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Abstract
There is a growing interest in the development of new iron chelators as novel promising therapeutic strategies for neurodegenerative disorders. In this article, a series of mono(catecholamine) derivatives, 2,3-bis(hydroxy)-N-(hydroxyacyl)benzamide, containing a pendant hydroxy, have been synthesized and fully characterized by nuclear magnetic resonance, Fourier transform infrared spectroscopy and mass spectrum. The thermodynamic stability of the chelators with FeIII, MgII and ZnII ions was then investigated. The chelators enable formation of (3 : 1) FeIII complexes with high thermodynamic stability and exhibited improved selectivity to FeIII ion. Meanwhile, the results of 1,1-diphenyl-2-picryl-hydrazyl assays of mono(catecholamine) derivatives indicated that they all possess excellent antioxidant properties. These results support the hypothesis that the mono(catecholamine) derivatives be used as high-affinity chelator for iron overload situations without depleting essential metal ions, such as MgII and ZnII ions.
Highlights
Iron is essential to the proper functioning of most organisms, but it is toxic when present in excess
The results of 1,1-diphenyl-2-picrylhydrazyl assays of mono(catecholamine) derivatives indicated that they all possess excellent antioxidant properties. These results support the hypothesis that the mono(catecholamine) derivatives be used as high-affinity chelator for iron overload situations without depleting essential metal ions, such as MgII and ZnII ions
The synthesis of the bidentate chelator mono(catecholamine) derivatives 4a–c are shown in figure 2
Summary
Iron is essential to the proper functioning of most organisms, but it is toxic when present in excess. Lots of hexadentate chelators were synthesized based on chelate moieties of siderophores, such as catecholamine [7,8,9,10], hydroxypyridinone [11,12,13,14,15], and hydroxamate [16] Most of these hexadentate chelators have a high FeIII binding ability, but almost all chelating agents with high molecular weight (greater than 500), high hydrogen bond donors (greater than 5) and high hydrogen bond acceptors (greater than 10), which lead to a poor absorption, have not attracted more attention as potential therapeutic chelators. While deferiprone is a very simple bidentate structure chelator which possesses low molecular weight (139), low hydrogen bond donors (1) and low hydrogen bond acceptors (3) it satisfies design guidelines [17] for good absorption. We reported the synthesis of mono(catecholamine) derivatives, the solution thermodynamic stability of these chelators with FeIII, MgII and ZnII ions in aqueous solution and antioxidant activity
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