Synthesis of Fluorine-18 Functionalized Nanoparticles for use as in vivo Molecular Imaging Agents

• Published in: Journal of the American Chemical Society 2008-05, Vol.130 (21), p.6731-6733
• Main Authors: Matson, John B, Grubbs, Robert H
• Format: Article
• Language: English
• Subjects: Bridged Bicyclo Compounds - chemistry; Catalysis; Diagnostic Imaging - methods; Electron Spin Resonance Spectroscopy; Fluorine Radioisotopes - chemistry; Heptanes - chemistry; Hydrophobic and Hydrophilic Interactions; Imides - chemical synthesis; Imides - chemistry; Isotope Labeling - methods; Mesylates - chemistry; Micelles; Microscopy, Atomic Force; Nanoparticles - chemistry; Polyethylene Glycols - chemistry; Radiopharmaceuticals - chemical synthesis; Radiopharmaceuticals - chemistry; Ruthenium - chemistry
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja802010d

Nanoparticles containing fluorine-18 were prepared from block copolymers made by ring opening metathesis polymerization (ROMP). Using the fast initiating ruthenium metathesis catalyst (H2IMes)(pyr)2(Cl)2RuCHPh, low polydispersity amphiphilic block copolymers were prepared from a cinnamoyl-containing hydrophobic norbornene monomer and a mesyl-terminated PEG-containing hydrophilic norbornene monomer. Self-assembly into micelles and subsequent cross-linking of the micelle cores by light-activated dimerization of the cinnamoyl groups yielded stable nanoparticles. Incorporation of fluorine-18 was achieved by nucleophilic displacement of the mesylates by the radioactive fluoride ion with 31% incorporation of radioactivity. The resulting positron-emitting nanoparticles are to be used as in vivo molecular imaging agents for use in tumor imaging.