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. 2020 Sep 14;63(20):11707–11724. doi: 10.1021/acs.jmedchem.0c00856

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Effect of 20, 22, 23, 30, and ciprofloxacin (3) on gyrase-catalyzed DNA supercoiling. Propargylation (20) decreased the inhibitory concentration only by a factor of 3.5 compared to 3. Gyrase inhibition as a putative mode of action was confirmed as all conjugates inhibit gyrase-catalyzed DNA supercoiling. Mean and standard deviations were determined from three independent experiments. A representative titration of E. coli gyrase with 22 in a supercoiling inhibition assay is shown. Controls: plasmid without gyrase and inhibitor (leftmost band) and plasmid with gyrase and without inhibitor (rightmost band). ON, open circular/nicked plasmid; R, relaxed topoisomers; SC, supercoiled topoisomers of E. coli DNA.