钌多吡啶配合物与DNA/RNA的键合机理及其抗肿瘤活性研究
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摘要
DNA是染色体的主要成分,是储存、复制和传递遗传信息的物质基础,其双链结构对于维持遗传物质的稳定性和复制的准确性极为重要,并与某些病变有关；RNA同样是生物体重要的组成物质,它参与蛋白质的生物合成,在基因调控过程中起着很重要的作用,并与一些疾病的诊断与治疗有关。
由于钌(Ⅱ)多吡啶配合物具有丰富的光化学、光物理以及氧化还原等特性,近年来,钌(Ⅱ)多吡啶配合物与DNA/RNA相互作用的研究引起了人们的广泛关注。这些配合物与DNA/RNA相互作用机理的研究有望筛选出在临床医学中与基因和病毒有关的“诊断试剂和化学治疗药物”。全文分为五章：
第一章,介绍了钌(Ⅱ)多吡啶配合物与DNA/RNA相互作用的理论基础、研究现状、方法及本文的选题意义。
第二章,合成和表征了新的带羰基的插入配体PTBM及钌(Ⅱ)多吡啶配合物[Ru(phen)2PTBM]2+(phen=1,10-邻菲咯琳)(1)和[Ru(bpy)2PTBM]2+(bpy=2,2-联吡啶)(2),运用光谱、粘度及凝胶电泳的方法研究了其与DNA的相互作用。这两个配合物与DNA相互作用的研究表明,两配合物以插入方式与DNA相互作用,且前者比后者的插入作用强；两种配合物均与DNA发生立体选择性结合。结果表明,辅助配体和羰基官能团对其键合模式及配合物对DNA的断裂效果影响很大。
第三章,合成和表征了新的带杂原子硫的插入配体BTCP及钌(Ⅱ)多吡啶配合物[Ru(bpy)2(BTCP)]2+(1),[Ru(phen)2(BTCP)]2+(2)和[Ru(dmb)2(BTCP)]2+(3)(dmb=4,4'-甲基,2,2’-联吡啶),并运用光谱、粘度、热变性等方法研究了其与DNA的相互作用。研究表明,配合物均以插入方式与DNA相互作用,且三种配合物与DNA结合时存在明显的立体选择性；DNA的热变性实验表明：该过程是一个焓驱动过程,且包含熵的补偿关系；在光照条件下,三种配合物均能有效地对DNA进行切割。
第四章,合成和表征了新的带柔性链的插入配体stcp和ptcp及钌(Ⅱ)多吡啶配合物[Ru(phen)2(stcp)]2+(1),[Ru(phen)2(ptcp)]2+(2),[Ru(4,7-dmp)2(stcp)]2+(3), [Ru(4.7-dmp)2(ptcp)]2+(4)和[Ru(bpy)2(stcp)]2+(5)(4,7-dmp=4,7-二甲基-1,10-邻菲咯啉),并运用光谱、粘度、循环伏安等方法研究了其与DNA/tRNA(1 and 5)的相互作用。研究表明,1和5与tRNA的作用类似于它们与DNA的插入模式,它们可以插入到tRNA局部形成的双链中；含双键stcp的配合物因能形成较大的共轭体系,能以插入的方式与DNA/RNA结合,而单键的ptcp却以静电的方式与DNA键合；核酸结构、配合物结构的不同对键合模式有影响,而且结构上的微小差异可以导致性质方面的显著差异。
第五章,利用MTT体对所合成的钌配合物进行了初步的体外抗肿瘤活性研究。实验结果表明,配合物对肝癌细胞(HepG2)和白血病细胞(HL-60)均呈现了不同特点和强度的抗癌活性。为了更清楚的观察配合物对细胞的抑制作用,进行了姬姆萨染色实验,观察到了明显的细胞凋亡。进一步关于作用机理的研究有助于我们开发出新的高效的抗癌药物。
DNA is the main composition of the chromosome, the main material basis of gene stroage, copy, expression. The double-stranded structure of DNA directly affects the stability of gene and accuracy of reproduction, It is also relative to pathological changes. RNA is also the important component material of biology. It takes part in the biosynthesis of protein and plays a significant role in regulation of gene expression. It is also relative to diagnosis and therapy of some diseases.
