Supramolecular approaches to the formation of nanostructures based on phosphonate-thiacalix[4]arenes, their selective lysozyme recognition

Yakimova, Luidmila S.; Vavilova, Alena A.; Shibaeva, K. S.; Sultanaev, Vildan; Mukhametzyanov, Timur A.; Стойков, И. И.

doi:10.1016/j.colsurfa.2020.125897

Cited by 11 publications

(3 citation statements)

References 53 publications

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“…Due to the ability to fix the macrocyclic ring in several conformations and the relative ease of its functionalization, functional groups can be arranged in a predetermined manner in space. It determines the tendency to self-assembly into nanostructures under the influence of the substrate (ions, molecules) [28][29][30].…”

Section: Introductionmentioning

confidence: 99%

Structure–Activity Relationship of the Thiacalix[4]arenes Family with Sulfobetaine Fragments: Self-Assembly and Cytotoxic Effect against Cancer Cell Lines

et al. 2022

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Regulating the structure of macrocyclic host molecules and supramolecular assemblies is crucial because the structure–activity relationship often plays a role in governing the properties of these systems. Herein, we propose and develop an approach to the synthesis of the family of sulfobetaine functionalized thiacalix[4]arenes with regulation of the self-assembly and cytotoxic effect against cancer cell lines. The dynamic light scattering method showed that the synthesized macrocycles in cone, partial cone and 1,3-alternate conformations form submicron-sized particles with Ag+ in water, but the particle size and polydispersity of the systems studied depend on the macrocycle conformation. Based on the results obtained by 1H and 1H-1H NOESY NMR spectroscopy and transmission electron microscopy for the macrocycles and their aggregates with Ag+, a coordination scheme for the Ag+ and different conformations of p-tert-butylthiacalix[4]arene functionalized with sulfobetaine fragments was proposed. The type of coordination determines the different shapes of the associates. Cytotoxic properties are shown to be controlled by the shape of associates, with the highest activity demonstrated by thiacalix[4]arenes in partial cone conformation. This complex partial cone/Ag+ is two times higher than the reference drug imatinib mesylate. High selectivity against cervical carcinoma cell line indicates the prospect of their using as components of new anticancer system.

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Section: Introductionmentioning

confidence: 99%

Structure–Activity Relationship of the Thiacalix[4]arenes Family with Sulfobetaine Fragments: Self-Assembly and Cytotoxic Effect against Cancer Cell Lines

et al. 2022

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“…These arrangements allow binding to the target substrate and determine the tendency to self-assemble into nanostructures [ 18 , 19 , 20 ]. Modified thiacalix[4]arenes are amphiphilic structures in which polar hydrophilic substituents are spatially separated from the hydrophobic macrocyclic fragment, which leads to the formation of micellar structures in aqueous solutions that can include various biologically significant molecules [ 21 , 22 , 23 ]. We have already successfully used this type of compounds for protein binding, incl.…”

Section: Introductionmentioning

confidence: 99%

Albumin/Thiacalix[4]arene Nanoparticles as Potential Therapeutic Systems: Role of the Macrocycle for Stabilization of Monomeric Protein and Self-Assembly with Ciprofloxacin

Yakimova

Kunafina

Mostovaya

et al. 2022

IJMS

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The therapeutic application of serum albumin is determined by the relative content of the monomeric form compared to dimers, tetramers, hexamers, etc. In this paper, we propose and develop an approach to synthesize the cone stereoisomer of p-tert-butylthiacalix[4]arene with sulfobetaine fragments stabilization of monomeric bovine serum albumin and preventing aggregation. Spectral methods (UV-vis, CD, fluorescent spectroscopy, and dynamic light scattering) established the influence of the synthesized compounds on the content of monomeric and aggregated forms of BSA even without the formation of stable thiacalixarene/protein associates. The effect of thiacalixarenes on the efficiency of protein binding with the antibiotic ciprofloxacin was shown by fluorescence spectroscopy. The binding constant increases in the presence of the macrocycles, likely due to the stabilization of monomeric forms of BSA. Our study clearly shows the potential of this macrocycle design as a platform for the development of the fundamentally new approaches for preventing aggregation.

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“…As a result, 1:1 host–guest complexes are formed [ 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 ]. In addition, the ability of water-soluble macrocycles, by analogy with non-macrocyclic surfactants, to form various types of associates such as liposomes [ 36 , 37 , 38 ], micelles [ 39 , 40 , 41 ], and liquid crystals [ 42 , 43 ], etc., is well known. It attracts great attention due to their potential application in various fields and especially in biomedicine as nanocontainers for medicinal and imaging agents [ 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 ].…”

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

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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.

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Supramolecular approaches to the formation of nanostructures based on phosphonate-thiacalix[4]arenes, their selective lysozyme recognition

Cited by 11 publications

References 53 publications

Structure–Activity Relationship of the Thiacalix[4]arenes Family with Sulfobetaine Fragments: Self-Assembly and Cytotoxic Effect against Cancer Cell Lines

Structure–Activity Relationship of the Thiacalix[4]arenes Family with Sulfobetaine Fragments: Self-Assembly and Cytotoxic Effect against Cancer Cell Lines

Albumin/Thiacalix[4]arene Nanoparticles as Potential Therapeutic Systems: Role of the Macrocycle for Stabilization of Monomeric Protein and Self-Assembly with Ciprofloxacin

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

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