Nitrone Modified Gold Nanoparticles: Synthesis, Characterization and Their Potential as 18F-Labeled PET Probes via I-SPANC

A bioorthogonal gold nanoparticle template displaying interfacial nitrone functional groups for bioorthogonal interfacial strain-promoted alkyne-nitrone cycloaddition (I-SPANC) reactions has been synthesized. The Nitrone-AuNPs were characterized in detail using ¹H NMR spectroscopy, TEM, TGA, and XPS and a nanoparticle raw formula was calculated. The ability to control the conjugation of molecules of interest at the molecular level onto the Nitrone-AuNPs template allowed us to create a methodology for the synthesis of AuNP-based radiolabeled probes with a high degree of loading using copper free, strained-promoted cycloaddition. To this end, we also describe the synthesis of a new prosthetic group containing a strained-alkyne capable of clicking hot ¹⁸F-label onto complementary azide or nitrone labelled agents.