Rapid, regiospecific syntheses of deuterium substituted 6-[18F]fluorodopamine (α,α-D2; β,β-D2 and α,α,β,β-D4) for mechanistic studies with positron emission tomography

✍ Scribed by Yu-Shin Ding; Joanna S. Fowler; Alfred P. Wolf

• Publisher: John Wiley and Sons
• Year: 1993
• Tongue: French
• Weight: 521 KB
• Volume: 33
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580330712

✦ Synopsis

Abstract

Doubly labeled (^18^F and deuterium) 6‐fluorodopamine (6‐FDA) isotopomers were prepared to probe the contribution of metabolism by monoamine oxidase (MAO) and dopamine β‐hydroxylase (DBH) on the kinetics of 6‐[^18^F]FDA in baboon heart. Specifically deuterated 6‐[^18^F]FDA‐α,α‐D~2~ and 6‐[^18^F]FDA‐β,β‐D~2~ were prepared by a six‐step synthesis starting from nucleophilic aromatic substitution with NCA [^18^F]fluoride on 6‐nitropiperonal or 6‐nitropiperonal‐D in a decay corrected radiochemical yield of 3‐10% (EOB). 6‐[^18^F]FDA‐α,α,β,β‐D~4~ was prepared in 4 steps in a radiochemical yield of 16‐20% (EOB) and specific activity 2‐5 Ci/μmol (EOB). The regiospecificity of deuterium substitution in the synthesis of 6‐[^18^F]FDA‐α,α,β,β‐D~4~ was verified using piperonal as a substrate.