Aleksandrova Yulia I, Shurpik Dmitriy N, Nazmutdinova Viktoriya A, Mostovaya Olga A, Subakaeva Evgenia V, Sokolova Evgenia A, Zelenikhin Pavel V, Stoikov Ivan I
A.M. Butlerov Chemistry Institute, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia.
Institute of Fundamental Medicine and Biology, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia.
Pharmaceutics. 2023 Jan 31;15(2):476. doi: 10.3390/pharmaceutics15020476.
New amino derivatives of pillar[5]arene were obtained in three stages with good yields. It was shown that pillar[5]arene containing thiaether and tertiary amino groups formed supramolecular complexes with low molecular weight model DNA. Pillar[5]arene formed complexes with a DNA nucleotide pair at a ratio of 1:2 (macrocycle/DNA base pairs), as demonstrated by UV-visible and fluorescence spectroscopy. The association constants of pillar[5]arene with DNA were lgKass1:1 = 2.38 and lgKass1:2 = 5.07, accordingly. By using dynamic light scattering and transmission electron microscopy, it was established that the interaction of pillar[5]arene containing thiaether and tertiary amino groups (concentration of 10-5 M) with a model nucleic acid led to the formation of stable nanosized macrocycle/DNA associates with an average particle size of 220 nm. It was shown that the obtained compounds did not exhibit a pronounced toxicity toward human adenocarcinoma cells (A549) and bovine lung epithelial cells (LECs). The hypothesis about a possible usage of the synthesized macrocycle for the aggregation of extracellular bacterial DNA in a biofilm matrix was confirmed by the example of . It was found that pillar[5]arene at a concentration of 10 M was able to reduce the thickness of the biofilm by 15%.
通过三个步骤以良好的产率获得了柱[5]芳烃的新型氨基衍生物。结果表明，含有硫醚和叔氨基的柱[5]芳烃与低分子量模型DNA形成了超分子复合物。紫外可见光谱和荧光光谱表明，柱[5]芳烃与DNA核苷酸对以1:2（大环/DNA碱基对）的比例形成复合物。相应地，柱[5]芳烃与DNA的缔合常数lgKass1:1 = 2.38和lgKass1:2 = 5.07。通过动态光散射和透射电子显微镜确定，含有硫醚和叔氨基的柱[5]芳烃（浓度为10-5 M）与模型核酸的相互作用导致形成稳定的纳米级大环/DNA缔合物，平均粒径为220 nm。结果表明，所获得的化合物对人腺癌细胞（A549）和牛肺上皮细胞（LEC）没有明显的毒性。以……为例证实了关于合成大环可能用于生物膜基质中细胞外细菌DNA聚集的假设。发现浓度为10 M的柱[5]芳烃能够使生物膜的厚度减少15%。
