Enhanced cellular uptake of amphiphilic gold nanoparticles with ester functionality

Kobayashi, Koichi; Niikura, Kenichi; Takeuchi, Chie; Sekiguchi, Shota; Ninomiya, Takafumi; Hagiwara, Kyoji; Mitomo, Hideyuki; Ito, Yoshihiro; Osada, Yoshihito; Ijiro, Kuniharu

doi:10.1039/c3cc48532c

Cited by 13 publications

(16 citation statements)

References 36 publications

(14 reference statements)

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“…27,28 We have previously demonstrated that thiolated-PEG ligands with a terminus consisting of a short alkyl chain provide AuNPs (10 nm in a diameter) with an amphiphilic property and facilitate the phase transfer of AuNPs from aqueous to organic solvents. 29,30 Stellacci et al…”

Section: Introductionmentioning

confidence: 98%

Amphiphilic Gold Nanoparticles Displaying Flexible Bifurcated Ligands as a Carrier for siRNA Delivery into the Cell Cytosol

Niikura

Kobayashi

Takeuchi

et al. 2014

ACS Appl. Mater. Interfaces

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The nanoparticle-based delivery of siRNA with a noncationic outermost surface at a low particle concentration is greatly desired. We newly synthesized a bifurcated ligand (BL) possessing hydrophobic and hydrophilic arms as a surface ligand for gold nanoparticles (AuNPs) to allow siRNA delivery. The concept underlying the design of this ligand is that amphiphilic property should allow AuNPs to permeate the cell cytosol thorough the endosomal membrane. BLs and quaternary cationic ligands were codisplayed on 40 nm AuNPs, which were subsequently coated with siRNA via electrostatic interaction. The number of siRNAs immobilized on a single nanoparticle was 26, and the conjugate showed a negative zeta potential due to siRNAs on the outermost surface of the AuNPs. Apparent gene silencing of luciferase expression in HeLa cells was achieved at an AuNP concentration as low as 60 pM. Almost no gene silencing was observed for AuNPs not displaying BLs. To reveal the effect of the BL, we compared the number of AuNPs internalized into HeLa cells and the localization in the cytosol between AuNPs displaying and those not displaying BLs. These analyses indicated that the role of BLs is not only the simple promotion of cellular uptake but also involves the enhancement of AuNPs permeation into the cytosol from the endosomes, leading to effective gene silencing.

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Section: Introductionmentioning

confidence: 98%

Amphiphilic Gold Nanoparticles Displaying Flexible Bifurcated Ligands as a Carrier for siRNA Delivery into the Cell Cytosol

Niikura

Kobayashi

Takeuchi

et al. 2014

ACS Appl. Mater. Interfaces

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“…The similar nanoparticle cell studies have shown that the particle clusters are uptaken by the cells via endocytosis. 58 The gold concentrations added to the cells were determined by ICP-MS and the results were summarized in Table S2 (ESI † ). The internalization of the 3 nm Den–AuNPs was the lowest, despite having the highest concentration in the original nanoparticle solution.…”

Section: Resultsmentioning

confidence: 99%

Stability, cytotoxicity and cell uptake of water-soluble dendron–conjugated gold nanoparticles with 3, 12 and 17 nm cores

2015

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This article describes the synthesis of water-soluble dendron-conjugated gold nanoparticles (Den-AuNPs) with various average core sizes and the evaluation of stability, cytotoxicity, cell permeability and uptake of these materials. The characterization of Den-AuNPs using various instruments including transmission electron microscopy (TEM), matrix-assisted laser desorption/ionization-time of flight mass spectrometry (MALDI-TOF-MS), 1H NMR, FT-IR, and UV-vis spectroscopy confirms the dendron conjugation to the glutathione-capped gold nanoparticles (AuNPs). The stability of AuNPs and Den-AuNPs in solutions of different pH and salt concentration is determined by monitoring changes in surface plasmon bands of gold using UV-vis spectroscopy. The stability of Den-AuNPs at different pH remained about the same compared to that of AuNPs. In comparison, the Den-AuNPs are found to be more stable than the precursor AuNPs maintaining their solubility in the aqueous solution with the salt concentration of up to 100 mM. The improved stability of Den-AuNPs suggests that the post-functionalization of thiol-capped gold nanoparticle surfaces with dendrons can further improve the physiological stability and biocompatibility of gold nanoparticle-based materials. Cytotoxicity studies of AuNPs and Den-AuNPs with and without flourophores are also performed by examining cell viability for 3T3 fibroblasts using a MTT cell proliferation assay. The conjugation of dendrons to the AuNPs with flourophore is able to decrease the cytotoxicity brought about by the flourophore. The successful uptake of Den-AuNPs in mouse fibroblast 3T3 cells shows the physiological viability of the hybrid materials.

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“…Niikura and coworkers demonstrated that an esterase-catalyzed hydrolysis of ester moieties can be used as to enhance the cellular uptake of amphiphilic AuNPs [76]. 10 nm AuNPs were functionalized with ester or ether-headed amphiphilic PEG ligands which enable NPs to dissolve both of polar and nonpolar solvents through systematic conformational changes (Fig.…”

Section: Engineering Responsive Biological Interactionsmentioning

confidence: 99%

“…(d) Esterase-induced cell internalization of AuNPs. Reprinted with permission from [76,77]. Figure 10d is based on information obtained in the report.…”

Section: Figurementioning

confidence: 99%

Using the power of organic synthesis for engineering the interactions of nanoparticles with biological systems

2016

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Summary The surface properties of nanoparticles (NPs) dictate their interaction with the outside world. The use of precisely designed molecular ligands to control NP surface properties provides an important toolkit for modulating their interaction with biological systems, facilitating their use in biomedicine. In this review we will discuss the application of the atom-by-atom control provided by organic synthesis to the generation of engineered nanoparticles, with emphasis on how the functionalization of NPs with these “small” organic molecules (Mw < 1,000) can be used to engineer NPs for a wide range of applications.

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Enhanced cellular uptake of amphiphilic gold nanoparticles with ester functionality

Cited by 13 publications

References 36 publications

Amphiphilic Gold Nanoparticles Displaying Flexible Bifurcated Ligands as a Carrier for siRNA Delivery into the Cell Cytosol

Amphiphilic Gold Nanoparticles Displaying Flexible Bifurcated Ligands as a Carrier for siRNA Delivery into the Cell Cytosol

Stability, cytotoxicity and cell uptake of water-soluble dendron–conjugated gold nanoparticles with 3, 12 and 17 nm cores

Using the power of organic synthesis for engineering the interactions of nanoparticles with biological systems

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