In recent years, studies of interaction of ruthenium(II) polypyridyl complexes with DNA have aroused intense interest because of their rich photophysical, photochemical and electrochemical properties. These studies about the binding mechanisms of these complexes with calf thymus DNA/RNA are very important to screen out the diagnosis reagent and chemical therapy medicine of some diseases related to gene and virus in clinic medicine. This thesis consists of five chapters.
In chapter 1,The theoretical foundation, the current situation, the research methods of interaction between ruthehium(Ⅱ) polypyridine complexes and DNA were introduced. The research significance of this thesis was summarized.
In chapter 2,A novel polypyridyl ligand PTBM(phenyl-(4,5,9,14-tetraaza-benzo[b] Triphenylenl,1-yl)-methanone) which containing carbonyl group and its complexes [Ru(phen)2(PTBM)]2+(1)and [Ru(bpy)2(PTBM)]2+(2)have been designed, synthesized and characterized by elemental analysis,H NMR and mass spectroscopy. The DNA-binding properties of the two complexes were investigated by UV-Vis, luminescence titration and quenching, viscosity measurements, CD spectra and photoactivated cleavage of DNA. The results indicate that both complexes bind to DNA via an intercalative mode and the DNA-binding affinity of 1 is greater than that of 2;the two complexes can interact with DNA enantioselectively; The result suggest that the ancillary and carbonyl group have significant effect on the complexes.
In chapter 3,A new polypyridyl ligand BTCP(2-benzo[b]thiophen-3-yl-1H-1,3,7,8-tetraa-zacyclopenta[1]phenanthrene) and its Ru complexes [Ru(bpy)2(BTCP)]2+(1), [Ru(phen)2(BTCP)]2+(2), and [Ru(dmb)2(BTCP)]2+(3)(dmb=4,4'-dimethyl-2,2'-bipyridine) have been designed, synthesized and characterized. The DNA binding properties of the three complexes were investigated by spectroscopic methods,viscosity measurements, thermal denaturation study and CD spectra. The results indicate that complexes 1,2 and 3 bind to DNA by an intercalative mode; The three complexes interact enantioselectively with DNA; The thermal denaturation study indicate that the process of complexes bind to DNA is the decrease ofΔGTθ,ΔAHθandΔSθ,it drived by enthalpy; When irradiated, they can cleave DNA effectively.
In chapter 4, two new polypyridyl ligands stcp and ptcp(where stcp=2-Styryl-lH-1,3,7,8-tetraaza-cyclopenta[/]phenanthrene, ptcp=2-Phenethyl-1H-1,3,7,8-tetraazacyclop-enta[/]phenanthrene) and its five Ru complexes have been designed, synthesized and characterized. The interactions of metal complexes with yeast tRNA and DNA have been investigated comparatively by spectroscopic and viscosity measurements. The results indicate that 1 can intercalate to local formation of double strand tRNA, Which is similar to the role of DNA; These complexes contain stcp bind to DNA via intercalative mode; However, those complexes contain ptcp bind to DNA via electrostatic mode; Taken together, these results indicate that the structures of nucleic acids and the difference of ancillary ligands have significant effects on the binding behaviors of metal complexes. A small difference in the structure leads a significant difference in the function. These fundamental results may be useful and serve as database for the development of futuristic tRNA based small molecule therapeutics.
