Investigation of DNA binding abilities of solid lipid nanoparticles based on p-tert-butylthiacalix[4]arene platform

Galukhin, Andrey; Erokhin, A.A.; Imatdinov, Ilnaz; Osin, Yu. N.

doi:10.1039/c5ra03814f

Cited by 7 publications

(3 citation statements)

References 21 publications

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“…Recently, several derivatives of thiacalix [4]arene with cationic functional groups have been synthesized and applied in the DNA study [28][29][30]. The aggregation and self-aggregation of the macrocycles were promoted by the DNA binding.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Sensing of Interactions between DNA and Charged Macrocycles

et al. 2021

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In this work, we investigated aggregation of native DNA and thiacalix[4]arene derivative bearing eight terminal amino groups in cone configuration using various redox probes on the glassy carbon electrode. It was shown that sorption transfer of the aggregates on the surface of the electrode covered with carbon black resulted in changes in electrostatic interactions and diffusional permeability of the surface layer. Such changes alter the signals of ferricyanide ion, methylene green and hydroquinone as redox probes to a degree depending on their specific interactions with DNA and own charge. Inclusion of DNA in the surface layer was independently confirmed by scanning electron microscopy, electrochemical impedance spectroscopy and experiments with doxorubicin as a model intercalator. Thermal denaturing of DNA affected the charge separation on the electrode interface and the signals of redox probes. Using hydroquinone, less sensitive to electrostatic interactions, made it possible to determine from 10 pM to 1.0 nM doxorubicin (limit of detection 3 pM) after 10 min incubation. Stabilizers present in the commercial medications did not alter the signal. The DNA sensors developed can find future application in the assessment of the complexes formed by DNA and macrocycles as delivery agents for small chemical species.

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Section: Introductionmentioning

confidence: 99%

Electrochemical Sensing of Interactions between DNA and Charged Macrocycles

et al. 2021

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“…In this work, we studied the influence of substituent nature in the structure of monosubstituted pillar[5]arenes on the size and stability of formed particles. We obtained SLN in water by nanoprecipitation using the THF-water solvent system according to the literature method [ 47 ]. The synthesized nanoparticles were characterized by DLS and electrophoretic light scattering methods ( Figures S17–S20 ).…”

Section: Resultsmentioning

confidence: 99%

Solid Lipid Nanoparticles Based on Monosubstituted Pillar[5]arenes: Chemoselective Synthesis of Macrocycles and Their Supramolecular Self-Assembly

et al. 2022

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Novel monosubstituted pillar[5]arenes with one or two terminal carboxyl groups were synthesized by the reaction of succinic anhydride with pillar[5]arene derivative containing a diethylenetriamine function. The ability for non-covalent self-assembly in chloroform, dimethyl sulfoxide, as well as in tetrahydrofuran-water system was studied. The ability of the synthesized macrocycles to form different types of associates depending on the substituent nature was established. The formation of stable particles with average diameter of 192 nm in chloroform and of 439 nm in DMSO was shown for pillar[5]arene containing two carboxyl fragments. Solid lipid nanoparticles (SLN) based on monosubstituted pillar[5]arenes were synthesized by nanoprecipitation in THF-water system. Minor changes in the structure of the macrocycle substituent can dramatically influence the stability and shape of SLN (spherical and rod-like structures) accordingly to DLS and TEM. The presence of two carboxyl groups in the macrocycle substituent leads to the formation of stable spherical SLN with an average hydrodynamic diameter of 364–454 nm. Rod-like structures are formed by pillar[5]arene containing one carboxyl fragment, which diameter is about of 50–80 nm and length of 700–1000 nm. The synthesized stable SLN open up great prospects for their use as drug storage systems.

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“…10,11 In p-tert-butylthiacalix [4]arene, the bond length between the aromatic residue and bridging group is 15% larger than that in methylene bridged p-tert-butylcalix [4]arene, 12,13 which allows for the design of conformationally more exible receptors compared with conventional calix [4]arene 14,15 for more effective recognition of biological anionic substrates. 16 Herein, we continue to develop our approach towards synthesis of preorganized guanidinium receptors based on stepwise functionalization of the lower rim of the p-tertbutylthiacalix [4]arene platform. 17,18 We studied aggregation and cytotoxicity of cationic thiacalixarenes functionalized with guanidinium fragments, as well as their binding affinity towards polynucleotide molecules.…”

Section: Introductionmentioning

confidence: 99%