Benassi Rois, Ferrari Erika, Grandi Romano, Lazzari Sandra, Saladini Monica
Department of Chemistry, University of Modena and Reggio Emilia, Via Campi 183, 41100 Modena, Italy.
J Inorg Biochem. 2007 Feb;101(2):203-13. doi: 10.1016/j.jinorgbio.2006.09.020. Epub 2006 Sep 29.
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.
在此，我们报告了新型糖基化苯基取代β-二酮的合成、表征及理论研究；根据缩合反应得到了两类化合物：中心衍生物和侧链衍生物。通过紫外可见（UV-vis）、电位滴定和核磁共振（NMR）技术测试了它们与铁（III）的螯合能力。中心衍生物的构象不允许任何金属螯合，而侧链衍生物通过β-二氧代部分与铁（III）结合。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稳定金属/配体（1/3）配合物。通过紫外可见光谱和电位滴定法评估了配体的pK(a)及其铁（III）配合物的稳定常数。最后报告了基于亲脂性和pFe(III)与其他铁螯合剂的比较。
