羧酸类芳酰腙配合物的结构、生物活性及与DNA作用初探
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摘要
本文以芳酰腙类有机小分子为主要配体，在查阅大量文献和分析发展动态的基础上，首次合成了3种芳酰腙有机配体及四个系列49种单核和双核稀土、过渡金属配合物，通过元素分析、摩尔电导率、IR、UV、FS、~1H NMR、热分析、单晶X射线四圆衍射、X-粉末衍射等诸多手段对物质的结构和物理化学性质进行了详细的、系统的分析和表征。同时，根据该类配体及配合物的性质，针对不同的动植物病菌作了生物活性筛选试验，求得了毒力回归方程。并用紫外-可见光谱、荧光光谱，荧光淬灭滴定等方法研究了样品与小牛胸腺DNA的作用强度及方式。具体内容如下：
1．有机小分子配体的合成：首次合成了3种含不同羧基的单酰腙和双酰腙有机配体(二丙酮酸缩对苯二甲双酰腙L2，二a-酮戊二酸缩对苯甲双酰腙L3，a-酮戊二酸缩水杨酰腙L4)，培养得到了两个配体的晶体结构(2-羰基丙酸水杨酰腙L1，L2)。通过红外、核磁、质谱、紫外-可见、荧光光谱、热重分析对其进行了表征。
2．L1分别与稀土、过渡金属形成的二元配合物：在混合溶剂中，2-羰基丙酸水杨酰腙(C_(10)H_(10)N_2O_4，H_3L)分别与RE(NO_3)_3·nH_2O (RE=La、Pr、Gd、Er)和过渡金属盐(CuCl_2·2H_2O)反应，合成了5种未见文献报道的配合物，测定了其晶体结构，稀土配合物的结构不尽相同，随着稀土离子半径的递减，其配位数也随之递减，配体的配位方式多样，表现出不同的价态；在Pr的配合物中，配体的羧基氧以μ_2形式桥连两个中心离子，形成双核配合物。而且并讨论了配合物的荧光性质。
3．L1和多吡啶类配体(2，2’-联吡啶bipy／1，10-菲啰啉phen)分别与稀土、过渡金属形成的超分子配合物：在混合溶剂中，以2-羰基丙酸水杨酰腙(C_(10)H_(10)N_2O_4，H_3L)，bipy分别与RE(NO_3)_3·nH_2O(RE=La、Ce、Pr、Nd、Sm、Eu、Gd、Tb、Dy、Er、Yb、Lu和Y)和过渡金属(Ni~(2+)，Cd~(2+))反应，合成了16种未见文献报道的配合物，经系统表征确定了配合物的组成和结构。稀土配合物具有相同的结构[RE(H_2L)(HL)(H_2O)_3]·0.5bipy·nH_2O，测定了三个代表性配合物的结构(Nd，Eu，Dy)，每个单元均为两个结构相似的9配位配合物，每个配合物中有两个2-羰基丙酸水杨酰腙和三个水分子参与了配位，同时还有一个bipy分子和水分子游离于晶格中，形成了三维网状的超分子化合物。过渡金属配合物NiHL(bipy)H_2O和[NiHL(phen)H_2O]·H_2O具有相似的结构，在空间呈畸变的八面体。双核配合物[CdHL(bipy)(H_2O)_2]_2·2H_2O中心金属离子配位数为7，在空间呈三方底四方底结构，且联吡啶环之间存在π-π堆积。
4．L2分别与稀土、过渡金属形成的二元配合物：在混合溶剂中，以丙酮酸缩对苯二甲双酰腙(C_(14)H_(14)N_4O_6)分别与RE(NO_3)_3·nH_2O((RE=La、Ce、Pr、Nd、Sm、Eu、Gd、Tb、Dy、Er、Yb、Lu和Y))和过渡金属盐(Cu~(2+)，Zn~(2+))反应，合成了15种未见文献报道的配合物，经系统表征确定了配合物的组成和结构，由于配体本身的结构特征使得该系列全为双核配合物，探讨了其成键特点及光谱性质。测试了配合物Cu_2(L)(pyridine)_6·2H_2O的晶体结构，配体采用脱氢共轭方式配位。
5．L4与稀土形成的二元配合物：在混合溶剂中，a-酮戊二酸缩水杨酰腙分别与RE(NO_3)_3·nH_2O(RE=La、Pr、Nd、Sm、Eu、Gd、Tb、Dy、Er、Yb、Lu和Y))反应，合成了13种未见文献报道的配合物，经系统表征确定了配合物的组成和结构，探讨了配合物的成键特点及光谱性质。
6．生物活性实验：选取不同类型具代表性的配体和配合物对动植物菌种进行生物活性筛选试验，植物菌种采用番茄灰霉病菌、烟草赤星病菌和小麦条锈病菌，方法是生长速率法和孢子萌发法。动物采用革兰氏阳性菌(金黄色葡萄球菌)，革兰氏阴性菌(大肠杆菌、鼠伤寒沙门菌)及人红白血病细胞系K562细胞。结果表明，配体及配合物对三种植物病菌及动物菌种大肠杆菌均有不同程度的抑菌活性，对效果较好的Dy(H_2L)(HL)·0.5bipy·5H_2O和L2进行了相关性分析，得到了毒力回归方程。对金黄色葡萄球菌、鼠伤寒沙门菌及人红白血病细胞系K562细胞抑制效果不明显。
7．用紫外-可见光谱、荧光光谱，荧光淬灭滴定等方法研究了三元超分子配合物及部分配体与小牛胸腺DNA的结合强度及机理，为进一步研究抑菌机理提供依据。
The main organic ligands are aryl-acylhydrazones in the paper. On the base of reading abundant literature and analyzing development state, four series-fifty compounds about aryl-acylhydrazones and their mono- and binuclear complexes were synthesized, and characterized by elemental analysis, IR, UV-Vis, FS,~1H NMR, thermoanalysis and XRD. At the same time, the bioactivity of some compounds against several plant and animal bacteria has been tested and gained the virulence recursive equation. The active mechanism and intensity of the compounds with CT-DNA were analyzed by UV, FS and fluorescence quench titration. The concrete content is following:
