Toward Pathogenic Biofilm Suppressors: Synthesis of Amino Derivatives of Pillar[5]arene and Supramolecular Assembly with DNA.

Autor: Aleksandrova YI; A.M. Butlerov Chemistry Institute, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia., Shurpik DN; A.M. Butlerov Chemistry Institute, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia., Nazmutdinova VA; A.M. Butlerov Chemistry Institute, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia., Mostovaya OA; A.M. Butlerov Chemistry Institute, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia., Subakaeva EV; Institute of Fundamental Medicine and Biology, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia., Sokolova EA; Institute of Fundamental Medicine and Biology, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia., Zelenikhin PV; Institute of Fundamental Medicine and Biology, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia., Stoikov II; A.M. Butlerov Chemistry Institute, Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russia.
Jazyk: angličtina
Zdroj: Pharmaceutics [Pharmaceutics] 2023 Jan 31; Vol. 15 (2). Date of Electronic Publication: 2023 Jan 31.
DOI: 10.3390/pharmaceutics15020476
Abstrakt: 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 St. Aureus . It was found that pillar[5]arene at a concentration of 10 -5 M was able to reduce the thickness of the St. Aureus biofilm by 15%.
Databáze: MEDLINE
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