Influence of the Spacer of Cationic Gemini Amphiphiles on the Hydration of Lipoplexes

Luciani, Paola; Bombelli, Cecilia; Colone, Marisa; Giansanti, Luisa; Ryhänen, Samppa J.; Säily, V. Matti J.; Mancini, Giovanna; Kinnunen, Paavo K.J.

doi:10.1021/bm070202o

Cited by 30 publications

(27 citation statements)

References 19 publications

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“…Different dicationic agents have been explored, with the structure of the head groups and spacers being varied. [36][37][38][39][40][41] To improve the stability and biocompatibility of amphiphile-DNA complexes, cationic surfactant/lipid mixtures have been used or biofragments have been introduced into the surfactant molecules. [42][43][44][45][46][47][48] A perspective approach in gene therapy has been connected with the use of oligonucleotides (ONus) and the development of cationic agents for their delivery.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Systems Based on Novel Mono‐ and Dicationic Pyrimidinic Amphiphiles and Oligonucleotides: A Self‐Organization and Complexation Study

et al. 2012

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Novel mono- and dicationic pyrimidinic surfactants are synthesized and their aggregation behavior is studied by methods of tensiometry and nuclear magnetic resonance (NMR) self-diffusion. To estimate their potentiality as gene delivery agents, the complexation with oligonucleotides (ONus) is explored by dynamic light scattering (DLS) and zeta-potential titration methods and ethidium bromide exclusion experiments. Bola-type pyrimidinic amphiphile (BPM) demonstrates rather a weak affinity to ONus. Although it induces mixed associations with ONus, only slight charge compensation changes occur at a large excess of bola, with no recharging reached. Similarly, the ethydium bromide exclusion study reveals a slow increase in the binding capacity toward an ONu with an increment in BPM concentration. The monocationic pyrimidinic surfactant (MPM) and its gemini analogue (GPM-1) are ranked as intermediates in both their aggregative activity and complexing properties toward ONus. They both form mixed associates with ONus well below the critical micelle concentrations (cmcs) of 2 and 15 mM respectively. However, GPM-1 has a much lower isoelectric point at the molar ratio surfactant/ONu r~1 compared to r~3 for MPM. This probably indicates a larger electrostatic contribution to the ONu complexation in the case of GPM-1. The most hydrophobic pyrimidinic surfactant (GPM-2), bearing three alkyl tails, demonstrates enhanced aggregative activity and binding capacity toward ONus as compared to former pyrimidinic surfactants. Due to effective aggregative (low cmc of 0.04 mM) plus binding properties (fraction of bound ONu β=0.76 at r=2.5), GPM-2 may be ranked as a promising agent for wider biological applications.

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Section: Introductionmentioning

confidence: 99%

Supramolecular Systems Based on Novel Mono‐ and Dicationic Pyrimidinic Amphiphiles and Oligonucleotides: A Self‐Organization and Complexation Study

et al. 2012

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“…3A, all MHAPC formulations showed enhanced negative ellipticity, a flattening of the positive bands and an overall red shift of the bands, that is, the typical features of the C form of DNA. 10,22) This suggested that the MHAPC-liposomes had strong complexation with DNA and surfactants did not alter the interaction. As shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Particle size and zeta potentials of lipoplexes are often reported when discussing their cellular association [6][7][8] ; however, another physiochemical property, the surface hydration of lipoplexes, is always neglected. Although the hydration levels of lipoplexes containing different liposomal formulations have been well established, [9][10][11] their effect on the cellular association of lipoplexes is still lacking.…”

mentioning

confidence: 99%

Surface Properties of Lipoplexes Modified with Mannosylerythritol Lipid-A and Tween 80 and Their Cellular Association

