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[(18)F]Fluoropyruvate: radiosynthesis and initial biological evaluation.

Keith Graham1, Andre Müller, Lutz Lehmann

  • 1Bayer Healthcare, Global Drug Discovery, Müllerstrasse 178, 13353, Berlin, Germany.

Journal of Labelled Compounds & Radiopharmaceuticals
|January 24, 2014
PubMed
Summary
This summary is machine-generated.

Researchers optimized the radiosynthesis of [(18)F]fluoropyruvate, achieving a 50% yield. However, low tumor cell uptake and bone uptake due to defluorination limit its use as a metabolic imaging agent.

Keywords:
PET imagingfluorine-18 radiolabelingfluoropyruvatepyruvate dehydrogenasepyruvate kinase

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Area of Science:

  • Radiochemistry
  • Nuclear Medicine
  • Organic Synthesis

Background:

  • Positron emission tomography (PET) imaging requires novel radiotracers for metabolic processes.
  • Fluoropyruvate is a potential metabolic tracer, but its radiosynthesis and biological evaluation are underexplored.

Purpose of the Study:

  • To develop and optimize the radiosynthesis of [(18)F]fluoropyruvate.
  • To evaluate the in vitro and in vivo properties of [(18)F]fluoropyruvate as a potential PET imaging agent.

Main Methods:

  • Synthesis of various precursors with different leaving groups (mesylate, tosylate, triflate, nonaflate) from ethyl 2,2-diethoxy-3-hydroxypropanoate.
  • Radiolabeling with [(18)F]fluoride, optimization of the hydrolysis step, and purification/formulation.
  • In vitro evaluation of [(18)F]fluoropyruvate uptake in A549 tumor cells.
  • In vivo pharmacokinetic assessment in nude mice.

Main Results:

  • Triflate precursor demonstrated superior [(18)F]fluoride incorporation.
  • Optimized acidic hydrolysis and purification yielded [(18)F]fluoropyruvate in approximately 50% decay-corrected yield.
  • In vitro studies showed low uptake (0.1% of applied dose/100,000 cells after 30 min) in A549 cells.
  • In vivo studies revealed significant bone uptake attributed to defluorination.

Conclusions:

  • [(18)F]fluoropyruvate can be synthesized with good yield.
  • The low tumor cell uptake and in vivo defluorination limit its potential as a PET imaging agent for metabolic processes.