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Heterocyclic Chemistry Applied to the Design of N-Acyl Homoserine Lactone Analogues as Bacterial Quorum Sensing Signals Mimics
Authors:Qiang Zhang  Sizhe Li  Maha Hachicha  Mohamed Boukraa  Laurent Soulre  Mohamed L Efrit  Yves Queneau
Institution:1.Univ Lyon, INSA Lyon, Université Claude Bernard Lyon 1, CPE Lyon, UMR 5246, CNRS, ICBMS, Institut de Chimie et de Biochimie Moléculaires et Supramoléculaires, Bât. E. Lederer, 1 Rue Victor Grignard, F-69622 Villeurbanne, France; (Q.Z.); (S.L.); (M.H.); (M.B.);2.Laboratoire de Synthèse Organique Sélective et Hétérocyclique, Faculté des Sciences de Tunis, Université de Tunis El Manar, El Manar, Tunis 2092, Tunisia
Abstract:N-acyl homoserine lactones (AHLs) are small signaling molecules used by many Gram-negative bacteria for coordinating their behavior as a function of their population density. This process, based on the biosynthesis and the sensing of such molecular signals, and referred to as Quorum Sensing (QS), regulates various gene expressions, including growth, virulence, biofilms formation, and toxin production. Considering the role of QS in bacterial pathogenicity, its modulation appears as a possible complementary approach in antibacterial strategies. Analogues and mimics of AHLs are therefore biologically relevant targets, including several families in which heterocyclic chemistry provides a strategic contribution in the molecular design and the synthetic approach. AHLs consist of three main sections, the homoserine lactone ring, the central amide group, and the side chain, which can vary in length and level of oxygenation. The purpose of this review is to summarize the contribution of heterocyclic chemistry in the design of AHLs analogues, insisting on the way heterocyclic building blocks can serve as replacements of the lactone moiety, as a bioisostere for the amide group, or as an additional pattern appended to the side chain. A few non-AHL-related heterocyclic compounds with AHL-like QS activity are also mentioned.
Keywords:acyl homoserine lactones  AHL  quorum sensing  bioisosteres  heterocyclic chemistry
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