不对称N，N'-双取代草酰胺化合物与DNA相互作用及抗肿瘤活性研究
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摘要
小分子化合物与生物大分子DNA的相互作用的研究是化学生物学领域重要的研究课题。DNA是生物体中最重要的遗传物质,它在遗传信息的储存、复制及转录中都具有非常重要的作用。一方面,DNA靶向化合物成为很重要的核酸探针选择对象;另一方面,临床上使用的许多抗癌药物都是以DNA为作用靶点。为了进一步探索和认识DNA的性质、结构、行为、形态,揭示生命的奥秘,人们研究了大量的小分子特别是过渡金属配合物与DNA之间的作用。小分子与DNA的相互作用的研究不仅有利于探索和开发新的核酸探针,而且有助于从分子水平上了解抗癌药物的作用机理,为设计临床上更为有效的抗癌药物提供理论指导。本文采用紫外光谱、荧光光谱、粘度法、电化学方法等研究了一系列草酰胺化合物与DNA的相互作用,总结了化合物与DNA相互作用的构效关系,并在此基础上采用SRB法研究了化合物的体外抗肿瘤活性。
本论文主要包括以下四个方面的工作:
一、设计并合成了4个结构新颖的不对称草酰胺配体,N-(2-羟基苯基)-N′-(3-二甲氨丙基)草酰胺(H3pdmapo) (L1)、N-(2-羟基苯基)-N′-(2-二甲氨乙基)草酰胺(H3pdmaeo) (L2)、N-(2-羟基苯基)-N′-(3-氨丙基)草酰胺(H3papo) (L3)、N-(2-二甲氨乙基)-N’-(3-二甲氨丙基)草酰胺(H2dmaepoxd) (L4),采用质谱、核磁、红外、元素分析等对其结构进行了表征,均为新化合物。
二、由已合成的草酰胺配体做桥联配体,通过变换合成方法,调控金属离子的种类、端基配体、抗衡阴离子、溶剂等条件实现了配合物种类、结构和配位方式的多样性,成功的合成了16个配合物: [Cu_2(pdmapo)(phen)(H_2O)](ClO_4) (1)、[Cu_2(pdmapo)(bpy)(CH_3OH)](ClO_4) (2)、[Cu_2(pdmapo)(dabt)](CH_3OH)(ClO_4) (3)、[Cu_2(pdmaeo)(phen)(H_2O)](CH_3OH)(ClO_4) (4)、[Cu_2(pdmaeo)(dabt)](CH_3OH)(ClO_4) (5)、[Cu_2(papo)(bpy)(H_2O)](ClO_4) (6)、[Cu_2(papo)(dmbpy)(CH_3OH)_0.5(H_2O)_0.5]- (H_2O)_0.5(ClO_4) (7)、[Cu_2(dmapoxd)(phen)_2](ClO_4)_2 (8)、[Cu_2(dmapoxd)(bpy)_2](ClO_4)_2 (9)、[Ni_2(dmapoxd)(bpy)_2(H_2O)_2](ClO_4)_2 (10)、[Cu_2(dmaepoxd)(N_3)_2]_n (11)、[Cu_2(dmaepoxd)(CH_3CH_2OH)(SCN)_2]_2n (12)、[Cu_2(dmaepoxd)(CH_3OH)(SCN)_2]_2n(13)、[Cu_2(dmaepoxd)(NO_2)_2]_n (14)、[Cu_2(dmaepoxd)(pic)_2]_n?nCH_3OH (15)、[Cu_2(dmaepoxd)(pma)]_n (16)。采用不同的培养方法分别得到了质量较好的单晶,解析了化合物的单晶结构,确定了化合物中金属原子的配位环境,研究了氢键、芳环堆积等弱相互作用在构筑化合物晶体结构中发挥的重要作用。
三、采用紫外光谱、荧光光谱、粘度法及电化学方法等研究了上述化合物与小牛胸腺DNA(CT-DNA)的相互作用,判断了化合物与DNA之间相互作用的模式并确定了它们相互作用的强度。研究表明,配体L1~L4及配合物(11)~(14)与DNA以沟槽模式相结合,而配合物(1)~(10)、(15)~(16)与DNA之间存在插入作用模式。在此基础上,分析了化合物自身结构和化合物与DNA相互作用模式及强度间的联系,总结了化合物与DNA相互作用的构效关系。
四、采用SRB法分别对不对称草酰胺配体L1~L4及多核金属配合物(1)~(16)进行了体外细胞毒活性测试,研究结果表明,部分化合物对人肝癌细胞(SMMC-7721)和人肺腺癌细胞(A549)表现出较强抑制活性,其中配合物(8)的活性最强,对两种肿瘤细胞株的半数抑制浓度(IC50)分别为20和16 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、低毒的无机抗癌药物的设计与合成提供了非常有价值的参考信息。
Studies on DNA interaction of organic and inorganic small molecules have gotten more and more interests in the recent years. Deoxyribonucleic acid (DNA) is an important genetic substance in organism. As the basis of genetic expression, it plays an important role in the process of storing, copying and transmitting germ messages. The recognition of DNA for natural and artificial molecules in the inhibition of cellular disorders and in therapy of certain diseases is very paramount importance in