侧臂式多氮大环配合物的合成、表征及生物活性的研究
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摘要
本文以侧臂式多氮席夫碱大环配合物为研究对象,以带吡啶、噻吩和苯环侧臂的希夫碱大环配合物的合成、表征、性质和生物为主要内容,以合成新型高效拟酶催化剂和抑菌剂,合成了六种新的配合物:[Mn_2H_2L~1(OAc)_2](ClO_4)_2·(H_2O)1,[Ni_2L~2(OAc)](ClO_4)·(CH_3OH)2,[Ni_2L~3(OAc)](ClO_4)·2(CH_3CN)3,[Ni_2L~4(OAc)](ClO_4)·2(CH_3CN)4,[Cu_2L~3(OAc)](ClO_4)·(CH_3CN)5和[Cu_4L~3(OAc)_2O_2](ClO_4)·(CH_3CN)6,并对它们及相关中间产物进行了一系列表征,如红外、元素分析、核磁共振谱和X-射线晶体衍射,借助循环伏安法和变温磁化率实验研究了配合物的电化学和磁学性质,测定了配合物1模拟过氧化氢酶的活性及配合物1、2、4的抑菌、切割超螺旋DNA的活性。
主要工作如下:
1.以吡啶甲胺和苯甲胺为原料合成了N,N-二(3-氨丙基)-2-吡啶甲胺盐酸盐和N,N-二(3-氨丙基)-2-苯甲胺,用IR和~1HNMR对其结构进行了表征;
2.首次合成了具有很大空穴的侧臂式不对称双核锰金属配合物1。通过X-射线单晶衍射发现,两个悬臂上吡啶N原子与两个金属离子呈反向配位,大环上的酚氧原子和两个希夫碱亚胺N原子未与金属配位,从而形成了一个很大的空穴。电化学测试表明配合物1在0--1.8 V范围内有两对氧化还原峰,且均为准可逆过程。变温磁化率实验则表明该配合物的两个Mn~(2+)之间具有弱的反铁磁性偶合。通过测量催化分解产生的放氧量随时间的变化,发现它能快速高效地催化分解过氧化氢,用紫外-可见光谱跟踪1催化分解发现可能有活性中间体(Mn~ⅡMn~Ⅳ(=O)H_2L~1(OAc)_2)产生。该配合物基本没有切割超螺旋DNA(pBR322)的活性,但是在与H_2O_2的共同作用下切割效果有明显提高,能将超螺旋DNA完全切割成带缺口的环状DNA(FormⅡ)和线状DNA(FormⅢ)。另外,它对大肠杆菌有良好的抑制作用。
3.通过模板法制备出了带噻吩环侧臂的双核镍大环配合物2和3和带苯环侧臂的双核镍大环配合物4。通过X-射线晶体衍射发现分子空间形态均为“马鞍状”,两个金属离子均是通过μ_2-醋酸根桥接,配合物2和3的噻吩乙胺悬臂上的S原子均未参与配位。循环伏安法表明三种配合物在0--1.8 V范围内均只有一对氧化还原峰。变温磁化率研究表明,配合物2和3的两个金属Ni~(2+)之间均存在弱的反铁磁性偶合。配合物2和4切割DNA的活性不高,但是对大肠杆菌有一定的抑菌作用。
4.以2,6-二甲酰基-4-氯苯酚和N,N-二(3-氨丙基)-2-噻吩乙胺直接缩合得到了一种新型对称的大环配体。此配体与不同比例的Cu~(2+)作用形成了四核铜配合物5及双核配合物6。晶体结构表明配合物5的Cu_4O_4中心呈“椅状”对称结构。配合物6中配体阳离子呈“马鞍”状,两个金属离子的配位环境与配合物2、3和4中的金属离子的配位环境相似。
This dissertation uses the novel symmetric polynitrogen-macrocyclic complexes with pendant-arm as research objects, focusing on the synthesis, characterization, modeling metalloenzyme, cleavage of DNA pBR322 and activity against the test bacterial organism of them. Aim to synthesize highly effective novel enzyme catalyzers and bactorial inhabitors, six new complexes, [Mn_2H_2L~1(OAc)_2](ClO_4)_2·(H2O) 1, [Ni_2L~2(OAc)](ClO_4)·(CH_3OH) 2, [Ni_2L~3(OAc)](ClO_4)·2(CH_3CN) 3, [Ni_2L~4(OAc)](ClO_4)·2(CH_3CN) 4, [Cu_2L~3(OAc)](ClO_4)·(CH_3CN) 5 and [Cu_4L~3(OAc)_2O_2](ClO_4)·(CH_3CN) 6, have been synthesized and characterized by element analyses, mass spectra, IR, ~1HNMR and X-ray diffractions techniques. The electro-chemistry characterization and magnetism interactions between metal ions of three complexes have been studied by the measurements of cyclic voltammograms and variable-temperature magnetic susceptibility. In addition, Catalase-like activity of disproportionating H_2O_2 into H_2O and O_2 of the dinuclear manganese(Ⅱ) complex 1, and the cleavage activity of plasmid DNA pBR322 and the inhabitory bacteria activity of the complexes 1、2、4 have been also investigated.
