系列DNA切割体系的构建及其生物活性研究
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摘要
本文以系列多吡啶配体为主要构筑元件,并辅以其它配体,设计合成了35个未见文献报道的配合物,应用元素分析、红外光谱和单晶衍射等方法对其组成和结构进行了详细的表征；采用电子吸收光谱、荧光光谱、圆二色谱和琼脂糖凝胶电泳等方法,从分子层次探讨配合物与DNA或BSA的相互作用机制；此外,筛选部分配合物,采用MTT法、细胞克隆形成、Hoechst33342荧光染色、细胞周期阻滞、Annexin V/PI(或Annexin V/7-AAD)双染、彗星实验和活性氧(ROS)等多种细胞生物学的实验方法,从细胞层次对其抗癌活性和机制进行初步研究,从而为新型配合物型抗肿瘤药物的研发提供有价值的信息。
本论文主要研究成果如下：
1、合成了五个新颖的多吡啶配体,利用核磁共振、元素分析、红外光谱以及X-射线单晶衍射等方法对其进行表征。
2、利用上述五个配体合成了十个未见文献报道的锌配合物,解析了其单晶结构。锌配合物与CT-DNA的作用均以中等强度的插入方式发生作用。1-4和6-7的DNA切割机理以及无氧实验的研究排除了氧参与的可能,初步判断可能以水解方式断裂DNA。1-4和6-7与BSA的键合作用以及其机理也被讨论。利用MTT法测定了配合物1-4和6-7对体外肿瘤细胞生长的抑制能力,所有配合物对HeLa细胞均有较明显的抑制能力,而单核锌配合物6对MCF-7和7对RL952细胞的抑制能力比较接近甚至更优于顺铂的。我们还对配合物3(对HeLa细胞)和6(对MCF-7细胞)进行克隆形成、Hoechst33342染色、细胞周期、以及Annexin V/7-AAD双染等实验来进一步探讨了配合物的抗肿瘤活性及机理。
3、利用上述五个配体合成了十二个未见文献报道的铜配合物,解析了其单晶结构。配合物与CT-DNA的作用均以中等强度的插入方式发生作用。在不加外界诱导剂下,四核铜配合物11表现出了强的断裂DNA的能力。加入诱导剂过氧化氢、谷胱甘肽后,配合物12-22切割DNA的能力都有非常大的提高并初步推断其可能以氧化方式断裂DNA。配合物11-19与BSA的键合作用以及其机理也被讨论。利用MTT法测定了配合物12-19对体外肿瘤细胞生长的抑制能力,结果显示所有配合物对这三个细胞系均明显的抑制能力,尤其双核配合物14表现出了较好的抗癌活性,比较接近甚至更优于顺铂的抗肿瘤活性。我们还对配合物12和14对HeLa细胞进行克隆形成、Hoechst33342染色、细胞周期、AnnexinV/PI双染、彗星实验、以及活性氧(ROS)的产生等实验来进一步探讨了配合物的抗肿瘤活性及机理。
4、利用上述五个配体共合成了五个未见文献报道的钴配合物,解析了其单晶结构。配合物与CT-DNA的作用均以中等强度的插入方式发生作用。在不加外界诱导剂时,钴配合物表现出了较好的化学核酸酶活性：27>23-25>26,机理研究23-25和27可能以水解方式断裂DNA,而配合物26可能以氧化方式断裂DNA。23-25与BSA的键合作用以及其机理也被讨论。
5、利用上述配体共合成了八个未见文献报道的镍配合物,其中镍配合物31-34是由混合配体构筑的,配合物30-34与CT-DNA的作用均以中等强度的插入方式发生作用。在无外界诱导剂、加入谷胱甘肽以及365nm紫外光下照射等条件下,研究了配合物对DNA的断裂程度并初步判断其可能以氧化方式断裂DNA。30-34与BSA的键合作用以及其机理也被讨论。利用MTT法测定了配合物30-34对体外肿瘤细胞生长的抑制能力,配合物34对HepG-2细胞的抑制能力比较接近顺铂的,我们通过Hoechst33342染色实验可初步探讨了配合物的抗肿瘤活性及机理。
本论文主要研究了多吡啶作为主要构筑元件的锌、铜、钴、镍配合物的化学核酸酶活性,计算了一些量化参数,归纳总结了过渡金属配合物的结构与生物活性的相关性,为设计合成高效新型的、结构简单的化学核酸酶以及为深入了解小分子金属配合物作为抗肿瘤药物的作用机理提供了有价值的信息。
Thirty-five new zinc(II), copper(II), cobalt(II) and nickel(ll) complexes, utilizing five interrelated polypyridyl ligands and other coligands, have been synthesized and characterized by element analyses and IR. The structures of these complexes have been determined by X-ray crystallographic methods. The interactions of the complexes with DNA have been explored by absorption, emission, circular dichroic spectral and gel electrophoresis. The protein binding abilities and mechanisms have been monitored by quenching emission in the presence of complexes using BSA as model protein. In addition, the antitumor activities and mechanisms for some complexes are investigated through MTT assay, colony-forming assay, Hoechst33342staining assay, Cell cycle arrest, Annexin V/PI (or Annexin V/7-AAD) analysis, comet assay and ROS generation experiments. This is beneficial for the research and development of metal antitumor drugs.
