𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Radiosynthesis of [18F]DPA-714, a selective radioligand for imaging the translocator protein (18 kDa) with PET

✍ Scribed by Annelaure Damont; Françoise Hinnen; Bertrand Kuhnast; Marie-Anne Schöllhorn-Peyronneau; Michelle James; Christopher Luus; Bertrand Tavitian; Michael Kassiou; Frédéric Dollé

Publisher
John Wiley and Sons
Year
2008
Tongue
French
Weight
193 KB
Volume
51
Category
Article
ISSN
0022-2135

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Recently, a novel series of 2‐phenylpyrazolo[1,5‐a]pyrimidineacetamides has been reported as selective ligands of the translocator protein (18 kDa). Within this series, DPA‐714 (N,N‐diethyl‐2‐(2‐(4‐(2‐fluoroethoxy)phenyl)‐5,7‐dimethylpyrazolo[1,5‐a]pyrimidin‐3‐yl)acetamide, K~i~=7.0 nM) is a compound, which had been designed with a fluorine atom in its structure, allowing labelling with fluorine‐18 (half‐life: 109.8 min) and in vivo imaging using positron emission tomography. DPA‐714 and its tosyloxy derivative (N,N‐diethyl‐2‐(2‐(4‐(2‐toluenesulfonyloxyethoxy)phenyl)‐5,7‐dimethylpyrazolo[1,5‐a]pyrimidin‐3‐yl)acetamide) as precursor for the labelling with fluorine‐18 were synthesized in two steps from DPA‐713 (N,N‐diethyl‐2‐(2‐(4‐methoxyphenyl)‐5,7‐dimethylpyrazolo[1,5‐a]pyrimidin‐3‐yl)acetamide) and obtained in 32 and 42% yields, respectively. [^18^F]DPA‐714 was synthesized using a simple one‐step process (a tosyloxy‐for‐fluorine nucleophilic aliphatic substitution), which has been fully automated on our Zymate‐XP robotic system. It involves: (A) reaction of K[^18^F]F‐Kryptofix^®^222 with the tosyloxy precursor (4.5–5.0 mg, 8.2–9.1 µmol) at 165°C for 5 min in dimethyl sufloxide (0.6 mL) followed by (B) C18 PrepSep cartridge pre‐purification and finally (C) semi‐preparative high‐performance liquid chromatography (HPLC) purification on a Waters X‐Terra™ RP18. Typically, 5.6–7.4 GBq of [^18^F]DPA‐714 (>95% chemically and radiochemically pure) could be obtained with specific radioactivities ranging from 37 to 111 GBq/µmol within 85–90 min (HPLC purification and SepPak^®^‐based formulation included), starting from a 37 GBq [^18^F]fluoride batch (overall non‐decay‐corrected and isolated radiochemical yield: 15–20%). Copyright © 2008 John Wiley & Sons, Ltd.

📜 SIMILAR VOLUMES

Radiosynthesis of [18F]PBR111, a selecti
Radiosynthesis of [18F]PBR111, a selective radioligand for imaging the translocator protein (18 kDa) with PET
✍ Frédéric Dollé; Françoise Hinnen; Annelaure Damont; Bertrand Kuhnast; Christophe 📂 Article 📅 2008 🏛 John Wiley and Sons 🌐 French ⚖ 137 KB

## Abstract PBR111 (2‐(6‐chloro‐2‐(4‐(3‐fluoropropoxy)phenyl)imidazo[1,2‐__a__]pyridin‐3‐yl)‐__N__,__N__‐diethylacetamide) is a novel, reported, high‐affinity and selective ligand for the translocator protein (18 kDa). PBR111 has been labelled with fluorine‐18 (half‐life: 109.8 min) using our Zymat

The development of PET radioligands for
The development of PET radioligands for imaging the translocator protein (18 kDa): What have we learned?
✍ Christopher Luus; Raphy Hanani; Aaron Reynolds; Michael Kassiou 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 French ⚖ 208 KB

## Abstract The translocator protein (TSPO; 18 kDa), formerly known as the peripheral benzodiazepine receptor (PBR), is minimally expressed in the healthy brain. On the other hand, increased levels of TSPO have been noted in brain disorders for which an immune response is elicited. This increase in

Radiosynthesis of [18F]LBT-999, a select
Radiosynthesis of [18F]LBT-999, a selective radioligand for the visualization of the dopamine transporter with PET
✍ Frédéric Dollé; Françoise Hinnen; Patrick Emond; Sylvie Mavel; Zoïa Mincheva; Wa 📂 Article 📅 2006 🏛 John Wiley and Sons 🌐 French ⚖ 161 KB

LBT-999 (8-((E)-4-fluoro-but-2-enyl)-3b-p-tolyl-8-aza-bicyclo[3.2.1]octane-2b-carboxylic acid methyl ester) is a cocaine derivative belonging to a new generation of highly selective dopamine transporter ligands (K D :9 nM). LBT-999 was labelled with fluorine-18 at its fluoromethylvinyl moiety using

One-step radiosynthesis of [18F]LBT-999:
One-step radiosynthesis of [18F]LBT-999: a selective radioligand for the visualization of the dopamine transporter with PET
✍ Frédéric Dollé; Julie Helfenbein; Françoise Hinnen; Sylvie Mavel; Zoïa Mincheva; 📂 Article 📅 2007 🏛 John Wiley and Sons 🌐 French ⚖ 153 KB

## Abstract LBT‐999 (8‐((__E__)‐4‐fluoro‐but‐2‐enyl)‐3‐beta‐__p__‐tolyl‐8‐aza‐bicyclo[3.2.1]octane‐2‐beta‐carboxylicacid methyl ester) is a recently developed cocaine derivative belonging to a new generation of highly selective dopamine transporter (DAT) ligands (__K__~D~: 9 nM for the DAT and IC~5

A 18F-Labeled Fluorobutyl-Substituted Sp
A 18F-Labeled Fluorobutyl-Substituted Spirocyclic Piperidine Derivative as a Selective Radioligand for PET Imaging of Sigma1 Receptors
✍ Dr. Aurélie Maisonial; Dr. Eva Große Maestrup; Dr. Steffen Fischer; Dr. Achim Hi 📂 Article 📅 2011 🏛 John Wiley and Sons 🌐 English ⚖ 491 KB 👁 1 views

## Abstract In this study, we synthesized and evaluated a new spirocyclic piperidine derivative 3, containing a 4‐fluorobutyl side chain, as a PET radioligand for neuroimaging of σ~1~ receptors. In vitro, compound 3 displayed high affinity for σ~1~ receptors (__K__~i~=1.2 nM) as well as high select

Radiosynthesis of 2-exo-(2′-[18F]Fluoro-
Radiosynthesis of 2-exo-(2′-[18F]Fluoro-3′-(4-fluorophenyl)-pyridin-5′-yl)-7-azabicyclo[2.2.1]heptane ([18F]F2PhEP), a potent epibatidine-based radioligand for nicotinic acetylcholine receptor PET imaging
✍ Gaëlle Roger; Françoise Hinnen; Héric Valette; Wadad Saba; Michel Bottlaender; F 📂 Article 📅 2006 🏛 John Wiley and Sons 🌐 French ⚖ 189 KB

2-exo-(2 0 -Fluoro-3 0 -(4-fluorophenyl)-pyridin-5 0 -yl)-7-azabicyclo[2.2.1]heptane (F 2 PhEP), a novel, epibatidine-based, a4b2-selective nicotinic acetylcholine receptor antagonist of low toxicity, as well as the corresponding N-Boc-protected chloro-and bromo derivatives as precursors for labelli