A.M. Butlerov Chemistry Institute, Kazan Federal University, 18 Kremlyovskaya Str., 420008 Kazan, Russia.
Int J Mol Sci. 2022 Jan 11;23(2):779. doi: 10.3390/ijms23020779.
Novel monosubstituted pillar[5]arenes containing both amide and carboxyl functional groups were synthesized. Solid lipid nanoparticles based on the synthesized macrocycles were obtained. Formation of spherical particles with an average hydrodynamic diameter of 250 nm was shown for pillar[5]arenes containing N-(amidoalkyl)amide fragments regardless of their concentration. It was established that pillar[5]arene containing N-alkylamide fragments can form spherical particles with two different sizes (88 and 223 nm) depending on its concentration. Mixed solid lipid nanoparticles based on monosubstituted pillar[5]arenes and surfactant (dodecyltrimethylammonium chloride) were obtained for the first time. The surfactant made it possible to level the effect of the macrocycle concentration. It was found that various types of aggregates are formed depending on the macrocycle/surfactant ratio. Changing the macrocycle/surfactant ratio allows to control the charge of the particles surface. This controlled property will lead to the creation of molecular-scale porous materials that selectively interact with various types of substrates, including biopolymers.
合成了含有酰胺和羧基官能团的新型单取代的[5]柱芳烃。基于合成的大环,得到了固体脂质纳米粒子。对于含有 N-(酰胺基烷基)酰胺片段的[5]柱芳烃,无论其浓度如何,均显示出形成平均水动力直径为 250nm 的球形颗粒。已经确定,含有 N-烷基酰胺片段的[5]柱芳烃可以根据其浓度形成两种不同尺寸(88nm 和 223nm)的球形颗粒。首次获得了基于单取代[5]柱芳烃和表面活性剂(十二烷基三甲基氯化铵)的混合固体脂质纳米粒子。表面活性剂使得能够平衡大环浓度的影响。发现,根据大环/表面活性剂的比例形成各种类型的聚集体。改变大环/表面活性剂的比例可以控制颗粒表面的电荷。这种可控特性将导致创建选择性与各种类型的底物(包括生物聚合物)相互作用的分子级多孔材料。