Issue 42, 2013
From the journal:

Chemical Communications

Synthesis of cephalosporin-3′-diazeniumdiolates: biofilm dispersing NO-donor prodrugs activated by β-lactamase†

Nageshwar Rao Yepuri,a   Nicolas Barraud,b   Nasim Shah Mohammadi,b   Bharat G. Kardak,a   Staffan Kjelleberg,bc   Scott A. Ricebc  and  Michael J. Kelso*a  

* Corresponding authors

a School of Chemistry, University of Wollongong, NSW, Australia
E-mail: mkelso@uow.edu.au
Fax: +61 2 4221 4287
Tel: +61 2 4221 5085

b School of Biotechnology and Biomolecular Sciences and Centre for Marine Bio-Innovation, University of New South Wales, Australia

c Singapore Centre on Environmental Life Sciences Engineering, Nanyang Technological University, Singapore

Abstract

Use of biofilm dispersing NO-donor compounds in combination with antibiotics has emerged as a promising new strategy for treating drug-resistant bacterial biofilm infections. This paper details the synthesis and preliminary evaluation of six cephalosporin-3′-diazeniumdiolates as biofilm-targeted NO-donor prodrugs. Each of the compounds is shown to selectively release NO following reaction with the bacteria-specific enzyme β-lactamase and to trigger dispersion of Pseudomonas aeruginosa biofilms in vitro.

Graphical abstract: Synthesis of cephalosporin-3′-diazeniumdiolates: biofilm dispersing NO-donor prodrugs activated by β-lactamase

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Article information

DOI
https://doi.org/10.1039/C3CC40869H
Article type
Communication
Submitted
01 Feb 2013
Accepted
15 Apr 2013
First published
15 Apr 2013

Chem. Commun., 2013,49, 4791-4793

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Synthesis of cephalosporin-3′-diazeniumdiolates: biofilm dispersing NO-donor prodrugs activated by β-lactamase

N. R. Yepuri, N. Barraud, N. S. Mohammadi, B. G. Kardak, S. Kjelleberg, S. A. Rice and M. J. Kelso, Chem. Commun., 2013, 49, 4791 DOI: 10.1039/C3CC40869H

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