Towards potential nanoparticle contrast agents: Synthesis of new functionalized PEG bisphosphonates

• Main Authors: Souad Kachbi-Khelfallah, Maelle Monteil, Margery Cortes-Clerget, Evelyne Migianu-Griffoni, Jean-Luc Pirat, Olivier Gager, Julia Deschamp, Marc Lecouvey
• Format: Article
• Language: English
• Published: Beilstein-Institut 2016-07-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: bisphosphonate; Fe2O3 nanoparticle; polyethylene glycol derivatives; surface ligand synthesis
• Online Access: https://doi.org/10.3762/bjoc.12.130

The use of nanotechnologies for biomedical applications took a real development during these last years. To allow an effective targeting for biomedical imaging applications, the adsorption of plasmatic proteins on the surface of nanoparticles must be prevented to reduce the hepatic capture and increase the plasmatic time life. In biologic media, metal oxide nanoparticles are not stable and must be coated by biocompatible organic ligands. The use of phosphonate ligands to modify the nanoparticle surface drew a lot of attention in the last years for the design of highly functional hybrid materials. Here, we report a methodology to synthesize bisphosphonates having functionalized PEG side chains with different lengths. The key step is a procedure developed in our laboratory to introduce the bisphosphonate from acyl chloride and tris(trimethylsilyl)phosphite in one step.