Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties

The alkyl-4-quinolones (AQs) are a class of metabolites produced primarily by members of the <i>Pseudomonas</i> and <i>Burkholderia</i> genera, consisting of a 4-quinolone core substituted by a range of pendant groups, most commonly at the C-2 position. The history of this cl...

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Main Authors: Muhammad Saalim, Jessica Villegas-Moreno, Benjamin R. Clark
Format: Article
Language:English
Published: MDPI AG 2020-12-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/25/23/5689
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author Muhammad Saalim
Jessica Villegas-Moreno
Benjamin R. Clark
author_facet Muhammad Saalim
Jessica Villegas-Moreno
Benjamin R. Clark
author_sort Muhammad Saalim
collection DOAJ
description The alkyl-4-quinolones (AQs) are a class of metabolites produced primarily by members of the <i>Pseudomonas</i> and <i>Burkholderia</i> genera, consisting of a 4-quinolone core substituted by a range of pendant groups, most commonly at the C-2 position. The history of this class of compounds dates back to the 1940s, when a range of alkylquinolones with notable antibiotic properties were first isolated from <i>Pseudomonas aeruginosa</i>. More recently, it was discovered that an alkylquinolone derivative, the Pseudomonas Quinolone Signal (PQS) plays a key role in bacterial communication and quorum sensing in <i>Pseudomonas aeruginosa</i>. Many of the best-studied examples contain simple hydrocarbon side-chains, but more recent studies have revealed a wide range of structurally diverse examples from multiple bacterial genera, including those with aromatic, isoprenoid, or sulfur-containing side-chains. In addition to their well-known antimicrobial properties, alkylquinolones have been reported with antimalarial, antifungal, antialgal, and antioxidant properties. Here we review the structural diversity and biological activity of these intriguing metabolites.
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spelling doaj.art-4eaa7721a3b44221822da4bbad766a462023-11-20T23:14:44ZengMDPI AGMolecules1420-30492020-12-012523568910.3390/molecules25235689Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological PropertiesMuhammad Saalim0Jessica Villegas-Moreno1Benjamin R. Clark2School of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Tianjin 300092, ChinaSchool of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Tianjin 300092, ChinaSchool of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Tianjin 300092, ChinaThe alkyl-4-quinolones (AQs) are a class of metabolites produced primarily by members of the <i>Pseudomonas</i> and <i>Burkholderia</i> genera, consisting of a 4-quinolone core substituted by a range of pendant groups, most commonly at the C-2 position. The history of this class of compounds dates back to the 1940s, when a range of alkylquinolones with notable antibiotic properties were first isolated from <i>Pseudomonas aeruginosa</i>. More recently, it was discovered that an alkylquinolone derivative, the Pseudomonas Quinolone Signal (PQS) plays a key role in bacterial communication and quorum sensing in <i>Pseudomonas aeruginosa</i>. Many of the best-studied examples contain simple hydrocarbon side-chains, but more recent studies have revealed a wide range of structurally diverse examples from multiple bacterial genera, including those with aromatic, isoprenoid, or sulfur-containing side-chains. In addition to their well-known antimicrobial properties, alkylquinolones have been reported with antimalarial, antifungal, antialgal, and antioxidant properties. Here we review the structural diversity and biological activity of these intriguing metabolites.https://www.mdpi.com/1420-3049/25/23/5689quinolonesquorum sensing<i>Pseudomonas aeruginosa</i>
spellingShingle Muhammad Saalim
Jessica Villegas-Moreno
Benjamin R. Clark
Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties
Molecules
quinolones
quorum sensing
<i>Pseudomonas aeruginosa</i>
title Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties
title_full Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties
title_fullStr Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties
title_full_unstemmed Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties
title_short Bacterial Alkyl-4-quinolones: Discovery, Structural Diversity and Biological Properties
title_sort bacterial alkyl 4 quinolones discovery structural diversity and biological properties
topic quinolones
quorum sensing
<i>Pseudomonas aeruginosa</i>
url https://www.mdpi.com/1420-3049/25/23/5689
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AT benjaminrclark bacterialalkyl4quinolonesdiscoverystructuraldiversityandbiologicalproperties