Department of Bacteriology, University of Wisconsin , 1550 Linden Drive, Madison, Wisconsin 53706, United States.
J Am Chem Soc. 2016 May 4;138(17):5568-75. doi: 10.1021/jacs.5b12929. Epub 2016 Apr 20.
Botulium neurotoxins (BoNTs) are among the most lethal toxins known to man. They are comprised of seven serotypes with BoNT/A being the most deadly; yet, there is no approved therapeutic for their intoxication or one that has even advanced to clinical trials. Botulinum neurotoxicity is ultimately governed through light chain (LC) protease SNARE protein cleavage leading to a loss of neurotransmitter release. Pharmacological attempts to ablate BoNT/A intoxication have sought to either nullify cellular toxin entry or critical biochemical junctions found within its intricate mechanism of action. In these regards, reports have surfaced of nonpeptidic small molecule inhibitors, but few have demonstrated efficacy in neutralizing cellular toxicity, a key prerequisite before rodent lethality studies can be initiated. On the basis of a lead discovered in our BoNT/A cellular assay campaign, we investigated a family of N-hydroxysuccinimide inhibitors grounded upon structure activity relationship (SAR) fundamentals. Molecules stemming from this SAR exercise were theorized to be protease inhibitors. However, this proposition was overturned on the basis of extensive kinetic analysis. Unexpectedly, inhibitor data pointed to thioredoxin reductase (TrxR), an essential component required for BoNT protease translocation. Also unforeseen was the inhibitors' mechanism of action against TrxR, which was found to be brokered through a suicide-mechanism utilizing quinone methide as the inactivating element. This new series of TrxR inhibitors provides an alternative means to negate the etiological agent responsible for BoNT intoxication, the LC protease.
肉毒神经毒素(BoNTs)是已知对人类最致命的毒素之一。它们由七种血清型组成,其中 BoNT/A 是最致命的;然而,目前还没有针对其中毒的批准治疗方法,也没有一种方法已经进入临床试验。肉毒神经毒性最终通过轻链(LC)蛋白酶 SNARE 蛋白裂解来控制,导致神经递质释放的丧失。药理学尝试消除 BoNT/A 中毒,试图消除细胞毒素进入或其复杂作用机制中发现的关键生化接头。在这些方面,已经出现了非肽小分子抑制剂的报道,但很少有报道证明其在中和细胞毒性方面的功效,这是启动啮齿动物致死性研究的关键前提。基于我们在 BoNT/A 细胞测定活动中发现的一个先导化合物,我们研究了一系列基于结构活性关系(SAR)原理的 N-羟基琥珀酰亚胺抑制剂。源自该 SAR 研究的分子被理论上认为是蛋白酶抑制剂。然而,这一假设被广泛的动力学分析推翻了。出人意料的是,抑制剂数据指向了硫氧还蛋白还原酶(TrxR),这是 BoNT 蛋白酶易位所必需的重要组成部分。同样出乎意料的是,抑制剂对 TrxR 的作用机制,发现它是通过利用醌甲醚作为失活元素的自杀机制来发挥作用的。这一系列新的 TrxR 抑制剂提供了一种否定 BoNT 中毒的致病因子 LC 蛋白酶的替代方法。