In chapter 5,the complexes we synthesized have been subjected to anti-cancer test in vitro by MTT method. Preliminary results indicate that some of the complexes show high activity against HepG2 and HL-60.In order to describe visually the decease of the cell after drug added, Wrights-Giemsa coloration experiment was also carried.we can see the typical apoptotic bodies of HepG2 cell in presence of complexes and cisplatin. More experiences and studies on mechanism can help pick out the efficient anticaner medicines.
由于钌(Ⅱ)多吡啶配合物具有丰富的光化学、光物理以及氧化还原等特性,近年来,钌(Ⅱ)多吡啶配合物与DNA/RNA相互作用的研究引起了人们的广泛关注。这些配合物与DNA/RNA相互作用机理的研究有望筛选出在临床医学中与基因和病毒有关的“诊断试剂和化学治疗药物”。全文分为五章：
第一章,介绍了钌(Ⅱ)多吡啶配合物与DNA/RNA相互作用的理论基础、研究现状、方法及本文的选题意义。
第二章,合成和表征了新的带羰基的插入配体PTBM及钌(Ⅱ)多吡啶配合物[Ru(phen)2PTBM]2+(phen=1,10-邻菲咯琳)(1)和[Ru(bpy)2PTBM]2+(bpy=2,2-联吡啶)(2),运用光谱、粘度及凝胶电泳的方法研究了其与DNA的相互作用。这两个配合物与DNA相互作用的研究表明,两配合物以插入方式与DNA相互作用,且前者比后者的插入作用强；两种配合物均与DNA发生立体选择性结合。结果表明,辅助配体和羰基官能团对其键合模式及配合物对DNA的断裂效果影响很大。
第三章,合成和表征了新的带杂原子硫的插入配体BTCP及钌(Ⅱ)多吡啶配合物[Ru(bpy)2(BTCP)]2+(1),[Ru(phen)2(BTCP)]2+(2)和[Ru(dmb)2(BTCP)]2+(3)(dmb=4,4'-甲基,2,2’-联吡啶),并运用光谱、粘度、热变性等方法研究了其与DNA的相互作用。研究表明,配合物均以插入方式与DNA相互作用,且三种配合物与DNA结合时存在明显的立体选择性；DNA的热变性实验表明：该过程是一个焓驱动过程,且包含熵的补偿关系；在光照条件下,三种配合物均能有效地对DNA进行切割。
第四章,合成和表征了新的带柔性链的插入配体stcp和ptcp及钌(Ⅱ)多吡啶配合物[Ru(phen)2(stcp)]2+(1),[Ru(phen)2(ptcp)]2+(2),[Ru(4,7-dmp)2(stcp)]2+(3), [Ru(4.7-dmp)2(ptcp)]2+(4)和[Ru(bpy)2(stcp)]2+(5)(4,7-dmp=4,7-二甲基-1,10-邻菲咯啉),并运用光谱、粘度、循环伏安等方法研究了其与DNA/tRNA(1 and 5)的相互作用。研究表明,1和5与tRNA的作用类似于它们与DNA的插入模式,它们可以插入到tRNA局部形成的双链中；含双键stcp的配合物因能形成较大的共轭体系,能以插入的方式与DNA/RNA结合,而单键的ptcp却以静电的方式与DNA键合；核酸结构、配合物结构的不同对键合模式有影响,而且结构上的微小差异可以导致性质方面的显著差异。
第五章,利用MTT体对所合成的钌配合物进行了初步的体外抗肿瘤活性研究。实验结果表明,配合物对肝癌细胞(HepG2)和白血病细胞(HL-60)均呈现了不同特点和强度的抗癌活性。为了更清楚的观察配合物对细胞的抑制作用,进行了姬姆萨染色实验,观察到了明显的细胞凋亡。进一步关于作用机理的研究有助于我们开发出新的高效的抗癌药物。
DNA is the main composition of the chromosome, the main material basis of gene stroage, copy, expression. The double-stranded structure of DNA directly affects the stability of gene and accuracy of reproduction, It is also relative to pathological changes. RNA is also the important component material of biology. It takes part in the biosynthesis of protein and plays a significant role in regulation of gene expression. It is also relative to diagnosis and therapy of some diseases.
