β-Alaninol and its derivatives were reported to exhibit interesting biological and pharmacological activities and showed potential application in formulating drug delivery vehicles. In the present study, we report the synthesis and characterization of N-acyl-β-alaninols (NABAOHs) bearing saturated acyl chains (n = 8–20) with respect to thermotropic phase behavior, supramolecular organization and interaction with diacylphosphatidylcholine, a major membrane lipid. Results obtained from DSC and powder XRD studies revealed that the transition temperatures (T_t), transition enthalpies (ΔH_t), transition entropies (ΔS_t) and d-spacings of NABAOHs show odd-even alteration. A linear dependence was observed in the values of ΔH_t and ΔS_t on the acyl chain length, independently for even and odd acyl chains in both dry and hydrated states; further, the even chainlength molecules exhibited higher values than the odd chainlength series. The crystals structures of N-lauroyl-β-alaninol and N-palmitoyl-β-alaninol, solved in monoclinic system in the P21/c space group, show that the NABAOHs adopt a tilted bilayer structure. A number of NH⋯O, O—H⋯O, and C—H⋯O hydrogen bonds between the hydroxyl and amide moieties of the head groups of NABAOH molecules belonging to adjacent and opposite layers stabilize the overall supramolecular organization of the self-assembled bilayer system. DSC studies on the interaction of N-myristoyl-β-alaninol (NMBAOH) with dimyristoylphosphatidylcholine (DMPC) indicate that these two lipids mix well up to 45 mol% NMBAOH, whereas phase separation was observed at higher contents of NMBAOH. Transmission electron microscopic studies reveal that mixtures containing 20−50 mol% NMBAOH form stable ULVs of 90−150 nm diameter, suitable for use in drug delivery applications.

据报道，β-丙氨醇及其衍生物表现出有趣的生物和药理活性，并显示出在配制药物载体方面的潜在应用。在本研究中，我们报告了带有饱和酰基链 ( n = 8-20)的N-酰基-β-丙氨醇 (NABAOH)的合成和表征，涉及热致相行为、超分子组织以及与主要膜二酰基磷脂酰胆碱的相互作用脂质。从 DSC 和粉末 XRD 研究获得的结果表明，转变温度 ( T _t )、转变焓 (Δ H _t )、转变熵 (Δ S _t ) 和d-NABAOH 的间距显示奇偶变化。Δ H _t和Δ S _t的值与酰基链长度呈线性相关，对于干态和水合状态的偶数和奇数酰基链，它们都是独立的；此外，偶数链长分子表现出比奇数链长系列更高的值。N-月桂酰-β-丙氨醇和N-棕榈酰-β-丙氨醇的晶体结构在P21/c空间群的单斜晶系中溶解，表明NABAOHs采用倾斜的双层结构。数 NH⋯O、O-H⋯O 和 C-H⋯O 属于相邻层和相对层的 NABAOH 分子的头部基团的羟基和酰胺部分之​​间的氢键稳定了自组装双层系统的整体超分子组织。N-肉豆蔻酰-β-丙氨醇 (NMBAOH) 与二肉豆蔻酰磷脂酰胆碱 (DMPC)相互作用的 DSC 研究表明，这两种脂质在高达 45 mol% NMBAOH 的情况下混合良好，而在 NMBAOH 含量较高时观察到相分离。透射电子显微镜研究表明，含有 20-50 mol% NMBAOH 的混合物可形成直径为 90-150 nm 的稳定 ULV，适用于药物输送应用。