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Salicylamide derivatives for iron and aluminium sequestration. From synthesis to complexation studies

Salicylamide derivatives for iron and aluminium sequestration. From synthesis to complexation studies
Salicylamide derivatives for iron and aluminium sequestration. From synthesis to complexation studies

This paper presents an easy, fast and economic synthesis of chelating agents for medical, environmental and analytical applications, and the evaluation of the stability of their complexes with Fe3+ and Al3+. Complex formation equilibria with Cu2+ and Zn2+ metal ions were also studied to evaluate if the chelating agents can perturb the homeostatic equilibria of these essential metal ions. Effective chelating agents for metal ions, in addition to their well-known medical uses, find an increasing number of applications in environmental remediation, agricultural applications (supplying essential elements in an easily available form), and in analytical chemistry as colorimetric reagents. Besides the stability of the complexes, the lack of toxicity and the low cost are the basic requisites of metal chelating agents. With these aims in mind, we utilized ethyl salicylate, a cheap molecule without toxic effects, and adopted a simple synthetic strategy to join two salicylate units through linear diamines of variable length. Actually, the mutual position of the metal binding oxygen groups, as well as the linker length, affected protonation and complex formation equilibria. A thorough study of the ligands is presented. In particular, the complex formation equilibria of the three ligands toward Fe3+, Al3+, Zn2+ and Cu2+ ions were investigated by combined potentiometric and spectrophotometric techniques. The results are encouraging: all the three ligands form stable complexes with all the investigated metal ions, involving the oxygen donor atoms from the 2-hydroxybenzamido unit, and nitrogen atoms in copper and zinc coordination.

Aluminium toxicity, Chelating agents, Iron toxicity, Metal complex stability, Potentiometry, UV-Vis spectrophotometry
0946-672X
Lachowicz, Joanna I.
0f100158-e84b-49ef-8724-6a8a69c953bc
Crespo-Alonso, Miriam
14268c27-dd92-499a-9573-e553b6b2aac3
Caltagirone, Claudia
9148afed-6af0-4fcd-b30e-daa3d7765dc0
Alberti, Giancarla
88305b16-43ca-46f9-9fea-a26b842c65fb
Biesuz, Raffaela
f1d55aac-f29a-4574-8031-b947d1bcc623
Orton, James O.
4e2a471f-9e11-4cb4-abb6-d0398047939f
Nurchi, Valeria M.
d87f1eb4-e3a0-4b61-b5e8-bbb5e7dbaf92
Lachowicz, Joanna I.
0f100158-e84b-49ef-8724-6a8a69c953bc
Crespo-Alonso, Miriam
14268c27-dd92-499a-9573-e553b6b2aac3
Caltagirone, Claudia
9148afed-6af0-4fcd-b30e-daa3d7765dc0
Alberti, Giancarla
88305b16-43ca-46f9-9fea-a26b842c65fb
Biesuz, Raffaela
f1d55aac-f29a-4574-8031-b947d1bcc623
Orton, James O.
4e2a471f-9e11-4cb4-abb6-d0398047939f
Nurchi, Valeria M.
d87f1eb4-e3a0-4b61-b5e8-bbb5e7dbaf92

Lachowicz, Joanna I., Crespo-Alonso, Miriam, Caltagirone, Claudia, Alberti, Giancarla, Biesuz, Raffaela, Orton, James O. and Nurchi, Valeria M. (2018) Salicylamide derivatives for iron and aluminium sequestration. From synthesis to complexation studies. Journal of Trace Elements in Medicine and Biology. (doi:10.1016/j.jtemb.2018.04.010).

Record type: Article

Abstract

This paper presents an easy, fast and economic synthesis of chelating agents for medical, environmental and analytical applications, and the evaluation of the stability of their complexes with Fe3+ and Al3+. Complex formation equilibria with Cu2+ and Zn2+ metal ions were also studied to evaluate if the chelating agents can perturb the homeostatic equilibria of these essential metal ions. Effective chelating agents for metal ions, in addition to their well-known medical uses, find an increasing number of applications in environmental remediation, agricultural applications (supplying essential elements in an easily available form), and in analytical chemistry as colorimetric reagents. Besides the stability of the complexes, the lack of toxicity and the low cost are the basic requisites of metal chelating agents. With these aims in mind, we utilized ethyl salicylate, a cheap molecule without toxic effects, and adopted a simple synthetic strategy to join two salicylate units through linear diamines of variable length. Actually, the mutual position of the metal binding oxygen groups, as well as the linker length, affected protonation and complex formation equilibria. A thorough study of the ligands is presented. In particular, the complex formation equilibria of the three ligands toward Fe3+, Al3+, Zn2+ and Cu2+ ions were investigated by combined potentiometric and spectrophotometric techniques. The results are encouraging: all the three ligands form stable complexes with all the investigated metal ions, involving the oxygen donor atoms from the 2-hydroxybenzamido unit, and nitrogen atoms in copper and zinc coordination.

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More information

Accepted/In Press date: 10 April 2018
e-pub ahead of print date: 16 April 2018
Keywords: Aluminium toxicity, Chelating agents, Iron toxicity, Metal complex stability, Potentiometry, UV-Vis spectrophotometry

Identifiers

Local EPrints ID: 424887
URI: http://eprints.soton.ac.uk/id/eprint/424887
ISSN: 0946-672X
PURE UUID: f162ee00-e44a-449a-b483-9a06dfd6e11b

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Date deposited: 05 Oct 2018 11:52
Last modified: 14 Sep 2021 19:52

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Contributors

Author: Joanna I. Lachowicz
Author: Miriam Crespo-Alonso
Author: Claudia Caltagirone
Author: Giancarla Alberti
Author: Raffaela Biesuz
Author: James O. Orton
Author: Valeria M. Nurchi

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