Self-assembling systems based on quaternized derivatives of 1,4-diazabicyclo[2.2.2]octane in nutrient broth as antimicrobial agents and carriers for hydrophobic drugs

Pashirova, Tatiana N.; Лукашенко, С. С.; Захаров, С. В.; Voloshina, Alexandra D.; Zhil’tsova, E. P.; Зобов, В. В.; Souto, Eliana B.; Zakharova, L. Ya.

doi:10.1016/j.colsurfb.2015.01.044

Cited by 40 publications

(17 citation statements)

References 74 publications

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“…Despite the key role of hydrophobicity of surfactants in their micellization and functional activity, this aspect is poorly studied for alkylated DABCO excepting isolated publications. Our work focused on the aggregation activity of mono-( 3 ) and di-( 4 ) and tetracationic ( 5 ) derivatives of DABCO (Figure 2) in water, chloroform, and biological fluids [138,141,142], their catalytic and biological activity [142,143], adsorption on the air/water interface [141,144] in both single solution and in the presence of calixarenes [145,146,147], organophosphorus substrates [148,149,150], and polymers [151]. As can be seen from the structural formulas (Figure 2), these surfactant series allow the comparison of the behavior of gemini surfactants bearing two charged fragments and two long-chain alkyl groups with dicationic surfactants bearing one long-chain alkyl fragment.…”

Section: Self-assembled Quaternized Derivatives Of 14-diazabicyclmentioning

confidence: 99%

Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications

Zakharova

Pashirova

Doktorovová

et al. 2019

IJMS

108

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The development of biotechnological protocols based on cationic surfactants is a modern trend focusing on the fabrication of antimicrobial and bioimaging agents, supramolecular catalysts, stabilizers of nanoparticles, and especially drug and gene nanocarriers. The main emphasis given to the design of novel ecologically friendly and biocompatible cationic surfactants makes it possible to avoid the drawbacks of nanoformulations preventing their entry to clinical trials. To solve the problem of toxicity various ways are proposed, including the use of mixed composition with nontoxic nonionic surfactants and/or hydrotropic agents, design of amphiphilic compounds bearing natural or cleavable fragments. Essential advantages of cationic surfactants are the structural diversity of their head groups allowing of chemical modification and introduction of desirable moiety to answer the green chemistry criteria. The latter can be exemplified by the design of novel families of ecological friendly cleavable surfactants, with improved biodegradability, amphiphiles with natural fragments, and geminis with low aggregation threshold. Importantly, the development of amphiphilic nanocarriers for drug delivery allows understanding the correlation between the chemical structure of surfactants, their aggregation behavior, and their functional activity. This review focuses on several aspects related to the synthesis of innovative cationic surfactants and their broad biological applications including antimicrobial activity, solubilization of hydrophobic drugs, complexation with DNA, and catalytic effect toward important biochemical reaction.

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Section: Self-assembled Quaternized Derivatives Of 14-diazabicyclmentioning

confidence: 99%

Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications

Zakharova

Pashirova

Doktorovová

et al. 2019

IJMS

108

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“…Surface tension measurements were performed using the du Nouy ring detachment method (Kruss K6 Tensiometer, Hamburg, Germany). The experimental details are described elsewhere [ 84 ]. Briefly, the planar and spherical ring was placed parallel to the air–solvent interface.…”

Section: Methodsmentioning

confidence: 99%

Nanoscale isoindigo-carriers: self-assembly and tunable properties

Pashirova

Богданов

Musin

et al. 2017

Beilstein J. Nanotechnol.