1. The synthesis of organic ligands: Three organic aryl-acylhydrazone ligands have been synthesized with different carboxyl group which was mono- and di-hydrazones firstly. They are bi-[N-(propionic acid)] terephthalal diacylhydrazone (C_(14)H_(14)H_4O_6, L2), bi(2-ketoglutaric acid) terephthalal diacylhydrazone (C_(18)H_(18)N_4O_(10), L3) and (2-ketoglutaric acid)-salicyloyl hydrazone(C_(12)H_(12)N_2O_6, L4), and obtained the crystal structures of two ligands Ll(N-(2-propionic acid)-salicyloyl hydrazone, C_(10)H_(10)N_2O_4) and L2. Four ligands determined by elemental analysis, IR, ~1H NMR, MS, UV, FS and thermoanalysis.
2. The binary complexes of rare earth or transition metal with L1: In mixed solution, Five unreported complexes of N-(2-propionic acid)-salicyloyl hydrazone with RE(NO_3)_3·nH_2O(RE= La、Pr、Gd、Er) and CuCl_2·2H_2O respectively were synthesized, And the crystal structures were determined by X-ray single crystal diffraction. The complex structures are different. Two negative univalent tridentate ligands were coordinated viaμ_2- bridging mode in the binuclear praseodymium(III) complex. The coordination number is decrease with rare earth ion radius decrease. The coordination modes and valence states are variety in the complexes. And the fluorescent properties were discussed.
3. The ternary supermolecule complexes of rare earth or transition metal with L1 and polypyridyl (bipy/phen): In mixed solution, sixteen complexes of N-(2-propionic acid)-salicyloyl hydrazone with rare earth nitrate(RE= La、Ce、Pr、Nd、Sm、Eu、Gd、Tb、Dy、Er、Yb、Lu and Y) and transition metal(Ni~(2+),Cd~(2+))were synthesized firstly. The component and structure of all rare earth complexes are similar except the crystal lattice waters. The crystal structures of three representative complexes(RE = Nd、Eu、Dy) were determined. RE(III) is 9-coordinated by carboxyl O and acyl O atoms and azomethine N atoms of two ligands (H_2L and HL forms) and O atom from three water molecules. The coordination polyhedron around RE(III) was described as a monocapped square antiprism. One free 2, 2-dipyridyl and two lattice waters connecting with coordinated water and ligands by hydrogen bonds lie in the crystal cell. The complexes formed a three-dimensional super molecule in space through hydrogen bonds. The structures of [NiHL(bipy)H_2O] and [NiHL(phen)H_2O]H_2O are similar where HL is the tridentate ligand the N-(2-propionic acid)-salicyloyl hydrazone, bipy/phen a bidentate 2, 2-dipyridyl/1,10- and one water, thus generating a distorted octahedral coordination for Ni(II). To binuclear complex [CdHL(bipy)(H_2O)_2]_2·2H_2O, Two center ions Cd(II) are connected by twoμ_2-bridging carboxyl oxygen. The Cd(II) is seven-coordinated via one water, one tridentate ligand and one bidentate bipy. The coordination polyhedron of Cd(II) can be described as a distorted quadrilateral- triangle underside. The strongπ-πstacking interaction exist between two adjacent bipys.
