fac-[TcO3(tacn)]+: A Versatile Precursor for the Labelling of Pharmacophores, Amino Acids and Carbohydrates through a New Ligand-Centred Labelling Strategy Academic Article uri icon

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abstract

  • Herein, we report a protocol for the synthesis of [(99m)TcO(3)(tacn)](+) ([1](+)) (tacn = 1,4,7-triazacyclononane) that is suitable for clinical translation. Bioconjugates containing pharmacophores ([TcO(NO(2)-Imi)(tacn)](+); [3](+)), artificial amino acids ([TcO(Fmoc-allyl-His)(tacn)](+); [5](+)), and glucose derivatives ([TcO(allyl-tetraacetylglucose)(tacn)](+); [7](+)) were synthesized by cycloaddition strategies and fully characterized ((99)Tc and (99m)Tc). These new technetium complexes are stable at neutral pH and demonstrate the potential and flexibility of the [3+2] cycloaddition labelling concept. In addition to the synthetic work, the first biodistribution studies of [1](+) and the small [3+2] cycloadduct [(99m)TcO(NO(2)-Imi)(tacn)](+) ([3](+)) were completed. The biodistribution studies suggest the stability of these complexes in vivo. Furthermore, it was demonstrated that the high hydrophilicity of the [(99m)TcO(3)(tacn)](+) building block is a complement to the complexes of the fac-{Tc(CO)(3)}(+) core.

authors

  • Braband, Henrik
  • Tooyama, Yuji
  • Fox, Thomas
  • Simms, Ryan
  • Forbes, John
  • Valliant, John F
  • Alberto, Roger

publication date

  • November 11, 2011