Gold Nanoparticle Enantiomers and Their Chiral-Morphology Dependence of Cellular Uptake

Chiral molecules are widely prevalent in nature and biological systems, and artificial chiral nanoparticles have drawn enormous interest owing to their unique optical and physical properties. However, nanoparticles with chiral morphologies and their potential role in biology have been rarely explored. Herein, we report a seed-mediated synthesis of enantiomorphic Au nanooctopods (NOPs) and their chiral-morphology dependence of cellular uptake. With a high yield (similar to 80%), the chiral NOPs possess eight uniform arms that bend from < 111 > to < 100 > directions, like a propeller structure. The chiral NOPs synthesized with L- or D-glutathione (GSH) have opposite handedness, resulting in opposite circular dichroism signals, which is consistent with finite-difference time-domain simulations. D-GSH NOPs demonstrate greater than 30% (ca. 15%) enhanced cellular uptake in GL261 and bEnd.3 cells compared with L-GSH NOPs (racemic NOPs). Moreover, D-GSH NOPs modified with poly(ethylene glycol) or L-GSH are also preferred by the cells, proving the chiral-morphology dependence of cellular uptake. Our study develops the exploration of the chiral-specific interaction in biological systems, providing potential applications for drug delivery, biosensing, and tumor detection. [GRAPHICS] .

Automated summary

The study presents a seed-mediated synthesis method for chiral gold nanooctopods with specific morphology, showing an influence on cellular uptake.