Design, synthesis and 64Cu labeling of fatty acid analogs containing dithiosemicarbazone chelate

Int J Rad Appl Instrum A. 1989;40(9):745-9. doi: 10.1016/0883-2889(89)90091-9.

Abstract

For the development of 62Cu labeled fatty acid analogs, two fatty acid analogs, containing dithiosemicarbazone (DTS) molecule as the 62Cu coordinating site, were designed and synthesized: a fatty acid analog containing DTS molecule at the omega-position, (a) the 12,13-dioxotetradecanoic acid di(N-methyl-thiosemicarbazone) (FA-DTS), and an omega-phenyl fatty acid analog containing DTS molecule at the para-position, (b) the p-carboxyundecylphenylglyoxal-di (N-methylthiosemicarbazone] (PFA-DTS). FA-DTS was synthesized by the reaction of ethyl diethoxyacetate with ethyl 11-bromonundecanate by successive decarboxylation and hydrolysis and final condensation with N-methylthiosemicarbazide. PFA-DTS was synthesized by the Friedel-Craft acylation of ethyl 11-phenylundecanate, selenium oxidation of the acetophenone derivative, followed by the condensation with N-methylthiosemicarbazide. Radiolabeling of FA-DTS and PFA-DTS with [64Cu]copper acetate was simple, rapid and quantitative. When injected into mice, both compounds were distributed and retained in the myocardium. These results offer a good basis for further development of 62Cu labeled fatty acid analogs.

MeSH terms

  • Animals
  • Chelating Agents
  • Copper Radioisotopes
  • Drug Design
  • Fatty Acids / chemical synthesis*
  • Fatty Acids / pharmacokinetics
  • Male
  • Mice
  • Radiochemistry
  • Thiosemicarbazones
  • Tissue Distribution

Substances

  • Chelating Agents
  • Copper Radioisotopes
  • Fatty Acids
  • Thiosemicarbazones
  • dithiosemicarbazone