氧氟沙星酰腙配合物的结构、抗氧化活性及与生物大分子的相互作用
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摘要
蛋白质、核酸等基本生命物质对一切生命现象都起着至关重要的作用。在分子水平上研究药物或配合物小分子与蛋白质、核酸等生物大分子的相互作用,是当前生命科学、药物化学的重要研究课题之一。本论文合成、表征了五个氧氟沙星酰腙衍生物及其稀土配合物,发现合成的配合物与配体相比,溶解性有了很大程度地提高,说明在配体中引进金属离子对药物的药剂相性质有较明显的影响；我们推测这些化合物可能有更好的生物活性,所以研究了部分化合物与小牛胸腺DNA (CT DNA)和牛血清白蛋白(BSA)的结合性质及抗氧化活性,得到了一系列有意义的结论。
全文一共分为五章：
第一章：综述了DNA和BSA与小分子作用的研究进展,总结了小分子与DNA和BSA相互作用的方式、影响因素以及研究方法,阐述了小分子与DNA和BSA相互作用的研究在药物筛选和生物化学中重要的理论和实际意义。概述了本论文的选题目的及意义。
第二章：在氧氟沙星母体上,引入羟取代基位置和数量不同的水杨醛衍生物,合成表征了三种新的水杨醛氧氟沙星酰腙配体H2L1,H2L2和H3L3及其稀土配合物ML1-3(M=Pr(Ⅲ), Nd(Ⅲ), Sm(Ⅲ));解析了PrL1和NdL1的晶体结构,其晶体组成分别为[PrL1(NO3)2(CH3OH)] NO3和[NdL1(NO3)2(CH3OH)] NO3。运用紫外可见吸收光谱、荧光光谱、圆二色谱、粘度等方法观察了以上化合物与DNA的相互作用。实验表明,这些化合物均以插入方式与DNA结合,取代基的差异只影响了它们与DNA的结合能力。DNA切割实验说明,配体H2L1,H2L2和H3L3对DNA没有明显的切割作用,但配合物ML1-3都能有效的切割DNA,表现出了一定的化学核酸酶活性。抗氧化活性实验表明,部分化合物对OH·和O2-·自由基具有清除能力,含有两个-OH的H3L3及SmL3对O2-·和OH的清除能力要强于含有一个-OH的H2L1及SmL1和H2L2及SmL2,说明羟基的数量对化合物的抗氧化活性有较大影响。
第三章：运用紫外可见吸收光谱、荧光光谱、圆二色谱等方法,研究了羟基取代基位置和数量不同的水杨醛氧氟沙星酰腙配体H2L1,H2L2和H3L3及其配合物ML1-3与BSA的相互作用。实验表明,这些化合物对BSA的荧光淬灭机理属于静态淬灭,结合位点数都约为1,计算了化合物与BSA作用时的结合常数和热力学参数,确定了它们与BSA之间的主要作用力类型；根据Forster能量传递原理计算了化合物与BSA分子肽链中色氨酸残基之间的距离；利用圆二色光谱研究了它们对BSA二级结构的影响。探讨了-OH位置和数量的变化对化合物与BSA作用的影响。
第四章：合成、表征了呋喃(噻吩)甲醛氧氟沙星酰腙HL4和HL5及其稀土配合物ML4 (M=La(Ⅲ), Nd(Ⅲ), Er(Ⅲ))和ML5(M=La(Ⅲ), Pr(Ⅲ)。研究发现,ML4和ML5具有类似的结构。运用光谱分析和粘度等手段观察了HL4、ML4和HL5、ML5与DNA的相互作用,分别计算了它们与DNA作用的结合常数和淬灭常数。对于HL4及ML4,结合常数和淬灭常数有如下顺序：K (HL4) 第五章：观察了2,6-二((安替比林-4-亚氨基)甲基)-4-甲酚(Dpmp)及其Co(Ⅱ)、Zn(Ⅱ)的配合物与DNA的相互作用,推测Dpmp及其配合物均以插入模式与DNA结合。通过凝胶电泳方法观察到,两种金属配合物都能够有效的切割pUC19 DNA,具有潜在的化学核酸酶活性。抗氧化活性研究表明,Dpmp及其配合物对O2-·和OH具有一定的清除能力。
The essential biological materials——protein and nucleic acid, have been playing vital roles in all kinds of biological phenomena. Exploring the interaction mechanisms on these biomacromolecules with small molecules, especially for those drug molecules, at the molecular level is of current interest in many research areas such as biology, clinical medicine chemistry, and so on. In this paper, we have reported the synthesis, characterization of five ofloxacin acylhydrazones and their metal complexes. The complexes are more soluble compare with the corresponding ligand, which may result in new biological activities, so some of them were evaluated for DNA and BSA binding properties and antioxidant activities. A series of significant conclusions have achieved from the results. The dissertation includes following five chapters:
In chapter one, the research progress in the interactions of DNA and BSA with small molecules, as well as the interaction mode, influence factors, research methods are reviewed. The important theoretical and practical significance of the research work in the drug screening and biochemistry are also discussed herein. Moreover, the aim and significance of this thesis have been outline.
