Macrocyclic complexes of yttrium, the lanthanides and the actini

Organic compounds -- part of the class 532-570 series – Organic compounds – Rare earth containing

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534 10, 5303915, 530402, 530409, 540465, 540475, 424 9361, 424 165, A61K 4900, A61K 39395, A61B 5055, C07F 500

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active

056962401

ABSTRACT:
Symmetrically di-functionalized water soluble macrocyclic complexes of lanthanide, actinide and yttrium ions were obtained by metal templated, Schiff-base, cyclic condensation of: (1) a functionalized 1,2-diaminoethane and a dicarbonyl compound selected from the group consisting of 2,6-dicarbonylpyridine, 2,6-diformylpyridine, 2,5-dicarbonylfuran, 2,5-diformylfuran, 2,5-dicarbonyl-thiophene and 2,5-diformylthiophene; or (2) 1,2-diaminoethane and a ring-substituted heterocyclic dicarbonyl compound selected from a group consisting of substituted 2,6-dicarbonylpyridine, substituted 2,6-diformylpyridine, substituted 2,5-dicarbonylfuran, substituted 2,5-diformylfuran; substituted 2,5-dicarbonyl thiophene, and substituted 2,5-diformylthiophene. Asymmetrically functionalized water soluble macrocyclic complexes of the lanthanide, actinide and yttrium ions were obtained by metal templated, Schiff-base, cyclic condensation of appropriately substituted diamine and dicarbonyl precursors, with such precursors contributing two heteroaromatic moieties (pyridine, furan, thiophene, or a combination thereof) to the resulting macrocyclic structure. The coordination complexes thus formed are kinetically stable in dilute aqueous solution. They are further reacted, or coupled, through a substituent on the 1,2-diaminoethane or on the pyridine, furan, or thiophene moieties, to one of the following: proteinaceous materials, polysaccharides, polynucleotides, other biologically compatible macromolecules or bridging molecules which, can be further reacted or coupled to the above mentioned substrates. These macrocyclic complexes are suitable in the preparation of reporter molecules and for magnetic resonance, radiation imaging and radiation therapy.

REFERENCES:
patent: 4678667 (1987-07-01), Meares et al.
Desreux et al. "Highly Stable Lanthanide Macrocyclic in Search of New Constrast Agents for NMR Imaging", Nucl. Med. Biol. vol. 15, No. 1, pp. 9-15 (1988).
DeCola et al., "Metal-templated Synthesis of Novel Macrocyclic Complexes of the Uranyl Ion", Inorganics Chimica Acta, 110, L1-L2, (1985).

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