4. The binary complexes of rare earth or transition metal with L2: Fifteen unreported binucleus complexes of bi[N-(propionic acid)] terephthalal diacylhydrazone with rare earth nitrate(RE= La、Ce、Pr、Nd、Sm、Eu、Gd、Tb、Dy、Er、Yb、Lu and Y)and transition metal(Cu~(2+), Zn~(2+))were synthesized. The component and structure of all rare earth complexes are similar except the crystal lattice waters by several characterization. The crystal structure of binuclear Cu complex was determined.
5. The binary complexes of rare earth with L4: Thirteen unreported complexes of (2-ketoglutaric acid)-salicyloyl hydrazone with RE(NO_3)_3·nH_2O (RE= La、Ce、Pr、Nd、Sm、Eu、Gd、Tb、Dy、Er、Yb、Lu and Y) were synthesized. The component and structure of all rare earth complexes are same but the crystal lattice waters in which are different by several characterization and discussed the bonding feature and spectral properties.
6. The biologic activity: The bioactivity of some compounds against three plant bacteria(Botrytis cirerea Pers.ex Tris., Alternaria alternata (Fries) keissler and Wheat rust). The animal bacteria are Gram-positive bacteria (Staphylococcin aureus), Gram-negative bacteria (Coliforms and Salmonella typhimurium) and leukemia K562. The result showed that all compounds possessed a certain bacteriostasis activity against three plant bacteria and Coliforms. By relativity analyses, the virulence regress equations were obtained for L2 and Dy (H_2L)(HL)·0.5bipy5H_2O. And the compounds are no palpable effect against Staphylococcin aureus, Salmonella typhimurium and leukemia K562.
7. The binding mechanism and intensity with CT-DNA were analyzed by UV, FS and fluorescence quench titration which can offer theoretical foundation for further study of bacteriostatic mechanism.
1．有机小分子配体的合成：首次合成了3种含不同羧基的单酰腙和双酰腙有机配体(二丙酮酸缩对苯二甲双酰腙L2，二a-酮戊二酸缩对苯甲双酰腙L3，a-酮戊二酸缩水杨酰腙L4)，培养得到了两个配体的晶体结构(2-羰基丙酸水杨酰腙L1，L2)。通过红外、核磁、质谱、紫外-可见、荧光光谱、热重分析对其进行了表征。
2．L1分别与稀土、过渡金属形成的二元配合物：在混合溶剂中，2-羰基丙酸水杨酰腙(C_(10)H_(10)N_2O_4，H_3L)分别与RE(NO_3)_3·nH_2O (RE=La、Pr、Gd、Er)和过渡金属盐(CuCl_2·2H_2O)反应，合成了5种未见文献报道的配合物，测定了其晶体结构，稀土配合物的结构不尽相同，随着稀土离子半径的递减，其配位数也随之递减，配体的配位方式多样，表现出不同的价态；在Pr的配合物中，配体的羧基氧以μ_2形式桥连两个中心离子，形成双核配合物。而且并讨论了配合物的荧光性质。
