钌(II)多吡啶配合物的合成及其生物活性研究
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摘要
论文概述了钌多吡啶配合物与DNA作用的研究现状,基础理论和研究方法;合成了文献未报道的五个系列的钌(II)多吡啶配合物,对所合成的配体和配合物进行了表征。研究了配合物的电化学性质和光谱学性质;用电子吸收光谱、流体力学、热变性和光断裂实验系统研究了配合物与DNA的作用方式;采用MTT(3-(4,5-二甲基噻-2)-2,5-二苯基四氮唑溴盐)法研究了配体和配合物的体外细胞毒性;研究了配合物清除羟基自由基的能力。本论文共分为五章。
第一章概述钌多吡啶配合物的结构特征、与DNA作用的方式、研究方法和研究现状。对钌多吡啶配合物研究的未来方向进行了展望,提出了论文的选题意义。
第二章以邻菲啰啉为原料，合成了未见报道的含氟配体Fpp(2-(3',3'-二氟-3,4-亚甲基二氧苯基)咪唑并[4,5-f][1,10]邻二氮杂菲)及两个钌(II)多吡啶配合物:[Ru(dmb)_2(Fpp)](ClO_4)_2和[Ru(bpy)_2(Fpp)](ClO_4)_2。用元素分析、电喷雾质谱、核磁共振氢谱对它们进行了表征;用电子吸收光谱、流体力学、热变性和光断裂实验研究了配合物与DNA的作用方式以及作用力的强弱,结果表明两个配合物均以插入方式与DNA结合,作用力的强弱顺序为:[Ru(bpy)_2(Fpp)]~(2+) > [Ru(dmb)_2(Fpp)]~(2+),即辅助配体对其的影响按dmb→bpy顺序由小到大变化,这主要由于辅助配体的疏水性引起的;并通过循环伏安法研究了这些配合物的电化学性质。
第三章合成了两个新的含氨基配体maip(2-(3-苯胺)咪唑并[4,5-f][1,10]邻二氮杂菲)和paip(2-(4-苯胺)咪唑并[4,5-f][1,10]邻二氮杂菲)及八个钌(II)多吡啶配合物([Ru(bpy)_2(maip)]~(2+), [Ru(bpy)_2(paip)]~(2+), [Ru(dmb)_2(maip)]~(2+), [Ru(dmb)_2(paip)]~(2+), [Ru(phen)_2(maip)]~(2+), [Ru (phen)_2(paip)]~(2+), [Ru(dmp)_2(maip)]~(2+)和[Ru (dmp)_2(paip)]~(2+))。用元素分析、电喷雾质谱、核磁共振氢谱对它们进行了表征;用电子吸收光谱、粘度实验、热变性实验、光断裂实验研究了配合物与DNA作用的方式以及作用力的强弱,
对于同样含有辅助配体的钌(II)多吡啶金属配合物来说,配体paip与DNA的结合作用比maip的更强,这可能是由于插入配体paip的氨基受对位基团的影响,比maip的氨基受邻位相同基团的影响电子更“富裕”,因而配体和DNA之间电子堆积作用更强,结合得更牢固;用MTT法研究了配体和配合物的体外细胞毒性和IC50值,比较了插入配体取代基位置不同对配合物与DNA作用力大小和抑制肿瘤细胞增殖的影响。我们发现其中有些配合物的IC50值与顺铂的比较接近,如[Ru(phen)_2(paip)]~(~(2+)) (4b)。有的甚至表现出比顺铂更好的活性,如[Ru(dmb)_2(maip)]~(2+) (3a)能有效地抑制BEL-7402肿瘤细胞增殖;依据Feton体系产生羟基自由基的原理,研究了配合物清除羟基自由基的能力。
第四章合成了一个新的对称配体(2-(3,5-二溴-4-羟基)咪唑并[4,5-f][1,10]菲啰啉, DBHIP)和两个钌(II)多吡啶配合物([Ru(bpy)_2(DBHIP)](ClO_4)_2和[Ru(phen)_2(DBHIP)](ClO_4)_2).用元素分析、电喷雾质谱、核磁共振氢谱和碳谱对它们进行了表征;通过电子吸收光谱、流体力学、热变性和光断裂实验研究了配合物与DNA的作用方式以及作用力的大小,发现这两个化合物与DNA作用力的大小为[Ru(bpy)_2(DBHIP)]~(2+) < [Ru(phen)_2(DBHIP)]~(2+);用MTT法研究了配体和配合物的体外细胞毒性以及IC50值,我们发现这三个化合物中,配体抑制肿瘤细胞增殖的效果最好,配合物1最弱,并研究了配合物清除羟基自由基的能力。
第五章合成了一个刚性平面配体(ITAP, isatino[1,2-b]-1,4,8,9- tetraazatriphenylene)及其钌(II)多吡啶配合物[Ru(dmb)_2(ITAP)](ClO_4)_2。用元素分析、电喷雾质谱、核磁共振碳谱对它们进行了表征;用循环伏安法研究了配合物的电化学性质;通过电子吸收光谱、流体力学、热变性和光断裂实验研究了配合物与DNA的作用,结果表明配合物以插入方式与DNA结合。
The current situation, the theoretical foundation and research methods of ruthehium polypyridine complexes with DNA were summarized. Five series of novel ligands and their ruthenium(II) complexes were synthesized and characterized. The effect of different complexes on DNA-binding properties was investigated by electronic absorption titration, viscosity measurements, DNA thermal denaturation and photoactivated cleavage experiment. The in vitro cytotoxic activity and the values of IC_(50) of some complexes were eluvateded by the method of MTT. Besides, the apoptosis activity and hydroxyl radical scavenging activity of ligand and their complexes were investigated. This dissertation concretely consists of the following five chapters.
