[18F]fluoro-beta-fluoromethylene-m-tyrosine analogs, potential PET agents for presynaptic dopamine terminals: synthesis and spectroscopic characterization

Int J Rad Appl Instrum A. 1992 Aug;43(8):969-77. doi: 10.1016/0883-2889(92)90215-z.

Abstract

18F-labeled (E)-beta-fluoromethylene-DL-m-tyrosine (FMMT) was prepared by the direct reaction of FMMT with [18F]acetylhypofluorite (AcOF) resulting into three product isomers. Extensive 1H, 13C and 19F-NMR spectroscopic analysis identify these products to be 2-fluoro, 6-fluoro-FMMT and 2,6-difluoro-FMMT. The HPLC isolated radiochemical EOB yields of these products were 22, 25 and 14%, respectively, based on starting [18F]AcOF. The specific activity at the end of a synthesis time of an hour was ca 200 mCi/mmol. With the possible advantage of "metabolic trapping" in dopamine nerve terminals via covalent binding to MAO and reduced metabolite formation, [18F]F-FMMT may potentially be the optimal PET tracer for CNS dopamine nerve terminals.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Brain / diagnostic imaging
  • Brain / physiology*
  • Dopamine / physiology*
  • Nerve Endings / diagnostic imaging*
  • Tomography, Emission-Computed*
  • Tyrosine / analogs & derivatives*
  • Tyrosine / chemical synthesis

Substances

  • Tyrosine
  • beta-fluoromethylene-3-tyrosine
  • Dopamine