Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 25, Pages 7834-7841Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201200132
Keywords
anhydrides; chelates; DOTA; imaging agents; protecting groups
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Funding
- CNRS
- University of Burgundy
- Conseil Regional de Bourgogne
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A DOTA derivative that contains an anhydride group was readily synthesized by reacting DOTAGA with acetic anhydride and its reactivity was investigated. Opening the anhydride with propylamine led to the selective formation of one of two possible regioisomers. The structure of the obtained isomer was unambiguously determined by 1D and 2D NMR experiments, including COSY, HMBC, and NOESY techniques. This bifunctional chelating agent offers a convenient and attractive approach for labeling biomolecules and, more generally, for the synthesis of a large range of DOTA derivatives. The scope of the reaction was extended to prepare DOTA-like compounds that contained various functional groups, such as isothiocyanate, thiol, ester, and amino acid moieties. This versatile building block was also used for the synthesis of a bimodal tag for SPECT or PET/optical imaging.
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