In chapter 1, the structural character of ruthenium polypyridyl complexes, the interaction modes, study methods and current study situations were summarized. The trend of the research in this field and the significance of these researches dissertation were put forward.
In chapter 2, a ligand, Fpp (2-(3',3'-difluoro-3,4-methylenedioxyphenyl)imidazo [4,5-f][1,10]phenanthroline) which contains elements of fluorin and oxygen and its ruthenium(II) polypyridyl complexes [Ru(dmb)_2(Fpp)]~(2+) and [Ru(bpy)_2(Fpp)]~(2+) were synthesized and characterized by elemental analysis, ES-MS and ~1H NMR and ~(13)C NMR, their electrochemical behaviors were studied by cyclic voltammetry. DNA-binding properties were investigated by electronic absorption titration, viscosity measurements, DNA thermal denaturation and photoactivated cleavage experiment. The results show that the two complexes combine with DNA in the mode of intercalation, the DNA-binding affinity of the two complexes is [Ru(bpy)_2(Fpp)]~(2+) > [Ru(dmb)_2(Fpp)]~(2+), which implies the effect of the ancillary ligand has an on going trend from dmb→bpy. This may be due to他the difference in hydrophobicity of these ancillary ligands. And the electrochemical behaviors of these complexes were analyzed.
In chapter 3, two new ligands maip (2-(3-nitrophenyl)imidazo[4,5-f][1,10] phenanthroline) and paip (2-(4-nitrophenyl)imidazo[4,5-f][1,10] phenanthroline) containing amino and their ruthenium(II) polypyridyl complexes ([Ru(bpy)2(maip)]~(2+), [Ru(bpy)_2(paip)]~(2+), [Ru(dmb)_2(maip)]~(2+), [Ru(dmb)_2(paip)]~(2+), [Ru(dmp)_2(maip)]~(2+), [Ru(dmp)_2(paip)]~(2+), [Ru(phen)_2(maip)]~(2+) and [Ru(phen)_2(paip)]~(2+)) were synthesized and characterized by elemental analysis, ES-MS and 1H NMR. The interaction of these complexes with DNA was investigated by electronic absorption titration, viscosity measurements, DNA thermal denaturation and photoactivated cleavage experiment. Results show that intercalative ligand paip has larger DNA binding affinity than maip, this may ascribe to that paip has richer electron than maip. The cell viability of these complexes was investigated by the method of MTT. The hydroxyl radical scavenging activity was also studied.
In chapter 4, a novel symmetric ligand DBHIP (2-(3,5-dibromo-4-hydroxyphenyl) imidazo[4,5-f][1,10]phenanthroline) and its ruthenium(II) polypyridyl complexes ([Ru(bpy)_2DBHIP](ClO_4)_2 and [Ru(phen)_2DBHIP](ClO_4)_2) were synthesized and characterized by elemental analysis, ES-MS, 1HNMR and 13C NMR. The DNA-binding properties were studied by electronic absorption titration, viscosity measurements, DNA thermal denaturation and photoactivated cleavage. The results show complex [Ru(phen)_2(DBHIP)]~(2+) has larger DNA affinity than complex [Ru(bpy)_2(DBHIP)]~(2+). Their electrochemical behaviors were also studied by cyclic voltammetry. The cytotoxicity in vitro and the values of IC_(50) of these complexes were obtained by the MTT method. The cytotoxicity of ligand was slightly weakened when the ligand bonded to the metal atom Ru to form complexes. The antioxidant activity of ligang and its complexes against hydroxyl radical scavenging activity was also explored.
