A new route towards fimbrolide analogues : importance of the exomethylene motif in LuxR dependent quorum sensing inhibition

Mohamad Sabbah (1) , Maud Bernollin (1) , Alain Doutheau (1) , Laurent Soulère (1) , Yves Queneau (2)

1 ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
2 COB - Chimie Organique et Bioorganique

Sixteen analogues of fimbrolides (brominated 3-substituted-5-methylene-2(5H)-furanones), naturally occurring bacterial quorum sensing (QS) inhibitors, were synthesized by a novel sequence. The importance of the methylene group, either brominated or non-brominated, in LuxR-dependent QS inhibition was demonstrated. One of the most active furanone-type QS inhibitors was identified, with an IC50 of 0.6 μM.

Domaines: Chimie organique

Mohamad Sabbah, Maud Bernollin, Alain Doutheau, Laurent Soulère, Yves Queneau. A new route towards fimbrolide analogues : importance of the exomethylene motif in LuxR dependent quorum sensing inhibition. MedChemComm, 2013, 4 (2), pp.363-366. ⟨10.1039/c2md20298k⟩. ⟨hal-01146328⟩