Efficient automated syntheses of high specific activity 6-[18F]fluorodopamine using a diaryliodonium salt precursor

Kiel D. Neumann, Linlin Qin, Amy L. Vavere, Bin Shen, Zheng Miao, Frederick T. Chin, Barry L. Shulkin, Scott E. Snyder, Stephen G. Dimagno

Research output: Contribution to journalArticle

12 Scopus citations

Abstract

6-[18F]Fluorodopamine (6-[18F]F-DA) is a positron emission tomography radiopharmaceutical used to image sympathetic cardiac innervation and neuroendocrine tumors. Imaging with 6-[18F]F-DA is constrained, in part, by the bioactivity and neurotoxicity of 6-[19F]fluorodopamine. Furthermore, routine access to this radiotracer is limited by the inherent difficulty of incorporation of [18F]fluoride into electron-rich aromatic substrates. We describe the simple and direct preparation of high specific activity (SA) 6-[18F]F-DA from no-carrier-added (n.c.a.) [18F]fluoride. Incorporation of n.c.a. [18F]fluoride into a diaryliodonium salt precursor was achieved in 50-75% radiochemical yields (decay corrected to end of bombardment). Synthesis of 6-[18F]F-DA on the IBA Synthera® and GE TRACERlab FX-FN automated platforms gave 6-[18F]F-DA in >99% chemical and radiochemical purities after HPLC purification. The final non-corrected yields of 6-[18F]F-DA were 25 ± 4% (n = 4, 65 min) and 31 ± 6% (n = 3, 75 min) using the Synthera and TRACERlab modules, respectively. Efficient access to high SA 6-[18F]F-DA from a diaryliodonium salt precursor and n.c.a. [18F]fluoride is provided by a relatively subtle change in reaction conditions - replacement of a polar aprotic solvent (acetonitrile) with a relatively nonpolar solvent (toluene) during the critical radiofluorination reaction. Implementation of this process on common radiochemistry platforms should make 6-[18F]F-DA readily available to the wider imaging community.

Original languageEnglish (US)
Pages (from-to)30-34
Number of pages5
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume59
Issue number1
DOIs
StatePublished - Jan 1 2016

Keywords

  • 6-[F]fluorodopamine
  • diaryliodonium salts
  • emission computed tomography
  • fluorine-18
  • positron emission tomography

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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    Neumann, K. D., Qin, L., Vavere, A. L., Shen, B., Miao, Z., Chin, F. T., Shulkin, B. L., Snyder, S. E., & Dimagno, S. G. (2016). Efficient automated syntheses of high specific activity 6-[18F]fluorodopamine using a diaryliodonium salt precursor. Journal of Labelled Compounds and Radiopharmaceuticals, 59(1), 30-34. https://doi.org/10.1002/jlcr.3367