ABSTRACT
A photochemical approach based on nitrile imine-mediated tetrazole-ene cycloaddition is introduced to functionalize gold nanorods with biomolecules. For this purpose, a bifunctional, photoreactive linker containing thioctic acid as the Au anchoring group and a tetrazole moiety for the light-induced reaction with maleimide-capped DNA was prepared. The tetrazole-based reaction on the nanoparticles' surface results in a fluorescent pyrazoline product allowing for the spectroscopic monitoring of the reaction. This first example of nitrile imine-mediated tetrazole-ene cycloaddition (NITEC)-mediated biofunctionalization of Au nanorods paves the way for the attachment of sensitive biomolecules, such as antibodies and other proteins, under mild conditions and expands the toolbox for the tailoring of nanomaterials.
Subject(s)
DNA/chemistry , Gold/chemistry , Maleimides/chemistry , Metal Nanoparticles/chemistry , Nanostructures/chemistry , Nanotubes/chemistry , Tetrazoles/chemistry , Cycloaddition Reaction , Imines/chemistry , Nitriles/chemistryABSTRACT
Photoreactive gold nanoparticles (NP) can be encoded in a spatially resolved fashion using direct laser writing techniques into variable patterns. The surface of the gold nanoparticles is imparted with photoreactivity by tethering photo-caged dienes ('photoenols'), which are able to undergo a rapid Diels-Alder cycloaddition with surface anchored enes. Subsequent to surface encoding, the particles feature residual caged dienes, which can be reactivated for secondary surface encoding.
Subject(s)
Gold/chemistry , Metal Nanoparticles/chemistry , Photochemical Processes , Alkenes/chemistryABSTRACT
A mild, efficient and ambient temperature photochemical approach for the synthesis of silver nanoparticle core-shell structures employing a zwitterionic polymer as well as polyethylene glycol is presented.
Subject(s)
Light , Metal Nanoparticles/chemistry , Polymers/chemistry , Silver/chemistry , Polyethylene Glycols/chemistry , Temperature , Triazoles/chemistryABSTRACT
DNA was modified with a photo-reactive caged diene allowing for the modification of dienophile containing proteins under mild irradiation conditions to afford fully functional DNA-protein conjugates.
