Heterocyclic Chemistry Applied to the Design of N-Acyl Homoserine Lactone Analogues as Bacterial Quorum Sensing Signals Mimics

被引:13
|
作者
Zhang, Qiang [1 ,3 ]
Li, Sizhe [1 ,4 ]
Hachicha, Maha [1 ,2 ]
Boukraa, Mohamed [1 ,2 ]
Soulere, Laurent [1 ]
Efrit, Mohamed L. [2 ]
Queneau, Yves [1 ]
机构
[1] Univ Claude Bernard Lyon 1, Univ Lyon, INSA Lyon, CPE Lyon,UMR 5246,CNRS,ICBMS, Bat E Lederer,1 Rue Victor Grignard, F-69622 Villeurbanne, France
[2] Univ Tunis El Manar, Lab Synth Organ Select & Heterocycl, Fac Sci Tunis, Tunis 2092, Tunisia
[3] Hubei Univ Educ, Sch Chem & Life Sci, 129 Second Gaoxin Rd, Wuhan 430205, Peoples R China
[4] Leiden Inst Chem, Bioorgan Synth Grp, DE-4-07,Einsteinweg 55, NL-2333 CC Leiden, Netherlands
来源
MOLECULES | 2021年 / 26卷 / 17期
关键词
acyl homoserine lactones; AHL; quorum sensing; bioisosteres; heterocyclic chemistry; BIOLOGICAL EVALUATION; DERIVATIVES; INHIBITORS; TRIAZOLE; BIOSYNTHESIS; BIOISOSTERES; ANTAGONISTS; MODULATION; DISCOVERY; VIRULENCE;
D O I
10.3390/molecules26175135
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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.
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页数:24
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