Dipartimento di Scienze Chimiche, Università di Cagliari, 09042 Monserrato, Cagliari, Italy.
J Inorg Biochem. 2010 May;104(5):560-9. doi: 10.1016/j.jinorgbio.2010.01.007. Epub 2010 Feb 6.
With the aim to design new chelators for the clinical treatment of different diseases involving the trivalent metal ions Fe(III) and Al(III), we present the equilibria of kojic acid and its derivative 6-[5-hydroxy-2-hydroxymethyl-pyran-4-one]-5-hydroxy-2-hydroxymethyl-pyran-4-one with these two metal ions. Potentiometric and spectrophotometric techniques for iron, and potentiometry and (1)H NMR for aluminum were used, supported by X-ray, electrospray ionization-mass spectrometry (ESI-MS), calorimetry and quantum chemical calculations. In this work, evidence is given on the formation of MeL, MeL(2), and MeL(3) complexes of both metal ions with kojic acid, confirmed by the X-ray structure of the FeL(3) complex, and of variously protonated Me(2)L(2) and MeL(2) complexes of 6-[5-hydroxy-2-hydroxymethyl-pyran-4-one]-5-hydroxy-2-hydroxymethyl-pyran-4-one. The extremely good pFe value for this second ligand gives confidence to, and opens perspectives for, the search of new kojic acid derivatives.
为了设计用于治疗涉及三价金属离子 Fe(III)和 Al(III)的不同疾病的新型螯合剂，我们研究了曲酸及其衍生物 6-[5-羟基-2-羟甲基-吡喃-4-酮]-5-羟基-2-羟甲基-吡喃-4-酮与这两种金属离子的平衡。使用了电位法和分光光度法（铁），电位法和（1）H NMR 法（铝），并结合 X 射线、电喷雾电离质谱（ESI-MS）、量热法和量子化学计算进行了研究。在这项工作中，通过 X 射线结构证实了金属离子与曲酸形成了 MeL、MeL(2)和 MeL(3)配合物，还证实了 6-[5-羟基-2-羟甲基-吡喃-4-酮]-5-羟基-2-羟甲基-吡喃-4-酮的各种质子化 Me(2)L(2)和 MeL(2)配合物的形成。第二个配体具有非常好的 pFe 值，这为寻找新的曲酸衍生物提供了信心和前景。
