Department of Pure and Applied Sciences, University of Urbino "Carlo Bo", via della Stazione 4, 61029 Urbino, Italy.
Department of Chemistry "Ugo Schiff", University of Florence, via della Lastruccia 3-13, 50019 Sesto Fiorentino, Italy.
Molecules. 2020 Feb 20;25(4):943. doi: 10.3390/molecules25040943.
Two maltol-based ligands, ,'-bis((3-hydroxy-4-pyron-2-yl)methyl)-1,4-piperazine () and ,','-tris((3-hydroxy-4-pyron-2-yl)methyl)--methylethylendiamine (), were synthesized and characterized. and , containing, respectively, two and three maltol units spaced by a diamine fragment, were designed to evaluate how biological and binding features are affected by structural modifications of the parent compound malten. The acid-base behavior and the binding properties towards transition, alkaline-earth (AE) and rare-earth (RE) cations in aqueous solution, studied by potentiometric, UV-Vis and NMR analysis, are reported along with biological studies on DNA and leukemia cells. Both ligands form stable complexes with Cu(II), Zn(II) and Co(II) that were studied as metallo-receptors for AE and RE at neutral pH. complexes are more affected than ones by hard cations, the -Cu(II) system being deeply affected by RE. The structural modifications altered the mechanism of action: partially maintains the ability to induce structural alterations of DNA, while provokes single strand (nicks) and to a lesser extent double strand breaks of DNA.
两种基于麦芽酚的配体，1,4-双（（3-羟基-4-吡喃-2-基）甲基）-1,4-哌嗪（）和1,4,7-三（（3-羟基-4-吡喃-2-基）甲基）-1,4,7-三甲基乙二胺（）被合成并进行了表征。配体和，分别含有两个和三个麦芽酚单元，由二胺片段隔开，旨在评估母体化合物麦芽酚的结构修饰如何影响生物和结合特性。在水溶液中通过电位法、UV-Vis 和 NMR 分析研究了酸-碱行为和对过渡、碱土 (AE) 和稀土 (RE) 阳离子的结合特性，并对 DNA 和白血病细胞进行了生物学研究。两种配体均与 Cu(II)、Zn(II) 和 Co(II) 形成稳定的配合物，这些配合物在中性 pH 下被研究为 AE 和 RE 的金属受体。与 1 相比，配体的配合物受硬阳离子的影响更大，-Cu(II) 体系受 RE 的影响更深。结构修饰改变了作用机制：配体保留了诱导 DNA 结构改变的能力，而配体引起单链（切口）和较小程度的 DNA 双链断裂。
