基于DNA相互作用的多核配合物的合成、结构及抗肿瘤活性研究
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摘要
本论文以DNA为靶点,以寻找新结构类型的高效、低毒的抗癌、抗菌多核配合物为目标,从分子设计出发,共合成得到了16个化合物的单晶结构,对其进行了结构表征,探讨了结构影响因素,并研究了其超分子结构;采用紫外-可见吸收光谱法、荧光光谱法、电化学和粘度法,从分子水平上研究了所得配合物与DNA的相互作用;在细胞水平上,研究了草酰胺桥联双核配合物的抗菌和抗肿瘤活性。本论文主要包括以下三部分:
一、合成得到了一个草酰胺配体硝酸盐的单晶结构,[H_4dmaeoxd](NO_3)_2 (1) [dmaeoxd = N,N'-双(二甲基氨基乙基)草酰胺];通过调控金属离子的种类、端基配体、抗衡阴离子、溶剂、pH值等条件定向合成了四个反式草酰胺桥联双核铜配合物:[Cu_2(dmaeoxd)(bpy)_2](ClO_4)_2 (2)、[Cu_2(dmaeoxd)(phen)_2](ClO_4)_2 (3)、、[Cu_2(dmaeoxd)(Me_2phen)_2](ClO_4)_2 (4)、[Cu_2(dmaeoxd)(SCN)_2(H_2O)_2] (5);四个顺式草酰胺桥联同/异双核配合物:[Ni(dmaeoxd)Ni(dmbp)_2](ClO_4)_2 (6)、[Cu(dmaeoxd)Ni(bpy)_2](ClO_4)_2·2CH_3OH (7)、[Cu(dmaeoxd)Zn(bpy)_2]- (ClO_4)_2·2H_2O (8)、[Cu(dmaeoxd)(H_2O)Ni(phen)_2](ClO_4)_2.0.5CH_3OH (9);三个一维聚合物: [Cu_2(dmaeoxd)(ox)]_n·nH_2O (10)、[Cu_2(H_2O)_2(dmaeoxd)- (bdc)]_n·4nH_2O (11)、[Cu_2(dmaeob)(H_2O)(phen)]_n(NO_3)_n·2nH_2O (12);一个二维聚合物: [Cu_6(oxen)_3(μ_3-OH)_2(H_2O)_2]_n(ClO_4)_(4n).2nH_2O (13) ;单核钒配合物[VO(ox)(bpy)(H_2O)]·2H_2O (14)、草酸根桥联双核锌配合物[Zn_2(ox)(bpy)_4](ClO_4)_2·H_2O (15)、美洛西康铜配合物[Cu(Miloxicamin)_2]·2DCM (16),利用元素分析、摩尔电导、红外光谱、电子光谱和单晶X-射线衍射对上述所得化合物进行了结构表征,探讨了结构影响因素,并研究了其超分子结构。
二、采用光谱法(电子吸收光谱和荧光光谱)、电化学方法和流体力学法研究了上述化合物与鲱鱼鱼精DNA(HS-DNA)的相互作用,发现大多数配合物与DNA的主要结合模式为嵌插结合,只有配合物(5)(静电结合)和配合物(11)(静电和沟槽结合)除外。此外,本文还研究了金属离子、端基配体种类及草酰胺顺反式结构对DNA相互作用的影响。
三、对所合成的草酰胺桥联双核配合物(反式同双核、顺式同双核、顺式异双核)进行了抗菌和体外细胞毒活性研究。1).采用滤纸片法和液体培养基稀释法研究了它们对几种常见菌的杀菌活性,研究表明,自由配体不具备抗菌活性,形成配合物后均表现出抗菌活性,这为发掘和利用多核配合物的新功能提供了有用的信息,也为进一步探讨此类体系的杀菌机理提供了丰富的素材。2).运用MTT和SRB法对双核配合物进行了体外细胞毒性试验,发现大多数配合物具有较强的细胞毒活性,其中DNA结合活性最好的反式双核铜配合物(3)和(4),对人肝癌细胞(SMMC-7721)和人肺腺癌细胞(A549)的半数抑制浓度(IC50)均达到20~30 ng/mL。
上述工作不仅丰富了无机药物化学的研究内容,而且为高效、低毒的无机化疗药物的设计与合成提供了非常有价值的参考信息。
This dissertation aims at finding anticancer and antibacterial polynuclear complexes targeting DNA with high activity and low toxicity. Sixteen compounds were synthesized, and characterized by means of X-ray single crystal diffraction, elemental analysis, molar conductivity and IR, and the influencing factors on structures of the compounds have been investigated. The actions of these compounds to DNA were also investigated by spectral, electrochemical and hydromechanical methods. Finally, the cytotoxic and antibacterial activities of the oxamido-bridged binuclear complexes were studied in vitro.
