芳酰腙类配合物的合成、晶体结构及性质研究
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摘要
本文基于金属元素与具有生物功能的含肽键芳酰腙类配体形成配合物的协同作用和应用前景，合成了24种未见文献报道的芳酰腙与过渡及稀土元素的配合物(含与另一配体的混配体配合物)，培养出了五个配合物的单晶；研究了配体及其配合物的荧光性质和抑菌活性，并初探了配合物与CT-DNA的作用机理，具体如下：
1．合成：在水醇混合溶剂中，以N-(2-异丙酸)．水杨酰腙(C_(10)H_(10)N_2O_4，H_3L~1)为配体与金属离子Cu~(2+)、Ni~(2+)、Zn~(2+)、Cr~(2+)、Mn~(2+)、Ni~(2+)、Cd~(2+)和Sm~(3+)的盐反应，合成了8种新颖的配合物，并且得到了其中3个配合物的单晶；以H_3L~、对羟基苯甲酸(phba)为配体与稀土盐反应，制得了4个新颖的稀土混配体配合物，培养出1个配合物的单晶;以N-(2-乙酸)水杨酰腙(H_3L~2)为配体和金属盐反应，合成出了11种金属配合物；以N-(2-乙酸)水杨酰腙(H_3L~2)、咪唑(C_3H_4N_2，Jm)为配体与过渡金属离子Cd~(2+)反应，合成了1种新颖的混配体配合物Cd_6(HE~2)_6(Im)_(12)(H_2O)_(10)，并且得到了该配合物的单晶。
2．表征：通过元素分析、红外光谱、紫外光谱、荧光光谱、X-射线粉末衍射、X-射线单晶衍射以及TG-DTG等手段对配合物的成键情况、结构和物理化学性质进行了表征，确定了配合物的组成并测定了部分配合物的晶体结构。
3．性质：在室温下研究了2种配体H_3L~1、H_3L~2及9种配合物Cd_6(HL~2)_6(Im)_(12)(H_2O)_(10)、Cd(H_2L~1)_2·6H_2O、Cd(H_2L~2)_2·3H_2O、Eu(H_2L~2)(HL~2)·4H_2O、[Sm_2(H_2L~1)_2(HL~1)_2(H_2O)_4]、[Pr_2(H_2L~1)_2(phba)_4(H_2O)_2]·2H_2O、[(Nd_2(H_2L~1)_2(phba)_4(H_2O)_2]·2H_2O、[(Sm_2(H_2L~1)_2(phba)_4(H_2O)_2]·5H_2O、[Eu_2(H_2L~1)_2(phba)·4(H_2O)_2]的固体荧光性质，结果显示所测试的所有Cd(Ⅱ)配合物均具有出优良的荧光性质，是潜在的荧光材料；用孢子萌发法测定了5种药剂H_3L~2、Y(H_2L~2)(HL~2)·4H_2O、Er(H_2L~2)(HL~2)·4H_2O、Y(NO_3)_3·4H_2O和Er(NO_3)_3·5H_2O对小麦条锈病菌孢子萌发的抑制作用。结果显示，配合物的抑菌活性明显优于配体和稀土硝酸盐；用生长速率法测定了6种药剂Y(H_2L~2)(HL~2)·2H_2O、H_3L~2、phba、[(Pr_2(H_2L~1)_2(phba)_4(H_2O)_2]·2H_2O、H_3L~1和Y(NO_3)_3·4H_2O对苹果树腐烂病病原真菌生长速率的影响。结果显示，配体H_3L~1和phba对该病菌有很好的抑菌效果，配合物均不理想。
4．配合物与CT-DNA作用的光谱研究：通过紫外光谱、荧光光谱和荧光猝灭光谱研究了配合物与CT-DNA的作用机理，结果显示配合物Cd_6(HL~2)_6(Im)_(12)(H_2O)_(10)、Co(H_2L~1)_2·3H_2O和[Sm(H_2L~1)(HL~1)(H_2O_4]是以插入方式与CT-DNA相互作用的，而配合物Cd(H_2L~1)_2·6H_2O与DNA的作用方式除部分插入式结合以外还存在静电式结合，配合物Zn(H_2L~1)_2和[(Pr_2(H_2L~1)_2(phba)_4(H_2O)_2]·2H_2O是以表面沟槽方式结合的。
According to the synergies and the applied prospect of the aryl-aroylhydrazone complexes containing peptide bond, twenty-four novel metal complexes with aryl-acylhydrazones were synthesized (containing the mixed ligands complexes with the other ligand), and five single crystals were also obtained. At the same time, the bioactivity and fluorescent property of some compounds have been studied. In addition, the mechanism of the interaction between complexes and calf thymus DNA was also probed into primarily.The main work is as follows
1. Synthesis. In a mixed solution of aqua-ethanol, eight novel metal ion (Cu~(2+),Ni~(2+),Zn~(2+),Cr~(2+),Mn~(2+),Ni~(2+),Cd~(2+),Sm~(3+) ) complexes with N-(2-propionic acid)-salicyloylhydrazone (C_(10)H_(10)N_2O_4,H_3L~1) have been synthesized, at the same time, and three single crystals are also obtained. Four rare earth complexes containing 4-hydroxybenzoic acid (phba) and H_3L~1 have been synthesized. One crystal