A gadolinium(III) complex of a carboxylic-phosphorus acid derivative of diethylenetriamine covalently bound to inulin, a potential macromolecular MRI contrast agent

A novel conjugate of a polysaccharide and a Gd(III) chelate with potential as contrast agent for magnetic resonance imaging (MRI) was synthesized. The structure of the chelate was derived from H5DTPA by replacing the central pendant arm by a phosphinic acid functional group, which was covalently bou...

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Veröffentlicht in:Bioconjugate chemistry Jg. 15; H. 4; S. 881
Hauptverfasser: Lebdusková, Petra, Kotek, Jan, Hermann, Petr, Vander Elst, Luce, Muller, Robert N, Lukes, Ivan, Peters, Joop A
Format: Journal Article
Sprache:Englisch
Veröffentlicht: United States 01.07.2004
Schlagworte:
Contrast Media - chemistry
Gadolinium - chemistry
Inulin - chemistry
Ligands
Magnetic Resonance Imaging - instrumentation
Molecular Structure
Organometallic Compounds - chemistry
Pentetic Acid - analogs & derivatives
Pentetic Acid - chemistry
Polyamines - chemistry
Protons
Spectrum Analysis
Water
ISSN:1043-1802
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Zusammenfassung:A novel conjugate of a polysaccharide and a Gd(III) chelate with potential as contrast agent for magnetic resonance imaging (MRI) was synthesized. The structure of the chelate was derived from H5DTPA by replacing the central pendant arm by a phosphinic acid functional group, which was covalently bound to the polysaccharide inulin. On the average, each monosaccharide unit of the inulin was attached to approximately one (0.9) chelate moiety. The average molecular weight is 23110 and the average number of Gd3+ ions per molecule is 24. The ligand binds the Gd3+ ion in an octadentate fashion via three nitrogen atoms, four carboxylate oxygen atoms, and one P-O oxygen atom, and its first coordination sphere is completed by a water molecule. This compound shows promising properties for application as a contrast agent for MRI thanks to a favorable residence lifetime of this water molecule (170 ns at 298 K), a relatively long rotational correlation time (866 ps at 298 K), and the presence of two water molecules in the second coordination sphere of the Gd3+ ion. Furthermore, its stability toward transmetalation with Zn(II) is as high as that of the clinically used [Gd(DTPA)(H2O)]2-.
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ISSN:1043-1802
DOI:10.1021/bc049966g