1. Synthesis and characterization of glucosyl-curcuminoids as Fe3+ suppliers in the treatment of iron deficiency
- Author
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Marco Ferrali, Sandra Lazzari, Beatrice Arezzini, Francesca Pignedoli, Ferdinando Spagnolo, Monica Saladini, and Erika Ferrari
- Subjects
Curcumin ,Magnetic Resonance Spectroscopy ,Stereochemistry ,Metal ions in aqueous solution ,Metal Binding Site ,Iron Chelating Agents ,Ferric Compounds ,General Biochemistry, Genetics and Molecular Biology ,Biomaterials ,Metal ,Moiety ,Molecule ,Chelation ,Binding site ,Anemia, Iron-Deficiency ,Molecular Structure ,Ligand ,Chemistry ,Metals and Alloys ,Hydrogen-Ion Concentration ,Curcuminoidic compounds - Metal complexes - β-Diketo ligands ,carbohydrates (lipids) ,visual_art ,visual_art.visual_art_medium ,Thermodynamics ,Spectrophotometry, Ultraviolet ,General Agricultural and Biological Sciences - Abstract
The Fe3+ chelating ability of some curcumin glucosyl derivatives (Glc-H; Glc-OH; Glc-OCH3) is tested by means of UV and NMR study. The pK a values of the ligands and the overall stability constants of Fe3+ and Ga3+ complexes are evaluated from UV spectra. The only metal binding site of the ligand is the β-diketo moiety in the keto-enolic form; the glucosyl moiety does not interact with metal ion but it contributes to the stability of metal/ligand 1:2 complexes by means of hydrophilic interactions. These glucosyl derivatives are able to bind Fe3+ in a wide pH rage, forming complex species thermodynamically more stable than those of other ligands commonly used in the treatment of iron deficiency. In addition they demonstrate to have a poor affinity for competitive biological metal ions such as Ca2+. All ligands and their iron complexes have a good lypophilicity (log P > −0.7) suggesting an efficient gastrointestinal absorption in view of their possible use as iron supplements in oral therapy. The ligand molecules are also tested for their antioxidant properties in “ex vivo” biological system.
- Published
- 2009
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