of them has been obtained.It addition, eleven metal complexes with N-(2-propionic acid)-salicyloyl hydrazone also have been synthesized in mixed solution of aqua-ethano. Moreover, a novel cadmium (Ⅱ) complex with N-(2-acetic acid)-salicyloyl hydrazone (C_9H_8N_2O_4, H_3L~2) and imidazole (Im) was prepared and characterized. The crystal structures of ligand H_3L~2 and cadmium (Ⅱ) complex were determined by X-ray single crystal diffractometry.
2. Characterization. The structures and photo-physical properties of above synthesized complexes have been characterized by elemental analyses, IR spectrum, UV-Vis spectrum, Fluorescent spectrum, X-ray powder diffraction, X-ray single diffraction and TG-DTG? the composing of the complexes are confirmed. Furthermore, the crystal structures of some complexes have been determined.
3. Property. The solid fluorescent properties of two ligands (H_3L~1,H_3L~2) and nine complexes (Cd(H_2L~1)_2·6H_2O,Cd_6(HL~2)_6(Im)_(12)(H_2O)_(10),Cd(H_2L~2)_2·3H_2O,Eu(H_2L~2)(HL~2)·4H_2O, [Sm_2(H_2L~1)_2(HL~1)_2(H_2O)_4],[Pr_2(H_2L~1)_2(phba)_4(H_2O)_2]·2H_2O,[(Nd_2(H_2L~1)_2(phba)_4(H_2O)_2]·2H_2O, [(Sm_2(H_2L~1)_2(phba)_4(H_2O)_2]·5H_2O,[Eu_2(H_2L~1)_2(phba)_4(H_2O)_2]·4H_2O) were researched in the room temperature, and the results showed that all cadmium (Ⅱ) complexes took on splendiferous fluorescent property and are potential fluorescent material. The compounds H_3L~2, Y(H_2L~2)(HL~2)·4H_2O, Er(H_2L~2)(HL~2)·4H_2O, Y(NO_3)_3·4H_2O and Er(NO_3)_3·5H_2O are selected to test for antimicrobial activity against Puccinia striiformis Westendorp by spore sprout method,and the results revealed that the complexes showed better bioactivity than ligand and rare earth nitrate. The bioactivity against the apple canker of the compounds Y(H_2L~2)(HL~2)·4H_2O, H_3L~2, Y(NO_3)_3·4H_2O, [(Pr_2(H_2L~1)_2(phba)_4(H_2O)_2]·2H_2O, H_3L~1andphba are tested by Photoelectric Turbidimetry method, and the reults showed that the ligand H_3L~1 and phba possessed excellent bioactivity.
4. Studies on the Interaction of the Complexes with DNA by Spectra: DNA binding mechanisms of the complexes are observed by UV-Vis spectrum and fluorescent spectrum analysis.The results showed that the complexes Cd_6(HL~2)_6(Im)_(12)(H_2O)_(10),Co(H_2L~1)_2·3H_2O and [Sm(H_2L~1)(HL~1)(H_2O)_4] possibly are bound to calf thymus DNA mainly by intercalation,while complex Cd(H_2L~1)_2·6H_2O interacts with calf thymus DNA by part intercalation and electrostatic effection. The complexes Zn(H_2L~1)2 and [(Pr_2(H_2L~1)_2(phba)_4(H_2O)_2]·2H_2O mainly interacts with calf thymus DNA by groove binding.
