Hydrazides of glycine-containing decasubstituted pillar [5]arenes were synthesized and characterized. Dynamic light scattering (DLS) and transmission electron microscopy (TEM) showed that self-assembly into monodisperse spherical nanoparticles (28 nm) was typical in water for pillarene hydrazides containing glycylglycide fragments (1×10 -3 M). Binding of the antitumor drug Floxuridine in water by the substituents of the macrocycle was established by NMR spectroscopy. It was shown by DLS and TEM, that heating of the macrocycle-Floxuridine system in a 1:1 ratio at 1×10 -4 M led to its self-organization into monodisperse spherical particles 132 nm in diameter.
Nanoscale lipid drug delivery systems are widely used due to their high efficiency and possibility to increase the drug bioavailability. The size, shape and morphology of these systems can significantly...
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%.
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