Issue 10, 2019

Synthesis and iron chelating properties of hydroxypyridinone and hydroxypyranone hexadentate ligands

Abstract

Chelation therapy has become an important therapeutic approach for some diseases. In attempt to identify clinically useful chelators, four hexadentate ligands were synthesized by conjugating the corresponding bidentate ligands (3-hydroxypyridin-4-one (3,4-HOPO), 3-hydroxypyridin-2-one (3,2-HOPO), 1-hydroxypyridin-2-one (1,2-HOPO), and 3-hydroxypyran-4-one) each with a free amino group to a tripodal acid. Their pKa values and affinities for iron(III) were investigated. The pFe3+ values of the hexadentate pyridinones 1 (3,4-HOPO), 3 (3,2-HOPO) and 4 (1,2-HOPO), and the pyranone 2 was found to follow the sequence 1 > 43 > 2, which is different to the pFe3+ value sequence of the corresponding bidentate forms (3,4-HOPO ≫ 3,2-HOPO > 1,2-HOPO > 3-hydroxypyranone). Hexadentate 3,4-HOPOs and 1,2-HOPOs have the greatest potential as iron scavenging agents.

Graphical abstract: Synthesis and iron chelating properties of hydroxypyridinone and hydroxypyranone hexadentate ligands

Article information

Article type
Paper
Submitted
20 Dec 2018
Accepted
19 Feb 2019
First published
20 Feb 2019

Dalton Trans., 2019,48, 3459-3466

Synthesis and iron chelating properties of hydroxypyridinone and hydroxypyranone hexadentate ligands

T. Zhou, X. Kong and R. C. Hider, Dalton Trans., 2019, 48, 3459 DOI: 10.1039/C8DT05014G

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