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N-[4-[4-(2-[¹¹C]甲氧基苯基)哌嗪-1-基]丁基]苯并[b]噻吩-2-甲酰胺的合成与放射性标记——一种潜在的用于PET成像检测D3受体的放射性示踪剂

Synthesis and radiolabeling of N-[4-[4-(2-[11C]methoxyphenyl)piperazin-1-yl]butyl]benzo[b]thiophene-2-carboxamide -- a potential radiotracer for D3 receptor imaging with PET.

作者信息

Kuhnast Bertrand, Valette Héric, Besret Laurent, Demphel Stéphane, Coulon Christine, Ottaviani Michèle, Guillermier Martine, Bottlaender Michel, Dollé Frédéric

机构信息

Service Hospitalier Frédéric Joliot, SHFJ/CEA/DSV, 4 place du Général Leclerc, 91401 Orsay, France.

出版信息

Nucl Med Biol. 2006 Aug;33(6):785-95. doi: 10.1016/j.nucmedbio.2006.05.007. Epub 2006 Jul 18.

DOI:10.1016/j.nucmedbio.2006.05.007
PMID:16934697
Abstract

FAUC346 (N-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]benzo[b]thiophene-2-carboxamide), an in vitro D(3)-selective ligand, and its normethyl derivative have been synthesized from commercially available 1-(2-substituted-phenyl)piperazines. FAUC346 has been labeled using [(11)C]methyl triflate in acetone containing aqueous NaOH (5 Eq) at -10 degrees C for 1 min, purified on semipreparative reverse-phase high-performance liquid chromatography (HPLC) and formulated as an intravenous injectable solution using a Sep-Pak Plus C(18) device. Up to 5.5 GBq of [(11)C]FAUC346 (N-[4-[4-(2-[methyl-(11)C]methoxyphenyl)piperazin-1-yl]butyl]benzo[b]thiophene-2-carboxamide), with a specific radioactivity of 45-75 GBq/micromol, could be obtained in 30-35 min, including HPLC purification and formulation starting from 44.4 GBq of [(11)C]carbon dioxide. Preliminary pharmacological evaluation of [(11)C]FAUC346 in rat brain clearly demonstrated in vivo selectivity for D(3) receptors and the absence of radiolabeled metabolite within the brain. These encouraging results, however, could not be confirmed in nonhuman primates; therefore, this radioligand does not appear to have the required pharmacological profile for a positron emission tomography probe for imaging D(3) receptors.

摘要

FAUC346（N-[4-[4-(2-甲氧基苯基)哌嗪-1-基]丁基]苯并[b]噻吩-2-甲酰胺），一种体外D(3)选择性配体，及其去甲基衍生物已由市售的1-(2-取代苯基)哌嗪合成。FAUC346在含有氢氧化钠水溶液（5当量）的丙酮中于-10℃用[(11)C]甲基三氟甲磺酸酯标记1分钟，通过半制备反相高效液相色谱（HPLC）纯化，并使用Sep-Pak Plus C(18)装置配制成静脉注射溶液。从44.4 GBq的[(11)C]二氧化碳开始，在30 - 35分钟内可获得高达5.5 GBq的[(11)C]FAUC346（N-[4-[4-(2-[甲基-(11)C]甲氧基苯基)哌嗪-1-基]丁基]苯并[b]噻吩-2-甲酰胺），比活度为45 - 75 GBq/微摩尔，包括HPLC纯化和制剂制备。[(11)C]FAUC346在大鼠脑中的初步药理学评估清楚地证明了其在体内对D(3)受体的选择性以及脑中不存在放射性标记代谢物。然而，这些令人鼓舞的结果在非人类灵长类动物中无法得到证实；因此，这种放射性配体似乎不具备作为用于成像D(3)受体的正电子发射断层扫描探针所需的药理学特性。

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