The study of complexation between dicationic surfactants and the DNA duplex using structural and spectroscopic methods

Andrzejewska, Weronika; Wilkowska, Michalina; Chrabąszczewska, Magdalena; Kozak, Maciej

doi:10.1039/c6ra24978g

Cited by 11 publications

(11 citation statements)

References 60 publications

(120 reference statements)

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“…The results of the gel electrophoresis experiment indicated better complexing properties of surfactants towards siRNA (for most of them at p/n = 1.5) than dsDNA. A similar effect has been observed previously for the lipoplexes obtained on the basis of imidazolium dichlorides [29,30]. A significant effect of the length of the spacer group of the studied surfactants on the binding efficiency of nucleic acid oligomers was observed.…”

Section: Discussionsupporting

confidence: 87%

“…The CD spectra deformations indicate significant conformation changes and the levorotatory character of the oligomer, which is directly related to deterioration of the complexing abilities. The changes in CD curves were similar to those taking place upon the transition of B-DNA to Z-DNA or X-DNA [35,52,53,54] which has been observed earlier for the mixtures of dsDNA with imidazolium surfactant [30].…”

Section: Discussionsupporting

confidence: 77%

“…These oligomers have been previously successfully used by us for tests of imidazolium gemini surfactants as components of nucleic acids delivery systems [29,30].…”

Section: Resultsmentioning

confidence: 99%

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Ammonium Gemini Surfactants Form Complexes with Model Oligomers of siRNA and dsDNA

Andrzejewska

Wilkowska

Skrzypczak

et al. 2019

IJMS

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Dimeric cationic surfactants (gemini-type) are a group of amphiphilic compounds with potential use in gene therapy as effective carriers for nucleic acid transfection (i.e., siRNA, DNA, and plasmid DNA). Our studies have shown the formation of lipoplexes composed of alkanediyl-α,ω-bis[(oxymethyl)dimethyldodecylammonium] chlorides and selected 21-base-pair nucleic acid (dsDNA and siRNA) oligomers. To examine the structure and physicochemical properties of these systems, optical microscopy, circular dichroism spectroscopy (CD), small-angle X-ray scattering of synchrotron radiation (SR-SAXS), and agarose gel electrophoresis (AGE) were used. The lengths of spacer groups of the studied surfactants had a significant influence on the surfactants’ complexing properties. The lowest charge ratio (p/n) at which stable lipoplexes were observed was 1.5 and the most frequently occurring microstructure of these lipoplexes were cubic and micellar phases for dsDNA and siRNA, respectively. The cytotoxicity tests on HeLa cells indicated the non-toxic concentration of surfactants to be at approximately 10 µM. The dicationic gemini surfactants studied form complexes with siRNA and dsDNA oligomers; however, the complexation process is more effective towards siRNA. Therefore these systems could be applied as transfection systems for therapeutic nucleic acids.

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Section: Discussionsupporting

confidence: 87%

Section: Discussionsupporting

confidence: 77%

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Ammonium Gemini Surfactants Form Complexes with Model Oligomers of siRNA and dsDNA

Andrzejewska

Wilkowska

Skrzypczak

et al. 2019

IJMS

Self Cite

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“…Efforts have been made to design novel QAS for gene delivery that would be able to deliver nucleic acids without complementary action of helper lipids. Inspired by rigid, planar structure of Chol, Andrzejewska et al synthetized cationic gemini surfactants that comprise a rigid cyclic moiety and condensed DNA of various length into stable aggregates, being the surfactant with longer spacer slightly more efficient in DNA binding [129].…”

Section: Quaternary Ammonium Surfactants In Pharmaceutical Applicamentioning

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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“…Particular attention is paid to the flexibly or rigidly linked bisimidazolium salts, the so-called gemini ILs. Gemini ILs can show interesting surfactant and liquid crystalline properties [ 4 – 12 ] and such salts were used in many applications, ranging from catalysis [ 13 ] to biological [ 14 – 16 ] or biochemical applications [ 17 – 19 ]. Recently, we have shown that it is possible to exchange the smaller anions (Br − ) with alkyl sulfate ions to yield new ILCs based on bisimidazolium salts with flexible methylene spacer and long alkyl tails [ 20 ].…”

Section: Introductionmentioning

confidence: 99%

Dielectric properties of a bisimidazolium salt with dodecyl sulfate anion doped with carbon nanotubes

Maximean

Cı̂rcu

Ganea

2018

Beilstein J. Nanotechnol.

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A new bisimidazolium salt with dodecyl sulfate as counterion has been designed and prepared. This salt shows a SmA phase that is stable at room temperature. The new ionic liquid crystal (ILC) was characterized by 1H NMR, 13C NMR and IR spectroscopy. Its liquid crystalline properties were analyzed by polarizing optical microscopy (POM), differential scanning calorimetry (DSC) and powder X-ray diffraction (XRD) studies. The dielectric spectra of the ILC doped with different concentrations of carbon nanotubes (CNT) were recorded over a wide frequency and temperature range of 10−1 to 107 Hz and 293–338 K, respectively. The values of the activation energy were found in the range of 0.46–0.61 eV; the characteristic time was obtained by fitting the spectra of the dielectric loss with the Havriliak–Negami functions. As a result of doping the ILC with CNT, the electric conductivity increases significantly. Ionic conductivity is dominant and it was indirectly observed through the electrode polarization (EP) effect. The very high dielectric permittivity values and the decrease of the electric conductivity at low frequencies confirm the presence of EP.

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The study of complexation between dicationic surfactants and the DNA duplex using structural and spectroscopic methods

Abstract: Dicationic (also known as gemini or dimeric) bis-alkylimidazolium surfactants belong to a group of non-viral transfection systems proposed for the successful introduction of different types of nucleic acids (i.e., siRNA, DNA oligomers, and plasmid DNA) into living cells.

Cited by 11 publications

References 60 publications

Ammonium Gemini Surfactants Form Complexes with Model Oligomers of siRNA and dsDNA

Ammonium Gemini Surfactants Form Complexes with Model Oligomers of siRNA and dsDNA

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

Dielectric properties of a bisimidazolium salt with dodecyl sulfate anion doped with carbon nanotubes

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