1．合成：在水醇混合溶剂中，以N-(2-异丙酸)．水杨酰腙(C_(10)H_(10)N_2O_4，H_3L~1)为配体与金属离子Cu~(2+)、Ni~(2+)、Zn~(2+)、Cr~(2+)、Mn~(2+)、Ni~(2+)、Cd~(2+)和Sm~(3+)的盐反应，合成了8种新颖的配合物，并且得到了其中3个配合物的单晶；以H_3L~、对羟基苯甲酸(phba)为配体与稀土盐反应，制得了4个新颖的稀土混配体配合物，培养出1个配合物的单晶;以N-(2-乙酸)水杨酰腙(H_3L~2)为配体和金属盐反应，合成出了11种金属配合物；以N-(2-乙酸)水杨酰腙(H_3L~2)、咪唑(C_3H_4N_2，Jm)为配体与过渡金属离子Cd~(2+)反应，合成了1种新颖的混配体配合物Cd_6(HE~2)_6(Im)_(12)(H_2O)_(10)，并且得到了该配合物的单晶。
2．表征：通过元素分析、红外光谱、紫外光谱、荧光光谱、X-射线粉末衍射、X-射线单晶衍射以及TG-DTG等手段对配合物的成键情况、结构和物理化学性质进行了表征，确定了配合物的组成并测定了部分配合物的晶体结构。
3．性质：在室温下研究了2种配体H_3L~1、H_3L~2及9种配合物Cd_6(HL~2)_6(Im)_(12)(H_2O)_(10)、Cd(H_2L~1)_2·6H_2O、Cd(H_2L~2)_2·3H_2O、Eu(H_2L~2)(HL~2)·4H_2O、[Sm_2(H_2L~1)_2(HL~1)_2(H_2O)_4]、[Pr_2(H_2L~1)_2(phba)_4(H_2O)_2]·2H_2O、[(Nd_2(H_2L~1)_2(phba)_4(H_2O)_2]·2H_2O、[(Sm_2(H_2L~1)_2(phba)_4(H_2O)_2]·5H_2O、[Eu_2(H_2L~1)_2(phba)·4(H_2O)_2]的固体荧光性质，结果显示所测试的所有Cd(Ⅱ)配合物均具有出优良的荧光性质，是潜在的荧光材料；用孢子萌发法测定了5种药剂H_3L~2、Y(H_2L~2)(HL~2)·4H_2O、Er(H_2L~2)(HL~2)·4H_2O、Y(NO_3)_3·4H_2O和Er(NO_3)_3·5H_2O对小麦条锈病菌孢子萌发的抑制作用。结果显示，配合物的抑菌活性明显优于配体和稀土硝酸盐；用生长速率法测定了6种药剂Y(H_2L~2)(HL~2)·2H_2O、H_3L~2、phba、[(Pr_2(H_2L~1)_2(phba)_4(H_2O)_2]·2H_2O、H_3L~1和Y(NO_3)_3·4H_2O对苹果树腐烂病病原真菌生长速率的影响。结果显示，配体H_3L~1和phba对该病菌有很好的抑菌效果，配合物均不理想。
4．配合物与CT-DNA作用的光谱研究：通过紫外光谱、荧光光谱和荧光猝灭光谱研究了配合物与CT-DNA的作用机理，结果显示配合物Cd_6(HL~2)_6(Im)_(12)(H_2O)_(10)、Co(H_2L~1)_2·3H_2O和[Sm(H_2L~1)(HL~1)(H_2O_4]是以插入方式与CT-DNA相互作用的，而配合物Cd(H_2L~1)_2·6H_2O与DNA的作用方式除部分插入式结合以外还存在静电式结合，配合物Zn(H_2L~1)_2和[(Pr_2(H_2L~1)_2(phba)_4(H_2O)_2]·2H_2O是以表面沟槽方式结合的。
According to the synergies and the applied prospect of the aryl-aroylhydrazone complexes containing peptide bond, twenty-four novel metal complexes with aryl-acylhydrazones were synthesized (containing the mixed ligands complexes with the other ligand), and five single crystals were also obtained. At the same time, the bioactivity and fluorescent property of some compounds have been studied. In addition, the mechanism of the interaction between complexes and calf thymus DNA was also probed into primarily.The main work is as follows
1. Synthesis. In a mixed solution of aqua-ethanol, eight novel metal ion (Cu~(2+),Ni~(2+),Zn~(2+),Cr~(2+),Mn~(2+),Ni~(2+),Cd~(2+),Sm~(3+) ) complexes with N-(2-propionic acid)-salicyloylhydrazone (C_(10)H_(10)N_2O_4,H_3L~1) have been synthesized, at the same time, and three single crystals are also obtained. Four rare earth complexes containing 4-hydroxybenzoic acid (phba) and H_3L~1 have been synthesized. One crystal of them has been obtained.It addition, eleven metal complexes with N-(2-propionic acid)-salicyloyl hydrazone also have been synthesized in mixed solution of aqua-ethano. Moreover, a novel cadmium (Ⅱ) complex with N-(2-acetic acid)-salicyloyl hydrazone (C_9H_8N_2O_4, H_3L~2) and imidazole (Im) was prepared and characterized. The crystal structures of ligand H_3L~2 and cadmium (Ⅱ) complex were determined by X-ray single crystal diffractometry.
