Pyrazole-type Cannabinoid Ligands conjugated with Fluoro-deoxy-carbohydrates as Potential PET-Imaging Agents

Synthesis and CB1/CB2 receptor affinity evaluation

Simona Frau, Sergio Dall'Angelo, Gemma L. Baillie, Ruth A. Ross, Marilena Pira, Chih-Chung Tseng, Paolo Lazzari, Matteo Zanda

Research output: Contribution to journalArticle

7 Citations (Scopus)

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 °C, 30 min). All of the title compounds showed relatively modest affinity for the CB1 receptor (high nanomolar range) and selectivities vs. the CB2.
Original languageEnglish
Pages (from-to)166-172
Number of pages7
JournalJournal of Fluorine Chemistry
Volume152
Early online date18 Mar 2013
DOIs
Publication statusPublished - Aug 2013

Fingerprint

rimonabant
Pyrazoles
Cannabinoid Receptor CB2
Cannabinoid Receptor CB1
Hydroxylamine
Oximes
Ribose
Cannabinoids
carbohydrates
conjugation
ligand
affinity
carbohydrate
glucose
Carbohydrates
Ligands
Imaging techniques
ribose
Glucose
ligands

Keywords

  • Fluoro-carbohydrates
  • PET imaging
  • cannabinoids

Cite this

Pyrazole-type Cannabinoid Ligands conjugated with Fluoro-deoxy-carbohydrates as Potential PET-Imaging Agents : Synthesis and CB1/CB2 receptor affinity evaluation. / Frau, Simona; Dall'Angelo, Sergio; Baillie, Gemma L. ; Ross, Ruth A. ; Pira, Marilena; Tseng, Chih-Chung; Lazzari, Paolo; Zanda, Matteo.

In: Journal of Fluorine Chemistry, Vol. 152, 08.2013, p. 166-172.

Research output: Contribution to journalArticle

Frau, Simona ; Dall'Angelo, Sergio ; Baillie, Gemma L. ; Ross, Ruth A. ; Pira, Marilena ; Tseng, Chih-Chung ; Lazzari, Paolo ; Zanda, Matteo. / Pyrazole-type Cannabinoid Ligands conjugated with Fluoro-deoxy-carbohydrates as Potential PET-Imaging Agents : Synthesis and CB1/CB2 receptor affinity evaluation. In: Journal of Fluorine Chemistry. 2013 ; Vol. 152. pp. 166-172.
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