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Extra resources for Contrast Agents I: Magnetic Resonance Imaging (Topics in Current Chemistry, 221)
Sample text
Frullano et al. The success of [Gd(DOTA)]– as a CA has initiated an intensive search for derivatives with improved properties, such as complexes of DO3A derivatives. The nonionic reagents Gd(HP-DO3A) and Gd(DO3A-butrol), in which one of the acetate groups of DOTA is replaced by a hydroxyalkyl group, have recently been introduced. The crystal structures of the parent Gd(DO3A) [67] and of the Gd(DO3MA) [83] derivatives show the 9-coordinate Gd3+ to be bound by the ligands in a heptadentate fashion.
The ligand tetracarboxyethyl DOTA derivative (TCE-DOTA) was synthesized as a mixture of the six stereoisomers defined by the absolute configuration of the four chiral carbons, RRRR/SSSS pair, RSSS/SRRR pair, RSRS and RRSS, which were separated, crystallized and their crystal structures determined [78, 79]. 5°) and opposite helicities [78, 79]. Thus, for an R configuration at carbon, the complex adopted a L (left-handed) arm helicity and a (dddd) chelate ring configuration. The (SSSS) enantiomer gave a D (right-handed) helicity and a (llll) chelate ring configuration.
This unusual behavior is ascribed to stacking properties of the carbostyril unit and to the presence of the a-oxygen atom in a position advantageous for coordination. The 13C NMR spectra of the La3+ and Lu3+ complexes of BOPTA display about 20 resonances in the aliphatic region at 60°C [28], which broaden upon lowering of the temperature. This suggests that a dynamic process is slowing down. It can be concluded that this compound occurs as at least two pairs of interconverting isomers [28]. In principle, the chirality in the benzyloxymethyl chain can give rise to doubling of the number of isomers, however, they are probably not observable in the NMR spectra of the diamagnetic La3+ and Lu3+ complexes due to small chemical shift differences between them.