In chapter two, three ofloxacin acylhydrazones with different number and location of hydroxyl substituting groups (H2L1, H2L2 and H3L3) and their metal complexes ML1-3(M=Pr(Ⅲ), Nd(Ⅲ), Sm(Ⅲ)) have been synthesized and characterized. The crystals structures of PrL1 and NdL1 characterized by single crystal X-ray diffraction showed that the complexes have a similar molecular structure. The interactions of above compounds with DNA were investigated by spectrophotometric methods and viscosity measurement, which suggested that the complexes bind with DNA in intercalation mode and the different position and number of substituting groups lead in different DNA binding affinity of the complexes. Experiments with pBR322 DNA show that the free ligand does not show any DNA-cleaving abilities and the complexes display chemical nuclease activity. Antioxidant tests in vitro show some complexes possess significant antioxidant activity against superoxide and hydroxyl radicals and the different number of substituting groups leads in different antioxidant activity of the complexes.
In chapter three, the interactions of H2L1, H2L2, H3L3 and their metal complexes ML1-3 with BSA have been studied using UV-visible, fluorescence spectroscopic and CD methods. The results suggested that the quenching mechanism of BSA fluorescence by complexes was proved to be a static quenching and the numbers of binding sites were about 1. The binding constants and types of interaction forces between BSA and compounds were obtained. The average binding distance between complexes and BSA has been determined on the basis of the Forster'theory. The CD data well supports the idea that the complexes had some effect on BSA'structure. The different position and number of hydroxyl substituting groups lead in different BSA binding affinity of the complexes.
In chapter four, two ofloxacin derivatives with different five-heterocyclic (HL4 and HL5) and their metal complexes (ML4(M=La(Ⅲ), Nd(Ⅲ, Er(Ⅲ)) and ML5(M=La(Ⅲ), Pr(Ⅲ), Sm(Ⅲ))) have been synthesized and characterized. ML4 and ML5 have a similar molecular structure. The interactions of complexes with DNA were investigated by spectrophotometric methods and viscosity measurement, which suggested that the complexes bind with DNA in groove mode. The data of the binding constants and quenching constants present the order of K (HL4)< K (LaL4)< K (NdL4) In chapter five, the interaction of a ligand 2, 6-di((phenazonyl-4-imino)methyl)-4-methylphenol (Dpmp) and its Co(Ⅱ) and Zn(Ⅱ) complex with CT DNA have been studied. The experiment results revealed that they can bind tightly to DNA probably via the intercalative mode. Both the two complexes have been found to promote cleavage ability of pUC19 DNA. In addition, the ligand and complexes showed considerable anti-oxidative activity to superoxide and hydroxyl radicals.
全文一共分为五章：
第一章：综述了DNA和BSA与小分子作用的研究进展,总结了小分子与DNA和BSA相互作用的方式、影响因素以及研究方法,阐述了小分子与DNA和BSA相互作用的研究在药物筛选和生物化学中重要的理论和实际意义。概述了本论文的选题目的及意义。
第二章：在氧氟沙星母体上,引入羟取代基位置和数量不同的水杨醛衍生物,合成表征了三种新的水杨醛氧氟沙星酰腙配体H2L1,H2L2和H3L3及其稀土配合物ML1-3(M=Pr(Ⅲ), Nd(Ⅲ), Sm(Ⅲ));解析了PrL1和NdL1的晶体结构,其晶体组成分别为[PrL1(NO3)2(CH3OH)] NO3和[NdL1(NO3)2(CH3OH)] NO3。运用紫外可见吸收光谱、荧光光谱、圆二色谱、粘度等方法观察了以上化合物与DNA的相互作用。实验表明,这些化合物均以插入方式与DNA结合,取代基的差异只影响了它们与DNA的结合能力。DNA切割实验说明,配体H2L1,H2L2和H3L3对DNA没有明显的切割作用,但配合物ML1-3都能有效的切割DNA,表现出了一定的化学核酸酶活性。抗氧化活性实验表明,部分化合物对OH·和O2-·自由基具有清除能力,含有两个-OH的H3L3及SmL3对O2-·和OH的清除能力要强于含有一个-OH的H2L1及SmL1和H2L2及SmL2,说明羟基的数量对化合物的抗氧化活性有较大影响。
第三章：运用紫外可见吸收光谱、荧光光谱、圆二色谱等方法,研究了羟基取代基位置和数量不同的水杨醛氧氟沙星酰腙配体H2L1,H2L2和H3L3及其配合物ML1-3与BSA的相互作用。实验表明,这些化合物对BSA的荧光淬灭机理属于静态淬灭,结合位点数都约为1,计算了化合物与BSA作用时的结合常数和热力学参数,确定了它们与BSA之间的主要作用力类型；根据Forster能量传递原理计算了化合物与BSA分子肽链中色氨酸残基之间的距离；利用圆二色光谱研究了它们对BSA二级结构的影响。探讨了-OH位置和数量的变化对化合物与BSA作用的影响。
