2023Future Medicinal ChemistryRequires access

Investigation of Halogenated Furanones As Inhibitors of Quorum sensing-regulated Bioluminescence in Vibrio Harveyi

Jorge Pinheiro, Thérèse Lyons, Vanessa Las Heras, Miguel Villoria Recio, Cormac G. M. Gahan, Timothy P. O’Sullivan

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Abstract

Aim: Vibrio harveyi is a Gram-negative marine bacterium that is a model system in the study of quorum sensing (QS). V. harveyi uses multichannel QS, mediated by three signaling molecules. The aim of this study was to synthesize and screen a diverse series of furanones for their potential to inhibit V. harveyi quorum sensing. Materials & methods: A library of halogenated furanones was prepared and derivatized using standard Pd-mediated coupling reactions and subsequently evaluated for their effects on V. harveyi bioluminescence. Results & conclusion: Several furanones inhibited QS-regulated bioluminescence, with gem-dichlorofuranone and tribromofuranone compounds proving especially effective. Importantly, a number of compounds were effective inhibitors of V. harveyi bioluminescence but did not have an impact on bacterial growth.

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Aim: Vibrio harveyi is a Gram-negative marine bacterium that is a model system in the study of quorum sensing (QS). V. harveyi uses multichannel QS, mediated by three signaling molecules. The aim of this study was to synthesize and screen a diverse series of furanones for their potential to inhibit V. harveyi quorum sensing. Materials & methods: A library of halogenated furanones was prepared and derivatized using standard Pd-mediated coupling reactions and subsequently evaluated for their effects on V. harveyi bioluminescence. Results & conclusion: Several furanones inhibited QS-regulated bioluminescence, with gem-dichlorofuranone and tribromofuranone compounds proving especially effective. Importantly, a number of compounds were effective inhibitors of V. harveyi bioluminescence but did not have an impact on bacterial growth.

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Available abstract

Aim: Vibrio harveyi is a Gram-negative marine bacterium that is a model system in the study of quorum sensing (QS). V. harveyi uses multichannel QS, mediated by three signaling molecules. The aim of this study was to synthesize and screen a diverse series of furanones for their potential to inhibit V. harveyi quorum sensing. Materials & methods: A library of halogenated furanones was prepared and derivatized using standard Pd-mediated coupling reactions and subsequently evaluated for their effects on V. harveyi bioluminescence. Results & conclusion: Several furanones inhibited QS-regulated bioluminescence, with gem-dichlorofuranone and tribromofuranone compounds proving especially effective. Importantly, a number of compounds were effective inhibitors of V. harveyi bioluminescence but did not have an impact on bacterial growth.

Key concepts: Vibrio harveyi, Bioluminescence, Quorum sensing, Chemistry, Microbiology, Bacteria, Combinatorial chemistry, Biochemistry

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