Department of Medicinal Chemistry, School of Pharmacy, Virginia Commonwealth University, 800 E Leigh Street, Richmond, VA, 23298, USA.
J Comput Aided Mol Des. 2020 Aug;34(8):879-895. doi: 10.1007/s10822-020-00309-x. Epub 2020 Mar 19.
Targeting the mu opioid receptor (MOR) by applying orthosteric ligands is the most frequently employed method to treat opioid use disorder (OUD). Unfortunately, most of MOR orthosteric ligands produce severe side effects, mainly due to their low selectivity over other opioid receptors. In contrast, some G protein-coupled receptor allosteric modulators have been reported to exhibit high subtype selectivity and can effectively modulate the potency and/or efficacy of orthosteric ligands. Recently, NAQ and its analog NCQ were identified as novel MOR bitopic modulators. Interestingly, NAQ and NCQ were similar in structure but exhibited different efficacy profiles to the MOR. NAQ exhibited an antagonism activity to the MOR while NCQ showed a partial agonism activity to the MOR. In the present study, molecular modeling methods were applied to explore the putative molecular mechanisms of their different functional profiles to the MOR. When NAQ binding with the inactive MOR, the 'address' portion of NAQ interacted with the MOR allosteric site but showed no significant allosteric modulation of the efficacy of the 'message' portion of NAQ. However, when NCQ binding with the inactive and active MOR, the 'address' portion of NCQ seemed to be able to positively modulate the efficacy of the 'message' portion of NCQ at varying levels. Evidentially, the substituents at the 1'- and 4'-positions of the isoquinoline ring of NCQ seemed to play a critical role in the modulatory function of the 'address' portion of NCQ. These findings will be invaluable to develop our next generation of MOR bitopic modulators with high affinity and subtype selectivity to potentially treat OUD.
通过应用正构配体靶向μ阿片受体(MOR)是治疗阿片类药物使用障碍(OUD)最常用的方法。不幸的是,大多数 MOR 正构配体产生严重的副作用,主要是由于它们对其他阿片受体的选择性低。相比之下,一些 G 蛋白偶联受体变构调节剂已被报道具有高亚型选择性,并能有效调节正构配体的效力和/或功效。最近,NAQ 和其类似物 NCQ 被鉴定为新型 MOR 双位点调节剂。有趣的是,NAQ 和 NCQ 在结构上相似,但对 MOR 的疗效谱不同。NAQ 对 MOR 表现出拮抗作用,而 NCQ 对 MOR 表现出部分激动作用。在本研究中,应用分子建模方法探讨了它们对 MOR 不同功能谱的可能分子机制。当 NAQ 与非活性 MOR 结合时,NAQ 的“地址”部分与 MOR 变构部位相互作用,但对 NAQ 的“消息”部分的效力没有显著的变构调节。然而,当 NCQ 与非活性和活性 MOR 结合时,NCQ 的“地址”部分似乎能够在不同水平上积极调节 NCQ 的“消息”部分的效力。显然,NCQ 异喹啉环的 1'和 4'位的取代基似乎在 NCQ 的“地址”部分的调节功能中起关键作用。这些发现对于开发具有高亲和力和亚型选择性的新一代 MOR 双位点调节剂,以潜在治疗 OUD,将是非常宝贵的。