title: Tetrazine Click Chemistry for the Modification of 1-Hydroxy-1,1-methylenebisphosphonic Acids: Towards Bio-orthogonal Functionalization of Gold Nanoparticles.
abstract: 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.
authors: Inserm, U1148, Laboratory for Vascular Translational Science, UFR SMBH, Université Paris 13, Sorbonne Paris Cité, 74 avenue M. Cachin, 93017, Bobigny, France.
authors: Romain
authors: R
authors: Aufaure
authors: Laboratoire PBS, CNRS (UMR 6270), Université de Rouen, Bd Maurice de Broglie, 76821, Mont Saint Aignan Cedex, France.
authors: Julie
authors: J
authors: Hardouin
authors: Laboratoire Interdisciplinaire Carnot de Bourgogne, UMR 6303 CNRS/Université de Bourgogne Franche-Comté, 9 av. A. Savary, BP 47870, 21 078, DIJON Cedex, France.
authors: Nadine
authors: N
authors: Millot
authors: Inserm, U1148, Laboratory for Vascular Translational Science, UFR SMBH, Université Paris 13, Sorbonne Paris Cité, 74 avenue M. Cachin, 93017, Bobigny, France.
authors: Laurence
authors: L
authors: Motte
authors: Inserm, U1148, Laboratory for Vascular Translational Science, UFR SMBH, Université Paris 13, Sorbonne Paris Cité, 74 avenue M. Cachin, 93017, Bobigny, France. guenin@univ-paris13.fr, yoann.lalatonne@aphp.fr.|Service de Médecine Nucléaire, Hôpital Avicenne Assistance Publique-Hôpitaux de Paris, 93009, Bobigny, France. guenin@univ-paris13.fr, yoann.lalatonne@aphp.fr.
authors: Yoann
authors: Y
authors: Lalatonne
authors: Inserm, U1148, Laboratory for Vascular Translational Science, UFR SMBH, Université Paris 13, Sorbonne Paris Cité, 74 avenue M. Cachin, 93017, Bobigny, France. yoann.lalatonne@aphp.fr.
authors: Erwann
authors: E
authors: Guénin
keywords: bisphosphonate; click chemistry; gold; inverse electron demand Diels-Alder; nanoparticles