title: A self-reporting tetrazole-based linker for the biofunctionalization of gold nanorods.
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.
authors: Center for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Wolfgang-Gaede-Str.1a, 76131 Karlsruhe (Germany).|Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstrasse 18, 76128 Karlsruhe (Germany).
authors: Lukas
authors: L
authors: Stolzer
authors: Center for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Wolfgang-Gaede-Str.1a, 76131 Karlsruhe (Germany).
authors: Antonina
authors: A
authors: Vigovskaya
authors: Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstrasse 18, 76128 Karlsruhe (Germany). christopher.barner-kowollik@kit.edu.|Institut für Biologische Grenzflächen, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen (Germany). christopher.barner-kowollik@kit.edu.
authors: Christopher
authors: C
authors: Barner-Kowollik
authors: Center for Functional Nanostructures (CFN), Karlsruhe Institute of Technology (KIT), Wolfgang-Gaede-Str.1a, 76131 Karlsruhe (Germany). ljiljana.fruk@kit.edu.
authors: Ljiljana
authors: L
authors: Fruk
mesh_terms: D061565:Cycloaddition Reaction; D004247:DNA / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D007097:Imines / Q000737:chemistry; D008301:Maleimides / Q000737:chemistry*; D053768:Metal Nanoparticles / Q000737:chemistry*; D049329:Nanostructures / Q000737:chemistry*; D043942:Nanotubes / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry; D013777:Tetrazoles / Q000737:chemistry*
chemical_list: D007097:Imines; D008301:Maleimides; D009570:Nitriles; D013777:Tetrazoles; C043592:maleimide; D006046:Gold; D004247:DNA
keywords: DNA; dipolar cycloaddition; gold; nanostructures; photochemistry