Ding

Hattori

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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For effective gene transfection into mammalian cells, numerous cationic lipids have been synthesized and formulated into cationic liposomes. [1][2][3] In general, the diverse cationic lipids contain a hydrophobic region, a linker and a cationic headgroup, which are substantially quite variable in different cationic lipids. However, in the cationic headgroup, the basic element is amine, which is responsible for DNA complexation as a protonized form. All four amine types, from primary to quaternary amine, have been reported in diverse cationic lipids and exhibited substantially different cellular association and gene transfection capabilities. 4,5) Understanding the key step in gene transfection, i.e. cellular association of lipoplexes, which is largely determined by the physiochemical properties of cationic liposomes and their lipoplexes, will provide valuable information for designing more effective cationic lipids and optimizing the liposomal formulation. Particle size and zeta potentials of lipoplexes are often reported when discussing their cellular association [6][7][8] ; however, another physiochemical property, the surface hydration of lipoplexes, is always neglected. Although the hydration levels of lipoplexes containing different liposomal formulations have been well established, 9-11) their effect on the cellular association of lipoplexes is still lacking.We reported previously that cationic liposomes, composed of dioleoylphosphatidylethanolamine (DOPE) and N,Nmethyl hydroxyethyl aminopropane carbamoyl cholesterol (MHAPC) or cholesteryl-3b-carboxyamindoethylene-N-hydroxyethylamine (OH-Chol), demonstrated distinctive differences in their cellular association and gene transfection efficiencies in vitro.12) The major differences between MHAPC and OH-Chol are the amine types and linkers shown in Fig. 1, with MHAPC having a tertiary amine linked to the cholesteryl skeleton by a carbamate ester, and OH-Chol having a secondary amine with an amido linker. To understand the different cellular association of lipoplexes composed of different cationic lipids, the effect of amine types and linkers on the surface properties, e.g. zeta potentials and surface hydration levels, was examined. Furthermore, mannosylerythritol lipid-A (MEL-A) is a newly developed biosurfactant 13) and modification of OH-Chol-liposomes with MEL-A markedly increased the gene transfection efficiency of plasmid DNA.14,15) Recent findings found that MEL-A induced membrane fusion between the target cells and cationic liposomes 16,17) ; however, the physiochemical mechanism of the fusion ability of MEL-A has not been fully understood. As a

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“…The potential nonviral liposomal genetic delivery systems were obtained empirically by modulating phospholipid and surfactant structures (particularly dicationic quaternary ammonium surfactants -gemini surfactants) [19][20][21].…”

Section: Introductionmentioning

confidence: 99%

“…So far, several studies have demonstrated the efficiency of Gemini surfactant mediated delivery of DNA in vivo [19][20][21].…”

Section: Introductionmentioning

confidence: 99%

SAXS Study of Influence of Gemini Surfactant, 1,1'-(1,4-butanediyl)bis 3-cyclododecyloxymethylimidazolium di-chloride, on the Fully Hydrated DMPC

et al. 2010

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The study has been performed on model systems of biological membranes obtained on the basis of 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) and cationic gemini surfactant -derivative of 1,1 -(1,4--butane)bis 3-alkyloxymethylimidazolium chlorides with cyclic chains. The small angle X-ray scattering SAXS results implied a gradual disappearance (as a function of surfactant concentration) of the lamellar phase typical of DMPC and formation of unilamellar phase -probably a bicellar phase.

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Influence of the Spacer of Cationic Gemini Amphiphiles on the Hydration of Lipoplexes

Cited by 30 publications

References 19 publications

Supramolecular Systems Based on Novel Mono‐ and Dicationic Pyrimidinic Amphiphiles and Oligonucleotides: A Self‐Organization and Complexation Study

Supramolecular Systems Based on Novel Mono‐ and Dicationic Pyrimidinic Amphiphiles and Oligonucleotides: A Self‐Organization and Complexation Study

Surface Properties of Lipoplexes Modified with Mannosylerythritol Lipid-A and Tween 80 and Their Cellular Association

SAXS Study of Influence of Gemini Surfactant, 1,1'-(1,4-butanediyl)bis 3-cyclododecyloxymethylimidazolium di-chloride, on the Fully Hydrated DMPC

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