Precise delivery of hydrophobic drugs has always been a great challenge for drug delivery systems. To overcome this problem, we designed and synthesized a novel supramolecular host biotin-acyclic cucurbituril (ACBB) at the first time, and we have developed a host–guest amphiphilic complex based on ACBB and amantadine-conjugated cannabinoids (AD-CBD) that self-assembles to form functionalized supramolecular micelles (FSMs) for cell-targeted drug delivery. The 1:1 stoichiometric ratio of the amphiphilic complex and its possible host–guest inclusion behaviors are obtained by fluorescence titration, nuclear magnetic resonance (NMR), Fourier transform-infrared spectroscopy (FT-IR) and thermal analysis (TGA and DSC). Using transmission electron microscope (TEM) and dynamic light scattering (DLS), we have observed that the shape of FSMs was spherical and size was 137–192 nm. In addition, MTT test results show that FSMs have good antitumor activity, taking MCF-7 as an example, the in vitro half-maximal inhibitory concentration (IC₅₀) values of FSMs were 1.53 μM and 5.02 μM, which were better than 30.83 μM of cisplatin. Confocal laser scanning microscopy (CLSM) results showed that FSMs loaded with Rhodamine B can specifically aggregate on the surface of tumor cells and the targeting ability has been directly verified. Flow cytometry results showed that FSMs could promote tumor cell apoptosis. All results indicated that FSMs had high bioavailability, stability, accurate targeting and excellent delivery efficiency, which had great application potential in the field of drug delivery.

疏水性药物的精确递送一直是药物递送系统面临的巨大挑战。为了克服这一问题，我们首次设计并合成了一种新型的超分子宿主生物素-无环葫芦脲（ACBB），并开发了一种基于ACBB和金刚烷胺偶联大麻素（AD-CBD）的主客两亲复合物。 -组装形成功能化的超分子胶束 (FSM)，用于细胞靶向药物递送。通过荧光滴定、核磁共振 (NMR)、傅里叶变换红外光谱 (FT-IR) 和热分析 (TGA 和 DSC) 获得了两亲复合物的 1:1 化学计量比及其可能的主客体包合行为。使用透射电子显微镜 (TEM) 和动态光散射 (DLS)，我们观察到 FSM 的形状为球形，尺寸为 137-192 nm。此外，MTT试验结果表明FSMs具有良好的抗肿瘤活性，以MCF-7为例，体外半数最大抑制浓度（IC₅₀ ) FSM 的值为 1.53 μM 和 5.02 μM，优于顺铂的 30.83 μM。共聚焦激光扫描显微镜（CLSM）结果表明，负载罗丹明B的FSMs可以特异性地聚集在肿瘤细胞表面，靶向能力得到了直接验证。流式细胞仪结果显示FSMs可以促进肿瘤细胞凋亡。结果表明，FSMs具有较高的生物利用度、稳定性、精准的靶向性和优异的递送效率，在药物递送领域具有巨大的应用潜力。