Improved, one-pot synthesis of 6-[18 F]fluorodopamine and quality control testing for use in patients with neuroblastoma

J Labelled Comp Radiopharm. 2018 Dec;61(14):1069-1080. doi: 10.1002/jlcr.3685. Epub 2018 Oct 22.

Abstract

6-[18 F]Fluorodopamine ([18 F]F-DA) is taken into cells via the norepinephrine transporter (NET). Recent [18 F]F-DA positron emission tomography-computed tomography (PET-CT) imaging of adult neuroendocrine tumors shows a dramatic improvement in sensitivity over the standard-of-care, meta-iodobenzylguanidine (MIBG) single-photon emission computed tomography (SPECT)-CT. A new precursor (ALPdopamine™) allows no-carrier-added synthesis resulting in high-molar activity [18 F]F-DA. Automated synthesis of [18 F]F-DA was performed in a single reactor using a two-step procedure: 1) fluorination via thermolysis of a diaryliodonium salt precursor, followed by 2) acid hydrolysis. Phase transfer agents, Kryptofix 222 and two tetraalkylammonium salts, were investigated. Optimized synthesis of [18 F]F-DA was achieved in 56 to 60 minutes (26% end of synthesis [EOS], nondecay corrected). The product passed all Food and Drug Administration (FDA)-required quality control testing for human use. Accumulation of [18 F]F-DA in SK-N-BE(2)-C (high NET expression) cells was significantly higher than in SH-EP (minimal NET expression) cells (P < 0.0001). ALPdopamine provides an effective scaffold for the routine production of [18 F]F-DA for human use. Validation of uptake by neuroblastoma (NB) cell lines supports the use of [18 F]F-DA for imaging NB patients. A pediatric NB imaging trial using [18 F]F-DA PET has been approved (Investigational New Drug application (IND) no. 138638) based on the methods reported here. We expect [18 F]F-DA will be localized in NB tumors and that high-quality functional images will be obtained within minutes after injection.

Keywords: 6-[18F]fluorodopamine; F-DA; PET; fluorine-18; neuroblastoma.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Transport
  • Cell Line, Tumor
  • Chemistry Techniques, Synthetic
  • Dopamine / analogs & derivatives*
  • Dopamine / chemical synthesis
  • Dopamine / chemistry
  • Dopamine / metabolism
  • Humans
  • Neuroblastoma / diagnostic imaging*
  • Neuroblastoma / pathology
  • Positron Emission Tomography Computed Tomography
  • Quality Control
  • Radiochemistry

Substances

  • 6-fluorodopamine
  • Dopamine