Polycationic Derivatives of p-tert-Butylthiacalix[4]arene in 1,3-alternate Stereoisomeric Form: New DNA Condensing Agents

Ibragimova, R. R.; Burilov, Vladimir; Aimetdinov, Albert R.; Mironova, Diana A.; Evtugyn, Vladimir G.; Osin, Yu. N.; Solovieva, Svetlana E.; Антипин, И. С.

doi:10.6060/mhc161180b

Cited by 15 publications

(9 citation statements)

References 21 publications

(39 reference statements)

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“…[6] Imidazole-containing amphiphiles occupy a special place due to their unique properties: they can form supramolecular complexes with drugs, proteins, nucleic acids, and are also used as ionic liquids, basic components of nanogels and in organocatalysis. [7][8][9][10] The introduction of ethylene glycol fragments into amphiphilic molecules leads to an increase in their water solubility and improves biocompatibility. [11] The calixarene platform allows to combine various functional groups on one platform.…”

Section: Introductionmentioning

confidence: 99%

Amphiphilic N-Oligoethyleneglycol-imidazolium Derivatives of p-tert-Butylthiacalix[4]arene: Synthesis, Aggregation and Interaction with DNA

Gafiatullin¹,

Radaev²,

Osipova³

et al. 2021

MHC

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New water-soluble derivatives of p-tert-butylthiacalix [4]arene have been synthesized in the stereoisomeric form 1,3-alternate with butyl and tetradecyl groups on one side of the macrocyclic platform and tri/tetraethylene glycol substituents on the other. The aggregation characteristics of macrocycles in the aquatic environment (CAC, aggregate size, zeta potential) have been studied. It has been demonstrated that the resulting aggregates have the ability to solubilize the lipophilic azo dye Orange OT, and the solubilizing ability significantly increases on going from butyl to tetradecyl derivatives. Using the methods of dynamic and electrophoretic light scattering and fluorimetry with ethidium bromide as a probe, it was shown that the obtained macrocycles interact with the DNA of the calf thymus. It was found that the efficiency of the interaction is greatly influenced by the length of the oxyethyl fragments: macrocycles containing tetraethylene glycol fragments are more effective than triethylene glycol analogs, causing a 2-fold compaction of DNA.

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Section: Introductionmentioning

confidence: 99%

Amphiphilic N-Oligoethyleneglycol-imidazolium Derivatives of p-tert-Butylthiacalix[4]arene: Synthesis, Aggregation and Interaction with DNA

Gafiatullin¹,

Radaev²,

Osipova³

et al. 2021

MHC

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“…We recently synthesized a series of cationic receptors based on the p-tert -butylthiacalix[4]arene platform with 1,3-alternate conformation having polyammonium binding sites. They were shown to effectively interact with calf thymus DNA causing a 4-fold compaction of the latter [ 25 ]. Related macrocycles containing two cationic imidazolium fragments demonstrated a high affinity to ATP [ 26 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new p-tert-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates

Burilov¹,

Fatikhova²,

Dokuchaeva³

et al. 2018

Beilstein J. Org. Chem.

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The synthesis of new calix[4]arenes adopting a cone stereoisomeric form bearing two or four azide fragments on the upper rim and water-soluble triazolyl amphiphilic receptors with two or four polyammonium headgroups via copper-catalyzed azide–alkyne cycloaddition reaction has been performed for the first time. It was found that the synthesized macrocycles form stable aggregates with hydrodynamic diameters between 150–200 nm and electrokinetic potentials about +40 to +60 mV in water solutions. Critical aggregation concentration (CAC) values were measured using a micelle method with pyrene and eosin Y as dye probes. The CAC values of tetraalkyl-substituted macrocycles 12a,b (5 µM for both) are significantly lower than those for dialkyl-substituted macrocycles 10a,b (790 and 160 µM, respectively). Premicellar aggregates of macrocycles 10a,b and 12a,b with the dye eosin Y were used for nucleotides sensing through a dye replacement procedure. It is unusual that disubstituted macrocycles 10a,b bind more effectively a less charged adenosine 5'-diphosphate (ADP) than adenosine 5'-triphosphate (ATP). A simple colorimetric method based on polydiacetylene vesicles decorated with 10b was elaborated for the naked-eye detection of ADP with a detection limit of 0.5 mM.

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“…Use of 1,3-alternate stereoisomeric form allowed to design on the thiacalixarene platform two molecular domains (liophilic and polar receptor units) with quite different properties located on opposite sides of the macrocycles plane. Obtained cationic amphiphilic receptors showed a great opportunities in binding with biomolecules (BSA [21] calf timus DNA) [22] as well as with anionic surfactants [23] (lauril and laureth sulphates).…”

Section: Introductionmentioning

confidence: 99%

Unusual Reactivity of Aliphatic and Aromatic Amines with Bromoalkyl Derivatives of Thiacalix[4]arene in 1,3-Alternate Stereoisomeric Form

Nugmanov¹,

Ibragimova²,

Burilov³

et al. 2017

MHC

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Polycationic Derivatives of p-tert-Butylthiacalix[4]arene in 1,3-alternate Stereoisomeric Form: New DNA Condensing Agents

Cited by 15 publications

References 21 publications

Amphiphilic N-Oligoethyleneglycol-imidazolium Derivatives of p-tert-Butylthiacalix[4]arene: Synthesis, Aggregation and Interaction with DNA

Amphiphilic N-Oligoethyleneglycol-imidazolium Derivatives of p-tert-Butylthiacalix[4]arene: Synthesis, Aggregation and Interaction with DNA

Synthesis of new p-tert-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates

Unusual Reactivity of Aliphatic and Aromatic Amines with Bromoalkyl Derivatives of Thiacalix[4]arene in 1,3-Alternate Stereoisomeric Form

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