Synthesis and Structural Analysis of 1, 4, 7, 10‐Tetraazacyclododecane‐1, 4, 7, 10‐­tetraazidoethylacetic Acid (DOTAZA) Complexes. Issue 32 (26th October 2015)

• Record Type: Journal Article
• Authors: Kriemen, Ella; Holzapfel, Malte; Ruf, Erik; Rehbein, Julia; Maison, Wolfgang
• Is Part Of: European journal of inorganic chemistry. Issue 32(2015)
• Page Start: 5368
• Page End: 5378
• Publication Date: 2015-10-26
• Subjects: Macrocyclic ligands -- Imaging agents -- Structure elucidation -- Bifunctional chelators -- Density functional calculations; Chemistry, Inorganic -- Periodicals; Organometallic chemistry -- Periodicals; Bioinorganic chemistry -- Periodicals; Solid state chemistry -- Periodicals; 546
• DOI: 10.1002/ejic.201500789
• Languages: English
• ISSNs: 1434-1948

Abstract

Abstract: Herein, we present the synthesis and structural analysis of metal complexes of enantiomerically pure 1, 4, 7, 10‐tetraazacyclododecane‐1, 4, 7, 10‐tetraazidoethylacetic acid (DOTAZA). DOTAZA is a new tunable analog of DOTA, a clinically approved chelator for various pharmaceutically relevant metal ions. In this work, we investigate the complexation chemistry of DOTAZA and report the crystal structures of a number of complexes with pharmaceutically relevant metal ions such as Gd 3+ [magnetic resonance imaging (MRI)], Eu 3+ (luminescence spectroscopy), Y 3+ [positron emission tomography (PET)], In 3+ [single‐photon‐emission computed tomography (SPECT)], and Na + . These structures provide useful information for imaging applications and demonstrate the potential of DOTAZA to form stable complexes. Owing to its clickable azide functionalities, it may be used for the development of tailored imaging reagents that retain the positive complexation chemistry of the parent compound DOTA. Abstract : We report the synthesis of two enantiomers of 1, 4, 7, 10‐tetraazacyclododecane‐1, 4, 7, 10‐tetraazidoethylacetic acid (DOTAZA), a modular DOTA derivative that allows for fine tuning of its pharmacokinetic properties for imaging applications by click chemistry. Metal complexes of DOTAZA are analyzed by NMR spectroscopy, X‐ray diffraction, and DFT calculations.