Structure, Stability, and Biodistribution of Cationic [M(CO)3]+ (M = Re, 99Tc, 99mTc) Complexes with Tridentate Amine Ligands
- 1 January 2005
- journal article
- Published by Taylor & Francis in Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry
- Vol. 35 (1) , 27-34
- https://doi.org/10.1081/sim-200047534
Abstract
Bifunctional chelating molecules linking the fac-Tc-99m(CO)(3)](+) core with targeting biomolecules are required for the development of specific diagnostic radiopharmaceuticals. Diethylenetriamine (1) and N-(pyridin-2-ylmethyl)ethane-1,2-diamine (2) both react readily with (99mT)c(H2O)(3)(CO)(3)](+) in 0.9% saline at micromolar concentrations to form the cationic complexes Tc-99m(1)(CO)(3)](+) (5) and Tc-99m(2)(CO)(3)](+) (6) in quantitative yields. The crystal structures of the corresponding Re or Tc-99 complexes were determined and exhibit in particular the small size of 5. Challenging both Tc-99m complexes 5 and 6 with a 10(4) excess of histidine or cysteine showed no decomposition or ligand exchange after 24 hours and both compounds were also stable against reoxidation to (TcO4)-Tc-99m](-). In normal mice, complex 5 revealed a good and fast clearance from the blood, and most organs. Only limited accumulation in the large intestine was visible after 4 hours. Complex 6 was also excreted relatively quickly from the blood but retention was observed in some tissues after 4 h. In order to illustrate the potential of both ligands to be further functionalized, two derivatives containing potentially DNA binding functionalities, N-(2-Amino-ethyl)-N'-pyren-1-ylmethyl-ethane-1,2-diamine (3) and N-(quinolin-2-ylmethyl)ethane-1,2-diamine (4) were synthesized. The respective Re or Tc-99 complexes were fully characterized. Based on these results, it appears that functionalization of biomolecules with acyclic triamine ligands is biologically relevant. Complex 5 in particular could be used to mimic a terminal amino group in, e. g., a peptide due to its small size and positive chargeKeywords
This publication has 10 references indexed in Scilit:
- Preparation of No-Carrier-Added Technetium-99m Complexes via Metal-Assisted Cleavage from a Solid PhaseBioconjugate Chemistry, 2003
- Rhenium(I) Carbonyl Complexes of 2,4,6-Tris(2-pyridyl)-1,3,5-triazine (TPT). Rhenium(I)-Promoted Methoxylation of the Triazine Ring Carbon Atom in Dinuclear Rhenium ComplexesInorganic Chemistry, 2001
- Synthesis and Properties of Boranocarbonate: A Convenient in Situ CO Source for the Aqueous Preparation of [99mTc(OH2)3(CO)3]+Journal of the American Chemical Society, 2001
- 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 BiomoleculesBioconjugate Chemistry, 2000
- TechnetiumPublished by Wiley ,2000
- SIR97: a new tool for crystal structure determination and refinementJournal of Applied Crystallography, 1999
- A Novel Organometallic Aqua Complex of Technetium for the Labeling of Biomolecules: Synthesis of [99mTc(OH2)3(CO)3]+ from [99mTcO4]- in Aqueous Solution and Its Reaction with a Bifunctional LigandJournal of the American Chemical Society, 1998
- Reactions with the technetium and rhenium carbonyl complexes (NEt4)2[MX3(CO)3]. Synthesis and structure of [Tc(CN-But)3(CO)3](NO3) and (NEt4)[Tc2(μ-SCH2CH2OH)3(CO)6]Polyhedron, 1996
- New 2-pyridyl polyamines. Synthesis, spectra, and proton dissociation constantsJournal of the Chemical Society C: Organic, 1968
- Über die Alkaloide aus Strychnos melinoniana BaillonHelvetica Chimica Acta, 1952