Department of Medicine, Columbia University, 630 W 168th Street, BB8-444, New York, NY, 10032, USA.
Department of Medicine, Columbia University, 630 W 168th Street, BB8-444, New York, NY, 10032, USA.
Toxicol Lett. 2018 Jul;291:1-10. doi: 10.1016/j.toxlet.2018.03.028. Epub 2018 Mar 31.
Organophosphate compounds (OPCs) are commonly used as pesticides and were developed as nerve agents for chemical warfare. Exposure to OPCs results in toxicity due to their covalent binding and inhibition of acetylcholinesterase (AChE). Treatment for toxicity due to OPC exposure has been largely focused on the reactivation of AChE by oxime-based compounds via direct nucleophilic attack on the phosphorous center. However, due to the disadvantages to existing oxime-based reactivators for treatment of OPC poisoning, we considered non-oxime mechanisms of reactivation. A high throughput screen of compound libraries was performed to discover previously unidentified reactivation compounds, followed by studies on their analogs. In the process, we discovered multiple non-oxime classes of compounds, the most robust of which we have already reported [1]. Herein, we report other classes of compounds we identified in our screen that are efficient at reactivation. During biochemical characterization, we also found some compounds with other activities that may inspire novel therapeutic approaches to OPC toxicity. Specifically, we found compounds that [1] increase the rate of substrate hydrolysis by AChE and, [2] protect the enzyme from inhibition by OPC. Further, we discovered that a subset of reactivator compounds recover activity from both AChE and the related enzyme butyrylcholinesterase (BuChE). We now report these compounds, their activities and discuss how each relates to therapeutic approaches that would provide alternatives to traditional oxime-based reactivation.
有机磷化合物(OPCs)通常被用作农药,也被开发为化学战中的神经毒剂。由于它们的共价结合和对乙酰胆碱酯酶(AChE)的抑制作用,接触 OPC 会导致毒性。针对 OPC 暴露引起的毒性的治疗方法主要集中在通过肟类化合物对磷中心的直接亲核攻击来使 AChE 重新激活。然而,由于现有肟类再激活剂在治疗 OPC 中毒方面存在缺点,我们考虑了非肟类再激活机制。对化合物库进行了高通量筛选,以发现以前未被识别的再激活化合物,然后对其类似物进行研究。在此过程中,我们发现了多种非肟类化合物,其中最有效的一种我们已经报道过[1]。在此,我们报告我们在筛选中发现的其他类别的有效再激活化合物。在生化特性研究过程中,我们还发现了一些具有其他活性的化合物,这些化合物可能为 OPC 毒性的治疗方法提供新的思路。具体来说,我们发现一些化合物[1]可以提高 AChE 水解底物的速率,[2]可以保护酶免受 OPC 的抑制。此外,我们发现一组再激活化合物可以从 AChE 和相关酶丁酰胆碱酯酶(BuChE)中恢复活性。我们现在报告这些化合物、它们的活性,并讨论它们如何与治疗方法相关,这些方法将为传统肟类再激活提供替代方法。