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芳酰腙类配体及其金属配合物的合成、表征及性能研究
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摘要
本论文中,主要通过苯甲酰肼、邻羟基苯甲酰肼、对羟基苯甲酰肼与柚皮素或4-甲基-7-羟基-8-乙酰基香豆素反应,合成了一些芳酰腙类有机配体。并利用熔点、核磁共振波谱、质谱,对这些有机配体进行了结构验证。
     之后,合成了这些芳酰腙类有机配体的金属配合物,并且通过元素分析(C、H、N)、金属滴定,测定了配合物的组成;通过红外光谱、电导率的测定等方法,推测了金属配合物可能的配位形式。
     最终,研究了这些芳酰腙类有机配体及其配合物的生物药理性能(如:与脱氧核糖核酸(DNA)的结合模式、清除活性氧自由基的性能),或荧光性质。
     本论文中所包含的六章内容分别为:
     第一章、对DNA的基本结构,药物小分子与DNA的作用模式、检测方法,活性氧自由基的体外产生方法、检测方法,以及类黄酮物质的分类,香豆素类物质的生物药理活性和光学性质,做了系统的概述。
     第二章、通过柚皮素和邻羟基苯甲酰肼的缩合,得到了有机配体:柚皮素(2'-羟基苯甲酰)腙。进而合成、表征了相应的铜(Ⅱ)、锌(Ⅱ)、镍(Ⅱ)金属配合物。最后,研究了配体、配合物清除活性氧自由基(超氧自由基和羟基自由基)的性能。结果表明:配体及其配合物均表现出了良好的清除活性氧自由基的能力,其中铜(Ⅱ)配合物对超氧自由基的清除作用极为突出。
     第三章、利用有机配体:柚皮素(2'-羟基苯甲酰)腙,合成了其钇(Ⅲ)、铕(Ⅲ)金属配合物。进而研究了配体、配合物与DNA的作用模式,以及它们清除羟基自由基的性能。实验显示:配体和配合物都可以通过插入模式与小牛胸腺DNA作用。在三者中,铕(Ⅲ)金属配合物显示了最强的结合能力。在清除羟基自由基方面,钇(Ⅲ)、铕(Ⅲ)配合物的性能,均低于配体及其铜(Ⅱ)、锌(Ⅱ)、镍(Ⅱ)配合物的性能。
     第四章、首先,合成了4-甲基-7-羟基-8-乙酰基香豆素。之后,通过4-甲基-7-羟基-8-乙酰基香豆素分别和苯甲酰肼、对羟基苯甲酰肼的缩合,得到了有机配体:4-甲基-7-羟基-8-乙酰基香豆素(苯甲酰)腙和4-甲基-7-羟基-8-乙酰基香豆素(4'-羟基苯甲酰)腙。进而合成、表征了相应的铜(Ⅱ)、锌(Ⅱ)金属配合物。最后,研究了配体、配合物与DNA的作用模式。试验显示:铜(Ⅱ)、锌(Ⅱ)金属配合物采用不同的模式和DNA作用。
     第五章、以4-甲基-7-羟基香豆素和亚氨基二乙酸为起始物,合成了含二羧酸功能基团的香豆素类配体:7-(N,N-二乙酸氨基甲酰甲氧基)-4-甲基香豆素。进而合成了该配体的铕(Ⅲ)、铽(Ⅲ)金属配合物,并研究了该配体及其金属配合物的固体荧光性质。试验显示:铕(Ⅲ)配合物可以发出铕(Ⅲ)离了的红色特征荧光。
     第六章、以荧光素和1-苯基-3-甲基-4-苯甲酰基-5-吡唑啉酮作为起始原料,通过两步合成,得到了化学传感器:1-苯基-3-甲基-5-羟基吡唑-4-苯甲酰基(荧光素)腙。进而利用紫外-可见吸收光谱和荧光光谱,研究了该传感器,对水溶液中金属离子的识别响应。实验显示:在加入铜(Ⅱ)离子后,该传感器的水溶液立即由无色变为深黄色;同样条件下加入其他常见碱金属、碱土金属、过渡金属离子,却不能引起该传感器溶液颜色的变化。另外,该传感器和铜(Ⅱ)离子作用时的化学计量比、结合常数、结合机理也同时被研究。
In this dissertation, several aryl-acylhydrazones were synthesized, by the reaction of benzoyl hydrazine,2-hydroxy benzoyl hydrazine or 4-hydroxy benzoyl hydrazine with naringenin or 8-acetyl-7-hydroxy-4-methyl coumarin, separately. And melting point, NMR, and mass spectra were used to confirm these organic ligands.