The main contributions in this work are below:
1. Five novel polypyridyl ligands have been synthesized and characterized by1H NMR, element analyses, IR and X-ray crystallographic methods.
2. Ten new zinc(II) complexes have been synthesized with five interrelated polypyridyl ligands. The structures have been determined by X-ray crystallographic methods. Zinc(II) complexes bind to CT-DNA by partial intercalation binding mode. The DNA cleavage mechanism for complexes1-4and6-7and anaerobic experiments indicated the noninvolvement of molecular oxygen in the cleavage, such fact implies that DNA cleavage could be attributed to hydrolytic mechanism. The protein binding abilities and mechanisms have been monitored by quenching emission in the presence of complexes1-4and6-7using BSA as model protein. The MTT assay was done to test the ability of complexes1-4and6-7to inhibit cell growth, all of the complexes exhibit significant cytotoxic activity toward HeLa cell lines. Again, relatively the most potent cytotoxic effects were observed in MCF-7cells for complex6and in RL952cells for complex7, which were more or less equal to cisplatin against the same cell lines. The antitumor activities and mechanisms for the complexes3on HeLa cells and6on MCF-7cells were also investigated through colony-forming assay, Hoechst33342staining assay, Cell cycle arrest and Annexin V/7-AAD analysis.
3. Twelve new copper(II) complexes have been synthesized with five interrelated polypyridyl ligands. The structures have been determined by X-ray crystallographic methods. Copper(II) complexes bind to CT-DNA by partial intercalation binding mode. Complex11exhibits prominent DNA cleavage without any external agents. In the presence of H2O2or GSH (glutathione), the DNA cleavage efficiencies of complexes12-22exhibit remarkable increases and the oxidation mechanisms have been discussed. The protein binding abilities and mechanisms have been monitored by quenching emission in the presence of complexes11-19using BSA as model protein. The MTT assay was done to test the ability of complexes12-19to inhibit cell growth, all of the complexes exhibit significant cytotoxic activity toward the three cell lines. Again, relatively the most potent cytotoxic effects were observed for dinuclear complex14, which were almost equal or even better to cisplatin against the same cell lines. The antitumor activities and mechanisms for the complexes12and14on HeLa cells were also investigated through colony-forming assay, Hoechst33342staining assay, Cell cycle arrest, Annexin V/PI analysis, comet assay and ROS generation experiments.
4. Five new cobalt(II) complexes have been synthesized with five interrelated polypyridyl ligands. The structures have been determined by X-ray crystallographic methods. Cobalt(Ⅱ) complexes bind to CT-DNA by partial intercalation binding mode. They show obvious DNA cleavage activity without any external agents, which vary as27>23-25>26. The hydrolytic DNA cleavage mechanism for complexes23-25,27and the oxidation mechanisms of26have been discussed. The protein binding abilities and mechanisms have been monitored by quenching emission in the presence of complexes23-25using BSA as model protein.
5. Eight new nickel(II) complexes have been synthesized with polypyridyl ligands and mixed-ligands (31-34). The structures have been determined by X-ray crystallographic methods. Nickel(Ⅱ) complexes30-34bind to CT-DNA by partial intercalation binding mode. The DNA cleavage efficiencies of30-34exhibit remarkably different with change of external conditions, such as no additive agents, with the presence of GSH (glutathione) or on the photoirradiation at365nm. The oxidation mechanisms also have been discussed. The protein binding abilities and mechanisms have been monitored by quenching emission in the presence of complexes30-34using BSA as model protein. The MTT assay was done to test the ability of complexes30-34to inhibit cell growth, and the most potent cytotoxic effect was observed for complex34, which was more or less equal to cisplatin against the same cell lines. The antitumor mechanism for the complex34was also investigated through Hoechst33342staining assay.
