Palladium-mediated bioorthogonal conjugation of dual-functionalised nanoparticles and their cellular delivery

Abstract

Nanoparticles have gained considerable significance in the life sciences due to their ability to be internalised by living cells and the relative ease with which they can be functionalised with cargos ranging from molecular sensors to biomacromolecules. However, the scope of available bioconjugation methods is limited and new bioorthogonal methods are much sought after. Herein, we present dual functionalised (HO)₂B/H₂N-polymeric nanoparticles which can be conjugated via amide bond formation and/or Pd-mediated Suzuki–Miyaura cross-coupling in a chemoselective and bioorthogonal manner. These dual-functionalised particles were found to be efficiently taken up by mammalian cells without toxicity and were successfully employed in the cellular delivery and intracellular release of a “turn-on” molecular probe thereby demonstrating the potential use of the new particles for chemical biology applications.