     Later, the metal complexes of these organic ligands were prepared. Elemental analyses (C, H, N) and metal titration with EDTA were used to determine the component of the complexes. Infrared spectra and molar conductance measurements were used to presume the coordination structures.
     Finally, pharmacological properties or fluorescence properties of the ligands and the metal complexes were studied. For instance, the interaction with calf thymus DNA (CT-DNA) and antioxidant activities of the ligands and the metal complexes were investigated.
     In chapter 1, a simple review was made, including:the basic structure of DNA (deoxyribonucleic acid), the interaction of small molecules with DNA (interaction mode and detecting methods), some information about reactive oxygen species (generation methods and detecting methods in vitro), and some characters of flavonoid and coumarin.
     In chapter 2, a ligand, naringenin (2'-hydroxy benzoyl) hydrazone, was synthesized by the reaction of naringenin with 2-hydroxy benzoyl hydrazine. And its Cu(Ⅱ), Zn(Ⅱ), Ni(Ⅱ) complex have also been prepared and characterized. Finally, the antioxidant activities (superoxide radical and hydroxyl radical scavenging activities) of the free ligand and its complexes were determined in vitro. These compounds were found to possess good antioxidant activity. In particular, the Cu(Ⅱ) complex displayed excellent activity on the superoxide radical.
     In chapter 3, Y(Ⅲ) complex and Eu(Ⅲ) complex of the naringenin (2'-hydroxy benzoyl) hydrazone were synthesized. Experimental evidences indicate that these three compounds can strongly bind to CT-DNA via an intercalation mechanism. For the interaction ability with DNA, Eu(Ⅲ) complex was better than Y(Ⅲ) complex and the free ligand. Furthermore, the hydroxyl radical scavenging activities of the Y(Ⅱ) complex and Eu(Ⅲ) complex were lower than the free ligand and the Cu(Ⅱ), Zn(Ⅱ), Ni(Ⅱ) complexes of the ligand.
     In chapter 4, first,8-acetyl-7-hydroxy-4-methyl coumarin was prepared. Then by the reaction of 8-acetyl-7-hydroxy-4-methyl coumarin with benzoyl hydrazine or 4-hydroxy benzoyl hydrazine separately, two ligands,7-hydroxy-4-methyl-8-acetyl coumarin (benzoyl) hydrazone and 7-hydroxy-4-methyl-8-acetyl coumarin (4'-hydroxylbenzoyl) hydrazone, were synthesized. The Cu(II), Zn(II) complexes of the two ligands were also prepared. Finally, the interaction of the ligands and the metal complexes with CT-DNA was investigated. Experimental data shown that Cu(II), Zn(II) complexes bound with CT-DNA by different mode.
     In chapter 5, a new coumarin derivative was got, by using 7-hydroxy-4-methyl coumarin was used as staring material. And its Eu(III) and Tb(III) complexes were also prepared. Fluorescence emission spectrum shown that Eu(III) complex can give characteristic emission of Eu(III) ion.
     In chapter 6, a fluorescein-based colorimetric chemosensor,1-phenyl-3-methyl-5-hydroxypyrazole-4-benzoyl (fluorescein) hydrazone, was synthesized by the reaction between fluorescein hydrazide and 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone. And its sensing behavior toward metal ions was investigated. Addition of Cu2+ to an aqueous solution of the chemosensor made the color change from colorless to deep yellow in a very short time. However, under the same conditions, other common alkali- alkaline earth-, transition-and rare earth metal ions induced no or very little color change. The stoichiometry, association constant, and binding mode of the chemosensor with Cu2+ were also investigated.
引文
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