An Unsaturated Quinolone N-Oxide of Pseudomonas aeruginosa Modulates Growth and Virulence of Staphylococcus aureus

Angewandte Chemie
Dávid Szamosvári, Thomas Böttcher

Abstract

The pathogen Pseudomonas aeruginosa produces over 50 different quinolones, 16 of which belong to the class of 2-alkyl-4-quinolone N-oxides (AQNOs) with various chain lengths and degrees of saturation. We present the first synthesis of a previously proposed unsaturated compound that is confirmed to be present in culture extracts of P. aeruginosa, and its structure is shown to be trans-Δ1 -2-(non-1-enyl)-4-quinolone N-oxide. This compound is the most active agent against S.  aureus, including MRSA strains, by more than one order of magnitude whereas its cis isomer is inactive. At lower concentrations, the compound induces small-colony variants of S. aureus, reduces the virulence by inhibiting hemolysis, and inhibits nitrate reductase activity under anaerobic conditions. These studies suggest that this unsaturated AQNO is one of the major agents that are used by P. aeruginosa to modulate competing bacterial species.

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Citations

Mar 16, 2018·Organic & Biomolecular Chemistry·Dávid SzamosváriThomas Böttcher
Nov 7, 2017·Nucleic Acids Research·Weiliang HuangAngela Wilks
Mar 29, 2018·The Journal of Biological Chemistry·Nydia Morales-SotoJoshua D Shrout
Nov 21, 2019·Chembiochem : a European Journal of Chemical Biology·Lachlan DowBernard Lepetit
May 22, 2020·Chemical Communications : Chem Comm·Dávid SzamosváriThomas Böttcher
Jun 24, 2020·Environmental Microbiology·Bartosz Gerard GdaniecThilo Köhler
Jun 17, 2018·The Journal of Biological Chemistry·Neha Garg, Marvin Whiteley
Dec 6, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Muhammad SaalimBenjamin R Clark
May 13, 2021·Journal of the American Chemical Society·Magdalena Jancheva, Thomas Böttcher
Jun 15, 2021·Chemical Science·Michaela ProthiwaThomas Böttcher
Apr 7, 2018·Analytical Chemistry·Sage J B DunhamJonathan V Sweedler
Aug 4, 2018·Organic Letters·Ashley M KretschBo Li
Oct 20, 2018·Journal of the American Chemical Society·Michaela ProthiwaThomas Böttcher

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