Synthesis, radio-synthesis and in vitro evaluation of terminally fluorinated derivatives of HU-210 and HU-211 as novel candidate PET tracers

Chiara Zanato, Alessia Pelagalli, Katie F. M. Marwick, Monica Piras, Sergio Dall'Angelo, Andrea Spinaci, Roger G. Pertwee, David J. A. Wyllie, Giles E. Hardingham, Matteo Zanda

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Abstract

We report the synthesis of terminally fluorinated HU-210 and HU-211 analogues (HU-210F and HU-211F, respectively) and their biological evaluation as ligands of cannabinoid receptors (CB1 and CB2) and N-methyl D-aspartate receptor (NMDAR). [18F]-labelled HU-210F was radiosynthesised from the bromo-substituted precursor. In vitro assays showed that both HU-210F and HU-211F retain the potent pharmacological profile of HU-210 and HU-211, suggesting that [18F]-radiolabelled HU-210F and HU-211F could have potential as PET tracers for in vivo imaging.
Original languageEnglish
Pages (from-to)2086-2096
Number of pages11
JournalOrganic & Biomolecular Chemistry
Volume15
Issue number9
Early online date10 Feb 2017
DOIs
Publication statusPublished - 2017

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Radio
tracers
Derivatives
aspartates
evaluation
synthesis
Cannabinoid Receptor CB2
analogs
Cannabinoid Receptor CB1
ligands
profiles
N-Methyl-D-Aspartate Receptors
Assays
Pharmacology
Ligands
Imaging techniques
HU 211
In Vitro Techniques

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Synthesis, radio-synthesis and in vitro evaluation of terminally fluorinated derivatives of HU-210 and HU-211 as novel candidate PET tracers. / Zanato, Chiara; Pelagalli, Alessia ; Marwick, Katie F. M. ; Piras, Monica; Dall'Angelo, Sergio; Spinaci, Andrea; Pertwee, Roger G.; Wyllie, David J. A. ; Hardingham, Giles E. ; Zanda, Matteo.

In: Organic & Biomolecular Chemistry, Vol. 15, No. 9, 2017, p. 2086-2096.

Research output: Contribution to journalArticle

Zanato, Chiara ; Pelagalli, Alessia ; Marwick, Katie F. M. ; Piras, Monica ; Dall'Angelo, Sergio ; Spinaci, Andrea ; Pertwee, Roger G. ; Wyllie, David J. A. ; Hardingham, Giles E. ; Zanda, Matteo. / Synthesis, radio-synthesis and in vitro evaluation of terminally fluorinated derivatives of HU-210 and HU-211 as novel candidate PET tracers. In: Organic & Biomolecular Chemistry. 2017 ; Vol. 15, No. 9. pp. 2086-2096.
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abstract = "We report the synthesis of terminally fluorinated HU-210 and HU-211 analogues (HU-210F and HU-211F, respectively) and their biological evaluation as ligands of cannabinoid receptors (CB1 and CB2) and N-methyl D-aspartate receptor (NMDAR). [18F]-labelled HU-210F was radiosynthesised from the bromo-substituted precursor. In vitro assays showed that both HU-210F and HU-211F retain the potent pharmacological profile of HU-210 and HU-211, suggesting that [18F]-radiolabelled HU-210F and HU-211F could have potential as PET tracers for in vivo imaging.",
author = "Chiara Zanato and Alessia Pelagalli and Marwick, {Katie F. M.} and Monica Piras and Sergio Dall'Angelo and Andrea Spinaci and Pertwee, {Roger G.} and Wyllie, {David J. A.} and Hardingham, {Giles E.} and Matteo Zanda",
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T1 - Synthesis, radio-synthesis and in vitro evaluation of terminally fluorinated derivatives of HU-210 and HU-211 as novel candidate PET tracers

AU - Zanato, Chiara

AU - Pelagalli, Alessia

AU - Marwick, Katie F. M.

AU - Piras, Monica

AU - Dall'Angelo, Sergio

AU - Spinaci, Andrea

AU - Pertwee, Roger G.

AU - Wyllie, David J. A.

AU - Hardingham, Giles E.

AU - Zanda, Matteo

N1 - We thank the EPSRC National Mass Spectrometry Service Centre (Swansea, UK), for performing HRMS analyses.

PY - 2017

Y1 - 2017

N2 - We report the synthesis of terminally fluorinated HU-210 and HU-211 analogues (HU-210F and HU-211F, respectively) and their biological evaluation as ligands of cannabinoid receptors (CB1 and CB2) and N-methyl D-aspartate receptor (NMDAR). [18F]-labelled HU-210F was radiosynthesised from the bromo-substituted precursor. In vitro assays showed that both HU-210F and HU-211F retain the potent pharmacological profile of HU-210 and HU-211, suggesting that [18F]-radiolabelled HU-210F and HU-211F could have potential as PET tracers for in vivo imaging.

AB - We report the synthesis of terminally fluorinated HU-210 and HU-211 analogues (HU-210F and HU-211F, respectively) and their biological evaluation as ligands of cannabinoid receptors (CB1 and CB2) and N-methyl D-aspartate receptor (NMDAR). [18F]-labelled HU-210F was radiosynthesised from the bromo-substituted precursor. In vitro assays showed that both HU-210F and HU-211F retain the potent pharmacological profile of HU-210 and HU-211, suggesting that [18F]-radiolabelled HU-210F and HU-211F could have potential as PET tracers for in vivo imaging.

U2 - 10.1039/C6OB02796B

DO - 10.1039/C6OB02796B

M3 - Article

VL - 15

SP - 2086

EP - 2096

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1477-0520

IS - 9

ER -