For the first time, terpene-functionalized pillar[5]arenes containing geranyl, perillyl or farnesyl fragments were synthesized. The obtained compounds did not have a pronounced cytotoxic effect on cells in the studied concentration range (0.025–1 mg/mL). The ability of the obtained compounds to self-assemble in aqueous solutions was evaluated by DLS method. It was shown that the synthesized compounds are formed monodisperse nanosized aggregates with a diameter of 87–180 nm (PDI 0.18–0.33). The morphology of the formed aggregates was studied by transmission electron microscopy. The incorporation of the obtained amphiphilic macrocycles into the lipid bilayer of model lipid biomembranes was definitely confirmed by turbidimetry. Synthesized pillar [5]arenes form a complex with the aza dye methyl orange in a 1:2 ratio (logK = 2.12, logK = 8.63) This complex retains stability both in neutral (pH 7.4) and in an acidic environment (pH 2.7).

中文翻译：

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柱[5]芳烃平台上的萜烯功能化​​大环两亲物作为生物成像系统：合成、亲膜活性以及与偶氮染料的络合


首次合成了含有香叶基、紫苏基或法呢基片段的萜烯功能化​​柱[5]芳烃。所获得的化合物在研究浓度范围（0.025–1 mg/mL）内对细胞没有明显的细胞毒性作用。采用DLS方法评价了所得化合物在水溶液中自组装的能力。结果表明，合成的化合物形成单分散纳米尺寸聚集体，直径为 87-180 nm（PDI 0.18-0.33）。通过透射电子显微镜研究形成的聚集体的形态。通过比浊法明确证实了所获得的两亲性大环化合物并入模型脂质生物膜的脂质双层中。合成的柱 [5] 芳烃与氮杂染料甲基橙以 1:2 的比例形成复合物（logK = 2.12，logK = 8.63）该复合物在中性（pH 7.4）和酸性环境（pH 2.7）中均保持稳定性。