Department of Chemistry, Faculty of Sciences, Shiraz University, Shiraz 71454, Iran.
Department of Chemistry, Faculty of Sciences, Shiraz University, Shiraz 71454, Iran.
Spectrochim Acta A Mol Biomol Spectrosc. 2017 May 5;178:125-135. doi: 10.1016/j.saa.2017.01.037. Epub 2017 Jan 21.
Two water-soluble mono-nuclear macrocyclic lanthanum(III) complexes of 2,6-diformyl-4-methylphenol with 1,3-diamino-2-propanol (C) or 1,3-propylenediamine (C) were synthesized and characterized by UV-Vis, FT-IR, C and H NMR spectroscopy and elemental analysis. C complex was structurally characterized by single-crystal X-ray diffraction, which revealed that the complex was mononuclear and ten-coordinated. The coordination sites around lanthanum(III) were occupied with a five-dentate ligand, two bidentate nitrates, and one water molecule. The interaction of complexes with DNA was studied in buffered aqueous solution at pH7.4. UV-Vis absorption spectroscopy, emission spectroscopy, circular dichroism (CD) and viscometric measurements provided clear evidence of the intercalation mechanism of binding. The obtained intrinsic binding constants (K) 9.3×10 and 1.2×10M for C and C, respectively confirmed that C is better intercalator than C. The DNA docking studies suggested that the complexes bind with DNA in a groove binding mode with the binding affinity of C>C. Moreover, agarose gel electrophoresis study of the DNA-complex for both compounds revealed that the C intercalation cause ethidium bromide replacement in a competitive manner which confirms the suggested mechanism of binding. Finally, the anticancer experiments for the treated cancerous cell lines with both synthesized compounds show that these hydrophilic molecules need a suitable carrier to pass through the hydrophobic nature of cell membrane efficiently.
两种水溶性单核大环镧(III)配合物,由 2,6-二醛基-4-甲基苯酚与 1,3-二氨基-2-丙醇(C)或 1,3-丙二胺(C)合成,并通过紫外可见光谱、傅里叶变换红外光谱、C 和 H 核磁共振光谱和元素分析进行了表征。C 配合物的结构通过单晶 X 射线衍射进行了表征,结果表明该配合物为单核和十配位。镧(III)周围的配位位被一个五齿配体、两个双齿硝酸盐和一个水分子占据。在 pH7.4 的缓冲水溶液中研究了配合物与 DNA 的相互作用。紫外可见吸收光谱、荧光光谱、圆二色性(CD)和粘度测量提供了结合的嵌入机制的明确证据。分别获得的固有结合常数(K)9.3×10 和 1.2×10M 对于 C 和 C,证实 C 是比 C 更好的嵌入剂。DNA 对接研究表明,配合物以沟结合模式与 DNA 结合,结合亲和力为 C>C。此外,两种化合物的 DNA-复合物的琼脂糖凝胶电泳研究表明,C 的嵌入以竞争性方式取代溴化乙锭,这证实了所建议的结合机制。最后,用两种合成化合物处理癌细胞系的抗癌实验表明,这些亲水分子需要合适的载体才能有效地穿过细胞膜的疏水性。