mark S. Huang, Johnny X. Zuegg, Johannes Mamidyala, Sreeman K. Ramu, Soumya Kavanagh, Angela M. Cooper, Matthew A. An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants |
title | An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants |
title_full | An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants |
title_fullStr | An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants |
title_full_unstemmed | An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants |
title_short | An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants |
title_sort | azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4141890/ https://www.ncbi.nlm.nih.gov/pubmed/25023540 http://dx.doi.org/10.1016/j.bmc.2014.05.054 |
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