inorganic biochemistry. The binding of small molecules, especially transition metal complexes, to DNA and molecular identification are very important in life science. It can provide useful information to design novel and efficient drugs for disease diagnosis and chemotherapeutic agents. The main purpose of this article is to study the structure-activity relationship of the oxamide compounds and DNA. The DNA-binding properties of these oxamide compounds have been examined using electronic absorption, fluorescence, viscometry and electrochemical technique, and their antitumor activities have also been studied in vitro by SRB assay.
1. Four novel dissymmetrical N,N’-bis(substituent)oxamide ligand, N-phenolato- N’-(3-dimethylaminopropyl)oxamide (H3pdmapo) (L1), N-phenolato-N’-(2-dimethyl- aminoethyl)oxamide (H3pdmaeo) (L2), N-phenolato-N’-(3-aminopropyl)oxamide (H3papo) (L3) and N-2-(dimethylamino)ethyl-N’-3-(dimethylamino)propyl oxamide (H2dmaepoxd) (L4) have been synthesized and characterized by MS, 1H NMR, IR and elemental analyses.
2. Sixteen complexes with these dissymmetrical N,N’-bis(substituent)oxamides as ligands, [Cu_2(pdmapo)(phen)(H_2O)](ClO4) (1), [Cu_2(pdmapo)(bpy)(CH_3OH)](ClO_4) (2), [Cu_2(pdmapo)(dabt)](CH_3OH)(ClO_4) (3), [Cu_2(pdmaeo)(phen)(H_2O)](CH_3OH)- (ClO_4) (4), [Cu_2(pdmaeo)(dabt)](CH_3OH)(ClO_4) (5), [Cu_2(papo)(bpy)(H_2O)](ClO_4) (6), [Cu_2(papo)(dmbpy)(CH_3OH)_0.5(H_2O)0.5](H_2O)0.5(ClO_4) (7), [Cu_2(dmapoxd)- (phen)_2](ClO_4)_2 (8), [Cu_2(dmapoxd)(bpy)_2](ClO_4)_2 (9), [Ni_2(dmapoxd)(bpy)_2(H_2O)_2]- (ClO_4)_2 (10), [Cu_2(dmaepoxd)(N_3)_2]_n (11), [Cu_2(dmaepoxd)(CH_3CH_2OH)(SCN)_2]_2n (12), [Cu_2(dmaepoxd)(CH3OH)(SCN)2]2n (13), [Cu_2(dmaepoxd)(NO2)2]n (14), [Cu_2(dmaepoxd)(pic)_2]n?nCH_3OH (15) and [Cu_2(dmaepoxd)(pma)]n (16), have been synthesized and characterized by X-ray single crystal diffraction. The coordination environments of the metal atoms in the complexes are explored. Hydrogen bonds andπ-πstacking interactions which stabilize the crystal structure in these complexes are also discussed.
3. The DNA-binding properties of the compounds have been studied by electronic absorption, fluorescence, viscometry and electrochemical technique. The results suggest that the ligands L1~L4 and complexes (11)~(14) bind to DNA via a groove binding mode while complexes (1)~(10) and (15)~(16) bind intercalatively to DNA. The structure-activity relationship of these oxamide compounds binding to DNA has been examined.