第四章：合成、表征了呋喃(噻吩)甲醛氧氟沙星酰腙HL4和HL5及其稀土配合物ML4 (M=La(Ⅲ), Nd(Ⅲ), Er(Ⅲ))和ML5(M=La(Ⅲ), Pr(Ⅲ)。研究发现,ML4和ML5具有类似的结构。运用光谱分析和粘度等手段观察了HL4、ML4和HL5、ML5与DNA的相互作用,分别计算了它们与DNA作用的结合常数和淬灭常数。对于HL4及ML4,结合常数和淬灭常数有如下顺序：K (HL4)
The essential biological materials——protein and nucleic acid, have been playing vital roles in all kinds of biological phenomena. Exploring the interaction mechanisms on these biomacromolecules with small molecules, especially for those drug molecules, at the molecular level is of current interest in many research areas such as biology, clinical medicine chemistry, and so on. In this paper, we have reported the synthesis, characterization of five ofloxacin acylhydrazones and their metal complexes. The complexes are more soluble compare with the corresponding ligand, which may result in new biological activities, so some of them were evaluated for DNA and BSA binding properties and antioxidant activities. A series of significant conclusions have achieved from the results. The dissertation includes following five chapters:
In chapter one, the research progress in the interactions of DNA and BSA with small molecules, as well as the interaction mode, influence factors, research methods are reviewed. The important theoretical and practical significance of the research work in the drug screening and biochemistry are also discussed herein. Moreover, the aim and significance of this thesis have been outline.
In chapter two, three ofloxacin acylhydrazones with different number and location of hydroxyl substituting groups (H2L1, H2L2 and H3L3) and their metal complexes ML1-3(M=Pr(Ⅲ), Nd(Ⅲ), Sm(Ⅲ)) have been synthesized and characterized. The crystals structures of PrL1 and NdL1 characterized by single crystal X-ray diffraction showed that the complexes have a similar molecular structure. The interactions of above compounds with DNA were investigated by spectrophotometric methods and viscosity measurement, which suggested that the complexes bind with DNA in intercalation mode and the different position and number of substituting groups lead in different DNA binding affinity of the complexes. Experiments with pBR322 DNA show that the free ligand does not show any DNA-cleaving abilities and the complexes display chemical nuclease activity. Antioxidant tests in vitro show some complexes possess significant antioxidant activity against superoxide and hydroxyl radicals and the different number of substituting groups leads in different antioxidant activity of the complexes.
In chapter three, the interactions of H2L1, H2L2, H3L3 and their metal complexes ML1-3 with BSA have been studied using UV-visible, fluorescence spectroscopic and CD methods. The results suggested that the quenching mechanism of BSA fluorescence by complexes was proved to be a static quenching and the numbers of binding sites were about 1. The binding constants and types of interaction forces between BSA and compounds were obtained. The average binding distance between complexes and BSA has been determined on the basis of the Forster'theory. The CD data well supports the idea that the complexes had some effect on BSA'structure. The different position and number of hydroxyl substituting groups lead in different BSA binding affinity of the complexes.
In chapter four, two ofloxacin derivatives with different five-heterocyclic (HL4 and HL5) and their metal complexes (ML4(M=La(Ⅲ), Nd(Ⅲ, Er(Ⅲ)) and ML5(M=La(Ⅲ), Pr(Ⅲ), Sm(Ⅲ))) have been synthesized and characterized. ML4 and ML5 have a similar molecular structure. The interactions of complexes with DNA were investigated by spectrophotometric methods and viscosity measurement, which suggested that the complexes bind with DNA in groove mode. The data of the binding constants and quenching constants present the order of K (HL4)< K (LaL4)< K (NdL4)
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