Synthesis and characterization of glucosyl-curcuminoids as Fe3+ suppliers in the treatment of iron deficiency.
The Fe(3+) chelating ability of some curcumin glucosyl derivatives (Glc-H; Glc-OH; Glc-OCH(3)) is tested by means of UV and NMR study. The pK(a) values of the ligands and the overall stability constants of Fe(3+) and Ga(3+) complexes are evaluated from UV spectra. The only metal binding site of the ligand is the beta-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 Fe(3+) 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 Ca(2+). 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.
Ferrari
Erika
E
Department of Chemistry, University of Modena and Reggio Emilia, Modena, Italy.
Arezzini
Beatrice
B
Ferrali
Marco
M
Lazzari
Sandra
S
Pignedoli
Francesca
F
Spagnolo
Ferdinando
F
Saladini
Monica
M
D018798:Anemia, Iron-Deficiency / Q000188:drug therapy; D003474:Curcumin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry* / Q000627:therapeutic use; D005290:Ferric Compounds / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007502:Iron Chelating Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013056:Spectrophotometry, Ultraviolet; D013816:Thermodynamics
D005290:Ferric Compounds; D007502:Iron Chelating Agents; D003474:Curcumin