Quantitative Replacement of Cetyl Trimethylammonium Bromide by Cationic Thiol Ligands on the Surface of Gold Nanorods and Their Extremely Large Uptake by Cancer Cells

Vigderman, Leonid; Manna, Pramit; Zubarev, Eugene R.

doi:10.1002/anie.201107304

Cited by 176 publications

(181 citation statements)

References 52 publications

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“…[41] Furthermore, although the CTAB-Au NTs have good stability in DI water (well-dispersed after several weeks), during a 30 minincubation with serum-containing medium, CTAB-Au NTs agglomerate and precipitate with time, which also precludes their biological application. Therefore, surface modification is necessary to achieve biocompatible and low-cytotoxic nanotubes with colloid stability in a buffer medium.…”

Section: Surface Modification Of the Au Ntsmentioning

confidence: 99%

Engineering Gold Nanotubes with Controlled Length and Near‐Infrared Absorption for Theranostic Applications

Marston

McLaughlan

et al. 2015

Adv Funct Materials

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Section: Surface Modification Of the Au Ntsmentioning

confidence: 99%

Engineering Gold Nanotubes with Controlled Length and Near‐Infrared Absorption for Theranostic Applications

Marston

McLaughlan

et al. 2015

Adv Funct Materials

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“…35 The presence of residual CTAB on the GNRs, as determined by quantitative 1 H-NMR (Table S1 †), is not surprising given the difficulty of removing this small ligand -a problem often highlighted by others. 22,36 However, the effective CTAB concentration in the exposure experiments is 2-7 nM corresponding to 20-50 molecules per GNR, or approximately 0.1% of a full CTAB bilayer. This is low enough so as to expect little cytotoxicity or pro-inflammatory response, as observed by the absence of any significant difference in the level of LDH, TNF-α, and IL-8 with respect to the negative control (Fig.…”

Section: Shape-dependent Endocytosis Of Gold Nanorodsmentioning

confidence: 99%

Decoupling the shape parameter to assess gold nanorod uptake by mammalian cells

et al. 2016

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The impact of nanoparticles (NPs) upon biological systems can be fundamentally associated with their physicochemical parameters. A further often-stated tenet is the importance of NP shape on rates of endocytosis. However, given the convoluted parameters concerning the NP-cell interaction, it is experimentally challenging to attribute any findings to shape alone. Herein we demonstrate that shape, below a certain limit, which is specific to nanomedicine, is not important for the endocytosis of spherocylinders by either epithelial or macrophage cells in vitro. Through a systematic approach, we reshaped a single batch of gold nanorods into different aspect ratios resulting in near-spheres and studied their cytotoxicity, ( pro-)inflammatory status, and endocytosis/exocytosis. It was found that on a length scale of ∼10-90 nm and at aspect ratios less than 5, NP shape has little impact upon their entry into either macrophages or epithelial cells. Conversely, nanorods with an aspect ratio above 5 were preferentially endocytosed by epithelial cells, whereas there was a lack of shape dependent uptake following exposure to macrophages in vitro. These findings have implications both in the understanding of nanoparticle reshaping mechanisms, as well as in the future rational design of nanomaterials for biomedical applications.

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“…68,69 Previously, only few types of GNRs that are covalently functionalized with thiolated PEG and thiolated CTAB analogue can survive up to 5-6 rounds of centrifugation in water or in organic phase. 23,69 The high stability of the ionomer-modified GNRs herein is thus remarkable given that the nanorod stabilization is achieved exclusively through the noncovalent binding. temperature from 23 to 60 ºC causes negligible changes in the spectra, with the dispersions remaining stable without precipitates.…”

Section: Ctab-coated Gnrmentioning

confidence: 99%

“…10 In addition, CTAB-coated GNRs, though soluble/stable in aqueous solution containing sufficient free CTAB, tend to quickly aggregate in most organic solvents due to the destabilization of the CTAB bilayer, while their solubility in organic media is highly desired in order for further functionalization with organic functional groups to fine-tune their properties. 18 As such, surface functionalization of the GNRs by mercaptohexadecyl)trimethylammonium bromide (a thiolated CTAB analogue), 23 alkyl thiol acids/esters, [24][25][26] and thiolated DNA. 27,28 These sulfur-containing molecules can bind strongly to the rod surface by forming the covalent Au-S bond.…”

Section: Introductionmentioning

confidence: 99%

Efficient, robust surface functionalization and stabilization of gold nanorods with quaternary ammonium-containing ionomers as multidentate macromolecular ligands

et al. 2016

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Surface functionalization of gold nanorods (GNRs) is critical to their applications in various fields. While there are several existing strategies, we report in this article a new general strategy for the surface functionalization of GNRs with quaternary ammonium-containing ionomers as a novel class of multidentate macromolecular surface ligands. A range of tetralkylammoniumcontaining hyperbranched polyethylene-and linear poly(n-butyl acrylate)-based ionomers has been specifically designed and employed in the strategy. Acting as multidentate macromolecular analogues of cetyltrimethylammonium bromide (CTAB), the ionomers have been demonstrated to bind onto the GNR surface by displacing the surface-bound CTAB species via ligand exchange to render CTAB-free ionomer-modified GNRs. By properly designing the enabling ionomers, we have shown that the modified GNRs can be endowed with some desired properties, such as excellent dispersibility in various organic solvents, robust stability under multiple rounds (up to 12 investigated) of high-speed centrifugation in organic solvents, amphiphilicity with dispersibility in both aqueous and organic media, fluorescence, and capability in carrying hydrophobic guest species. This strategy thus provides potential new ways for the construction of novel multifunctional GNR nanocomposites.3

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Quantitative Replacement of Cetyl Trimethylammonium Bromide by Cationic Thiol Ligands on the Surface of Gold Nanorods and Their Extremely Large Uptake by Cancer Cells

Cited by 176 publications

References 52 publications

Engineering Gold Nanotubes with Controlled Length and Near‐Infrared Absorption for Theranostic Applications

Engineering Gold Nanotubes with Controlled Length and Near‐Infrared Absorption for Theranostic Applications

Decoupling the shape parameter to assess gold nanorod uptake by mammalian cells

Efficient, robust surface functionalization and stabilization of gold nanorods with quaternary ammonium-containing ionomers as multidentate macromolecular ligands

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