4. The cytotoxicities of ligands L1~L4 and its complexes (1)~(16) are examined in vitro by SRB assay. The results indicate that some compounds showed different cytotoxic activities against SMMC-7721 and A549 cell lines. Among these compounds, complex (8) has the strongest effects, with IC50 values 20 and 16 ng/mL in the two human tumor cell lines, respectively.
The researches of the paper not only enriched the content of inorganic medicinal chemistry, but also supplied valuable information for design and synthesis of inorganic antitumor medicinal with high activity and low toxicity.
本论文主要包括以下四个方面的工作:
一、设计并合成了4个结构新颖的不对称草酰胺配体,N-(2-羟基苯基)-N′-(3-二甲氨丙基)草酰胺(H3pdmapo) (L1)、N-(2-羟基苯基)-N′-(2-二甲氨乙基)草酰胺(H3pdmaeo) (L2)、N-(2-羟基苯基)-N′-(3-氨丙基)草酰胺(H3papo) (L3)、N-(2-二甲氨乙基)-N’-(3-二甲氨丙基)草酰胺(H2dmaepoxd) (L4),采用质谱、核磁、红外、元素分析等对其结构进行了表征,均为新化合物。
二、由已合成的草酰胺配体做桥联配体,通过变换合成方法,调控金属离子的种类、端基配体、抗衡阴离子、溶剂等条件实现了配合物种类、结构和配位方式的多样性,成功的合成了16个配合物: [Cu_2(pdmapo)(phen)(H_2O)](ClO_4) (1)、[Cu_2(pdmapo)(bpy)(CH_3OH)](ClO_4) (2)、[Cu_2(pdmapo)(dabt)](CH_3OH)(ClO_4) (3)、[Cu_2(pdmaeo)(phen)(H_2O)](CH_3OH)(ClO_4) (4)、[Cu_2(pdmaeo)(dabt)](CH_3OH)(ClO_4) (5)、[Cu_2(papo)(bpy)(H_2O)](ClO_4) (6)、[Cu_2(papo)(dmbpy)(CH_3OH)_0.5(H_2O)_0.5]- (H_2O)_0.5(ClO_4) (7)、[Cu_2(dmapoxd)(phen)_2](ClO_4)_2 (8)、[Cu_2(dmapoxd)(bpy)_2](ClO_4)_2 (9)、[Ni_2(dmapoxd)(bpy)_2(H_2O)_2](ClO_4)_2 (10)、[Cu_2(dmaepoxd)(N_3)_2]_n (11)、[Cu_2(dmaepoxd)(CH_3CH_2OH)(SCN)_2]_2n (12)、[Cu_2(dmaepoxd)(CH_3OH)(SCN)_2]_2n(13)、[Cu_2(dmaepoxd)(NO_2)_2]_n (14)、[Cu_2(dmaepoxd)(pic)_2]_n?nCH_3OH (15)、[Cu_2(dmaepoxd)(pma)]_n (16)。采用不同的培养方法分别得到了质量较好的单晶,解析了化合物的单晶结构,确定了化合物中金属原子的配位环境,研究了氢键、芳环堆积等弱相互作用在构筑化合物晶体结构中发挥的重要作用。
三、采用紫外光谱、荧光光谱、粘度法及电化学方法等研究了上述化合物与小牛胸腺DNA(CT-DNA)的相互作用,判断了化合物与DNA之间相互作用的模式并确定了它们相互作用的强度。研究表明,配体L1~L4及配合物(11)~(14)与DNA以沟槽模式相结合,而配合物(1)~(10)、(15)~(16)与DNA之间存在插入作用模式。在此基础上,分析了化合物自身结构和化合物与DNA相互作用模式及强度间的联系,总结了化合物与DNA相互作用的构效关系。
四、采用SRB法分别对不对称草酰胺配体L1~L4及多核金属配合物(1)~(16)进行了体外细胞毒活性测试,研究结果表明,部分化合物对人肝癌细胞(SMMC-7721)和人肺腺癌细胞(A549)表现出较强抑制活性,其中配合物(8)的活性最强,对两种肿瘤细胞株的半数抑制浓度(IC50)分别为20和16 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、低毒的无机抗癌药物的设计与合成提供了非常有价值的参考信息。
Studies on DNA interaction of organic and inorganic small molecules have gotten more and more interests in the recent years. Deoxyribonucleic acid (DNA) is an important genetic substance in organism. As the basis of genetic expression, it plays an important role in the process of storing, copying and transmitting germ messages. The recognition of DNA for natural and artificial molecules in the inhibition of cellular disorders and in therapy of certain diseases is very paramount importance in inorganic biochemistry. The binding of small molecules, especially transition metal complexes, to DNA and molecular identification are very important in life science. It can provide useful information to design novel and efficient drugs for disease diagnosis and chemotherapeutic agents. The main purpose of this article is to study the structure-activity relationship of the oxamide compounds and DNA. The DNA-binding properties of these oxamide compounds have been examined using electronic absorption, fluorescence, viscometry and electrochemical technique, and their antitumor activities have also been studied in vitro by SRB assay.
