Automated synthesis of F-18 radiolabelled indole containing Oncrasin-like molecules; a comparison of iodonium salts and boronic ester chemistry
Alexander F McDonald, Yit Wooi Goh, Jonathan M White, Andrew M Scott, Uwe Ackermann
EJNMMI RADIOPHARMACY AND CHEMISTRY | SPRINGERNATURE | Published : 2020
BACKGROUND: Oncrasin-1 is a small molecule which was identified from a screen of KRAS mutant cancer cells and has shown specificity for KRAS mutant cell killing. We aimed to develop a radiolabelled form of Oncrasin-1 to enable in-vivo imaging of mutant KRAS expression in malignant tumours. This work outlines the synthesis of 3 fluorinated derivatives and development of iodonium salt and boronic ester precursors for radiolabelling with the 18F isotope. RESULTS: In our hands, synthesis of iodonium salts were not easily accessible due to the 3-carbaldehyde indole structure being preferentially oxidized by conditions required for iodonium salt formation, rather than benzyl iodide. Synthesis and ..View full abstract
Funding for this project was provided by the University of Melbourne, the Olivia Newton-John Cancer Research Institute, and Austin Health.