Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.
J Med Chem. 2012 Nov 26;55(22):9669-81. doi: 10.1021/jm300908t. Epub 2012 Nov 8.
Quorum sensing is a mechanism of chemical communication among bacteria that enables collective behaviors. In V. cholerae, the etiological agent of the disease cholera, quorum sensing controls group behaviors including virulence factor production and biofilm formation. The major V. cholerae quorum-sensing system consists of the extracellular signal molecule called CAI-1 and its cognate membrane bound receptor called CqsS. Here, the ligand binding activity of CqsS is probed with structural analogues of the natural signal. Enabled by our discovery of a structurally simplified analogue of CAI-1, we prepared and analyzed a focused library. The molecules were designed to probe the effects of conformational and structural changes along the length of the fatty acid tail of CAI-1. Our results, combined with pharmacophore modeling, suggest a molecular basis for signal molecule recognition and receptor fidelity with respect to the fatty acid tail portion of CAI-1. These efforts provide novel probes to enhance discovery of antivirulence agents for the treatment of V. cholerae.
群体感应是一种细菌之间的化学通讯机制,使细菌能够表现出群体行为。在霍乱弧菌(Vibrio cholerae)中,这种疾病的病原体,群体感应控制着包括毒力因子产生和生物膜形成在内的群体行为。主要的霍乱弧菌群体感应系统由称为 CAI-1 的细胞外信号分子和其同源的膜结合受体 CqsS 组成。在这里,我们用天然信号的结构类似物来探测 CqsS 的配体结合活性。在我们发现 CAI-1 的结构简化类似物的基础上,我们制备并分析了一个聚焦文库。这些分子被设计用来探测 CAI-1 脂肪酸尾部长度上的构象和结构变化的影响。我们的结果,结合药效团建模,为信号分子识别和受体保真度提供了一个分子基础,涉及 CAI-1 的脂肪酸尾部部分。这些努力为发现治疗霍乱弧菌的抗毒力因子提供了新的探针。