Synthesis and characterization of new beta-diketo derivatives with iron chelating ability.
Here we report the synthesis, the characterization and a theoretical study on new glycosylated phenyl substituted beta-diketones; two classes of compounds are obtained according to the condensation reaction: central and side derivatives. Their iron(III) chelating ability is tested by means of UV-visible (UV-vis), potentiometric and NMR techniques. The conformation of central derivatives does not allow any metal chelation, while side derivatives bind iron(III) through the beta-dioxo moiety. The glycosyl moiety does not interact with metal ion but it helps to stabilize metal/ligand (1/3) complexes by means of hydrophylic interactions. The pK(a) of the ligands and the stability constants of their Fe(III) complexes are evaluated by means of UV-vis spectroscopy and potentiometry. A comparison with other iron-chelating agents, on the basis of lipophilicity and the pFe(III), is finally reported.
Benassi
Rois
R
Department of Chemistry, University of Modena and Reggio Emilia, Via Campi 183, 41100 Modena, Italy.
Ferrari
Erika
E
Grandi
Romano
R
Lazzari
Sandra
S
Saladini
Monica
M
D018360:Crystallography, X-Ray; D003474:Curcumin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004355:Drug Stability; D006031:Glycosylation; D006801:Humans; D006863:Hydrogen-Ion Concentration; D007502:Iron Chelating Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000493:pharmacokinetics / Q000494:pharmacology; D019190:Iron Overload / Q000188:drug therapy; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011199:Potentiometry; D013053:Spectrophotometry; D013056:Spectrophotometry, Ultraviolet
D007502:Iron Chelating Agents; D007659:Ketones; D008024:Ligands; D003474:Curcumin