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Radiosynthesis of 2-[6-chloro-2-(4-iodophenyl)imidazo[1,2-a]pyridin-3-yl]-N-ethyl-N-[11C]methyl-acetamide, [11C]CLINME, a novel radioligand for imaging the peripheral benzodiazepine receptors with PET

✍ Scribed by C. Thominiaux; F. Mattner; I. Greguric; H. Boutin; F. Chauveau; B. Kuhnast; M.-C. Grégoire; C. Loc′h; H. Valette; M. Bottlaender; Ph. Hantraye; B. Tavitian; A. Katsifis; F. Dollé

Publisher
John Wiley and Sons
Year
2007
Tongue
French
Weight
145 KB
Volume
50
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Recently, a new 2‐(iodophenyl)imidazo[1,2‐a]pyridineacetamide series has been developed as iodine‐123‐labelled radioligands for imaging the peripheral benzodiazepine receptors using single photon emission tomography. Within this series, 2‐[6‐chloro‐2‐(4‐iodophenyl)‐imidazo[1,2‐a]pyridin‐3‐yl]‐N‐ethyl‐N‐methyl‐acetamide (CLINME) was considered as an appropriate candidate for positron emission tomography imaging and was isotopically labelled with carbon‐11 (T~1/2~: 20.38 min) at the methylacetamide side chain from the corresponding nor‐analogue using [^11^C]methyl iodide and the following experimental conditions: (1) trapping at −10°C of [^11^C]methyl iodide in a 1/2 (v:v) mixture of DMSO/DMF (300 µl) containing 0.7–1.0 mg of the precursor for labelling and 3–5 mg of powdered potassium hydroxide (excess); (2) heating the reaction mixture at 110°C for 3 min under a nitrogen stream; (3) diluting the residue with 0.6 ml of the HPLC mobile phase; and (4) purification using semi‐preparative HPLC (Zorbax^®^ SB18, Hewlett Packard, 250 × 9.4 mm). Typically, starting from a 1.5 Ci (55.5 GBq) [^11^C]CO~2~ production batch, 120−150 mCi (4.44–5.55 GBq) of [^11^C]CLINME were obtained (16–23% decay‐corrected radiochemical yield, n=12) within a total synthesis time of 24–27 min (Sep‐pak^®^Plus‐based formulation included). Specific radioactivities ranged from 0.9 to 2.7 Ci/µmol (33.3–99.9 GBq/µmol) at the end of radiosynthesis. Copyright © 2007 John Wiley & Sons, Ltd.

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