In this paper, we have mainly investigated the chemical nuclease activities of transition metal complexes with polypyridyl ligands. Some quantitative parameters are calculated, and we also summarized the structure of transition metal complexes associated with the biological activity. All of these will be beneficial for designing efficient and simple chemical nuclease and understanding the mechanism on the metal antitumor drug.
本论文主要研究成果如下：
1、合成了五个新颖的多吡啶配体,利用核磁共振、元素分析、红外光谱以及X-射线单晶衍射等方法对其进行表征。
2、利用上述五个配体合成了十个未见文献报道的锌配合物,解析了其单晶结构。锌配合物与CT-DNA的作用均以中等强度的插入方式发生作用。1-4和6-7的DNA切割机理以及无氧实验的研究排除了氧参与的可能,初步判断可能以水解方式断裂DNA。1-4和6-7与BSA的键合作用以及其机理也被讨论。利用MTT法测定了配合物1-4和6-7对体外肿瘤细胞生长的抑制能力,所有配合物对HeLa细胞均有较明显的抑制能力,而单核锌配合物6对MCF-7和7对RL952细胞的抑制能力比较接近甚至更优于顺铂的。我们还对配合物3(对HeLa细胞)和6(对MCF-7细胞)进行克隆形成、Hoechst33342染色、细胞周期、以及Annexin V/7-AAD双染等实验来进一步探讨了配合物的抗肿瘤活性及机理。
3、利用上述五个配体合成了十二个未见文献报道的铜配合物,解析了其单晶结构。配合物与CT-DNA的作用均以中等强度的插入方式发生作用。在不加外界诱导剂下,四核铜配合物11表现出了强的断裂DNA的能力。加入诱导剂过氧化氢、谷胱甘肽后,配合物12-22切割DNA的能力都有非常大的提高并初步推断其可能以氧化方式断裂DNA。配合物11-19与BSA的键合作用以及其机理也被讨论。利用MTT法测定了配合物12-19对体外肿瘤细胞生长的抑制能力,结果显示所有配合物对这三个细胞系均明显的抑制能力,尤其双核配合物14表现出了较好的抗癌活性,比较接近甚至更优于顺铂的抗肿瘤活性。我们还对配合物12和14对HeLa细胞进行克隆形成、Hoechst33342染色、细胞周期、AnnexinV/PI双染、彗星实验、以及活性氧(ROS)的产生等实验来进一步探讨了配合物的抗肿瘤活性及机理。
4、利用上述五个配体共合成了五个未见文献报道的钴配合物,解析了其单晶结构。配合物与CT-DNA的作用均以中等强度的插入方式发生作用。在不加外界诱导剂时,钴配合物表现出了较好的化学核酸酶活性：27>23-25>26,机理研究23-25和27可能以水解方式断裂DNA,而配合物26可能以氧化方式断裂DNA。23-25与BSA的键合作用以及其机理也被讨论。
5、利用上述配体共合成了八个未见文献报道的镍配合物,其中镍配合物31-34是由混合配体构筑的,配合物30-34与CT-DNA的作用均以中等强度的插入方式发生作用。在无外界诱导剂、加入谷胱甘肽以及365nm紫外光下照射等条件下,研究了配合物对DNA的断裂程度并初步判断其可能以氧化方式断裂DNA。30-34与BSA的键合作用以及其机理也被讨论。利用MTT法测定了配合物30-34对体外肿瘤细胞生长的抑制能力,配合物34对HepG-2细胞的抑制能力比较接近顺铂的,我们通过Hoechst33342染色实验可初步探讨了配合物的抗肿瘤活性及机理。
本论文主要研究了多吡啶作为主要构筑元件的锌、铜、钴、镍配合物的化学核酸酶活性,计算了一些量化参数,归纳总结了过渡金属配合物的结构与生物活性的相关性,为设计合成高效新型的、结构简单的化学核酸酶以及为深入了解小分子金属配合物作为抗肿瘤药物的作用机理提供了有价值的信息。
Thirty-five new zinc(II), copper(II), cobalt(II) and nickel(ll) complexes, utilizing five interrelated polypyridyl ligands and other coligands, have been synthesized and characterized by element analyses and IR. The structures of these complexes have been determined by X-ray crystallographic methods. The interactions of the complexes with DNA have been explored by absorption, emission, circular dichroic spectral and gel electrophoresis. The protein binding abilities and mechanisms have been monitored by quenching emission in the presence of complexes using BSA as model protein. In addition, the antitumor activities and mechanisms for some complexes are investigated through MTT assay, colony-forming assay, Hoechst33342staining assay, Cell cycle arrest, Annexin V/PI (or Annexin V/7-AAD) analysis, comet assay and ROS generation experiments. This is beneficial for the research and development of metal antitumor drugs.
