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Influence of the Denticity of Ligand Systems on the in Vitro and in Vivo Behavior of 99mTc(I)−Tricarbonyl Complexes:  A Hint for the Future Functionalization of Biomolecules

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Center for Radiopharmaceutical Science of the ETH Zürich, Paul Scherrer Institute, CH-5232 Villigen, Switzerland, Department of Inorganic Chemistry, University of Zürich, CH-8057 Zürich, Switzerland, Forschungszentrum Rossendorf, Institut für Radiochemie, D-01062 Dresden, Germany
Cite this: Bioconjugate Chem. 2000, 11, 3, 345–351
Publication Date (Web):April 7, 2000
https://doi.org/10.1021/bc990127h
Copyright © 2000 American Chemical Society

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    Abstract

    Functionalization of biologically relevant molecules for the labeling with the novel fac-[99mTc(OH2)3(CO)3]+ precursor has gained considerable attention recently. Therefore, we tested seven different tridentate (histidine L1, iminodiacetic acid L2, N-2-picolylamineacetic acid L3, N,N-2-picolylaminediacetic acid L4) and bidentate (histamine L5, 2-picolinic acid L6, 2,4-dipicolinic acid L7) ligand systems, with the potential to be bifunctionalized and attached to a biomolecule. The ligands allowed mild radiolabeling conditions with fac-[99mTc(OH2)3(CO)3]+ (30 min, 75 °C). The ligand concentrations necessary to obtain yields of >95% of the corresponding organometallic complexes 1-7 ranged from 10-6 to 10-4 M. Complexes of the general formula “fac-[99mTcL(CO)3]” (L = tridentate ligand) and “fac-[99mTc(OH2)L‘(CO)3]” (L‘ = bidentate ligand), respectively, were produced. Challenge studies with cysteine and histidine revealed significant displacement of the ligands in complexes 57 but only little exchange with complexes 14 after 24 h at 37 °C in PBS buffer. However, no decomposition to 99mTcO4- was observed under these conditions. All complexes showed a hydrophilic character (log Po/w values ranging from −2.12 to 0.32). Time-dependent FPLC analyses of compounds 17 incubated in human plasma at 37 °C showed again no decomposition to 99mTcO4- after 24 h at 37 °C. However, the complexes with bidentate ligands (57) became almost completely protein bound after 60 min, whereas the complexes with tridentate coordinated ligands (14) showed no reaction with serum proteins. The compounds were tested for their in vivo stability and the biodistribution characteristics in BALB/c mice. The complexes with tridentate coordinated ligand systems (14) revealed generally a good and fast clearance from all organs and tissues. On the other hand, the complexes with only bidentate coordinated ligands (57) showed a significantly higher retention of activity in the liver, the kidneys, and the blood pool. Detailed radiometric analyses of murine plasma samples, 30 min p.i. of complex fac-[99mTcL1(CO)3], 1, revealed almost no reaction of the radioactive complex with the plasma proteins. By contrast, in plasma samples of mice, which were injected with complex fac-[99mTc(OH2)L5(CO)3]+, 5, the entire radioactivity coeluded with the proteins. On the basis of these in vitro and in vivo experiments, it appears that functionalization of biomolecules with tridentate-chelating ligand systems is preferable for the labeling with fac-[99mTc(OH2)3(CO)3]+, since this will presumably result in radioactive bioconjugates with better pharmacokinetic profiles.

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     Center for Radiopharmaceutical Science.

     Department of Inorganic Chemistry.

    §

     Forschungszentrum Rossendorf.

    *

     To whom correspondence should be addressed. Telephone:  ++41-56-310-2813. Fax:  ++41-56-310-2849. E-mail:  [email protected].

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