Supramolecular systems based on cationic imidazole-containing amphiphiles bearing hydroxyethyl fragment: Aggregation properties and functional activity

Kuznetsova, Darya A.; Gabdrakhmanov, Dinar R.; Лукашенко, С. С.; Voloshina, Alexandra D.; Sapunova, Аnastasiia S.; Кулик, Н. В.; Nizameev, Irek R.; Kadirov, Marsil K.; Kashapov, Ruslan R.; Zakharova, L. Ya.

doi:10.1016/j.molliq.2019.111058

Cited by 46 publications

(26 citation statements)

References 58 publications

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“…To gain a more detailed understanding on the mechanism of cytotoxicity of these imidazole and imidazolium salts on bacteria, we studied the possible structure–activity relationship between their antibacterial activities and their aggregation behavior in bacterial cell medium [ 23 , 38 ].…”

Section: Discussionmentioning

confidence: 99%

“…In this regard, the imidazolium skeleton can be transformed into ionic liquids with promisingly potent pharmacological properties [ 18 , 19 , 20 , 21 ]. Consequently, monoimidazolium [ 22 , 23 , 24 ] and bisimidazolium [ 25 , 26 , 27 , 28 ] salts have been explored as a new generation of antibacterial agents. In this context, amino acid-based monoimidazolium salts with good bacterial toxicity have been reported in the literature [ 29 ].…”

Section: Introductionmentioning

confidence: 99%

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Imidazole and Imidazolium Antibacterial Drugs Derived from Amino Acids

et al. 2020

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The antibacterial activity of imidazole and imidazolium salts is highly dependent upon their lipophilicity, which can be tuned through the introduction of different hydrophobic substituents on the nitrogen atoms of the imidazole or imidazolium ring of the molecule. Taking this into consideration, we have synthesized and characterized a series of imidazole and imidazolium salts derived from L-valine and L-phenylalanine containing different hydrophobic groups and tested their antibacterial activity against two model bacterial strains, Gram-negative E. coli and Gram-positive B. subtilis. Importantly, the results demonstrate that the minimum bactericidal concentration (MBC) of these derivatives can be tuned to fall close to the cytotoxicity values in eukaryotic cell lines. The MBC value of one of these compounds toward B. subtilis was found to be lower than the IC50 cytotoxicity value for the control cell line, HEK-293. Furthermore, the aggregation behavior of these compounds has been studied in pure water, in cell culture media, and in mixtures thereof, in order to determine if the compounds formed self-assembled aggregates at their bioactive concentrations with the aim of determining whether the monomeric species were in fact responsible for the observed antibacterial activity. Overall, these results indicate that imidazole and imidazolium compounds derived from L-valine and L-phenylalanine—with different alkyl lengths in the amide substitution—can serve as potent antibacterial agents with low cytotoxicity to human cell lines.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Imidazole and Imidazolium Antibacterial Drugs Derived from Amino Acids

et al. 2020

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“…As illustrated above, amphiphilic systems are of particular interest in biomedical applications [ 2 ], which can be supported by their use as hydrotropic additives [ 129 ], nanocontainers for poorly soluble drugs [ 130 , 131 , 132 , 133 ], antimicrobial preparations [ 134 , 135 ], complexing agents for negatively charged biomolecules such as DNA and BSA [ 136 , 137 , 138 , 139 , 140 ], etc. They have been successfully used for the fabrication of drug and gene delivery systems demonstrating numerous advantages compared to non-formulated drugs, i.e., improved bioavailability, higher stability and prolonged circulation in bioenvironment, lower side effects, etc.…”

Section: Self-assembled Amphiphilic Systems As Smart Drug Nanocarrmentioning

confidence: 99%

Self-Assembly of Amphiphilic Compounds as a Versatile Tool for Construction of Nanoscale Drug Carriers

Kashapov

Gaynanova

Gabdrakhmanov

et al. 2020

IJMS

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This review focuses on synthetic and natural amphiphilic systems prepared from straight-chain and macrocyclic compounds capable of self-assembly with the formation of nanoscale aggregates of different morphology and their application as drug carriers. Since numerous biological species (lipid membrane, bacterial cell wall, mucous membrane, corneal epithelium, biopolymers, e.g., proteins, nucleic acids) bear negatively charged fragments, much attention is paid to cationic carriers providing high affinity for encapsulated drugs to targeted cells. First part of the review is devoted to self-assembling and functional properties of surfactant systems, with special attention focusing on cationic amphiphiles, including those bearing natural or cleavable fragments. Further, lipid formulations, especially liposomes, are discussed in terms of their fabrication and application for intracellular drug delivery. This section highlights several features of these carriers, including noncovalent modification of lipid formulations by cationic surfactants, pH-responsive properties, endosomal escape, etc. Third part of the review deals with nanocarriers based on macrocyclic compounds, with such important characteristics as mucoadhesive properties emphasized. In this section, different combinations of cyclodextrin platform conjugated with polymers is considered as drug delivery systems with synergetic effect that improves solubility, targeting and biocompatibility of formulations.

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“…1, е-л), на основе которых созданы эффективные наноконтейнеры [14], микроэмульсии [15] и липосомальные системы [16] для доставки лекарственных веществ. Обнаружена высокая антимикробная активность имидазолиевых ПАВ против грамположительных бактерий [17][18] и кишечной палочки [19]. Большое количество работ посвящено комплексообразованию с синтетическими и природными полиэлектролитами [18][19][20][21][22][23][24][25][26][27].…”

Section: супрамолекулярные системы на основе катионных пав: влияние пunclassified

“…1, е) не влияет на агрегационные свойства систем, но снижает температуру Крафта [29]. Для имидазолсодержащих ПАВ с гидроксильными и гидроксиэтильными заместителями [17,[30][31] [35]. Для лиотропной жидкокристаллической системы на его основе найден более широкий температурный диапазон существования мезофазы по сравнению с термотропной.…”

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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Supramolecular systems based on cationic imidazole-containing amphiphiles bearing hydroxyethyl fragment: Aggregation properties and functional activity

Cited by 46 publications

References 58 publications

Imidazole and Imidazolium Antibacterial Drugs Derived from Amino Acids

Imidazole and Imidazolium Antibacterial Drugs Derived from Amino Acids

Self-Assembly of Amphiphilic Compounds as a Versatile Tool for Construction of Nanoscale Drug Carriers

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

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