Synthesis, in vitro and in vivo characterization of (64)Cu(I) complexes derived from hydrophilic tris(hydroxymethyl)phosphane and 1,3,5-triaza-7-phosphaadamantane ligands

J Biol Inorg Chem. 2008 Feb;13(2):307-15. doi: 10.1007/s00775-007-0322-y. Epub 2007 Nov 27.

Abstract

Four novel (64)Cu complexes ([(64)Cu(thp)(4)](+) (1), [(64)Cu(TPA)(4)](+) (2), [HC(CO(2))(pz(Me2))(2) (64)Cu(thp)(2)] (3) and [HC(CO(2))(tz)(2) (64)Cu(thp)(2)] (4), [where thp is tris(hydroxymethyl)phosphine, TPA is 1,3,5-triaza-7-phosphaadamantane, pz(Me2) is 3,5-dimethylpyrazole and tz is 1,2,4-triazole] were successfully synthesized and characterized. The complexes were produced in high radiochemical purity and yield (more than 98%) without the need for further purification. Their logP values and serum stabilities were measured and in vitro behavior was observed in cultured EMT-6 cells. The logP values (+/- standard deviation) obtained were -2.26 +/- 0.04 (1), 0.01 +/- 0.01 (2), -1.24 +/- 0.03 (3) and -2.06 +/- 0.03 (4). Complex 3 demonstrated the highest serum stability, with approximately 33% of the complex still intact after 1-h incubation. Complex 2 showed a rapid cell-association with EMT-6 cells, with more than 8.5% association at 2 h. This association was significantly higher (P < 0.001) than for the other three compounds after a 2-h incubation (1, 1.21%; 3, 0.63%; 4, 2.75%). Biodistribution and small-animal positron emission tomography/computed tomography was undertaken with 1 in mice bearing EMT-6 tumors. EMT-6 tumor uptake was high at 1 h (7.71 +/- 2.17 %ID/g) and decreased slowly over 24 h (4 h, 4.90 +/- 0.78 %ID/g; 24 h, 3.74 +/- 0.73 %ID/g). The PET/CT images show that the EMT-6 tumors can be visualized at all time points. In this proof-of-concept study, we have successfully synthesized and characterized a novel series of versatile water-soluble Cu(I) complexes containing monophosphine ligands. We also report the use of 1 as a building block for new radiopharmaceuticals, perhaps the first time such a method has been used in the production of copper radiopharmaceuticals.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Adamantane / analogs & derivatives*
  • Adamantane / blood
  • Adamantane / chemical synthesis
  • Adamantane / pharmacokinetics
  • Animals
  • Cell Line, Tumor
  • Copper Radioisotopes / chemistry*
  • Copper Radioisotopes / pharmacokinetics
  • Copper Radioisotopes / therapeutic use
  • Female
  • Ligands
  • Mice
  • Mice, Inbred BALB C
  • Organophosphorus Compounds / blood
  • Organophosphorus Compounds / chemical synthesis
  • Organophosphorus Compounds / pharmacokinetics*
  • Phosphines / blood
  • Phosphines / chemical synthesis
  • Phosphines / pharmacokinetics*
  • Positron-Emission Tomography
  • Radiopharmaceuticals / blood
  • Radiopharmaceuticals / chemical synthesis
  • Radiopharmaceuticals / pharmacokinetics*
  • Rats

Substances

  • 1,3,5-triaza-7-phosphaadamantane
  • Copper Radioisotopes
  • Ligands
  • Organophosphorus Compounds
  • Phosphines
  • Radiopharmaceuticals
  • Adamantane
  • tris(hydroxymethyl)phosphine