Iron(III) and aluminum(III) complexes with hydroxypyrone ligands aimed to design kojic acid derivatives with new perspectives

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• 作者：Valeria Marina Nurchi ; Guido Crisponi ; Joanna Izabela Lachowicz ; Sergio Murgia ; Tiziana Pivetta ; Maurizio Remelli ; Antonio Rescigno ; Juan Nicló ; s-Gutí ; errez ; Josefa Marí ; a Gonzá ; lez-P&
• 关键词：Kojic acid ; Fe(III) ; Al(III) ; pFe ; Solution equilibria ; Thermodynamic measurements ; X-ray structure ; Molecular modeling ; Synthesis
• 刊名：Journal of Inorganic Biochemistry
• 出版年：2010
• 出版时间：May 2010
• 年：2010
• 卷：104
• 期：5
• 页码：560-569
• 全文大小：1177 K

文摘

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 ¹H 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, MeL₂, and MeL₃ complexes of both metal ions with kojic acid, confirmed by the X-ray structure of the FeL₃ complex, and of variously protonated Me₂L₂ and MeL₂ 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.