Pyrazole-type cannabinoid ligands conjugated with fluoro-deoxy-carbohydrates as potential PET-imaging agents: Synthesis and CB1/CB2 receptor affinity evaluation

Authors :: Gemma L. Baillie
Simona Frau
Paolo Lazzari
Matteo Zanda
Chih-Chung Tseng
Marilena Pira
Ruth A. Ross
Sergio Dall'Angelo
Source :: Journal of fluorine chemistry, 152 (2013): 166–172. doi:10.1016/j.jfluchem.2013.03.006, info:cnr-pdr/source/autori:Frau, Simona; Dall'Angelo, Sergio; Baillie, Gemma L.; Ross, Ruth A.; Pira, Marilena; Tseng, Chih-Chung; Lazzari, Paolo; Zanda, Matteo/titolo:Pyrazole-type cannabinoid ligands conjugated with fluoro-deoxy-carbohydrates as potential PET-imaging agents: Synthesis and CB1%2FCB2 receptor affinity evaluation/doi:10.1016%2Fj.jfluchem.2013.03.006/rivista:Journal of fluorine chemistry (Print)/anno:2013/pagina_da:166/pagina_a:172/intervallo_pagine:166–172/volume:152
Publication Year :: 2013
Publisher :: Elsevier BV, 2013.
Abstract: 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 degrees C, 30 min). All of the title compounds showed relatively modest affinity for the CBI receptor (high nanomolar range) and selectivities vs. the CB2. (C) 2013 Elsevier B.V. All rights reserved.

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