Synthesis and characterization of glucosyl-curcuminoids as Fe³⁺ suppliers in the treatment of iron deficiency

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...

Full description

Saved in:
Bibliographic Details
Published in:Biometals 2009-10, Vol.22 (5), p.701-710
Main Authors: Ferrari, Erika, Arezzini, Beatrice, Ferrali, Marco, Lazzari, Sandra, Pignedoli, Francesca, Spagnolo, Ferdinando, Saladini, Monica
Format: Article
Language:English
Subjects:
Anemia, Iron-Deficiency - drug therapy
Biochemistry
Biomedical and Life Sciences
Cell Biology
Chemical synthesis
Curcumin - analogs & derivatives
Curcumin - chemical synthesis
Curcumin - chemistry
Curcumin - therapeutic use
Ferric Compounds - chemistry
Hydrogen-Ion Concentration
Iron
Iron Chelating Agents - chemical synthesis
Iron Chelating Agents - chemistry
Life Sciences
Magnetic Resonance Spectroscopy
Medicine/Public Health
Metal ions
Metals
Microbiology
Molecular Structure
Nutrient deficiency
Pharmacology/Toxicology
Plant Physiology
Spectrophotometry, Ultraviolet
Thermodynamics
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0966-0844
1572-8773
DOI:10.1007/s10534-009-9213-8