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Over the last decade isoindigo derivatives have attracted much attention due to their high potential in pharmacy and in the chemistry of materials. In addition, isoindigo derivatives can be modified to form supramolecular structures with tunable morphologies for the use in drug delivery. Amphiphilic long-chain dialkylated isoindigos have the ability to form stable solid nanoparticles via a simple nanoprecipitation technique. Their self-assembly was investigated using tensiometry, dynamic light scattering, spectrophotometry, and fluorometry. The critical association concentrations and aggregate sizes were measured. The hydrophilic–lipophilic balance of alkylated isoindigo derivatives strongly influences aggregate morphology. In the case of short-chain dialkylated isoindigo derivatives, supramolecular polymers of 200 to 700 nm were formed. For long-chain dialkylated isoindigo derivatives, micellar aggregates of 100 to 200 nm were observed. Using micellar surfactant water-soluble forms of monosubstituted 1-hexadecylisoindigo as well as 1,1′-dimethylisoindigo were prepared for the first time. The formation of mixed micellar structures of different types in micellar anionic surfactant solutions (sodium dodecyl sulfate) was determined. These findings are of practical importance and are of potential interest for the design of drug delivery systems and new nanomaterials.

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“…При введении гидротропных добавок ККМ ДАБКО-16 резко снижается (с 1 мМ до 0,08 мМ в присутствии 0,5 мМ салицилата натрия), а гидродинамический диаметр агрегатов возрастает (с 2,3 нм до 25 нм), что, вероятно, связано с образованием цилиндрических мицелл, а водные растворы ДАБКО-16салицилат натрия проявляют свойства упругого геля [36]. Введение эквимолярного количества Nметил-D-глюкамина в раствор с монокватеризо-ванным производным ДАБКО способствует увеличению солюбилизирующей способности по отношению к кверцетину (в 4 раза), а также позволяет в 2 раза снизить концентрацию ПАВ в антимикробной композиции, тем самым снижая ее токсичность [37]. Комплексом физико-химических методов было установлено, что 1-этил-4-алкил-1,4диазониабицикло[2.2.2]октан дибромиды (Di-ДАБКО-n) (рис.…”

Section: супрамолекулярные системы на основе катионных пав: влияние пunclassified

Polyfunctional Nanosystems on Amphiphilic and Hybrid Platform: Self-Assembly, Mesogenic Properties and Application

Zhil’tsova¹,

Ibatullina²,

Mirgorodskaya³

et al. 2020

Liq. Cryst. and their Appl.

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Обзор посвящен анализу современных публикаций в области самоорганизации амфифильных соединений, формирования полифункциональных наносистем различной морфологии, их прикладного потенциала в нано-и биотехнологиях. Рассмотрены самоорганизующиеся системы на основе амфифильных соединений, преимущественно катионных ПАВ, а также на гибридной платформе металл/амфифил. Для серии катионных ПАВ проведен анализ влияния структуры головной группы на функциональную активность (солюбилизирующие, каталитические, антимикробные свойства). Продемонстрированы перспективы их использования в качестве мицеллярных наноконтейнеров для гидрофобных спектральных зондов и лекарственных средств, невирусных векторов и антимикробных препаратов. Обсуждены гибридные системы на амфифильной платформе, в том числе металломицеллярные композиции, включающие металлы различной природы, установлена корреляция структура-активность при варьировании структуры ПАВ и природы металла. Отдельный раздел посвящен металломезогенам на амфифильной платформе, разработке наноматериалов различного назначения на их основе, применению в биомедицине, оптике, катализе. Спецификой таких систем является комбинация свойств, типичных для ПАВ (самоорганизация и поверхностная активность), и особенностей, характерных для координационных соединений (окислительно-восстановительные, каталитические, магнитные и оптические свойства). Введение иона металла может способствовать увеличению температурного интервала и концентрационной области существования мезофаз. Дополнительные возможности расширения морфологического поведения и функциональной активности предоставляет использование макроциклической матрицы, позволяющей создавать новые жидкокристаллические материалы.

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Self-assembling systems based on quaternized derivatives of 1,4-diazabicyclo[2.2.2]octane in nutrient broth as antimicrobial agents and carriers for hydrophobic drugs

Cited by 40 publications

References 74 publications

Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications

Cationic Surfactants: Self-Assembly, Structure-Activity Correlation and Their Biological Applications

Nanoscale isoindigo-carriers: self-assembly and tunable properties

Polyfunctional Nanosystems on Amphiphilic and Hybrid Platform: Self-Assembly, Mesogenic Properties and Application

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