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Title: Structure-activity relationship of brominated 3-alkyl-5-methylene-2(5H)-furanones and alkylmaleic anhydrides as inhibitors of Salmonella biofilm formation and quorum sensing regulated bioluminescence in Vibrio harveyi
Authors: Steenackers, Hans
Levin, Jeremy
Janssens, Joost
De Weerdt, Ami
Balzarini, Jan
Vanderleyden, Jozef
De Vos, Dirk
De Keersmaecker, Sigrid # ×
Issue Date: Jul-2010
Publisher: Pergamon
Series Title: Bioorganic & Medicinal Chemistry vol:18 issue:14 pages:5224-5233
Abstract: A library of 25 1'-unsubstituted and 1'-bromo or 1'-acetoxy 3-alkyl-5-methylene-2(5H)-furanones and two 3-alkylmaleic anhydrides was synthesized using existing and new methods. This library was tested for the antagonistic effect against the biofilm formation by Salmonella Typhimurium and the quorum sensing regulated bioluminescence of Vibrio harveyi. The length of the 3-alkyl chain and the bromination pattern of the ring structure were found to have a major effect on the biological activity of the 1'-unsubstituted furanones. Remarkably, the introduction of a bromine atom on the 1' position of the 3-alkyl chain did drastically enhance the activity of the furanones in both biological test systems. The introduction of an acetoxy function in this position did in general not improve the activity. Finally, the potential of the (bromo)alkylmaleic anhydrides as a new and chemically easily accessible class of biofilm and quorum sensing inhibitors was demonstrated.
URI: 
ISSN: 0968-0896
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Laboratory of Virology and Chemotherapy (Rega Institute)
Centre for Surface Chemistry and Catalysis
Centre of Microbial and Plant Genetics
× corresponding author
# (joint) last author

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