Bioconjugation of Gold Nanoparticles through the Oxidative Coupling of ortho-Aminophenols and Anilines

While there are a number of methods for attaching gold nanoparticles (AuNPs) to biomolecules, the existing strategies suffer from nonspecific AuNP adsorption, reagents that are unstable in aqueous solutions, and/or long reaction times. To improve upon existing AuNP bioconjugation strategies, we have adapted a recently reported potassium ferricyanide-mediated oxidative coupling reaction for the attachment of aniline-functionalized AuNPs to o-aminophenol-containing oligonucleotides, peptides, and proteins. The aniline-AuNPs are stable in aqueous solutions, show little-to-no nonspecific adsorption with biomolecules, and react rapidly (30 min) with o-aminophenols under mild conditions (pH 6.5, 1 mM oxidant).