. This dissertation consists of three sections as follows:
1. The crystal structure of a oxamide dinitrate, (1) [H_4dmaeoxd](NO_3)_2 [H_2dmaeoxd = N,N'-bis[2-(dimethylamino)ethyl]oxamide], has been obtained. The diversity of complexes with different structures is carried out by successful synthetic strategy of controlling species of metal ions, counter anions, pH values and solvents in the course of synthesis. Four dinuclear complexes bridged by trans-dmaeoxd2-: [Cu_2(dmaeoxd)(bpy)_2](ClO_4)_2 (2), [Cu_2(dmaeoxd)(phen)_2](ClO_4)_2 (3),、[Cu_2(dmaeoxd)(Me_2phen)_2](ClO_4)_2 (4), [Cu_2(dmaeoxd)(SCN)_2(H_2O)_2] (5); Four dinuclear complexes bridged by cis-dmaeoxd2-: [Ni(dmaeoxd)Ni(dmbp)_2](ClO_4)_2 (6), [Cu(dmaeoxd)Ni(bpy)_2](ClO_4)_2·2CH_3OH (7), [Cu(dmaeoxd)Zn(bpy)_2]- (ClO_4)_2·2H_2O (8), [Cu(dmaeoxd)(H_2O)Ni(phen)_2](ClO_4)_2.0.5CH_3OH (9); three 1-D polynuclear complexes: [Cu_2(dmaeoxd)(ox)]_n·nH_2O (10), [Cu_2(H_2O)_2(dmaeoxd)- (bdc)]_n·4nH_2O (11), [Cu_2(dmaeob)(H_2O)(phen)]_n(NO_3)_n·2nH_2O (12); one 2-D polynuclear complex,[Cu_6(oxen)_3(μ_3-OH)_2(H_2O)_2]_n(ClO_4)_(4n).2nH_2O (13); the others: [VO(ox)(bpy)(H_2O)]·2H_2O (14), [Zn_2(ox)(bpy)_4](ClO_4)_2·H_2O (15), [Cu(Miloxicamin)_2]·2DCM (16) have been synthesized and characterized by X-ray single crystal diffraction, elemental analysis, IR spectra. The coordination mode and supermolecular structure of the compounds were also studied.
2. DNA binding studies of the compounds with HS-DNA have been studied by the spectroscopic (absorption and emission spectra), electrochemical and hydromechanical measurements. The results show that the interaction mode of most complexes is intercalation, except for complex (5) and complex (11). The effects of metal ions, terminal ligands and cis/trans conformation of oxamide on DNA interactions were also studied.
3. The cytotoxic and antibacterial activities of the oxamido-bridged binuclear complexes (trans-homo-, cis-homo- and cis-heterobinuclear) were studied in vitro. 1). The antibacterial activities of the complexes were tested by the paper disc method and the microdilution broth method, and all the complexes display antibacterial activities. 2). The cytotoxicities of the complexes were tested by MTT and SRB methods. The results show that most of the complexes have the cytotoxic activities. Complexes (3) and (4) with the strongest DNA binding activities have the strongest effects on SMMC-7721 and A549 cell lines, with the IC50 = 20~30 ng/mL.
