Ferrari Erika, Arezzini Beatrice, Ferrali Marco, Lazzari Sandra, Pignedoli Francesca, Spagnolo Ferdinando, Saladini Monica
Department of Chemistry, University of Modena and Reggio Emilia, Modena, Italy.
Biometals. 2009 Oct;22(5):701-10. doi: 10.1007/s10534-009-9213-8. Epub 2009 Feb 11.
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.
通过紫外光谱和核磁共振研究测试了一些姜黄素葡萄糖基衍生物（Glc-H；Glc-OH；Glc-OCH(3)）的Fe(3+)螯合能力。从紫外光谱评估配体的pK(a)值以及Fe(3+)和Ga(3+)配合物的总稳定性常数。配体唯一的金属结合位点是酮-烯醇形式的β-二酮部分；葡萄糖基部分不与金属离子相互作用，但通过亲水相互作用有助于金属/配体1:2配合物的稳定性。这些葡萄糖基衍生物能够在很宽的pH范围内结合Fe(3+)，形成热力学上比治疗缺铁常用的其他配体更稳定的络合物物种。此外，它们对竞争性生物金属离子如Ca(2+)的亲和力较低。所有配体及其铁配合物都具有良好的亲脂性（log P > -0.7），鉴于它们可能用作口服治疗中的铁补充剂，表明其具有有效的胃肠道吸收。还在“离体”生物系统中测试了配体分子的抗氧化性能。
