N-sulfonyl homoserine lactones as antagonists of bacterial quorum sensing
N-sulfonyl homoserine lactones as antagonists of bacterial quorum sensing
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DOI：
10.1016/j.bmcl.2004.07.088
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发表时间：
2004-10-18
影响因子：
2.7
通讯作者：
Doutheau, A
中科院分区：
文献类型：
--
作者：
Castang, S;Chantegrel, B;Doutheau, A
本文合成了11个新的N-酰基高丝氨酸内酯类似物，其中羧酰胺键被磺酰胺键取代。评价这些化合物竞争性抑制3-氧代己酰基-L-高丝氨酸内酯作用的能力，3-氧代己酰基-L-高丝氨酸内酯是群体感应转录调节因子LuxR的天然配体，其进而激活模式细菌费氏弧菌中生物发光的表达。发现几种化合物显示拮抗剂活性。分子模拟表明，后者防止级联的结构重排必要的活性LuxR二聚体的形成。(C)2004爱思唯尔有限公司保留所有权利。
A series of 11 new analogues of N-acylhomoserine lactones in which the carboxamide bond was replaced by a sulfonamide one, has been synthesised. These compounds were evaluated for their ability to competitively inhibit the action of 3-oxohexanoyl-L-homoserine lactone, the natural ligand of the quorum sensing transcriptional regulator LuxR, which in turn activates expression of bioluminescence in the model bacterium Vibrio fischeri. Several compounds were found to display antagonist activity. Molecular modeling suggests that the latter prevent a cascade of structural rearrangements necessary for the formation of the active LuxR dimer. (C) 2004 Elsevier Ltd. All rights reserved.