These researches not only enriched the content of inorganic medicinal chemistry, but also supplied valuable information for design and synthesis of inorganic chemotherapeutic medicine with high activity and low toxicity.
一、合成得到了一个草酰胺配体硝酸盐的单晶结构,[H_4dmaeoxd](NO_3)_2 (1) [dmaeoxd = N,N'-双(二甲基氨基乙基)草酰胺];通过调控金属离子的种类、端基配体、抗衡阴离子、溶剂、pH值等条件定向合成了四个反式草酰胺桥联双核铜配合物:[Cu_2(dmaeoxd)(bpy)_2](ClO_4)_2 (2)、[Cu_2(dmaeoxd)(phen)_2](ClO_4)_2 (3)、、[Cu_2(dmaeoxd)(Me_2phen)_2](ClO_4)_2 (4)、[Cu_2(dmaeoxd)(SCN)_2(H_2O)_2] (5);四个顺式草酰胺桥联同/异双核配合物:[Ni(dmaeoxd)Ni(dmbp)_2](ClO_4)_2 (6)、[Cu(dmaeoxd)Ni(bpy)_2](ClO_4)_2·2CH_3OH (7)、[Cu(dmaeoxd)Zn(bpy)_2]- (ClO_4)_2·2H_2O (8)、[Cu(dmaeoxd)(H_2O)Ni(phen)_2](ClO_4)_2.0.5CH_3OH (9);三个一维聚合物: [Cu_2(dmaeoxd)(ox)]_n·nH_2O (10)、[Cu_2(H_2O)_2(dmaeoxd)- (bdc)]_n·4nH_2O (11)、[Cu_2(dmaeob)(H_2O)(phen)]_n(NO_3)_n·2nH_2O (12);一个二维聚合物: [Cu_6(oxen)_3(μ_3-OH)_2(H_2O)_2]_n(ClO_4)_(4n).2nH_2O (13) ;单核钒配合物[VO(ox)(bpy)(H_2O)]·2H_2O (14)、草酸根桥联双核锌配合物[Zn_2(ox)(bpy)_4](ClO_4)_2·H_2O (15)、美洛西康铜配合物[Cu(Miloxicamin)_2]·2DCM (16),利用元素分析、摩尔电导、红外光谱、电子光谱和单晶X-射线衍射对上述所得化合物进行了结构表征,探讨了结构影响因素,并研究了其超分子结构。
二、采用光谱法(电子吸收光谱和荧光光谱)、电化学方法和流体力学法研究了上述化合物与鲱鱼鱼精DNA(HS-DNA)的相互作用,发现大多数配合物与DNA的主要结合模式为嵌插结合,只有配合物(5)(静电结合)和配合物(11)(静电和沟槽结合)除外。此外,本文还研究了金属离子、端基配体种类及草酰胺顺反式结构对DNA相互作用的影响。
三、对所合成的草酰胺桥联双核配合物(反式同双核、顺式同双核、顺式异双核)进行了抗菌和体外细胞毒活性研究。1).采用滤纸片法和液体培养基稀释法研究了它们对几种常见菌的杀菌活性,研究表明,自由配体不具备抗菌活性,形成配合物后均表现出抗菌活性,这为发掘和利用多核配合物的新功能提供了有用的信息,也为进一步探讨此类体系的杀菌机理提供了丰富的素材。2).运用MTT和SRB法对双核配合物进行了体外细胞毒性试验,发现大多数配合物具有较强的细胞毒活性,其中DNA结合活性最好的反式双核铜配合物(3)和(4),对人肝癌细胞(SMMC-7721)和人肺腺癌细胞(A549)的半数抑制浓度(IC50)均达到20~30 ng/mL。
上述工作不仅丰富了无机药物化学的研究内容,而且为高效、低毒的无机化疗药物的设计与合成提供了非常有价值的参考信息。
This dissertation aims at finding anticancer and antibacterial polynuclear complexes targeting DNA with high activity and low toxicity. Sixteen compounds were synthesized, and characterized by means of X-ray single crystal diffraction, elemental analysis, molar conductivity and IR, and the influencing factors on structures of the compounds have been investigated. The actions of these compounds to DNA were also investigated by spectral, electrochemical and hydromechanical methods. Finally, the cytotoxic and antibacterial activities of the oxamido-bridged binuclear complexes were studied in vitro.
