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Please use this identifier to cite or link to this item: http://apo.ansto.gov.au/dspace/handle/10238/9025

Title: Triamidetriamine bearing macrobicyclic and macrotricyclic ligands: potential applications in the development of copper-64 radiopharmaceuticals
Authors: Tan, KV
Pellegrini, PA
Skelton, BW
Hogan, CF
Greguric, I
Barnard, PJ
Keywords: Ligands
Copper 64
Radiopharmaceuticals
Synthesis
Amino acids
Cysteine
Histidine
Crystallography
Issue Date: 16-Dec-2013
Publisher: American Chemical Society
Citation: Tan, K. V., Pellegrini, P. A., Skelton, B. W., Hogan, C. F., Greguric, I., & Barnard, P. J. (2014). Triamidetriamine Bearing Macrobicyclic and Macrotricyclic Ligands: Potential Applications in the Development of Copper-64 Radiopharmaceuticals. Inorganic Chemistry, 53(1), 468-477. doi:10.1021/ic4024508
Abstract: A versatile and straightforward synthetic approach is described for the preparation of triamide bearing analogues of sarcophagine hexaazamacrobicyclic cage ligands without the need for a templating metal ion. Reaction of 1,1,1-tris(aminoethyl)ethane (tame) with 3 equiv of 2-chloroacetyl chloride, yields the tris(α-chloroamide) synthetic intermediate 6, which when treated with either 1,1,1-tris(aminoethyl)ethane or 1,4,7-triazacyclononane furnished two novel triamidetriamine cryptand ligands (7 and 8 respectively). The Co(III) and Cu(II) complexes of cryptand 7 were prepared; however, cryptand 8 could not be metalated. The cryptands and the Co(III) complex 9 have been characterized by elemental analysis, 1H and 13C NMR spectroscopy, and X-ray crystallography. These studies confirm that the Co(III) complex 9 adopts an octahedral geometry with three facial deprotonated amido-donors and three facial amine donor groups. The Cu(II) complex 10 was characterized by elemental analysis, single crystal X-ray crystallography, cyclic voltammetry, and UV–visible absorption spectroscopy. In contrast to the Co(III) complex (9), the Cu(II) center adopts a square planar coordination geometry, with two amine and two deprotonated amido donor groups. Compound 10 exhibited a quasi-reversible, one-electron oxidation, which is assigned to the Cu2+/3+ redox couple. These cryptands represent interesting ligands for radiopharmaceutical applications, and 7 has been labeled with 64Cu to give 64Cu-10. This complex showed good stability when subjected to l-cysteine challenge whereas low levels of decomplexation were evident in the presence of l-histidine. © 2013 American Chemical Society
URI: https://doi.org/10.1021/ic4024508
http://apo.ansto.gov.au/dspace/handle/10238/9025
ISSN: 1520-510X
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