The Legacy of AAZTA—Synthesis and Coordination Chemistry of Two AAZTA Structural Analogs

Abstract

AAZTA (6-amino-6-methylperhydro-1,4-diazepinetetraacetic acid) is a mesocyclic chelating agent forming stable complexes with several metal ions. Over the past 20 years since its inception, AAZTA and its bifunctional derivatives have gained a growing role in several applications ranging from MRI contrast agents to diagnostics and nuclear medicine. The recent market restrictions applied to nitroethane preclude the easy preparation of AAZTA, prompting the search for a suitable alternative. In this work, we report the synthesis of two structural analogs (AAZTA-Bn and AAZTA-Et) from commercially available chemicals and the thermodynamic and kinetic study of their complexing ability towards selected metal ions. A comparison of the complexing properties of AAZTA-Bn and AAZTA-Et with the former AAZTA allows us to identify the possible heir of this efficient chelating agent.