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

Min Wang, Mingzhang Gao, Gary D. Hutchins, Qi Huang Zheng

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

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).

Original languageEnglish (US)
Pages (from-to)2748-2753
Number of pages6
JournalEuropean Journal of Medicinal Chemistry
Volume44
Issue number6
DOIs
StatePublished - Jun 2009

Keywords

  • [C]FEDAA1106
  • Brain and tumor imaging
  • Peripheral benzodiazepine receptor
  • Positron emission tomography

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

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