6533b83afe1ef96bd12a7a95
RESEARCH PRODUCT
Tetrazine Click Chemistry for the Modification of 1-Hydroxy-1,1-methylenebisphosphonic Acids: Towards Bio-orthogonal Functionalization of Gold Nanoparticles.
Nadine MillotRomain AufaureErwann GuéninJulie HardouinLaurence MotteYoann Lalatonnesubject
chemistry.chemical_classificationChemistryAlkeneOrganic ChemistryNanoparticle02 engineering and technologyGeneral Chemistry010402 general chemistry021001 nanoscience & nanotechnology01 natural sciencesCatalysis0104 chemical sciencesTetrazinechemistry.chemical_compoundX-ray photoelectron spectroscopyColloidal goldPolymer chemistryClick chemistryMoleculeSurface modification0210 nano-technologydescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-09-20 | Chemistry (Weinheim an der Bergstrasse, Germany) |