. This dissertation consists of three sections as follows:
1. The crystal structure of a oxamide dinitrate, (1) [H_4dmaeoxd](NO_3)_2 [H_2dmaeoxd = N,N'-bis[2-(dimethylamino)ethyl]oxamide], has been obtained. The diversity of complexes with different structures is carried out by successful synthetic strategy of controlling species of metal ions, counter anions, pH values and solvents in the course of synthesis. Four dinuclear complexes bridged by trans-dmaeoxd2-: [Cu_2(dmaeoxd)(bpy)_2](ClO_4)_2 (2), [Cu_2(dmaeoxd)(phen)_2](ClO_4)_2 (3),、[Cu_2(dmaeoxd)(Me_2phen)_2](ClO_4)_2 (4), [Cu_2(dmaeoxd)(SCN)_2(H_2O)_2] (5); Four dinuclear complexes bridged by cis-dmaeoxd2-: [Ni(dmaeoxd)Ni(dmbp)_2](ClO_4)_2 (6), [Cu(dmaeoxd)Ni(bpy)_2](ClO_4)_2·2CH_3OH (7), [Cu(dmaeoxd)Zn(bpy)_2]- (ClO_4)_2·2H_2O (8), [Cu(dmaeoxd)(H_2O)Ni(phen)_2](ClO_4)_2.0.5CH_3OH (9); three 1-D polynuclear complexes: [Cu_2(dmaeoxd)(ox)]_n·nH_2O (10), [Cu_2(H_2O)_2(dmaeoxd)- (bdc)]_n·4nH_2O (11), [Cu_2(dmaeob)(H_2O)(phen)]_n(NO_3)_n·2nH_2O (12); one 2-D polynuclear complex,[Cu_6(oxen)_3(μ_3-OH)_2(H_2O)_2]_n(ClO_4)_(4n).2nH_2O (13); the others: [VO(ox)(bpy)(H_2O)]·2H_2O (14), [Zn_2(ox)(bpy)_4](ClO_4)_2·H_2O (15), [Cu(Miloxicamin)_2]·2DCM (16) have been synthesized and characterized by X-ray single crystal diffraction, elemental analysis, IR spectra. The coordination mode and supermolecular structure of the compounds were also studied.
2. DNA binding studies of the compounds with HS-DNA have been studied by the spectroscopic (absorption and emission spectra), electrochemical and hydromechanical measurements. The results show that the interaction mode of most complexes is intercalation, except for complex (5) and complex (11). The effects of metal ions, terminal ligands and cis/trans conformation of oxamide on DNA interactions were also studied.
3. The cytotoxic and antibacterial activities of the oxamido-bridged binuclear complexes (trans-homo-, cis-homo- and cis-heterobinuclear) were studied in vitro. 1). The antibacterial activities of the complexes were tested by the paper disc method and the microdilution broth method, and all the complexes display antibacterial activities. 2). The cytotoxicities of the complexes were tested by MTT and SRB methods. The results show that most of the complexes have the cytotoxic activities. Complexes (3) and (4) with the strongest DNA binding activities have the strongest effects on SMMC-7721 and A549 cell lines, with the IC50 = 20~30 ng/mL.
These researches not only enriched the content of inorganic medicinal chemistry, but also supplied valuable information for design and synthesis of inorganic chemotherapeutic medicine with high activity and low toxicity.
引文
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