Molecular Bio-computation and Drug Design Laboratory, School of Health Sciences, University of KwaZulu-Natal, Westville Campus, Durban, 4001, South Africa.
J Mol Model. 2021 Jul 26;27(8):231. doi: 10.1007/s00894-021-04848-4.
The Retinoid X Receptor (RXR) is an attractive target in the treatment of colon cancer. Different therapeutic binders with high potency have been used to specifically target RXR. Among these compounds is a novel analogue of berberine, B12. We provided structural and molecular insights into the therapeutic activity properties of B12 relative to its parent compound, berberine, using force field estimations and thermodynamic calculations. Upon binding of B12 to RXR, the high instability elicited by RXR was markedly reduced; similar observation was seen in the berberine-bound RXR. However, our analysis revealed that B12 could have a more stabilizing effect on RXR when compared to berberine. Interestingly, the mechanistic behaviour of B12 in the active site of RXR opposed its impact on RXR protein. This disparity could be due to the bond formation and breaking elicited between B12/berberine and the active site residues. We observed that B12 and berberine could induce a disparate conformational change in regions Gly250-Asp258 located on the His-RXRα/LBD domain. Comparatively, the high agonistic and activation potential reported for B12 compared to berberine might be due to its superior binding affinity as evidenced in the thermodynamic estimations. The total affinity for B12 (-25.76 kcal/mol) was contributed by electrostatic interactions from Glu243 and Glu239. Also, Arg371, which plays a crucial role in the activity of RXR, formed a strong hydrogen bond with B12; however, a weak interaction was elicited between Arg371 and berberine. Taken together, our study has shown the RXRα activating potential of B12, and findings from this study could provide a framework in the future design of RXRα binders specifically tailored in the selective treatment of colon cancer.
维甲酸 X 受体(RXR)是治疗结肠癌的一个有吸引力的靶点。已经使用了不同的具有高效力的治疗结合物来特异性靶向 RXR。这些化合物包括小檗碱的一种新型类似物,B12。我们使用力场估计和热力学计算,提供了 B12 相对于其母体化合物小檗碱的治疗活性特性的结构和分子见解。B12 与 RXR 结合后,RXR 引起的高不稳定性明显降低;在与小檗碱结合的 RXR 中也观察到了类似的观察结果。然而,我们的分析表明,与小檗碱相比,B12 可以对 RXR 产生更稳定的作用。有趣的是,B12 在 RXR 的活性部位的机械行为与其对 RXR 蛋白的影响相反。这种差异可能是由于 B12/小檗碱与活性部位残基之间的键形成和断裂引起的。我们观察到 B12 和小檗碱可以诱导位于 His-RXRα/LBD 结构域上的 Gly250-Asp258 区域的不同构象变化。相比之下,与小檗碱相比,B12 报道的高激动剂和激活潜力可能是由于其在热力学估计中表现出的优越结合亲和力。B12 的总亲和力(-25.76 kcal/mol)由来自 Glu243 和 Glu239 的静电相互作用贡献。此外,Arg371 在 RXR 的活性中起关键作用,与 B12 形成强氢键;然而,Arg371 与小檗碱之间仅产生弱相互作用。总之,我们的研究表明了 B12 对 RXRα 的激活潜力,并且这项研究的结果可以为未来专门针对结肠癌的 RXRα 结合物的设计提供框架。