A self-reporting tetrazole-based linker for the biofunctionalization of gold nanorods.

Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 9513783 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3765 (Electronic) Linking ISSN: 09476539 NLM ISO Abbreviation: Chemistry Subsets: MEDLINE

Original Publication: Weinheim, Germany : Wiley-VCH

DNA/*chemistry ; Gold/*chemistry ; Maleimides/*chemistry ; Metal Nanoparticles/*chemistry ; Nanostructures/*chemistry ; Nanotubes/*chemistry ; Tetrazoles/*chemistry; Cycloaddition Reaction ; Imines/chemistry ; Nitriles/chemistry

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.
(© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Keywords: DNA; dipolar cycloaddition; gold; nanostructures; photochemistry

0 (Imines)
0 (Maleimides)
0 (Nitriles)
0 (Tetrazoles)
2519R1UGP8 (maleimide)
7440-57-5 (Gold)
9007-49-2 (DNA)

Date Created: 20150826 Date Completed: 20160509 Latest Revision: 20161125

20221213

10.1002/chem.201502070

26303592