A novel class of cannabinoid ligands was synthesized in good overall yields by means of oxime-bio-conjugation between hydroxylamine-functionalized Rimonabant-type pyrazoles and fluoro-deoxy-carbohydrates (d-2-fluoro-deoxy-glucose, FDG, and d-5-fluoro-5-deoxy-ribose, FDR). FDR proved to be superior to FDG for bio-conjugation, as it occurred in milder conditions and at faster rate (rt, 20 min vs. 100 °C, 30 min). All of the title compounds showed relatively modest affinity for the CB1 receptor (high nanomolar range) and selectivities vs. the CB2.
- PET imaging
Frau, S., Dall'Angelo, S., Baillie, G. L., Ross, R. A., Pira, M., Tseng, C-C., Lazzari, P., & Zanda, M. (2013). Pyrazole-type Cannabinoid Ligands conjugated with Fluoro-deoxy-carbohydrates as Potential PET-Imaging Agents: Synthesis and CB1/CB2 receptor affinity evaluation. Journal of Fluorine Chemistry, 152, 166-172. https://doi.org/10.1016/j.jfluchem.2013.03.006