Synthesis of pillar[5]arenes with a PH-containing fragment

Nazarova, A. A.; Makhmutova, L. I.; Stoikov, Ivan I.

doi:10.1134/s1070363217090080

Cited by 10 publications

(3 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The choice of this class of macrocyclic compounds was based on synthetic availability and possibility of regoiselective functionalization [ 22 , 23 , 24 , 25 ]. Moreover, the macrocyclic cavity of pillar[5]arene can take an active part in the formation of host-guest complexes, and also makes it possible to obtain different types of associates (supramolecular polymers, micelles, vesicles, rotaxanes and pseudorotaxanes) [ 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 ].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2022

View full text Add to dashboard Cite

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.

show abstract

Section: Introductionmentioning

confidence: 99%

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

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Most of the IPEC can be obtained in aqueous media without the use of organic solvents and chemical crosslinking agents by mixing oppositely charged solutions of polyelectrolytes in different ratios. A promising direction in the design of IPEC is the use of macrocyclic compounds, which, due to the presence of a macrocyclic cavity, make it possible to obtain materials with a specified structure and properties [ 60 , 61 , 62 ]. The interaction of the macrocyclic platform with oppositely charged polyelectrolyte molecules leads to a change in the properties of the supramolecular complex due to the cooperative aggregation of its components [ 39 , 63 ].…”

Section: Introductionmentioning

confidence: 99%

Self-Assembling Systems Based on Pillar[5]arenes and Surfactants for Encapsulation of Diagnostic Dye DAPI

Nazarova

Khannanov

Boldyrev

et al. 2021

IJMS

View full text Add to dashboard Cite

In this paper, we report the development of the novel self-assembling systems based on oppositely charged Pillar[5]arenes and surfactants for encapsulation of diagnostic dye DAPI. For this purpose, the aggregation behavior of synthesized macrocycles and surfactants in the presence of Pillar[5]arenes functionalized by carboxy and ammonium terminal groups was studied. It has been demonstrated that by varying the molar ratio in Pillar[5]arene-surfactant systems, it is possible to obtain various types of supramolecular systems: host–guest complexes at equimolar ratio of Pillar[5]arene-surfactant and interpolyelectrolyte complexes (IPECs) are self-assembled materials formed in aqueous medium by two oppositely charged polyelectrolytes (macrocycle and surfactant micelles). It has been suggested that interaction of Pillar[5]arenes with surfactants is predominantly driven by cooperative electrostatic interactions. Synthesized stoichiometric and non-stoichiometric IPECs specifically interact with DAPI. UV-vis, luminescent spectroscopy and molecular docking data show the structural feature of dye-loaded IPEC and key role of the electrostatic, π–π-stacking, cation–π interactions in their formation. Such a strategy for the design of supramolecular Pillar[5]arene-surfactant systems will lead to a synergistic interaction of the two components and will allow specific interaction with the third component (drug or fluorescent tag), which will certainly be in demand in pharmaceuticals and biomedical diagnostics.

show abstract

“…[16][17][18][19] Varying pillar[n]arene substituents allows their physical properties to be changed and opens up the possibility of working in fields previously inaccessible to paracyclophanes. [20][21][22][23] In this regard the study of the complexation of metal cations by monosubstituted pillar[n]arenes, as well as the influence of the substituents nature on their binding ability, is of special interest.…”

Section: Introductionmentioning

confidence: 99%

Monosubstituted pillar[5]arene functionalized with (amino)phosphonate fragments are “smart” building blocks for constructing nanosized structures with some s- and p-metal cations in the organic phase

et al. 2019

View full text Add to dashboard Cite

show abstract

Synthesis of pillar[5]arenes with a PH-containing fragment

Cited by 10 publications

References 23 publications

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

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

Self-Assembling Systems Based on Pillar[5]arenes and Surfactants for Encapsulation of Diagnostic Dye DAPI

Monosubstituted pillar[5]arene functionalized with (amino)phosphonate fragments are “smart” building blocks for constructing nanosized structures with some s- and p-metal cations in the organic phase

Contact Info

Product

Resources

About