3．L1和多吡啶类配体(2，2’-联吡啶bipy／1，10-菲啰啉phen)分别与稀土、过渡金属形成的超分子配合物：在混合溶剂中，以2-羰基丙酸水杨酰腙(C_(10)H_(10)N_2O_4，H_3L)，bipy分别与RE(NO_3)_3·nH_2O(RE=La、Ce、Pr、Nd、Sm、Eu、Gd、Tb、Dy、Er、Yb、Lu和Y)和过渡金属(Ni~(2+)，Cd~(2+))反应，合成了16种未见文献报道的配合物，经系统表征确定了配合物的组成和结构。稀土配合物具有相同的结构[RE(H_2L)(HL)(H_2O)_3]·0.5bipy·nH_2O，测定了三个代表性配合物的结构(Nd，Eu，Dy)，每个单元均为两个结构相似的9配位配合物，每个配合物中有两个2-羰基丙酸水杨酰腙和三个水分子参与了配位，同时还有一个bipy分子和水分子游离于晶格中，形成了三维网状的超分子化合物。过渡金属配合物NiHL(bipy)H_2O和[NiHL(phen)H_2O]·H_2O具有相似的结构，在空间呈畸变的八面体。双核配合物[CdHL(bipy)(H_2O)_2]_2·2H_2O中心金属离子配位数为7，在空间呈三方底四方底结构，且联吡啶环之间存在π-π堆积。
4．L2分别与稀土、过渡金属形成的二元配合物：在混合溶剂中，以丙酮酸缩对苯二甲双酰腙(C_(14)H_(14)N_4O_6)分别与RE(NO_3)_3·nH_2O((RE=La、Ce、Pr、Nd、Sm、Eu、Gd、Tb、Dy、Er、Yb、Lu和Y))和过渡金属盐(Cu~(2+)，Zn~(2+))反应，合成了15种未见文献报道的配合物，经系统表征确定了配合物的组成和结构，由于配体本身的结构特征使得该系列全为双核配合物，探讨了其成键特点及光谱性质。测试了配合物Cu_2(L)(pyridine)_6·2H_2O的晶体结构，配体采用脱氢共轭方式配位。
5．L4与稀土形成的二元配合物：在混合溶剂中，a-酮戊二酸缩水杨酰腙分别与RE(NO_3)_3·nH_2O(RE=La、Pr、Nd、Sm、Eu、Gd、Tb、Dy、Er、Yb、Lu和Y))反应，合成了13种未见文献报道的配合物，经系统表征确定了配合物的组成和结构，探讨了配合物的成键特点及光谱性质。
6．生物活性实验：选取不同类型具代表性的配体和配合物对动植物菌种进行生物活性筛选试验，植物菌种采用番茄灰霉病菌、烟草赤星病菌和小麦条锈病菌，方法是生长速率法和孢子萌发法。动物采用革兰氏阳性菌(金黄色葡萄球菌)，革兰氏阴性菌(大肠杆菌、鼠伤寒沙门菌)及人红白血病细胞系K562细胞。结果表明，配体及配合物对三种植物病菌及动物菌种大肠杆菌均有不同程度的抑菌活性，对效果较好的Dy(H_2L)(HL)·0.5bipy·5H_2O和L2进行了相关性分析，得到了毒力回归方程。对金黄色葡萄球菌、鼠伤寒沙门菌及人红白血病细胞系K562细胞抑制效果不明显。
7．用紫外-可见光谱、荧光光谱，荧光淬灭滴定等方法研究了三元超分子配合物及部分配体与小牛胸腺DNA的结合强度及机理，为进一步研究抑菌机理提供依据。
The main organic ligands are aryl-acylhydrazones in the paper. On the base of reading abundant literature and analyzing development state, four series-fifty compounds about aryl-acylhydrazones and their mono- and binuclear complexes were synthesized, and characterized by elemental analysis, IR, UV-Vis, FS,~1H NMR, thermoanalysis and XRD. At the same time, the bioactivity of some compounds against several plant and animal bacteria has been tested and gained the virulence recursive equation. The active mechanism and intensity of the compounds with CT-DNA were analyzed by UV, FS and fluorescence quench titration. The concrete content is following:
1. The synthesis of organic ligands: Three organic aryl-acylhydrazone ligands have been synthesized with different carboxyl group which was mono- and di-hydrazones firstly. They are bi-[N-(propionic acid)] terephthalal diacylhydrazone (C_(14)H_(14)H_4O_6, L2), bi(2-ketoglutaric acid) terephthalal diacylhydrazone (C_(18)H_(18)N_4O_(10), L3) and (2-ketoglutaric acid)-salicyloyl hydrazone(C_(12)H_(12)N_2O_6, L4), and obtained the crystal structures of two ligands Ll(N-(2-propionic acid)-salicyloyl hydrazone, C_(10)H_(10)N_2O_4) and L2. Four ligands determined by elemental analysis, IR, ~1H NMR, MS, UV, FS and thermoanalysis.
