title: DOTAGA-anhydride: a valuable building block for the preparation of DOTA-like chelating agents.
abstract: 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.
authors.affiliation: Institut de Chimie Moléculaire de l'Université de Bourgogne, UMR CNRS 6302, 9 avenue Alain Savary, 21000 Dijon, France.
authors.forename: Claire
authors.initials: C
authors.lastname: Bernhard
authors.forename: Mathieu
authors.initials: M
authors.lastname: Moreau
authors.forename: Damien
authors.initials: D
authors.lastname: Lhenry
authors.forename: Christine
authors.initials: C
authors.lastname: Goze
authors.forename: Frédéric
authors.initials: F
authors.lastname: Boschetti
authors.forename: Yoann
authors.initials: Y
authors.lastname: Rousselin
authors.forename: François
authors.initials: F
authors.lastname: Brunotte
authors.forename: Franck
authors.initials: F
authors.lastname: Denat
mesh_terms: D000812:Anhydrides / Q000138:chemical synthesis* / Q000737:chemistry; D002614:Chelating Agents / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: D000812:Anhydrides; D002614:Chelating Agents; C574967:DOTAGA-anhydride; D006571:Heterocyclic Compounds; D006573:Heterocyclic Compounds, 1-Ring; C071349:1,4,7,10-tetraazacyclododecane- 1,4,7,10-tetraacetic acid