Cationic amphiphiles bearing imidazole fragment: From aggregation properties to potential in biotechnologies

Samarkina, Darya A.; Gabdrakhmanov, Dinar R.; Лукашенко, С. С.; Khamatgalimov, Ayrat R.; Коваленко, В. И.; Zakharova, L. Ya.

doi:10.1016/j.colsurfa.2017.07.018

Cited by 46 publications

(37 citation statements)

References 41 publications

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“…In our case T m values did not change (~40.9 °C) up to a molar calixarene/DPPC ratio of 0.07, after which the increase of calixarene concentration promotes the ordering of the lipid in membranes ( Figure 4 ), which is in line with an increase in the T m value (43.3 °C). An increase in the temperature of the main phase transition, correlated with the stabilizing effect on the lipid packing, was demonstrated earlier [ 47 ] and was explained in terms of an increase in the distribution coefficient value for amphiphile in the gel phase in comparison with the distribution coefficient in the liquid phase.…”

Section: Resultssupporting

confidence: 52%

New Amphiphilic Imidazolium/Benzimidazolium Calix[4]arene Derivatives: Synthesis, Aggregation Behavior and Decoration of DPPC Vesicles for Suzuki Coupling in Aqueous Media

et al. 2020

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In this study, new types of amphiphilic calix[4]arene derivatives bearing N-alkyl/aryl imidazolium/benzimidazolium fragments were designed and synthesized by two step transformation: Regioselective Blanc chloromethylation of distal-di-O-butyl calix[4]arene and subsequent interaction with N-Substituted imidazole/benzimidazole. Critical aggregation concentration (CAC) values were estimated using pyrene fluorescent probe. Obtained macrocycles were found to form submicron particles with electrokinetic potential +44–+57 mV in aqueous solution. For the first time it was found that amphiphilic calixarene causes the fast transformation of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) multilamellar vesicles into unilamellar ones and leads to the ordering of the lipid in membranes at the molar calixarene/DPPC ratio more than 0.07. In situ complexes of calixarene aggregates with Pd(OAc)2 were found to be active in Suzuki–Miyaura coupling of 1-bromo-4-nitrobenzene with phenylboronic acid in water. It was shown that bulky N-substituents of heterocycle decrease the catalytic activity of the aggregates. These result can be assigned to the inhibition effect of Pd(II) complex in situ formation by bulky substituents located on the aggregate surface. Embedding of the most active palladium N-heterocyclic carbene (NHC) complex with methylimidazolium headgroups into DPPC vesicles enhances its catalytic activity in Suzuki–Miyaura coupling.

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Section: Resultssupporting

confidence: 52%

New Amphiphilic Imidazolium/Benzimidazolium Calix[4]arene Derivatives: Synthesis, Aggregation Behavior and Decoration of DPPC Vesicles for Suzuki Coupling in Aqueous Media

et al. 2020

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“…( A ) Chloride and bromide derivatives of 1-methyl-3-[3,4-bis(alkoxy)benzyl]-4 H -imidazolium ( 182 ). ( B ) 1-(2-Hydroxyethyl)alkylimidazolium ( 183 ) and ( C ) 1-alkyl-3-methylimidazolium ( 184 ) bromides ( n = 14, 16, 18). ( D ) 1,3-dimethyl-4,5-dipentadecyl-2-(5-(trimethylammonio)pentyl)imidazolium iodide ( 185 ).…”

Section: Ionic Liquids In Nucleic Acid Deliverymentioning

confidence: 99%

“…Lipoplexes with 1-(2-hydroxyethyl)hexadecylimidazolium bromide efficiently penetrated M-HeLa cells and delivered their cargo into the cytoplasm. Similarly, a series of imidazolium amphiphiles ([C n Mim][Br], n = 14, 16, 18) (Figure 6C ) was tested for the ability to from polyplexes with a DNA decamer and to penetrate a lipid bilayer (dipalmitoylphosphocholine liposomes, DPPC) (Table 6 ) ( 184 ). The size and charge of the amphiphile/DNA polyplexes were independent of the alkyl side chain length, which, however, had an impact on the binding and the ability to intercalate into the lipid bilayer.…”

