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Eur J Med Chem. 2009 Jun;44(6):2748-53. doi: 10.1016/j.ejmech.2008.08.001. Epub 2008 Aug 13.

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

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Department of Radiology, Indiana University School of Medicine, 1345 West 16th Street, L3-208, Indianapolis, IN 46202-2111, USA.


Peripheral benzodiazepine receptor (PBR) is associated with neuroinflammation and tumor progression. [(11)C]DAA1106 and [(18)F]FEDAA1106 are two promising radioligands for positron emission tomography (PET) imaging of PBR. This study was designed to develop a new radiolabeled analog of [(11)C]DAA1106 and [(18)F]FEDAA1106, [(11)C]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 [(11)C]CH(3)OTf and isolated by high pressure liquid chromatography (HPLC) purification to provide target radioligand N-(5-fluoro-2-phenoxyphenyl)-N-(2-(2-fluoroethoxy)-5-[(11)C]methoxybenzyl)acetamide ([(11)C]FEDAA1106, [(11)C]10) in 60-70% radiochemical yields, decay corrected to end of bombardment (EOB), based on [(11)C]CO(2). The specific activity of the target radiotracer [(11)C]10 was in a range of 111-185GBq/micromol at the end of synthesis (EOS).

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