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

doi:10.1016/j.jfluchem.2013.03.006

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 journal › Article › peer-review

8 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 language	English
Pages (from-to)	166-172
Number of pages	7
Journal	Journal of Fluorine Chemistry
Volume	152
Early online date	18 Mar 2013
DOIs	https://doi.org/10.1016/j.jfluchem.2013.03.006
Publication status	Published - Aug 2013

Keywords

Fluoro-carbohydrates
PET imaging
cannabinoids

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10.1016/j.jfluchem.2013.03.006

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title = "Pyrazole-type Cannabinoid Ligands conjugated with Fluoro-deoxy-carbohydrates as Potential PET-Imaging Agents: Synthesis and CB1/CB2 receptor affinity evaluation",

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.",

keywords = "Fluoro-carbohydrates, PET imaging, cannabinoids",

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

year = "2013",

month = aug,

doi = "10.1016/j.jfluchem.2013.03.006",

language = "English",

volume = "152",

pages = "166--172",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier BV",

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TY - JOUR

T1 - Pyrazole-type Cannabinoid Ligands conjugated with Fluoro-deoxy-carbohydrates as Potential PET-Imaging Agents

T2 - Synthesis and CB1/CB2 receptor affinity evaluation

AU - Frau, Simona

AU - Dall'Angelo, Sergio

AU - Baillie, Gemma L.

AU - Ross, Ruth A.

AU - Pira, Marilena

AU - Tseng, Chih-Chung

AU - Lazzari, Paolo

AU - Zanda, Matteo

PY - 2013/8

Y1 - 2013/8

N2 - 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.

AB - 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.

KW - Fluoro-carbohydrates

KW - PET imaging

KW - cannabinoids

U2 - 10.1016/j.jfluchem.2013.03.006

DO - 10.1016/j.jfluchem.2013.03.006

M3 - Article

SN - 0022-1139

VL - 152

SP - 166

EP - 172

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

ER -

Pyrazole-type Cannabinoid Ligands conjugated with Fluoro-deoxy-carbohydrates as Potential PET-Imaging Agents: Synthesis and CB1/CB2 receptor affinity evaluation

Abstract

Keywords

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