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

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 cont...

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Bibliographic Details
Published in:Inorganics 2024-09, Vol.12 (9), p.235
Main Authors: Forgione, Federico, Ranga, Madalina, Travagin, Fabio, Boccalon, Mariangela, Baranyai, Zsolt, Giovenzana, Giovanni B, Lattuada, Luciano
Format: Article
Language:English
Subjects:
AAZTA
Acetic acid
Acids
Analogs
chelating agent
Chelating agents
Chelation
Chemical reaction, Rate of
Chemical synthesis
Contrast agents
Contrast media
coordination
Coordination compounds
Ethanol
Health aspects
Hydrogenation
Ligands
Magnetic resonance imaging
mesocyclic
metal complexes
Metal ions
Methods
Nuclear medicine
Observations
Potash
Potassium
stability
Testing
Thermal properties
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Summary: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.
ISSN:2304-6740
2304-6740
DOI:10.3390/inorganics12090235