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一些含有修饰菲咯啉配体的新型表面活性剂铜(II)配合物的合成、胶束化行为、抗菌性能及嵌入DNA结合作用

Synthesis, micellization behavior, antimicrobial and intercalative DNA binding of some novel surfactant copper(II) complexes containing modified phenanthroline ligands.

作者信息

Nagaraj Karuppiah, Ambika Subramanian, Rajasri Shanmugasundaram, Sakthinathan Subramanian, Arunachalam Sankaralingam

机构信息

School of Chemistry, Bharathidasan University, Tiruchirapalli 620024, India.

School of Chemistry, Bharathidasan University, Tiruchirapalli 620024, India.

出版信息

Colloids Surf B Biointerfaces. 2014 Oct 1;122:151-157. doi: 10.1016/j.colsurfb.2014.05.011. Epub 2014 Jun 28.

Abstract

The novel surfactant copper(II) complexes, Cu(ip)2DA21, Cu(dpqc)2DA22, Cu(dppn)2DA23, where ip=imidazo[4,5-f][1,10]phenanthroline, dpqc=dipyrido3,2-a:2',4'-cphenazine, dppn=benzo[1]dipyrido[3,2-a':2',3'-c]phenazine and DA-dodecylamine, were synthesized and characterized by physico-chemical and spectroscopic methods. In these complexes 1-3, the geometry of copper metal ions was described as square pyramidal. The critical micelle concentration (CMC) value of these surfactant copper(II) complexes in aqueous solution was found out from conductance measurements. Specific conductivity data at different temperatures served for the evaluation of the temperature-dependent CMC and the thermodynamics of micellization (ΔGm°, ΔHm° and ΔSm°). The binding interaction of these complexes with DNA (calf thymus DNA) in Tris buffer was studied by physico-chemical techniques. In the presence of the DNA UV-vis spectrum of complexes showed red shift of the absorption band along with significant hypochromicity indicating intercalation of our complexes with nucleic acids. Competitive binding study with ethidium bromide (EB) shows that the complexes exhibit the ability to displace the nucleic acid-bound EB indicating that the complexes bind to nucleic acids in strong competition with EB for the intercalative binding site. Observed changes in the circular dichoric spectra of DNA in the presence of surfactant complexes support the strong binding of complexes with DNA. CV results also confirm this mode of binding. Some significant thermodynamic parameters of the binding of the titled complexes to DNA have also been determined. The results reveal that the extent of DNA binding of 3 was greater than that of 1 and 2. The antibacterial and antifungal screening tests of these complexes have shown good results compared to its precursor chloride complexes.

摘要

新型表面活性剂铜(II)配合物,Cu(ip)2DA2 1、Cu(dpqc)2DA2 2、Cu(dppn)2DA2 3,其中ip = 咪唑并[4,5-f][1,10]菲咯啉,dpqc = 二吡啶并3,2-a:2',4'-c吩嗪,dppn = 苯并[1]二吡啶并[3,2-a':2',3'-c]吩嗪且DA = 十二烷基胺,通过物理化学和光谱方法进行了合成与表征。在这些配合物1 - 3中,铜金属离子的几何构型被描述为四方锥型。通过电导率测量得出了这些表面活性剂铜(II)配合物在水溶液中的临界胶束浓度(CMC)值。不同温度下的比电导率数据用于评估温度依赖性CMC以及胶束化的热力学性质(ΔGm°、ΔHm°和ΔSm°)。通过物理化学技术研究了这些配合物与Tris缓冲液中DNA(小牛胸腺DNA)的结合相互作用。在DNA存在的情况下,配合物的紫外可见光谱显示吸收带发生红移并伴有显著的减色现象,表明我们的配合物与核酸发生了嵌入作用。与溴化乙锭(EB)的竞争结合研究表明,这些配合物具有取代与核酸结合的EB的能力,这表明配合物与EB在嵌入结合位点上存在与核酸的强竞争结合。在表面活性剂配合物存在下观察到的DNA圆二色光谱变化支持了配合物与DNA的强结合。循环伏安结果也证实了这种结合模式。还测定了标题配合物与DNA结合的一些重要热力学参数。结果表明,3与DNA的结合程度大于1和2。与它们的前体氯化物配合物相比,这些配合物的抗菌和抗真菌筛选试验显示出良好的结果。

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