Amphiphilic O-functionalized calix[4]resocinarenes with tunable structural behavior

Pashirova, Tatiana N.; Гибадуллина, Э. М.; Бурилов, А. Р.; Kashapov, Ruslan R.; Zhil’tsova, E. P.; Syakaev, Victor V.; Habicher, Wolf D.; Rümmeli, Mark H.; Latypov, Shamil K.; Коновалов, А. И.; Zakharova, L. Ya.

doi:10.1039/c3ra46146g

Cited by 18 publications

(7 citation statements)

References 64 publications

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“…The factor of hydrophobicity is differently displayed in the case of macrocyclic amphiphiles, i.e., calixarenes compared to conventional surfactants [166]. Unlike typical surfactants, the influence of alkyl chain length on the size and morphology of aggregates, their surface and functional activity have critical character, in particular, the change in the association model occurs in the case of R = C 5 H 11 (Figure 6).…”

Section: Self-assembled Quaternized Derivatives Of 14-diazabicyclmentioning

confidence: 99%

“…The idea of modification of the surfactant-calixarene nanocarriers can be improved by the knowledge of other structural factors controlling the morphological behavior and solubilization activity of superamphiphilic compositions. The modulation of properties can be achieved by the variation of the nature of dispersion media, component ratio, and even the nature of counter-ions [166,167].…”

Section: Self-assembled Quaternized Derivatives Of 14-diazabicyclmentioning

confidence: 99%

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

Zakharova

Pashirova

Doktorovová

et al. 2019

IJMS

115

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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%

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

115

View full text Add to dashboard Cite

show abstract

“…81 After that, Zakharova et al investigated the application of polyethyleneimine and amphiphilic sulfonatomethylated resorcinarenes in a catalytic system and synthesized amphiphilic O-functionalized resocinarenes with tunable structural behavior. 82,83 Amphiphilic resorcinarenes were also utilized in nanomaterials. Lately, Yan, Shen, and co-workers reported a series of amphiphilic resorcinarenes bearing amino groups as hydrophilic parts and they generated multiwalled microtubes with wall thicknesses of about 300 nm, diameters of several millimetres and lengths of several centimetres in water.…”

Section: Macrocyclic Amphiphiles Based On Resorcinarenesmentioning

confidence: 99%

Macrocyclic amphiphiles

et al. 2015

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In this critical review, we summarize recent results in the investigation of macrocyclic amphiphiles, amphiphiles based on macrocyclic frameworks. These interesting molecules have drawn a lot of attention over the past decades due to their unique superiority in self-assembly processes and other advantages. Compared with traditional linear amphiphiles, macrocyclic amphiphiles can be tailored to promote their self-assembly into various well-defined architectures by locating hydrophilic and hydrophobic chains on the respective sides. Since macrocyclic amphiphiles can be regarded as "surfactants" with host-guest recognition sites, they may be highly beneficial for applications where guest molecules must be stabilized, transported or protected in aqueous media. Considering the abundant research results on the host-guest chemistry of macrocycles, the use of macrocyclic amphiphiles in the fabrication of multidimensional and hierarchical self-assemblies may also provide interesting new topological structures. Moreover, the interactions of their self-assemblies can be mediated by molecular recognition, which may further our understanding of biological processes.

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“…Inspired by natural amphiphiles, a number of articial amphiphiles have been designed and synthesized, such as polymers, [6][7][8][9] liposomes, 10 dendrimers, 11 and so on. Supramolecular amphiphiles based on macrocyclic molecules such as cyclodextrins, 12,13 cucurbiturils, 14 calixarenes [15][16][17] were also extensively designed and studied.…”

Section: Introductionmentioning

confidence: 99%

Preparation and application of tubular assemblies based on amphiphilic tetramethoxyresorcinarenes

et al. 2015

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Amphiphilic O-functionalized calix[4]resocinarenes with tunable structural behavior

Cited by 18 publications

References 64 publications

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

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

Macrocyclic amphiphiles

Preparation and application of tubular assemblies based on amphiphilic tetramethoxyresorcinarenes

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