Towards the synthesis of new sequestring hexadentate bisphosphonic ligands for iron ion chelation

Abstract

This work presents the design and the synthesis of precursors of hexadentate bisphosphonic ligands able to complex iron cation. This study describes coupling reaction between natural siderophore entity and bisphosphonic acids. These latter have properties of complexing heavy metals. These compounds were obtained from amidation reaction between a protected and activated bisphosphonic compound and serine trilactone. In the intermediate species, all the hydroxyl groups of phosphorus are esterified with ethyl group. The coupling method gave access to triserinelactone-bisphosphonate conjugates in good yields.

Graphical Abstract

Keywords:

• Triserine lactone
• hexadentate bisphosphonic ligands
• chelation of iron

Acknowledgments

We gratefully thank Université Sorbonne Paris Nord, Centre National de la Recherche Scientifique (CNRS), Ministère de l’Enseignement Supérieur et de la Recherche (MESR), Ministère de l’Enseignement Supérieur et de la Recherche Scientifique Tunisie and GDR Phosphore 2008 (CNRS) for financial support. We also acknowledge the NMR-PF facility (University Sorbonne Paris Nord, France).

Disclosure statement

No potential conflict of interest was reported by the authors.