Understanding how stereochemistry affects interactions with cell membranes is important for effective drug development. Chirality has been shown to greatly effect pharmaceutical distribution and metabolism within the cell. However it has been thought that interactions with, and passive diffusion through, the membrane are not stereochemically selective. Various studies have produced conflicting results regarding whether interactions with lipid bilayers are or can be stereoselective. In the current work, stereoselective interactions between a pair of atropisomers, R-(+)/(S)-(−) 1,1′-Bi-2-naphthol, and sphingomyelin nanodisc bilayers, are demonstrated. This is accomplished using nanodisc electrokinetic chromatography, demonstrating that this approach is sensitive to subtle differences in affinity between small molecule probes and lipid bilayers. Using the same approach, no evidence of stereoselectivity was observed using enantiomer or diastereomer probes of varied chemistry and structure.

了解立体化学如何影响与细胞膜的相互作用对于有效的药物开发非常重要。手性已被证明极大地影响细胞内的药物分布和代谢。然而，人们认为与膜的相互作用以及通过膜的被动扩散不具有立体化学选择性。关于与脂质双层的相互作用是否是或可以是立体选择性的，各种研究产生了相互矛盾的结果。在当前的工作中，证明了一对阻转异构体、R-(+)/(S)-(−) 1,1'-Bi-2-萘酚和鞘磷脂纳米盘双层之间的立体选择性相互作用。这是使用纳米盘电动色谱法完成的，证明该方法对小分子探针和脂质双层之间的亲和力的细微差异敏感。使用相同的方法，使用不同化学和结构的对映异构体或非对映异构体探针没有观察到立体选择性的证据。