Ethylenediamine- and propylenediaminediacetic acid derivatives as ligands for the “fac-[M(CO)3]+” core (M = Re, 99mTc)

The reaction of Re(CO)5Cl with o- or p-N-(nitrophenyl)ethylenediaminediacetic acid (H2L1, H2L2) and o- or p-N-(nitrophenyl)propylenediaminediacetic acid (H2L3, H2L4) in methanol leads to the formation of stable anionic [Et3NH][Re(CO)3(L)] · H2O complexes 1–4. These compounds have been characterized by means of IR, mass spectrometry, elemental analysis, NMR and conductimetry, as well as X-ray crystallography for 2 and 3. The [Re(CO)3]+ moiety is coordinated via the nitrogen of the iminodiacetic acid unit and two oxygens of monodentate carboxylate groups. In each case, the nitro group of the aromatic ring remains uncoordinated. The analogous technetium-99m complexes 1′ and 3′ were also prepared quantitatively by the reaction of H2L1 and H2L3, respectively, with the fac-[99mTc(CO)3(H2O)3]+ precursor in ethanol. The corresponding Re and 99mTc compounds were shown to possess the same structure by means of HPLC studies. The high affinity of these ligands for the Tc(I) or Re(I) core, coupled with the easiness of their derivatization (by reduction of the nitro group in amino group), implies that the utilization of this ligand system to develop target-specific radiopharmaceuticals for diagnosis and therapy is promising.

Graphical abstractFour novel tricarbonylrhenium(I) complexes of the general formula [Et3NH][Re(CO)3(L)] · H2O (L = (nitrophenyl)ethylenediamine- or (nitrophenyl)-propylenediaminediacetate derivatives) are reported with X-ray crystal structures of two representative complexes. The analogous 99mTc(CO)3 complexes have also been investigated. A comparative HPLC study shows that the corresponding Re and 99mTc compounds have the same structure.Figure optionsDownload full-size imageDownload as PowerPoint slide