DOI: 10.1186/s41181-017-0029-5Pages: 1-12

An efficient preparation of labelling precursor of [11C]L-deprenyl-D2 and automated radiosynthesis

1. Centro Uruguayo de Imagenología Molecular (CUDIM)

2. Universidad de la República, Departamento de Química Orgánica, Facultad de Química

3. Universidad de la República, Cátedra de Radioquímica, Facultad de Química

Correspondence to:
Eduardo Savio
Tel: +598 24803238
Email: eduardo.savio@cudim.org

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Abstract

Background

The synthesis of [11C]L-deprenyl-D2 for imaging of astrocytosis with positron emission tomography (PET) in neurodegenerative diseases has been previously reported. [11C]L-deprenyl-D2 radiosynthesis requires a precursor, L-nordeprenyl-D2, which has been previously synthesized from L-amphetamine as starting material with low overall yields. Here, we present an efficient synthesis of L-nordeprenyl-D2 organic precursor as free base and automated radiosynthesis of [11C]L-deprenyl-D2 for PET imaging of astrocytosis. The L-nordeprenyl-D2 precursor was synthesized from the easily commercial available and cheap reagent L-phenylalanine in five steps. Next, N-alkylation of L-nordeprenyl-D2 free base with [11C]MeOTf was optimized using the automated commercial platform GE TRACERlab® FX C Pro.

Results

A simple and efficient synthesis of L-nordeprenyl-D2 precursor of [11C]L-deprenyl-D2 as free base has been developed in five synthetic steps with an overall yield of 33%. The precursor as free base has been stable for 9 months stored at low temperature (−20 °C). The labelled product was obtained with 44 ± 13% (n = 12) (end of synthesis, decay corrected) radiochemical yield from [11C]MeI after 35 min synthesis time. The radiochemical purity was over 99% in all cases and specific activity was (170 ± 116) GBq/μmol.

Conclusions

A high-yield synthesis of [11C]L-deprenyl-D2 has been achieved with high purity and specific activity. L-nordeprenyl-D2 precursor as free amine was applicable for automated production in a commercial synthesis module for preclinical and clinical application.

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  • Accepted: Jul 14, 2017
  • Online: Jul 24, 2017

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