Role of Surface Hydrophobicity of Dicationic Amphiphile-Stabilized Gold Nanoparticles on A549 Lung Cancer Cells.

Herein, we report the surface functionality of dicationic cysteamine conjugated cholic acid (DCaC), dicationic cysteamine conjugated deoxycholic acid (DCaDC), and dicationic cysteamine conjugated lithocholic acid (DCaLC) templated gold nanoparticles (AuNPs) on mammalian cells. The haemocompatibility of the synthesized NPs was evaluated by in vitro hemolysis and erythrocyte sedimentation rate using human red blood cells (RBCs). In all of the systems, no toxicity was observed on human erythrocytes (RBCs) up to the concentration of 120 µg/mL. The anticancer activity of these dicationic amphiphile-stabilized AuNPs on A549 lung cancer cells was demonstrated by in vitro cell viability assay, intracellular reactive oxygen species estimation by DCFH-DA, apoptosis analysis using AO-EtBr fluorescence staining, DNA fragmentation analysis by agarose gel electrophoresis, and western blot analysis of caspase-3 expression. These results suggest that the cytotoxicity of AuNPs to A549 cells increase with the dose and hydrophobicity of amphiphiles and were found to be in the order: DCaLC-AuNPs > DCaDC-AuNPs > DCaC-AuNPs.

Auric Chloride Induced Micellization on Fractal Patterned Dicationic Amphiphiles and Stabilization of Gold Nanoparticles.

The present article reports the development of sunlight-mediated rapid synthesis of bile acid derived dicationic amphiphiles, namely, dicationic cysteamine-conjugated cholic acid (DCaC), dicationic cysteamine-conjugated deoxycholic acid (DCaDC), and dicationic cysteamine-conjugated lithocholic acid (DCaLC) by adopting thiol-yne click chemistry approach. The auric chloride (AuHCl4) induced micellization of amphiphiles from fractal pattern to chainlike aggregates was examined by critical micelle concentration measurements, quenching studies, field emission scanning electron microscopy, and optical microscopy techniques. The micelles thus formed act as ideal templates for the stabilization of gold nanoparticles (AuNPs) and exhibit good stability for more than 6 months. The synthesized AuNPs were characterized using UV-visible spectroscopy, high-resolution transmission electron microscopy, DLS, zeta potential, and contact angle measurements. These NPs showed high salt tolerance, and the levels were found to be 420, 460, and 580 mM for DCaC-, DCaDC-, and DCaLC-capped AuNPs, respectively.

Hierarchical Self-Assembly of Bile-Acid-Derived Dicationic Amphiphiles and Their Toxicity Assessment on Microbial and Mammalian Systems.

A thiol-yne click chemistry approach was adopted for the first time to prepare highly water-soluble bile acid derived dicationic amphiphiles. The synthesized amphiphiles dicationic cysteamine conjugated cholic acid (DCaC), dicationic cysteamine conjugated deoxycholic acid (DCaDC), and dicationic cysteamine conjugated lithocholic acid (DCaLC) exhibited hierarchically self-assembled microstructures at various concentrations in an aqueous medium. Interestingly at below critical micellar concentration (CMC) the amphiphiles showed distinct fractal patterns such as fractal grass, microdendrites and fern leaf like fractals for DCaC, DCaDC and DCaLC respectively. The fractal dimension (Df) analysis indicated that the formation of fractal like aggregates is a diffusion limited aggregation (DLA) process. The preliminary aggregation studies such as determination of CMC, fluorescence quenching, wettability and contact angle measurements were elaborately investigated. The morphology of the aggregates were analyzed by SEM and OPM techniques. Further, we demonstrated the antimicrobial and hemolytic activity for the cationic amphiphiles. DCaC had potent antimicrobial activity and showed no toxicity on human RBCs indicating that DCaC could be used in biomedical applications, in addition to their industrial and laboratory applications such as detergency, surface cleaning, and disinfection agent.

Sodium cholate-templated blue light-emitting Ag subnanoclusters: in vivo toxicity and imaging in zebrafish embryos.

We report a novel green chemical approach for the synthesis of blue light-emitting and water-soluble Ag subnanoclusters, using sodium cholate (NaC) as a template at a concentration higher than the critical micelle concentration (CMC) at room temperature. However, under photochemical irradiation, small anisotropic and spherically shaped Ag nanoparticles (3-11 nm) were obtained upon changing the concentration of NaC from below to above the CMC. The matrix-assisted laser desorption ionization time-of-flight and electrospray ionization mass spectra showed that the cluster sample was composed of Ag4 and Ag6. The optical properties of the clusters were studied by UV-visible and luminescence spectroscopy. The lifetime of the synthesized fluorescent Ag nanoclusters (AgNCs) was measured using a time-correlated single-photon counting technique. High-resolution transmission electron microscopy was used to assess the size of clusters and nanoparticles. A protocol for transferring nanoclusters to organic solvents is also described. Toxicity and bioimaging studies of NaC templated AgNCs were conducted using developmental stage zebrafish embryos. From the survival and hatching experiment, no significant toxic effect was observed at AgNC concentrations of up to 200 µL/mL, and the NC-stained embryos exhibited blue fluorescence with high intensity for a long period of time, which shows that AgNCs are more stable in living system.