1. Four novel dissymmetrical N,N’-bis(substituent)oxamide ligand, N-phenolato- N’-(3-dimethylaminopropyl)oxamide (H3pdmapo) (L1), N-phenolato-N’-(2-dimethyl- aminoethyl)oxamide (H3pdmaeo) (L2), N-phenolato-N’-(3-aminopropyl)oxamide (H3papo) (L3) and N-2-(dimethylamino)ethyl-N’-3-(dimethylamino)propyl oxamide (H2dmaepoxd) (L4) have been synthesized and characterized by MS, 1H NMR, IR and elemental analyses.
2. Sixteen complexes with these dissymmetrical N,N’-bis(substituent)oxamides as ligands, [Cu_2(pdmapo)(phen)(H_2O)](ClO4) (1), [Cu_2(pdmapo)(bpy)(CH_3OH)](ClO_4) (2), [Cu_2(pdmapo)(dabt)](CH_3OH)(ClO_4) (3), [Cu_2(pdmaeo)(phen)(H_2O)](CH_3OH)- (ClO_4) (4), [Cu_2(pdmaeo)(dabt)](CH_3OH)(ClO_4) (5), [Cu_2(papo)(bpy)(H_2O)](ClO_4) (6), [Cu_2(papo)(dmbpy)(CH_3OH)_0.5(H_2O)0.5](H_2O)0.5(ClO_4) (7), [Cu_2(dmapoxd)- (phen)_2](ClO_4)_2 (8), [Cu_2(dmapoxd)(bpy)_2](ClO_4)_2 (9), [Ni_2(dmapoxd)(bpy)_2(H_2O)_2]- (ClO_4)_2 (10), [Cu_2(dmaepoxd)(N_3)_2]_n (11), [Cu_2(dmaepoxd)(CH_3CH_2OH)(SCN)_2]_2n (12), [Cu_2(dmaepoxd)(CH3OH)(SCN)2]2n (13), [Cu_2(dmaepoxd)(NO2)2]n (14), [Cu_2(dmaepoxd)(pic)_2]n?nCH_3OH (15) and [Cu_2(dmaepoxd)(pma)]n (16), have been synthesized and characterized by X-ray single crystal diffraction. The coordination environments of the metal atoms in the complexes are explored. Hydrogen bonds andπ-πstacking interactions which stabilize the crystal structure in these complexes are also discussed.
3. The DNA-binding properties of the compounds have been studied by electronic absorption, fluorescence, viscometry and electrochemical technique. The results suggest that the ligands L1~L4 and complexes (11)~(14) bind to DNA via a groove binding mode while complexes (1)~(10) and (15)~(16) bind intercalatively to DNA. The structure-activity relationship of these oxamide compounds binding to DNA has been examined.
4. The cytotoxicities of ligands L1~L4 and its complexes (1)~(16) are examined in vitro by SRB assay. The results indicate that some compounds showed different cytotoxic activities against SMMC-7721 and A549 cell lines. Among these compounds, complex (8) has the strongest effects, with IC50 values 20 and 16 ng/mL in the two human tumor cell lines, respectively.
The researches of the paper not only enriched the content of inorganic medicinal chemistry, but also supplied valuable information for design and synthesis of inorganic antitumor medicinal with high activity and low toxicity.
引文
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