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fac-TcO(3)(tacn)](+): A versatile precursor for the labelling of pharmacophores, amino acids and carbohydrates through a new ligand-centred labelling strategy


Braband, H; Tooyama, Y; Fox, T; Simms, R; Forbes, J; Valliant, J F; Alberto, R (2011). fac-TcO(3)(tacn)](+): A versatile precursor for the labelling of pharmacophores, amino acids and carbohydrates through a new ligand-centred labelling strategy. Chemistry - A European Journal, 17(46):12967-12974.

Abstract

Herein, we report a protocol for the synthesis of (99m)TcO(3)(tacn)](+) (1](+)) (tacn=1,4,7-triazacyclononane) that is suitable for clinical translation. Bioconjugates containing pharmacophores (TcO(NO(2)-Imi)(tacn)](+); 3](+)), artificial amino acids (TcO(Fmocallyl-His)(tacn)](+); 5](+)), and glucose derivatives (TcO(allyl-tetraacetyl-glucose) (tacn)](+); 7](+)) were synthesized by cycloaddition strategies and fully characterized ((99)Tc and (99m)Tc). These new technetium complexes are stable at neutral pH and demonstrate the potential and flexibility of the 3+2] cycloaddition labelling concept. In addition to the synthetic work, the first biodistribution studies of 1]+ and the small 3+2] cycloadduct (99m)TcO(NO(2)-Imi)(tacn)](+) (3](+)) were completed. The biodistribution studies suggest the stability of these complexes in vivo. Furthermore, it was demonstrated that the high hydrophilicity of the (99m)TcO(3)(tacn)](+) building block is a complement to the complexes of the fac-{Tc(CO)(3)}(+) core.

Abstract

Herein, we report a protocol for the synthesis of (99m)TcO(3)(tacn)](+) (1](+)) (tacn=1,4,7-triazacyclononane) that is suitable for clinical translation. Bioconjugates containing pharmacophores (TcO(NO(2)-Imi)(tacn)](+); 3](+)), artificial amino acids (TcO(Fmocallyl-His)(tacn)](+); 5](+)), and glucose derivatives (TcO(allyl-tetraacetyl-glucose) (tacn)](+); 7](+)) were synthesized by cycloaddition strategies and fully characterized ((99)Tc and (99m)Tc). These new technetium complexes are stable at neutral pH and demonstrate the potential and flexibility of the 3+2] cycloaddition labelling concept. In addition to the synthetic work, the first biodistribution studies of 1]+ and the small 3+2] cycloadduct (99m)TcO(NO(2)-Imi)(tacn)](+) (3](+)) were completed. The biodistribution studies suggest the stability of these complexes in vivo. Furthermore, it was demonstrated that the high hydrophilicity of the (99m)TcO(3)(tacn)](+) building block is a complement to the complexes of the fac-{Tc(CO)(3)}(+) core.

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11 citations in Web of Science®
11 citations in Scopus®
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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:November 2011
Deposited On:05 Mar 2012 12:16
Last Modified:07 Dec 2017 13:16
Publisher:Wiley-Blackwell
ISSN:0947-6539
Publisher DOI:https://doi.org/10.1002/chem.201101275
Other Identification Number:ISI:000297737900022

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