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An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants.

ABSTRACT: 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.

SUBMITTER: Phetsang W

PROVIDER: S-EPMC4141890 | biostudies-literature | 2014 Aug

REPOSITORIES: biostudies-literature

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An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants.

Phetsang Wanida W Blaskovich Mark A T MA Butler Mark S MS Huang Johnny X JX Zuegg Johannes J Mamidyala Sreeman K SK Ramu Soumya S Kavanagh Angela M AM Cooper Matthew A MA

Bioorganic & medicinal chemistry 20140614 16

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 demonstra ...[more]

PMID: 25023540

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