In recent years, studies of interaction of ruthenium(II) polypyridyl complexes with DNA have aroused intense interest because of their rich photophysical, photochemical and electrochemical properties. These studies about the binding mechanisms of these complexes with calf thymus DNA/RNA are very important to screen out the diagnosis reagent and chemical therapy medicine of some diseases related to gene and virus in clinic medicine. This thesis consists of five chapters.
In chapter 1,The theoretical foundation, the current situation, the research methods of interaction between ruthehium(Ⅱ) polypyridine complexes and DNA were introduced. The research significance of this thesis was summarized.
In chapter 2,A novel polypyridyl ligand PTBM(phenyl-(4,5,9,14-tetraaza-benzo[b] Triphenylenl,1-yl)-methanone) which containing carbonyl group and its complexes [Ru(phen)2(PTBM)]2+(1)and [Ru(bpy)2(PTBM)]2+(2)have been designed, synthesized and characterized by elemental analysis,H NMR and mass spectroscopy. The DNA-binding properties of the two complexes were investigated by UV-Vis, luminescence titration and quenching, viscosity measurements, CD spectra and photoactivated cleavage of DNA. The results indicate that both complexes bind to DNA via an intercalative mode and the DNA-binding affinity of 1 is greater than that of 2;the two complexes can interact with DNA enantioselectively; The result suggest that the ancillary and carbonyl group have significant effect on the complexes.
In chapter 3,A new polypyridyl ligand BTCP(2-benzo[b]thiophen-3-yl-1H-1,3,7,8-tetraa-zacyclopenta[1]phenanthrene) and its Ru complexes [Ru(bpy)2(BTCP)]2+(1), [Ru(phen)2(BTCP)]2+(2), and [Ru(dmb)2(BTCP)]2+(3)(dmb=4,4'-dimethyl-2,2'-bipyridine) have been designed, synthesized and characterized. The DNA binding properties of the three complexes were investigated by spectroscopic methods,viscosity measurements, thermal denaturation study and CD spectra. The results indicate that complexes 1,2 and 3 bind to DNA by an intercalative mode; The three complexes interact enantioselectively with DNA; The thermal denaturation study indicate that the process of complexes bind to DNA is the decrease ofΔGTθ,ΔAHθandΔSθ,it drived by enthalpy; When irradiated, they can cleave DNA effectively.
In chapter 4, two new polypyridyl ligands stcp and ptcp(where stcp=2-Styryl-lH-1,3,7,8-tetraaza-cyclopenta[/]phenanthrene, ptcp=2-Phenethyl-1H-1,3,7,8-tetraazacyclop-enta[/]phenanthrene) and its five Ru complexes have been designed, synthesized and characterized. The interactions of metal complexes with yeast tRNA and DNA have been investigated comparatively by spectroscopic and viscosity measurements. The results indicate that 1 can intercalate to local formation of double strand tRNA, Which is similar to the role of DNA; These complexes contain stcp bind to DNA via intercalative mode; However, those complexes contain ptcp bind to DNA via electrostatic mode; Taken together, these results indicate that the structures of nucleic acids and the difference of ancillary ligands have significant effects on the binding behaviors of metal complexes. A small difference in the structure leads a significant difference in the function. These fundamental results may be useful and serve as database for the development of futuristic tRNA based small molecule therapeutics.
In chapter 5,the complexes we synthesized have been subjected to anti-cancer test in vitro by MTT method. Preliminary results indicate that some of the complexes show high activity against HepG2 and HL-60.In order to describe visually the decease of the cell after drug added, Wrights-Giemsa coloration experiment was also carried.we can see the typical apoptotic bodies of HepG2 cell in presence of complexes and cisplatin. More experiences and studies on mechanism can help pick out the efficient anticaner medicines.
引文
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