Section: Ionic Liquids In Nucleic Acid Deliverymentioning

confidence: 99%

Ionic liquids: prospects for nucleic acid handling and delivery

Egorova

Posvyatenko

Larin

et al. 2021

Nucleic Acids Research

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Operations with nucleic acids are among the main means of studying the mechanisms of gene function and developing novel methods of molecular medicine and gene therapy. These endeavours usually imply the necessity of nucleic acid storage and delivery into eukaryotic cells. In spite of diversity of the existing dedicated techniques, all of them have their limitations. Thus, a recent notion of using ionic liquids in manipulations of nucleic acids has been attracting significant attention lately. Due to their unique physicochemical properties, in particular, their micro-structuring impact and tunability, ionic liquids are currently applied as solvents and stabilizing media in chemical synthesis, electrochemistry, biotechnology, and other areas. Here, we review the current knowledge on interactions between nucleic acids and ionic liquids and discuss potential advantages of applying the latter in delivery of the former into eukaryotic cells.

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“…TGA analysis of the DNA-IL functional nanostructures revealed that nanostructures consist of about 16 wt% ionic liquid, which may stabilize the pDNA and eventually enhance transformation efficiency. Samarkina et al studied the behavior of supramolecular systems based on homologous series of amphiphiles bearing imidazolium fragment (C n H 2n +1Im + Br − , where n = 14, 16, 18) toward the aggregation behavior, solubilization activity toward the hydrophobic guest, interaction with DNA decamer as well as integration with the lipid bilayer (Samarkina et al, 2017 ). The elongation of hydrophobic moiety by two methylene groups was noted to decrease critical micelle concentration by 4-folds without any change in the solubility.…”

Section: Ionic Liquid-deoxyribonucleic Acid (Dna) Interactionmentioning

confidence: 99%

Use of Ionic Liquids in Protein and DNA Chemistry

Shukla

Mikkola

2020

Front. Chem.

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Ionic liquids (ILs) have been receiving much attention as solvents in various areas of biochemistry because of their various beneficial properties over the volatile solvents and ILs availability in myriad variants (perhaps as many as 108) owing to the possibility of paring one cation with several anions and vice-versa as well as formulations as zwitterions. Their potential as solvents lies in their tendency to offer both directional and non-directional forces toward a solute molecule. Because of these forces, ionic liquids easily undergo intermolecular interactions with a range of polar/non-polar solutes, including biomolecules such as proteins and DNA. The interaction of genomic species in aqueous/non-aqueous states assists in unraveling their structure and functioning, which have implications in various biomedical applications. The charge density of ionic liquids renders them hydrophilic and hydrophobic, which retain intact over long-range of temperatures. Their ability in stabilizing or destabilizing the 3D-structure of a protein or the double-helical structure of DNA has been assessed superior to the water and volatile organic solvents. The aptitude of an ion in influencing the structure and stability of a native protein depends on their ranking in the Hofmeister series. However, at several instances, a reverse Hofmeister ordering of ions and specific ion-solute interaction has been observed. The capability of an ionic liquid in terms of the tendency to promote the coiling/uncoiling of DNA structure is noted to rely on the basicity, electrostatic interaction, and hydrophobicity of the ionic liquid in question. Any change in the DNA's double-helical structure reflects a change in its melting temperature (Tm), compared to a standard buffer solution. These changes in DNA structure have implications in biosensor design and targeted drug-delivery in biomedical applications. In the current review, we have attempted to highlight various aspects of ionic liquids that influence the structure and properties of proteins and DNA. In short, the review will address the issues related to the origin and strength of intermolecular interactions, the effect of structural components, their nature, and the influence of temperature, pH, and additives on them.

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Cationic amphiphiles bearing imidazole fragment: From aggregation properties to potential in biotechnologies

Cited by 46 publications

References 41 publications

New Amphiphilic Imidazolium/Benzimidazolium Calix[4]arene Derivatives: Synthesis, Aggregation Behavior and Decoration of DPPC Vesicles for Suzuki Coupling in Aqueous Media

New Amphiphilic Imidazolium/Benzimidazolium Calix[4]arene Derivatives: Synthesis, Aggregation Behavior and Decoration of DPPC Vesicles for Suzuki Coupling in Aqueous Media

Ionic liquids: prospects for nucleic acid handling and delivery

Use of Ionic Liquids in Protein and DNA Chemistry

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