2. The binary complexes of rare earth or transition metal with L1: In mixed solution, Five unreported complexes of N-(2-propionic acid)-salicyloyl hydrazone with RE(NO_3)_3·nH_2O(RE= La、Pr、Gd、Er) and CuCl_2·2H_2O respectively were synthesized, And the crystal structures were determined by X-ray single crystal diffraction. The complex structures are different. Two negative univalent tridentate ligands were coordinated viaμ_2- bridging mode in the binuclear praseodymium(III) complex. The coordination number is decrease with rare earth ion radius decrease. The coordination modes and valence states are variety in the complexes. And the fluorescent properties were discussed.
3. The ternary supermolecule complexes of rare earth or transition metal with L1 and polypyridyl (bipy/phen): In mixed solution, sixteen complexes of N-(2-propionic acid)-salicyloyl hydrazone with rare earth nitrate(RE= La、Ce、Pr、Nd、Sm、Eu、Gd、Tb、Dy、Er、Yb、Lu and Y) and transition metal(Ni~(2+),Cd~(2+))were synthesized firstly. The component and structure of all rare earth complexes are similar except the crystal lattice waters. The crystal structures of three representative complexes(RE = Nd、Eu、Dy) were determined. RE(III) is 9-coordinated by carboxyl O and acyl O atoms and azomethine N atoms of two ligands (H_2L and HL forms) and O atom from three water molecules. The coordination polyhedron around RE(III) was described as a monocapped square antiprism. One free 2, 2-dipyridyl and two lattice waters connecting with coordinated water and ligands by hydrogen bonds lie in the crystal cell. The complexes formed a three-dimensional super molecule in space through hydrogen bonds. The structures of [NiHL(bipy)H_2O] and [NiHL(phen)H_2O]H_2O are similar where HL is the tridentate ligand the N-(2-propionic acid)-salicyloyl hydrazone, bipy/phen a bidentate 2, 2-dipyridyl/1,10- and one water, thus generating a distorted octahedral coordination for Ni(II). To binuclear complex [CdHL(bipy)(H_2O)_2]_2·2H_2O, Two center ions Cd(II) are connected by twoμ_2-bridging carboxyl oxygen. The Cd(II) is seven-coordinated via one water, one tridentate ligand and one bidentate bipy. The coordination polyhedron of Cd(II) can be described as a distorted quadrilateral- triangle underside. The strongπ-πstacking interaction exist between two adjacent bipys.
4. The binary complexes of rare earth or transition metal with L2: Fifteen unreported binucleus complexes of bi[N-(propionic acid)] terephthalal diacylhydrazone with rare earth nitrate(RE= La、Ce、Pr、Nd、Sm、Eu、Gd、Tb、Dy、Er、Yb、Lu and Y)and transition metal(Cu~(2+), Zn~(2+))were synthesized. The component and structure of all rare earth complexes are similar except the crystal lattice waters by several characterization. The crystal structure of binuclear Cu complex was determined.
5. The binary complexes of rare earth with L4: Thirteen unreported complexes of (2-ketoglutaric acid)-salicyloyl hydrazone with RE(NO_3)_3·nH_2O (RE= La、Ce、Pr、Nd、Sm、Eu、Gd、Tb、Dy、Er、Yb、Lu and Y) were synthesized. The component and structure of all rare earth complexes are same but the crystal lattice waters in which are different by several characterization and discussed the bonding feature and spectral properties.
6. The biologic activity: The bioactivity of some compounds against three plant bacteria(Botrytis cirerea Pers.ex Tris., Alternaria alternata (Fries) keissler and Wheat rust). The animal bacteria are Gram-positive bacteria (Staphylococcin aureus), Gram-negative bacteria (Coliforms and Salmonella typhimurium) and leukemia K562. The result showed that all compounds possessed a certain bacteriostasis activity against three plant bacteria and Coliforms. By relativity analyses, the virulence regress equations were obtained for L2 and Dy (H_2L)(HL)·0.5bipy5H_2O. And the compounds are no palpable effect against Staphylococcin aureus, Salmonella typhimurium and leukemia K562.
7. The binding mechanism and intensity with CT-DNA were analyzed by UV, FS and fluorescence quench titration which can offer theoretical foundation for further study of bacteriostatic mechanism.
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