OPA quantification of amino groups at the surface of Lipidic NanoCapsules (LNCs) for ligand coupling improvement

Perrier, Thomas; Fouchet, Florian; Bastiat, Guillaume; Saulnier, Patrick; Benoı̂t, Jean-Pierre

doi:10.1016/j.ijpharm.2011.07.028

Cited by 8 publications

(3 citation statements)

References 41 publications

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“…Increase in size and in ζ-potential (in the case of LNC-LC) confirmed the success of surface modification of LNC. Post-inserted quantities, 15% for LNC-LC and 5% for LNC-LD, were in line with previous studies where 12% LC [11], 7% DSPE-PEG 2000 -maleimide [39], and 12% DSPE-PEG 2000 -amino [40] were detected on the LNC surface. In the first study presenting the LD insertion on the LNC surface, 10% LD / LNC mass was detected after integration of the NMR signal [29].…”

Section: Discussionsupporting

confidence: 92%

Surface modification of lipid nanocapsules with polysaccharides: From physicochemical characteristics to in vivo aspects

et al. 2013

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Attaching polysaccharides to the surface of nanoparticles offers the possibility of modifying the physicochemical and biological properties of the core particles. The surface of lipid nanocapsules (LNCs) was modified by post-insertion of amphiphilic lipochitosan (LC) or lipodextran (LD). Modelling of these LNCs by the drop tensiometer technique revealed that the positively charged LC made the LNC surface more rigid, whereas the neutral, higher M(W) LD had no effect on the surface elasticity. Both LNC-LC and LNC-LD activated the complement system more than the blank LNC, thus suggesting increased capture by the mononuclear phagocyte system. In vitro, the positively charged LNC-LC were more efficiently bound by the model HEK293(β3) cells compared to LNC and LNC-LD. Finally, it was observed that neither LC nor LD changed the in vivo biodistribution properties of LNCs in mice. These polysaccharide-coated LNCs, especially LNC-LC, are promising templates for targeting ligands (e.g. peptides, proteins) or therapeutic molecules (e.g. siRNA).

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Section: Discussionsupporting

confidence: 92%

Surface modification of lipid nanocapsules with polysaccharides: From physicochemical characteristics to in vivo aspects

et al. 2013

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“…OPA (280 µL) was added to each sample and the fluorescence was recorded with a Fluoroskan (Thermo Fisher Scientific) with an excitation wavelength of 355 nm and an emission wavelength of 460 nm. 29 A calibration curve ranging from 0.013-0.83 mg/mL of chitosan was obtained.…”

Section: Quantification Of Bound Chitosan On the Lnc Surfacementioning

confidence: 99%

Anti-epidermal growth factor receptor siRNA carried by chitosan-transacylated lipid nanocapsules increases sensitivity of glioblastoma cells to temozolomide

Messaoudi¹,

Saulnier²,

Boesen³

et al. 2014

IJN

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Epidermal growth factor receptor (EGFR) is a crucial protein that plays an important role in the maintenance and development of glioblastomas. The silencing or knockdown of EGFR is possible by administering a small interfering ribonucleic acid (siRNA). Lipid nanocapsules (LNCs) covered by chitosan were developed in our laboratory by a transacylation process. The resulting nanocapsules have a positive zeta potential that enables electrostatic interactions with the negatively-charged siRNA. Prior to transfection, the cytotoxicity of the nanocapsules by (3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium) (MTS) test was performed on the U87MG cell line to determine non-toxic levels of the LNCs to avoid cell mortality. Treatment of the U87MG cells with the chitosan-transacylated LNCs/anti-EGFR siRNA complex resulted in a reduction of EGFR expression by 51.95%±6.03% ( P ≤0.05) after 96 hours of incubation. It also increased the cellular sensitivity to temozolomide in comparison to untreated cells with siRNA. The largest increase in mortality was 62.55%±3.55% ( P <0.05). This successful knockdown provides proof for the concept of surface grafting of siRNA onto LNCs to modify cell sensitivity to temozolomide. The method could be implemented in future clinical models regarding the experimental treatment of glioblastoma cancer.

