Uncharged water-soluble amide derivatives of pillar[5]arene: synthesis and supramolecular self-assembly with tetrazole-containing polymers

Shurpik, D. N.; Nazarova, A. A.; Makhmutova, L. I.; Kizhnyaev, V. N.; Стойков, И. И.

doi:10.1007/s11172-020-2728-4

Cited by 6 publications

(4 citation statements)

References 28 publications

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“…Molecular recognition in water is a basis for various vital processes. A significant number of synthesized macrocyclic compounds (cyclodextrins, cucurbiturils, calixarenes, and their thia-analogues, pillararenes) are capable of binding guest molecules in water [45][46][47][48][49][50]. Furthermore, the introduction of small peptide fragments into the structure of macrocycles has shown the possibility of creating water-soluble receptors, which adopt a well-defined and precisely controlled secondary structure [51,52].…”

Section: Resultsmentioning

confidence: 99%

Towards Protection of Nucleic Acids from Herbicide Attack: Self-Assembly of Betaines Based on Pillar[5]arene with Glyphosate and DNA

Nazarova

Padnya

Khannanov

et al. 2023

IJMS

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Herbicides are one of the main parts of pesticides used today. Due to the high efficiency and widespread use of glyphosate-based herbicides, the search for substances reducing their genotoxicity is an important interdisciplinary task. One possible approach for solving the problem of herbicide toxicity is to use compounds that can protect DNA from damage by glyphosate derivatives. For the first time, a method for developing DNA-protecting measures against glyphosate isopropylamine salt (GIS) damage was presented and realized, based on low-toxicity water-soluble pillar[5]arene derivatives. Two- and three-component systems based on pillar[5]arene derivatives, GIS, and model DNA from salmon sperm, as well as their cytotoxicity, were studied. The synthesized pillar[5]arene derivatives do not interact with GIS, while GIS is able to bind DNA from salmon sperm with lgKa = 4.92. The pillar[5]arene betaine derivative containing fragments of L-phenylalanine and the ester derivative with diglycine fragments bind DNA with lgKa = 5.24 and lgKa = 4.88, respectively. The study of the associates (pillar[5]arene-DNA) with GIS showed that the interaction of GIS with DNA is inhibited only by the betaine pillar[5]arene containing fragments of L-Phe (lgKa = 3.60). This study has shown a possible application of betaine pillar[5]arene derivatives for nucleic acid protection according to its competitive binding with biomacromolecules.

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Section: Resultsmentioning

confidence: 99%

Towards Protection of Nucleic Acids from Herbicide Attack: Self-Assembly of Betaines Based on Pillar[5]arene with Glyphosate and DNA

Nazarova

Padnya

Khannanov

et al. 2023

IJMS

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“…Membrane damage occurs through hole formation, and some cationic polymers/oligomers can move across the cell membrane and bind to intracellular DNA or RNA to prevent intracellular synthesis [ 46 ]. In previous works, we showed [ 47 ] that polymers based on tetrazole in the presence of pillar[5]arene are capable of forming nanoscale associates. In [ 47 ], uncharged pillar[5]arenes containing hydroxyl groups were used.…”

Section: Resultsmentioning

confidence: 99%

“…In previous works, we showed [ 47 ] that polymers based on tetrazole in the presence of pillar[5]arene are capable of forming nanoscale associates. In [ 47 ], uncharged pillar[5]arenes containing hydroxyl groups were used. We have shown that the macrocyclic platform plays a key role in the formation of supramolecular associates.…”

Section: Resultsmentioning

confidence: 99%

Towards Universal Stimuli-Responsive Drug Delivery Systems: Pillar[5]arenes Synthesis and Self-Assembly into Nanocontainers with Tetrazole Polymers

et al. 2021

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In this work, we have proposed a novel universal stimulus-sensitive nanosized polymer system based on decasubstituted macrocyclic structures—pillar[5]arenes and tetrazole-containing polymers. Decasubstituted pillar[5]arenes containing a large, good leaving tosylate, and phthalimide groups were first synthesized and characterized. Pillar[5]arenes containing primary and tertiary amino groups, capable of interacting with tetrazole-containing polymers, were obtained with high yield by removing the tosylate and phthalimide protection. According to the fluorescence spectroscopy data, a dramatic fluorescence enhancement in the pillar[5]arene/fluorescein/polymer system was observed with decreasing pH from neutral (pH = 7) to acidic (pH = 5). This indicates the destruction of associates and the release of the dye at a pH close to 5. The presented results open a broad range of opportunities for the development of new universal stimulus-sensitive drug delivery systems containing macrocycles and nontoxic tetrazole-based polymers.

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“…This class of synthetically accessible p -cyclophanes was obtained in high yield by the condensation of 1,4-dimethoxybenzene and paraformaldehyde. Pillar[n]arenes play a great role in contemporary research because they are used as building blocks to create supramolecular polymers and sensors that are sensitive to a wide range of substrates [ 34 , 35 ].…”

Section: Resultsmentioning

confidence: 99%

Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes

Nazarova

Shurpik

Padnya

et al. 2020

IJMS

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Novel water-soluble multifunctional pillar[5]arenes containing amide-ammonium-amino acid moiety were synthesized. The compounds demonstrated a superior ability to bind (1S)-(+)-10-camphorsulfonic acid (S-CSA) and methyl orange dye depending on the nature of the substituent, resulting in the formation one-to-one complexes with both guests. The formation of host-guest complexes was confirmed by ultraviolet (UV), circular dichroism (CD) and 1H NMR spectroscopy. This work demonstrates the first case of using S-CSA as a chiral template for the non-covalent self-assembly of architectures based on pillar[5]arenes. It was shown that pillar[5]arenes with glycine or L-alanine fragments formed aggregates with average hydrodynamic diameters (d) of 165 and 238 nm, respectively. It was established that the addition of S-CSA to the L-alanine-containing derivative led to the formation of micron-sized aggregates with d of 713 nm. This study may advance the design novel stereoselective catalysts and transmembrane amino acid channels.

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Uncharged water-soluble amide derivatives of pillar[5]arene: synthesis and supramolecular self-assembly with tetrazole-containing polymers

Cited by 6 publications

References 28 publications

Towards Protection of Nucleic Acids from Herbicide Attack: Self-Assembly of Betaines Based on Pillar[5]arene with Glyphosate and DNA

Towards Protection of Nucleic Acids from Herbicide Attack: Self-Assembly of Betaines Based on Pillar[5]arene with Glyphosate and DNA

Towards Universal Stimuli-Responsive Drug Delivery Systems: Pillar[5]arenes Synthesis and Self-Assembly into Nanocontainers with Tetrazole Polymers

Self-Assembly of Supramolecular Architectures by the Effect of Amino Acid Residues of Quaternary Ammonium Pillar[5]arenes

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