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Additional info for Contrast Agents I: Magnetic Resonance Imaging (Topics in Current Chemistry, 221)

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The introduction of only one chiral center in DOTA by derivatizing one acetate a-carbon with a para-nitrophenyl group (DOTA-pNB) [80] also results in four possible diastereomers upon chelation. The Ho3+ and Yb3+ complexes of DOTA-pNB again give 1H NMR spectra showing the presence of only two isomers. In these cases, like for some of the [Eu(TCE-DOTA)]5– ligand isomers, 1H EXSY has shown that the two isomers exchange through inversion of the macrocyclic ring, whereas no rearrangement of the acetate groups is observed.

The smaller extent of encapsulation of the Ln3+ ions by the DO2A ligand leads to a less rigid macrocyclic [3333] structure than in the DOTA chelates, as indicated by the 1H NMR resonances of its CH2 protons [133]. Detailed crystal and solution structure and dynamics studies have been reported for the Ln3+ complexes of the achiral tetraamide ligands DOTAM, DTMA and DOTTA. Crystal structures have been reported for [Eu(DOTAM)(H2O)](CF3SO3)3 [117], [Gd(DTMA)(H2O)](ClO4)3 [129] and [Dy(DTMA)(H2O)](PF6)3 [131].

17O NMR [49, 50], luminescence [47, 51] and NMRD measurements [46] have shown that, for both 9- and 10-coordinate Ln(TTHA)3– complexes, the inner coordination sphere of the metal ion is fully occupied by donating groups of the ligand, leaving no space for the coordination of water. Consequently, the water proton relaxation enhancement has no inner sphere contribution and the [Gd(TTHA)]3– complex is not very suitable for application 36 L. Frullano et al. as CA. It has been considered for many years as a model for the outer sphere contribution to the total relaxivity of acyclic polyaminocarboxylates [52], but at present, the outer sphere contribution is usually evaluated with the use of the Freed equations [53].

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