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Mixed tridentate pi-donor and monodentate pi -acceptor ligands as chelating systems for rhenium-188 and technetium-99m nitrido radiopharmaceuticals
A new molecular metallic fragment for labeling biologically active molecules with99mTc and188Re is described. This system is composed of a combination of tridentate pi-donor and monodentate pi-acceptor ligands bound to a [M=N]2+ group (M =99m Tc,188Re) in a pseudo square-pyramidal geometry. A simple structural model of the new metallic fragment was obtained by reacting the ligand 2, 2?-iminodiethanethiol [H2NS2 = NH(CH2CH2SH)2] and monodentate tertiary phosphines with the [M=N]2+ group (M =99m Tc,188Re). In the resulting complexes (dubbed3+1complexes), the tridentate ligand binds the [M=N]2+ core through the two deprotonated, negatively charged, thiol sulfur atoms and the neutral, protonated, amine nitrogen atom. The residual fourth position of the five-coordinated arrangement is occupied by a phosphine ligand. The chemical identity of these model99m Tc and188Re compounds was established by comparison with the chromatographic properties of the corresponding complexes obtained at the macroscopic level with the long?lived 99gTc and natural Re isotopes. The investigation was further extended to comprise a series of ligands formed by simple combinations of two basic amino acids or pseudo-amino acids to yield potential tridentate chelating systems having [S, N, S] and [N, N, S] as sets of pi-donor atoms. Labeling yields and in vitro stability were investigated using different ancillary ligands. Results showed that SNS-type ligands afforded the highest labeling yields and the most robust 3+1 nitrido complexes with both99m Tc and188Re. Thus, the new chelating system can be conveniently employed for labeling peptides and other biomolecules with the [M=N]2+ group.
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Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate