Synthetic homoserine lactone-derived sulfonylureas as inhibitors of Vibrio fischeri quorum sensing regulator.
A series of 9 homoserine lactone-derived sulfonylureas substituted by an alkyl chain, some of them bearing a phenyl group at the extremity, have been prepared. All compounds were found to inhibit the action of 3-oxo-hexanoyl-L-homoserine lactone, the natural inducer of bioluminescence in the bacterium Vibrio fischeri, the aliphatic compounds being more active than their phenyl-substituted counterparts. Molecular modelling studies performed on the most active compound in each series suggest that the antagonist activity could be related to the perturbation of the hydrogen-bond network in the ligand-protein complexes.
Frezza
Marine
M
INSA Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, Laboratoire de Chimie Organique, Bât J. Verne, 20 av A. Einstein, 69621 Villeurbanne Cedex, France.
Soulère
Laurent
L
Reverchon
Sylvie
S
Guiliani
Nicolas
N
Jerez
Carlos
C
Queneau
Yves
Y
Doutheau
Alain
A
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D048908:Aliivibrio fischeri / Q000187:drug effects*; D001665:Binding Sites; D008024:Ligands; D015394:Molecular Structure; D053038:Quorum Sensing / Q000187:drug effects*; D013329:Structure-Activity Relationship; D013453:Sulfonylurea Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D008024:Ligands; D013453:Sulfonylurea Compounds; C088386:homoserine lactone; D015107:4-Butyrolactone