pH-sensitive N,N-(dimethyl)-N-alkanamine-N-oxides as gene delivery vectors

Liskayová, Gilda; Hubčík, Lukáš; Šišková, Katarína; Paulíková, I; Galliková, Dominika; Devı́nsky, Ferdinand; Funari, Sérgio S.; Uhrı́ková, Daniela

doi:10.1007/s11696-017-0171-2

Cited by 4 publications

(16 citation statements)

References 53 publications

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“…A recent study revealed the rich structural polymorphism of DNA-C12NO/DOPE complexes as a function of their composition, pH, and temperature . The follow-up to the biological study indicated a low cytotoxicity of C n NO/DOPE ( n = 12) complexes on liver hepatocellular carcinoma cells . On the basis of these results, we extended the study to the homological series of C n NO.…”

Section: Introductionmentioning

confidence: 88%

“…Herring testes DNA (DNA) solution was prepared as described in our previous work . Briefly, DNA was dissolved in a 150 mmol/L NaCl solution.…”

Section: Methodsmentioning

confidence: 99%

“…Afterward, the function mentioned above was extrapolated to λ < 330 nm. By subtraction of the extrapolated scattering function from the measured spectrum, we obtained the absorption maximum of DNA, A 260 . , …”

Section: Methodsmentioning

confidence: 99%

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pH-Sensitive N,N-Dimethylalkane-1-amine N-Oxides in DNA Delivery: From Structure to Transfection Efficiency

Liskayová¹,

Hubčík²,

Búcsi³

et al. 2019

Langmuir

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pH-sensitive liposomes composed of homologues of series of N,N-dimethylalkane-1-amine N-oxides (CnNO, n = 8−18, where n is the number of carbon atoms in the alkyl substituent) and neutral phospholipid dioleoylphosphatidylethanolamine (DOPE) were prepared at two molar ratios (CnNO/DOPE = 0.4:1 and 1:1) and tested for their in vitro transfection activity. Several techniques (SAXS/ WAXS, UV−vis, zeta potential measurements, confocal microscopy) were applied to characterize the system in an effort to unravel the relationship among the transfection efficiency, structure, and composition of the lipoplexes. The transfection efficiency of CnNO/DOPE for plasmid DNA in U2OS cells follows a quasi-parabolic dependence on CnNO's alkyl substituent length with a maximum at n = 16. The transfection efficiency of CnNO/DOPE (n = 12−18) lipoplexes was found to be higher than that of commercially available Lipofectamine 2000. C16NO/DOPE also positively transfected HEK 293T and HeLa cells. Small-angle X-ray scattering (SAXS) shows large structural diversity depending on the complex's composition and pH. Transfection efficiencies mediated by two structures, either a condensed lamellar (L α c ) or epitaxially connected L α c and a condensed inverted hexagonal (H II c ) phase (L α c & H II c ), were found to be very similar. The change in pH from acidic to neutral induces phase transition L α c & H II c → Q II + L α , with cubic phase Q II of the Pn3m space group. Q II detected in lipoplexes of most efficient composition CnNO/DOPE (n = 16 and 18) facilitates DNA release and promotes its internalization in the cell.

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Section: Introductionmentioning

confidence: 88%

“…Herring testes DNA (DNA) solution was prepared as described in our previous work . Briefly, DNA was dissolved in a 150 mmol/L NaCl solution.…”

Section: Methodsmentioning

confidence: 99%

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pH-Sensitive N,N-Dimethylalkane-1-amine N-Oxides in DNA Delivery: From Structure to Transfection Efficiency

Liskayová¹,

Hubčík²,

Búcsi³

et al. 2019

Langmuir

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“…Densitometry study (Belička et al 2014a) of dioleoylphosphatidylcholine (DOPC) mixtures with N,Ndimethyl-1-alkylamine-N-oxides (including DDAO) proved ideal mixing of DOPC and DDAO without any concentration dependent type of interaction within the studied range (0-30 wt% of DDAO). DDAO can play an important role in designing lipid-based systems for drug and DNA delivery (Hubčík et al 2015;Liskayová et al 2017). Differences in the geometric shape of the surfactant with alkyl chain shorter than phospholipid chains are causing creation of voids in the hydrophobic region of the bilayer, which is compensated by a trans-gauche isomerisation of alkyl and acyl chains.…”

Section: Introductionmentioning

confidence: 99%

Solubilisation of model membrane by DDAO surfactant – partitioning, permeabilisation and liposome-micelle transition

Želinská

Gallová²,

Huláková³

et al. 2020

gpb

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“…For this purpose, hundreds of lipids have been developed for gene transfer; however, lipoplexes still face a lack of transfection efficiency. In our laboratory, lipidic carriers for DNA have been studied previously (Hubčík et al 2014, Lengyel et al 2011, Liskayová et al 2017. The structure of lipid-based systems has been investigated and reviewed extensively for the past two decades (Uhríková et al 2007, Pullmannová et al 2012, Puri et al 2009.…”

mentioning

confidence: 99%

DOPE–oleic acid–Ca2+ as DNA condensing agent

Galliková

Liskayová

Búcsi

et al. 2018

European Pharmaceutical Journal

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Phospholipid-based non-viral carriers composed of neutral phospholipid dioleoylphosphatidylethanolamine (DOPE) and the binary mixture DOPE–oleic acid (OA) are examined as potential DNA delivery vectors. The process of DNA condensation in the presence of Ca2+ ions has been monitored through changes in emmision intensity of fluorescent probe ethidium bromide. The decline in fluorescence intensity with increasing Ca2+ concentration at two different time intervals was correlated with the binding capacity of complexes and possible release of DNA from the complex. The microstructure of DOPE–OA mixtures at different OA/DOPE molar ratios and that of DOPE–OA–DNA–Ca2+ complexes were determined using synchrotron small angle X-ray diffraction (SAXD). We identified inverted hexagonal phase HII as the dominant structure. OA affects the lattice parameter of HII formed by DOPE. With the increasing OA/DOPE molar ratio, the lattice parameter decreases, which results in significantly lower fraction of DNA bound to the OA-enriched complexes.

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pH-sensitive N,N-(dimethyl)-N-alkanamine-N-oxides as gene delivery vectors

Cited by 4 publications

References 53 publications

pH-Sensitive N,N-Dimethylalkane-1-amine N-Oxides in DNA Delivery: From Structure to Transfection Efficiency

pH-Sensitive N,N-Dimethylalkane-1-amine N-Oxides in DNA Delivery: From Structure to Transfection Efficiency

Solubilisation of model membrane by DDAO surfactant – partitioning, permeabilisation and liposome-micelle transition

DOPE–oleic acid–Ca2+ as DNA condensing agent

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