The main contributions in this work are below:
1. Five novel polypyridyl ligands have been synthesized and characterized by1H NMR, element analyses, IR and X-ray crystallographic methods.
2. Ten new zinc(II) complexes have been synthesized with five interrelated polypyridyl ligands. The structures have been determined by X-ray crystallographic methods. Zinc(II) complexes bind to CT-DNA by partial intercalation binding mode. The DNA cleavage mechanism for complexes1-4and6-7and anaerobic experiments indicated the noninvolvement of molecular oxygen in the cleavage, such fact implies that DNA cleavage could be attributed to hydrolytic mechanism. The protein binding abilities and mechanisms have been monitored by quenching emission in the presence of complexes1-4and6-7using BSA as model protein. The MTT assay was done to test the ability of complexes1-4and6-7to inhibit cell growth, all of the complexes exhibit significant cytotoxic activity toward HeLa cell lines. Again, relatively the most potent cytotoxic effects were observed in MCF-7cells for complex6and in RL952cells for complex7, which were more or less equal to cisplatin against the same cell lines. The antitumor activities and mechanisms for the complexes3on HeLa cells and6on MCF-7cells were also investigated through colony-forming assay, Hoechst33342staining assay, Cell cycle arrest and Annexin V/7-AAD analysis.
3. Twelve new copper(II) complexes have been synthesized with five interrelated polypyridyl ligands. The structures have been determined by X-ray crystallographic methods. Copper(II) complexes bind to CT-DNA by partial intercalation binding mode. Complex11exhibits prominent DNA cleavage without any external agents. In the presence of H2O2or GSH (glutathione), the DNA cleavage efficiencies of complexes12-22exhibit remarkable increases and the oxidation mechanisms have been discussed. The protein binding abilities and mechanisms have been monitored by quenching emission in the presence of complexes11-19using BSA as model protein. The MTT assay was done to test the ability of complexes12-19to inhibit cell growth, all of the complexes exhibit significant cytotoxic activity toward the three cell lines. Again, relatively the most potent cytotoxic effects were observed for dinuclear complex14, which were almost equal or even better to cisplatin against the same cell lines. The antitumor activities and mechanisms for the complexes12and14on HeLa cells were also investigated through colony-forming assay, Hoechst33342staining assay, Cell cycle arrest, Annexin V/PI analysis, comet assay and ROS generation experiments.
4. Five new cobalt(II) complexes have been synthesized with five interrelated polypyridyl ligands. The structures have been determined by X-ray crystallographic methods. Cobalt(Ⅱ) complexes bind to CT-DNA by partial intercalation binding mode. They show obvious DNA cleavage activity without any external agents, which vary as27>23-25>26. The hydrolytic DNA cleavage mechanism for complexes23-25,27and the oxidation mechanisms of26have been discussed. The protein binding abilities and mechanisms have been monitored by quenching emission in the presence of complexes23-25using BSA as model protein.
5. Eight new nickel(II) complexes have been synthesized with polypyridyl ligands and mixed-ligands (31-34). The structures have been determined by X-ray crystallographic methods. Nickel(Ⅱ) complexes30-34bind to CT-DNA by partial intercalation binding mode. The DNA cleavage efficiencies of30-34exhibit remarkably different with change of external conditions, such as no additive agents, with the presence of GSH (glutathione) or on the photoirradiation at365nm. The oxidation mechanisms also have been discussed. The protein binding abilities and mechanisms have been monitored by quenching emission in the presence of complexes30-34using BSA as model protein. The MTT assay was done to test the ability of complexes30-34to inhibit cell growth, and the most potent cytotoxic effect was observed for complex34, which was more or less equal to cisplatin against the same cell lines. The antitumor mechanism for the complex34was also investigated through Hoechst33342staining assay.
In this paper, we have mainly investigated the chemical nuclease activities of transition metal complexes with polypyridyl ligands. Some quantitative parameters are calculated, and we also summarized the structure of transition metal complexes associated with the biological activity. All of these will be beneficial for designing efficient and simple chemical nuclease and understanding the mechanism on the metal antitumor drug.
引文
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