2. Characterization. The structures and photo-physical properties of above synthesized complexes have been characterized by elemental analyses, IR spectrum, UV-Vis spectrum, Fluorescent spectrum, X-ray powder diffraction, X-ray single diffraction and TG-DTG? the composing of the complexes are confirmed. Furthermore, the crystal structures of some complexes have been determined.
3. Property. The solid fluorescent properties of two ligands (H_3L~1,H_3L~2) and nine complexes (Cd(H_2L~1)_2·6H_2O,Cd_6(HL~2)_6(Im)_(12)(H_2O)_(10),Cd(H_2L~2)_2·3H_2O,Eu(H_2L~2)(HL~2)·4H_2O, [Sm_2(H_2L~1)_2(HL~1)_2(H_2O)_4],[Pr_2(H_2L~1)_2(phba)_4(H_2O)_2]·2H_2O,[(Nd_2(H_2L~1)_2(phba)_4(H_2O)_2]·2H_2O, [(Sm_2(H_2L~1)_2(phba)_4(H_2O)_2]·5H_2O,[Eu_2(H_2L~1)_2(phba)_4(H_2O)_2]·4H_2O) were researched in the room temperature, and the results showed that all cadmium (Ⅱ) complexes took on splendiferous fluorescent property and are potential fluorescent material. The compounds H_3L~2, Y(H_2L~2)(HL~2)·4H_2O, Er(H_2L~2)(HL~2)·4H_2O, Y(NO_3)_3·4H_2O and Er(NO_3)_3·5H_2O are selected to test for antimicrobial activity against Puccinia striiformis Westendorp by spore sprout method,and the results revealed that the complexes showed better bioactivity than ligand and rare earth nitrate. The bioactivity against the apple canker of the compounds Y(H_2L~2)(HL~2)·4H_2O, H_3L~2, Y(NO_3)_3·4H_2O, [(Pr_2(H_2L~1)_2(phba)_4(H_2O)_2]·2H_2O, H_3L~1andphba are tested by Photoelectric Turbidimetry method, and the reults showed that the ligand H_3L~1 and phba possessed excellent bioactivity.
4. Studies on the Interaction of the Complexes with DNA by Spectra: DNA binding mechanisms of the complexes are observed by UV-Vis spectrum and fluorescent spectrum analysis.The results showed that the complexes Cd_6(HL~2)_6(Im)_(12)(H_2O)_(10),Co(H_2L~1)_2·3H_2O and [Sm(H_2L~1)(HL~1)(H_2O)_4] possibly are bound to calf thymus DNA mainly by intercalation,while complex Cd(H_2L~1)_2·6H_2O interacts with calf thymus DNA by part intercalation and electrostatic effection. The complexes Zn(H_2L~1)2 and [(Pr_2(H_2L~1)_2(phba)_4(H_2O)_2]·2H_2O mainly interacts with calf thymus DNA by groove binding.
引文
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