The work is composed of:
1. N, N-bis(3-aminopropyl)-2-pyridylmethylamine hydrochloride and N, N-bis(3-aminopropyl)-2-benzylmethylamine have been prepared from 2-pyridylmethylamine and 2-benzylmethylamme, respectively and characterized by IR and ~1HNMR.
2. The novel pendant-armed unsymmetric dinuclear manganese macrocyclic complexes with a big cavity has been synthesized firstly. The X-ray diffraction result of the complex reveals that the two nitrogen atoms of the two pendant arms exhibit trans- coordination mode with two metal ions , and the two imine N and one phenol O are not coordinated with metal ions, which leads to the formation of the big cavity. Electrochemistry study shows that the complex behaves two pair of pseudo-reversible redox peaks in the range of potential 0--1.8 V. The experimental data of susceptibility of the complex indicates weak antiferromagnetic exchange interactions between the two manganese (Ⅱ) in the complex. The record of oxygen volume produced by decomposition of H_2O_2 displays the relatively high efficiency of the complex 1, and the active intermediates Mn~ⅡMn~Ⅳ(=O)H_2L~1(OAc)_2 is quite probably occurred from the visible spectrum of process. The results of gel electrophoretic separations of plasmid pBR322 DNA induced by the complex shows it can not cleave basically pBR322, but in the presence of H_2O_2, complex 1 has obviously cleaving effect and can convert FormⅠplasmid DNA into FormⅡor FormⅢgradually, and make it disappeared finally. These complexes have antibiotic activities for Escherichia coli.
3. Two symmetric dinuclear nickel macrocyclic complexes with pendant arm containing thiophenol group 2 and 3 and one with benzyl pendant arm 4 have been synthesized by template reactions. The X-ray diffraction results of complexes show that shape of ligands are all like a saddle and two metal ions are bridged byμ_2-acetato in three complexes, and the S atoms on thiophenol group of pendant arm in complexes 2 and 3 are not involved in coordination. The CVs of the complexes show only one pseudo-reversible Ni~(Ⅱ/Ⅱ) and Ni~(Ⅰ/Ⅰ) waves. Magnetic susceptibility measurements of complex 2 and 3 reveal an anti-ferromagnetic interaction between two metal ions. The DNA cleavage ability of two complexes 2 and 4 with different pendant arm is poor. The tests of antibacterial activity of the two complexes toward Escherichia coli have been performed, and the experimental show they have ability of bacteriostasis.
4. The symmetric macrocyclic ligand has been synthesized by condensation reaction between 2, 6-diformyl-4-chlorophenol and N, N-bis(3-aminopropyl)- 2-pyridylmethylamine. Reacting this ligand with copper(Ⅱ) in different proportion, one tetranuclear and one dinucelar copper(Ⅱ) complexes have been obtained, respectively. The analyses of the crystal structures show that the Cu_4O_4 core of of complex 5 is in "chair" shape, and the cation of complex 6 is in "saddle" one. The coordination environment of two copper(Ⅱ) metal ions in complex 6 is similar to thoseof two nickel(Ⅱ) metal ions of above-mentioned three complexes.
主要工作如下:
1.以吡啶甲胺和苯甲胺为原料合成了N,N-二(3-氨丙基)-2-吡啶甲胺盐酸盐和N,N-二(3-氨丙基)-2-苯甲胺,用IR和~1HNMR对其结构进行了表征;
2.首次合成了具有很大空穴的侧臂式不对称双核锰金属配合物1。通过X-射线单晶衍射发现,两个悬臂上吡啶N原子与两个金属离子呈反向配位,大环上的酚氧原子和两个希夫碱亚胺N原子未与金属配位,从而形成了一个很大的空穴。电化学测试表明配合物1在0--1.8 V范围内有两对氧化还原峰,且均为准可逆过程。变温磁化率实验则表明该配合物的两个Mn~(2+)之间具有弱的反铁磁性偶合。通过测量催化分解产生的放氧量随时间的变化,发现它能快速高效地催化分解过氧化氢,用紫外-可见光谱跟踪1催化分解发现可能有活性中间体(Mn~ⅡMn~Ⅳ(=O)H_2L~1(OAc)_2)产生。该配合物基本没有切割超螺旋DNA(pBR322)的活性,但是在与H_2O_2的共同作用下切割效果有明显提高,能将超螺旋DNA完全切割成带缺口的环状DNA(FormⅡ)和线状DNA(FormⅢ)。另外,它对大肠杆菌有良好的抑制作用。
3.通过模板法制备出了带噻吩环侧臂的双核镍大环配合物2和3和带苯环侧臂的双核镍大环配合物4。通过X-射线晶体衍射发现分子空间形态均为“马鞍状”,两个金属离子均是通过μ_2-醋酸根桥接,配合物2和3的噻吩乙胺悬臂上的S原子均未参与配位。循环伏安法表明三种配合物在0--1.8 V范围内均只有一对氧化还原峰。变温磁化率研究表明,配合物2和3的两个金属Ni~(2+)之间均存在弱的反铁磁性偶合。配合物2和4切割DNA的活性不高,但是对大肠杆菌有一定的抑菌作用。
4.以2,6-二甲酰基-4-氯苯酚和N,N-二(3-氨丙基)-2-噻吩乙胺直接缩合得到了一种新型对称的大环配体。此配体与不同比例的Cu~(2+)作用形成了四核铜配合物5及双核配合物6。晶体结构表明配合物5的Cu_4O_4中心呈“椅状”对称结构。配合物6中配体阳离子呈“马鞍”状,两个金属离子的配位环境与配合物2、3和4中的金属离子的配位环境相似。