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“…Several studies have been published by Benoit and co-workers centered on modifying and grafting NEs with targeted ligands by a postinsertion method. − They also developed a layer-by-layer (LBL) approach to modify the surface of LNEs based on electrostatic interactions between the coating polyelectrolytes ( e.g ., cationic lipopolysaccharide; lipochitosan (LC)) and the LNEs along with introducing a model therapeutic polyelectrolyte ( i.e ., fondaparinux (FP) sodium, a heparin-like synthetic pentasaccharide) in the LBL process . Another study modified LNEs coated with both amphiphilic lipochitosan (LC) and lipodextran (LD), and the positively charged LC-LNEs were more efficiently bound to model HEK293(β3) cells compared to unmodified LNEs.…”

Section: Introductionmentioning

confidence: 99%

Strategies for High Grafting Efficiency of Functional Ligands to Lipid Nanoemulsions for RGD-Mediated Targeting of Tumor Cells In Vitro

Attia

Swasy

Akasov

et al. 2020

ACS Appl. Bio Mater.

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Lipid nanoemulsions (LNEs) are promising nanocarriers for delivering high payloads of lipophilic molecules. Nonetheless, the dynamic nature at their aqueous interfaces results in poor surface chemistry and thus ligand functionalization can be challenging. Herein, two independent strategies, postconjugation and preconjugation, were explored to prepare LNEs grafted covalently with model ligands, fluorescein dye and RGD peptide, respectively. Fluorescein was successfully conjugated with high grafting efficiency to an amine-functionalized lipid nanoemulsion (NH2-LNE) as determined by spectrophotometric analysis. First, we formulated NH2-LNEs by a low-energy spontaneous emulsification technique in the presence of oleylamine (OA) within the oily core of the nanodroplets, thus creating primary amine-reactive sites at the oil/water interface. These amines were used to incorporate fluorescein, yielding fluorescent LNEs with grafting efficiencies of 33, 69, and 69% at NH2-LNEs with [OA]oil = 0.18, 0.34, and 0.49 M, respectively. We also developed RGD-labeled LNEs (RGD-LNEs) and evaluated the nanomaterial with model cell lines that overexpress αVβ3 integrins on their surfaces. To this end, we initially synthesized an RGD–Oleate fatty acid–peptide conjugate by solid-phase synthesis. The lipophilic segment of this conjugate readily embedded into the oily core of the LNE, and the hydrophilic head (RGD moiety) was oriented toward the LNE interface. In vitro cytotoxicity and cellular uptake studies were undertaken on different cancer cell lines including HaCaT human umbilical vein endothelial cells (HUVECs), MCF-7, and U-87 MG and compared to uptake experiments with RAW 264.7 macrophages. Confocal imaging and flow cytometry showed that RGD-LNEs were preferentially taken up by all of the tumor cell lines but showed very slight accumulation in RAW macrophages. Unmodified LNE controls did not show any appreciable cellular uptake. This work provides a simple and reliable methodology for the incorporation of multiple ligands on a single surface to facilitate active tumor targeting with LNE-based drug/imaging carriers for theranostic applications.

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OPA quantification of amino groups at the surface of Lipidic NanoCapsules (LNCs) for ligand coupling improvement

Cited by 8 publications

References 41 publications

Surface modification of lipid nanocapsules with polysaccharides: From physicochemical characteristics to in vivo aspects

Surface modification of lipid nanocapsules with polysaccharides: From physicochemical characteristics to in vivo aspects

Anti-epidermal growth factor receptor siRNA carried by chitosan-transacylated lipid nanocapsules increases sensitivity of glioblastoma cells to temozolomide

Strategies for High Grafting Efficiency of Functional Ligands to Lipid Nanoemulsions for RGD-Mediated Targeting of Tumor Cells In Vitro

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