402718-53-0Relevant academic research and scientific papers
Synthetic quinolone signal analogues inhibiting the virulence factor elastase of Pseudomonas aeruginosa
Szamosvári, Dávid,Reichle, Valentin F.,Jureschi, Monica,B?ttcher, Thomas
, p. 13440 - 13443 (2016/11/19)
We explore the chemical space of Pseudomonas quinolone signal analogs as privileged structures and report the discovery of a thioquinolone as a potent inhibitor of the important virulence factor elastase of the human pathogen Pseudomonas aeruginosa. We provide evidence that the derivative binds to the active site zinc of elastase and additionally acts as a fluorescent zinc sensor.
Structure-function analysis of the C-3 position in analogues of microbial behavioural modulators HHQ and PQS
Reen, F. Jerry,Clarke, Sarah L.,Legendre, Claire,McSweeney, Christina M.,Eccles, Kevin S.,Lawrence, Simon E.,O'Gara, Fergal,McGlacken, Gerard P.
supporting information, p. 8903 - 8910 (2013/01/15)
2-Heptyl-3-hydroxy-4-quinolone (PQS) and its precursor 2-heptyl-4-quinolone (HHQ) are key signalling molecules of the important nosocomial pathogen Pseudomonas aeruginosa. We have recently reported an interkingdom dimension to these molecules, influencing key virulence traits in a broad spectrum of microbial species and in the human pathogenic yeast Candida albicans. For the first time, targeted chemical derivatisation of the C-3 position was undertaken to investigate the structural and molecular properties underpinning the biological activity of these compounds in P. aeruginosa, and using Bacillus subtilis as a suitable model system for investigating modulation of interspecies behaviour.
Synthesis of 3-halo-analogues of HHQ, subsequent cross-coupling and first crystal structure of Pseudomonas quinolone signal (PQS)
McGlacken, Gerard P.,McSweeney, Christina M.,O'Brien, Timothy,Lawrence, Simon E.,Elcoate, Curtis J.,Reen, F. Jerry,O'Gara, Fergal
scheme or table, p. 5919 - 5921 (2010/11/18)
2-Aryl- and 2-alkyl-quinolin-4-ones and their N-substituted derivatives have several important biological functions such as the Pseudomonas quinolone signal (PQS) molecule participation in quorum sensing. Herein, we report the synthesis of its biological precursor, 2-heptyl-4-hydroxy-quinoline (HHQ) and possible isosteres of PQS; the C-3 Cl, Br and I analogues. N-Methylation of the iodide was also feasible and the usefulness of this compound showcased in Pd-catalysed cross-coupling reactions, thus allowing access to a diverse set of biologically important molecules. The first crystal structure of PQS is also included.
Novel autoinducer molecules and uses therefor
-
, (2008/06/13)
Novel bacterial quinolone signal molecules and, more particularly, pseudomonas quinolone signal (“PQS”) molecules, e.g., 2-heptyl-3-hydroxy-4-quinolone, and analogs and derivatives thereof are described. Therapeutic compositions containing the molecules, and therapeutic methods, methods of for regulating gene expression, methods for identifying modulators of the autoinducer molecules, and methods of modulating quorum sensing signalling in bacteria using the compounds of the invention are also described.
