Synthesis of [¹¹C]FEDAA1106 as a new PET imaging probe of peripheral benzodiazepine receptor expression

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• 作者：Min Wang ; Mingzhang Gao ; Gary D. Hutchins ; Qi-Huang Zheng
• 关键词：Positron emission tomography ; Peripheral benzodiazepine receptor ; [¹¹C]FEDAA1106 ; Brain and tumor imaging
• 刊名：European Journal of Medicinal Chemistry
• 出版年：2009
• 出版时间：June 2009
• 年：2009
• 卷：44
• 期：6
• 页码：2748-2753
• 全文大小：244 K

文摘

Peripheral benzodiazepine receptor (PBR) is associated with neuroinflammation and tumor progression. [¹¹C]DAA1106 and [¹⁸F]FEDAA1106 are two promising radioligands for positron emission tomography (PET) imaging of PBR. This study was designed to develop a new radiolabeled analog of [¹¹C]DAA1106 and [¹⁸F]FEDAA1106, [¹¹C]FEDAA1106, for PET imaging of PBR expression in brain and cancer. Precursor N-(5-fluoro-2-phenoxyphenyl)-N-(2-(2-fluoroethoxy)-5-hydroxybenzyl)acetamide (9) was synthesized in multiple steps with moderate to high chemical yields. Precursor 9 was labeled by [¹¹C]CH₃OTf and isolated by high pressure liquid chromatography (HPLC) purification to provide target radioligand N-(5-fluoro-2-phenoxyphenyl)-N-(2-(2-fluoroethoxy)-5-[¹¹C]methoxybenzyl)acetamide ([¹¹C]FEDAA1106, [¹¹C]10) in 60–70 % radiochemical yields, decay corrected to end of bombardment (EOB), based on [¹¹C]CO₂. The specific activity of the target radiotracer [¹¹C]10 was in a range of 111–185 GBq/μmol at the end of synthesis (EOS).