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Facile Synthesis of Water-Soluble Fullerene (C60) Nanoparticles via Mussel-Inspired Chemistry as Efficient Antioxidants.

ABSTRACT: Rational design and modification of the all-carbon fullerene cages to meliorate their nature of hydrophobicity is critical for biomedical applications. The outstanding electron affinity of fullerenes enables them to effectively eliminate reactive oxygen species (ROS), the excess of which may lead to health hazards or biological dysfunction. Herein reported is a facile, mild, and green approach to synthesizing the favorable water-soluble C60 nanoparticles capable of ROS-scavenging by combining the mussel-inspired chemistry with the Michael addition reaction. Various characterization techniques, including Fourier-transform infrared spectroscopy (FTIR), X-ray photoelectron spectra (XPS), thermogravimetric analysis (TGA), transmission electron cryomicroscopy (Cryo-TEM), and dynamic laser scattering (DLS) were carried out to confirm the satisfactory preparation of the hybrid C60-PDA-GSH nanoparticles, which exhibited apparent scavenging capacity of DPPH and hydroxyl radicals in vitro. Additionally, the biocompatible C60-PDA-GSH nanoparticles entered into cells and displayed a universal cytoprotective effect against oxidative press induced by H2O2 in four kinds of human cells at a low concentration of 2 ?g/mL. The ease and versatility of the strategy present in this work will not only trigger more fullerene-based materials by the immobilization of diverse functional molecules, but will also extend their possible applications.

SUBMITTER: Zhang X

PROVIDER: S-EPMC6955807 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Facile Synthesis of Water-Soluble Fullerene (C<sub>60</sub>) Nanoparticles via Mussel-Inspired Chemistry as Efficient Antioxidants.

Zhang Xiaoyan X Ma Yihan Y Fu Sheng S Zhang Aiqing A

Nanomaterials (Basel, Switzerland) 20191120 12

Rational design and modification of the all-carbon fullerene cages to meliorate their nature of hydrophobicity is critical for biomedical applications. The outstanding electron affinity of fullerenes enables them to effectively eliminate reactive oxygen species (ROS), the excess of which may lead to health hazards or biological dysfunction. Herein reported is a facile, mild, and green approach to synthesizing the favorable water-soluble C<sub>60</sub> nanoparticles capable of ROS-scavenging by c ...[more]

PMID: 31756936

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Project description:A new class of water-soluble C60 transfecting agents has been prepared using Hirsch-Bingel chemistry and assessed for their ability to act as gene-delivery vectors in vitro. In an effort to elucidate the relationship between the hydrophobicity of the fullerene core, the hydrophilicity of the water-solubilizing groups, and the overall charge state of the C60 vectors in gene delivery and expression, several different C60 derivatives were synthesized to yield either positively charged, negatively charged, or neutral chemical functionalities under physiological conditions. These fullerene derivatives were then tested for their ability to transfect cells grown in culture with DNA carrying the green fluorescent protein (GFP) reporter gene. Statistically significant expression of GFP was observed for all forms of the C60 derivatives when used as DNA vectors and compared to the ability of naked DNA alone to transfect cells. However, efficient in vitro transfection was only achieved with the two positively charged C60 derivatives, namely, an octa-amino derivatized C60 and a dodeca-amino derivatized C60 vector. All C60 vectors showed an increase in toxicity in a dose-dependent manner. Increased levels of cellular toxicity were observed for positively charged C60 vectors relative to the negatively charged and neutral vectors. Structural analyses using dynamic light scattering and optical microscopy offered further insights into possible correlations between the various derivatized C60 compounds, the C60 vector/DNA complexes, their physical attributes (aggregation, charge) and their transfection efficiencies. Recently, similar Gd@C60-based compounds have demonstrated potential as advanced contrast agents for magnetic resonance imaging (MRI). Thus, the successful demonstration of intracellular DNA uptake, intracellular transport, and gene expression from DNA using C60 vectors suggests the possibility of developing analogous Gd@C60-based vectors to serve simultaneously as both therapeutic and diagnostic agents.

Dataset Information

Facile Synthesis of Water-Soluble Fullerene (C60) Nanoparticles via Mussel-Inspired Chemistry as Efficient Antioxidants.

Publications

Facile Synthesis of Water-Soluble Fullerene (C<sub>60</sub>) Nanoparticles via Mussel-Inspired Chemistry as Efficient Antioxidants.

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