This dissertation uses the novel symmetric polynitrogen-macrocyclic complexes with pendant-arm as research objects, focusing on the synthesis, characterization, modeling metalloenzyme, cleavage of DNA pBR322 and activity against the test bacterial organism of them. Aim to synthesize highly effective novel enzyme catalyzers and bactorial inhabitors, six new complexes, [Mn_2H_2L~1(OAc)_2](ClO_4)_2·(H2O) 1, [Ni_2L~2(OAc)](ClO_4)·(CH_3OH) 2, [Ni_2L~3(OAc)](ClO_4)·2(CH_3CN) 3, [Ni_2L~4(OAc)](ClO_4)·2(CH_3CN) 4, [Cu_2L~3(OAc)](ClO_4)·(CH_3CN) 5 and [Cu_4L~3(OAc)_2O_2](ClO_4)·(CH_3CN) 6, have been synthesized and characterized by element analyses, mass spectra, IR, ~1HNMR and X-ray diffractions techniques. The electro-chemistry characterization and magnetism interactions between metal ions of three complexes have been studied by the measurements of cyclic voltammograms and variable-temperature magnetic susceptibility. In addition, Catalase-like activity of disproportionating H_2O_2 into H_2O and O_2 of the dinuclear manganese(Ⅱ) complex 1, and the cleavage activity of plasmid DNA pBR322 and the inhabitory bacteria activity of the complexes 1、2、4 have been also investigated.
The work is composed of:
1. N, N-bis(3-aminopropyl)-2-pyridylmethylamine hydrochloride and N, N-bis(3-aminopropyl)-2-benzylmethylamine have been prepared from 2-pyridylmethylamine and 2-benzylmethylamme, respectively and characterized by IR and ~1HNMR.
2. The novel pendant-armed unsymmetric dinuclear manganese macrocyclic complexes with a big cavity has been synthesized firstly. The X-ray diffraction result of the complex reveals that the two nitrogen atoms of the two pendant arms exhibit trans- coordination mode with two metal ions , and the two imine N and one phenol O are not coordinated with metal ions, which leads to the formation of the big cavity. Electrochemistry study shows that the complex behaves two pair of pseudo-reversible redox peaks in the range of potential 0--1.8 V. The experimental data of susceptibility of the complex indicates weak antiferromagnetic exchange interactions between the two manganese (Ⅱ) in the complex. The record of oxygen volume produced by decomposition of H_2O_2 displays the relatively high efficiency of the complex 1, and the active intermediates Mn~ⅡMn~Ⅳ(=O)H_2L~1(OAc)_2 is quite probably occurred from the visible spectrum of process. The results of gel electrophoretic separations of plasmid pBR322 DNA induced by the complex shows it can not cleave basically pBR322, but in the presence of H_2O_2, complex 1 has obviously cleaving effect and can convert FormⅠplasmid DNA into FormⅡor FormⅢgradually, and make it disappeared finally. These complexes have antibiotic activities for Escherichia coli.
3. Two symmetric dinuclear nickel macrocyclic complexes with pendant arm containing thiophenol group 2 and 3 and one with benzyl pendant arm 4 have been synthesized by template reactions. The X-ray diffraction results of complexes show that shape of ligands are all like a saddle and two metal ions are bridged byμ_2-acetato in three complexes, and the S atoms on thiophenol group of pendant arm in complexes 2 and 3 are not involved in coordination. The CVs of the complexes show only one pseudo-reversible Ni~(Ⅱ/Ⅱ) and Ni~(Ⅰ/Ⅰ) waves. Magnetic susceptibility measurements of complex 2 and 3 reveal an anti-ferromagnetic interaction between two metal ions. The DNA cleavage ability of two complexes 2 and 4 with different pendant arm is poor. The tests of antibacterial activity of the two complexes toward Escherichia coli have been performed, and the experimental show they have ability of bacteriostasis.
4. The symmetric macrocyclic ligand has been synthesized by condensation reaction between 2, 6-diformyl-4-chlorophenol and N, N-bis(3-aminopropyl)- 2-pyridylmethylamine. Reacting this ligand with copper(Ⅱ) in different proportion, one tetranuclear and one dinucelar copper(Ⅱ) complexes have been obtained, respectively. The analyses of the crystal structures show that the Cu_4O_4 core of of complex 5 is in "chair" shape, and the cation of complex 6 is in "saddle" one. The coordination environment of two copper(Ⅱ) metal ions in complex 6 is similar to thoseof two nickel(Ⅱ) metal ions of above-mentioned three complexes.
引文
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