Tetrazine Click Chemistry for the Modification of 1-Hydroxy-1,1-methylenebisphosphonic Acids: Towards Bio-orthogonal Functionalization of Gold Nanoparticles.
Fiche publication
Date publication
novembre 2016
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
Auteurs
Membres identifiés du Cancéropôle Est :
Pr MILLOT Nadine
Tous les auteurs :
Aufaure R, Hardouin J, Millot N, Motte L, Lalatonne Y, Guénin E
Lien Pubmed
Résumé
Inverse electron demand Diels-Alder (iEDDA) was evaluated for the functionalization of gold nanoparticles. The reaction was first modelled with the free coating molecule 1-hydroxy-1,1-methylenebisphosphonate bearing an alkene functionality (HMBPene). A model tetrazine 3,6-dipyridin-2-yl-1,2,4,5-tetrazine (pyTz) was used, kinetic of the reaction was calculated and coupling products were analysed by NMR and HRMS. The reaction was then transposed at the nanoparticle surface. Gold nanoparticles bearing an alkene functionality were obtained using a one-pot methodology with HMBPene and the tetrazine click chemistry was evaluated at their surface using pyTz. The successful coupling was assessed by XPS measurements. This click-methodology was extended to the conjugation of a NIR probe at the NP surface.
Référence
Chemistry. 2016 Nov;22(45):16022-16027