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Issue 6, 2015
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3-Aminooxazolidinone AHL analogs as hydrolytically-stable quorum sensingagonists in Gram-negative bacteria

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Abstract

Synthetic molecules that modulate quorum sensing, QS, in bacteria have great potential for use in synthetic biology applications as well as acting as anti-virulence and anti-biofilm agents. Acylhomoserine lactone (AHL)-based autoinducer analogs have been extensively developed as QS modulators but these suffer from both chemical and enzymatic degradations. Here, we reveal that 3-aminooxazolidinone acylhomoserine lactone analogs are hydrolytically stable and are as potent in activating LuxR-type receptors. Docking analysis revealed that 3-oxo-C12-3-aminooxazolidinone docked in LasR of P. aeruginosa, making similar interactions with the protein's active-site residues to the native ligand, 3-oxo-C12 HSL. Experimentally, 3-oxo-C12-3-aminooxazolidinone was equally as potent as the natural ligand in inducing bioluminescence in E. coli carrying a bioluminescent gene that was under the control of LasR. In C. violaceum CV026, the 3-aminooxazolidinone analogs could also modulate pigment (violacein) formation, albeit this time not as potent as the natural AHL ligands.

Graphical abstract: 3-Aminooxazolidinone AHL analogs as hydrolytically-stable quorum sensing agonists in Gram-negative bacteria

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Publication details

The article was received on 12 Jan 2015, accepted on 16 Apr 2015 and first published on 20 Apr 2015


Article type: Concise Article
DOI: 10.1039/C5MD00015G
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Citation: Med. Chem. Commun., 2015,6, 1086-1092
  • Open access: Creative Commons BY-NC license
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    3-Aminooxazolidinone AHL analogs as hydrolytically-stable quorum sensingagonists in Gram-negative bacteria

    M. Guo, Y. Zheng, R. Starks, C. Opoku-Temeng, X. Ma and H. O. Sintim, Med. Chem. Commun., 2015, 6, 1086
    DOI: 10.1039/C5MD00015G

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