Supramolecular systems based on amidoammonium and amidoaminocalix[4]resorcinarenes and polyacrylic acid

Morozova, Julia E.; Syakaev, Victor V.; Ermakova, A.; Shalaeva, Yana V.; Kazakova, E. Kh.; Коновалов, А. И.

doi:10.1016/j.colsurfa.2015.06.002

Cited by 15 publications

(5 citation statements)

References 24 publications

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“…In general, titration of MO-P10+ solution with heparin leads to increase in the A(470)/A(405) ratio ( Figure 6) indicating that interaction with heparin releases the MO from the host cavity. Analogous MO displacement behavior has also been observed before for a similar triplicate system consisting of cationic resorcinarenes, methyl orange and polyacrylic acid 51 . However, in the system presented here, the host-guest binding likely has more specificity as the pillararene cavity is more confined.…”

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confidence: 84%

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A supramolecular host–guest complex for heparin binding and sensing

et al. 2018

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Heparin is an anionic polysaccharide widely used in clinics as an anticoagulant. However, heparin usage requires an antidote and sensors for safe operation during and after surgeries. In this study, a host-guest complex capable of selective heparin binding and sensing is presented. Heparin binding affinity was studied in solution with a variety of polycationic macrocyclic hosts, a pillar[5]arene and multiple resorcin[4]arenes, by dynamic light scattering, dye displacement assay, isothermal titration calorimetry, and anti-Xa assay. The measurements reveal the significant importance of multivalency in electrostatic host-heparin binding in competitive, application-relevant media. Additionally, to monitor the heparin concentration, a host-guest indicator displacement assay was performed by following the free and bound state of the methyl orange dye in UV-Vis spectroscopic experiments. Furthermore, this colorimetric sensing based on the tertiary host-guest-heparin supramolecular assembly was utilized in the construction of a calibration curve in a range of blood plasma concentrations.

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confidence: 84%

“…The tube-like cavity of the bimodal pillar [5]arene is larger and more complementary to the rod-like MO. [51][52][53][54] Protamine was used as a control and no changes in the MO spectra were observed indicating that protamine does not bind MO (data not shown).…”

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confidence: 99%

A supramolecular host–guest complex for heparin binding and sensing

et al. 2018

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“…[14][15] Заслуживающей внимания стратегией модификации макроциклических соединений является введение в структуру различных функциональных групп и алкильных радикалов различной протяженности. [16][17][18] Это наделяет систему способностью к самоорганизации, [19][20] что позволяет качественно усовершенствовать функциональную активность систем. В частности, показана возможность использования функционали-зированной каликсареновой платформы для эффективного связывания и транспорта ДНК.…”

Section: Introductionunclassified

Supramolecular Catalysts Based on Novel Pyrimidinophane: Influence of Additives of Polymer and Lanthanum Ions

Gabdrakhmanov¹,

Валеева²,

Семенов³

et al. 2016

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Supramolecular systems based on the novel tetracationic amphiphilic pyrimidinophane, their mixtures with polymer (polyethyleneimine) and lanthanum ions were formed. Using spectrophotometry technique a catalytic activity of these systems was studied on the example of hydrolysis reaction of O-p-nitrophenyl-O-alkylchloromethylphosphonates (alkyl = ethyl (P1) and n-hexyl (P2)). At the first step the catalytic effect of individual solutions of pyrimidinophanes was examined. Pronounced substrate specificity for two different phosphonates was revealed: inhibition of hydrolysis for phosphonate with ethyl residue and catalysis of hydrolysis for phosphonate with n-hexyl moiety. Similar unusual effect for organized systems based on cationic surfactants could be a result of the influence of two opposite factors. On the one hand, pH decrease with the pyrimidinophane concentration was found. It corresponds to reducing of OH -ions concentration in reaction medium and, therefore inhibition of hydrolysis occurs. On the other hand, aggregation in aqueous solutions of pyrimidinophane induces reactant concentrating in surfactant aggregates that accelerates the reaction. Thereby depending on the domination of the first or the second factor inhibition or catalysis may be observed. Experimental kinetic data allow us to assume that phosphonate P2 because of its higher hydrophobicity and affinity to nonpolar core of micellar pseudophase possesses the higher capability to binding with pyrimidinophane aggregates in comparison with P1. Quantitative treatment of obtained kinetic data in terms of pseudophase model has revealed that binding ability of P2 with pyrimidinophane aggregates is almost 2 times greater than in the case of P1. Moreover, hydrolysis in catalytic complex proceeds more than 5 times faster for substrate with n-hexyl residue. This fact is also due to the high capability of P2 to concentrate within hydrophobic core of pyrimidinophane aggregates. Thus it can be concluded that in the case of P2 the domination of positive contribution over the negative contribution of pH decrease with surfactant concentration is achieved due to high capability of substrate to bind with pyrimidinophane aggregates and high rate of hydrolysis in catalytic complex. It results in catalysis of reaction. At the same time, moderate ability of P1 to bind with aggregates is not enough to compensate pH decrease, which results in inhibition of reaction. Upon the transition from individual solutions of pyrimidinophane to its binary mixture with polyethyleneimine the difference of kinetic constants between P1 and P2 tends to be preserved. However absolute values of these constants are much lower than in the case of individual solutions of pyrimidinophane. Probably, it is due to the fact that cooperative aggregation between surfactant and polymer prevents reactant concentration in surfactant/polymer aggregates. However, resulting catalytic effect of binary system for both phosphonates is higher than in the case of individual solutions of pyrimidinophane. It ...

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“…Among the compounds of interest are the resorcin [4]arenes, which have a cavity, an upper rim, and a lower rim. These macrocycles can be functionalized: the lower rim with hydrocarbon chains, which allow the hydrophobicity of the macrocycle to vary, and the upper rim, with various functional groups, such as the sulfonate group, the amino group, and others that give them the property of being soluble in water, which is necessary for processes related to drug delivery [32][33][34].…”

Section: Resorcinarenes and Their Applications In Drug Deliverymentioning

confidence: 99%

A Review of the Application of Resorcinarenes and SBA-15 in Drug Delivery

et al. 2022

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Due to the diseases that people face today, scientists dedicate a part of their research to the synthesis, characterization, and study of functional compounds for controlled drug delivery. On the one hand, resorcinarenes are macrocycles obtained by condensation reactions of resorcinol and aldehyde. They include an upper and a lower rim functioning with different groups that confer solubility to the macrocycle and favor interactions with other compounds, therefore the hydroxyl groups on the upper rim improve the formation of hydrogen bonds. Additionally, resorcinarenes feature a cavity studied for forming host-guest complexes. SBA-15, on the other hand, is a mesoporous silica characterized by ordered pores in its structure and a large surface area. As a result of its properties, it has been used for several purposes, including absorbents, drug delivery, catalysis, and environmental processes. This review shows the recent advances in synthesis methods, characterization, micelle formation, interaction with other compounds, and host-guest procedures, as well as techniques for evaluating toxicity, drug retention, and their preliminary uses in pharmacology for macrocycles, such as resorcin[4]arenes and SBA-15.

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Supramolecular systems based on amidoammonium and amidoaminocalix[4]resorcinarenes and polyacrylic acid

Cited by 15 publications

References 24 publications

A supramolecular host–guest complex for heparin binding and sensing

A supramolecular host–guest complex for heparin binding and sensing

Supramolecular Catalysts Based on Novel Pyrimidinophane: Influence of Additives of Polymer and Lanthanum Ions

A Review of the Application of Resorcinarenes and SBA-15 in Drug Delivery

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