In chapter 5, Ru (II) polypyridyl complex [Ru(dmb)_2ITAP](ClO_4)_2 (ITAP = isatino [1,2-b]-1,4,8,9-tetraazatriphenylene, dmb = 4,4'-dimethyl-2,2'-bipyridine) was synthesized and characterized by elemental analysis, ES-MS and 1H NMR. The electrochemical behaviors of this complex were studied by cyclic voltammetry. The DNA-binding properties were studied by electronic absorption titration, viscosity measurements, DNA thermal denaturation and photoactivated cleavage experiment. The results indicate that [Ru(dmb)_2ITAP](ClO_4)_2 interacts with DNA through intercalation mode.
第一章概述钌多吡啶配合物的结构特征、与DNA作用的方式、研究方法和研究现状。对钌多吡啶配合物研究的未来方向进行了展望,提出了论文的选题意义。
第二章以邻菲啰啉为原料，合成了未见报道的含氟配体Fpp(2-(3',3'-二氟-3,4-亚甲基二氧苯基)咪唑并[4,5-f][1,10]邻二氮杂菲)及两个钌(II)多吡啶配合物:[Ru(dmb)_2(Fpp)](ClO_4)_2和[Ru(bpy)_2(Fpp)](ClO_4)_2。用元素分析、电喷雾质谱、核磁共振氢谱对它们进行了表征;用电子吸收光谱、流体力学、热变性和光断裂实验研究了配合物与DNA的作用方式以及作用力的强弱,结果表明两个配合物均以插入方式与DNA结合,作用力的强弱顺序为:[Ru(bpy)_2(Fpp)]~(2+) > [Ru(dmb)_2(Fpp)]~(2+),即辅助配体对其的影响按dmb→bpy顺序由小到大变化,这主要由于辅助配体的疏水性引起的;并通过循环伏安法研究了这些配合物的电化学性质。
第三章合成了两个新的含氨基配体maip(2-(3-苯胺)咪唑并[4,5-f][1,10]邻二氮杂菲)和paip(2-(4-苯胺)咪唑并[4,5-f][1,10]邻二氮杂菲)及八个钌(II)多吡啶配合物([Ru(bpy)_2(maip)]~(2+), [Ru(bpy)_2(paip)]~(2+), [Ru(dmb)_2(maip)]~(2+), [Ru(dmb)_2(paip)]~(2+), [Ru(phen)_2(maip)]~(2+), [Ru (phen)_2(paip)]~(2+), [Ru(dmp)_2(maip)]~(2+)和[Ru (dmp)_2(paip)]~(2+))。用元素分析、电喷雾质谱、核磁共振氢谱对它们进行了表征;用电子吸收光谱、粘度实验、热变性实验、光断裂实验研究了配合物与DNA作用的方式以及作用力的强弱,
对于同样含有辅助配体的钌(II)多吡啶金属配合物来说,配体paip与DNA的结合作用比maip的更强,这可能是由于插入配体paip的氨基受对位基团的影响,比maip的氨基受邻位相同基团的影响电子更“富裕”,因而配体和DNA之间电子堆积作用更强,结合得更牢固;用MTT法研究了配体和配合物的体外细胞毒性和IC50值,比较了插入配体取代基位置不同对配合物与DNA作用力大小和抑制肿瘤细胞增殖的影响。我们发现其中有些配合物的IC50值与顺铂的比较接近,如[Ru(phen)_2(paip)]~(~(2+)) (4b)。有的甚至表现出比顺铂更好的活性,如[Ru(dmb)_2(maip)]~(2+) (3a)能有效地抑制BEL-7402肿瘤细胞增殖;依据Feton体系产生羟基自由基的原理,研究了配合物清除羟基自由基的能力。
第四章合成了一个新的对称配体(2-(3,5-二溴-4-羟基)咪唑并[4,5-f][1,10]菲啰啉, DBHIP)和两个钌(II)多吡啶配合物([Ru(bpy)_2(DBHIP)](ClO_4)_2和[Ru(phen)_2(DBHIP)](ClO_4)_2).用元素分析、电喷雾质谱、核磁共振氢谱和碳谱对它们进行了表征;通过电子吸收光谱、流体力学、热变性和光断裂实验研究了配合物与DNA的作用方式以及作用力的大小,发现这两个化合物与DNA作用力的大小为[Ru(bpy)_2(DBHIP)]~(2+) < [Ru(phen)_2(DBHIP)]~(2+);用MTT法研究了配体和配合物的体外细胞毒性以及IC50值,我们发现这三个化合物中,配体抑制肿瘤细胞增殖的效果最好,配合物1最弱,并研究了配合物清除羟基自由基的能力。
第五章合成了一个刚性平面配体(ITAP, isatino[1,2-b]-1,4,8,9- tetraazatriphenylene)及其钌(II)多吡啶配合物[Ru(dmb)_2(ITAP)](ClO_4)_2。用元素分析、电喷雾质谱、核磁共振碳谱对它们进行了表征;用循环伏安法研究了配合物的电化学性质;通过电子吸收光谱、流体力学、热变性和光断裂实验研究了配合物与DNA的作用,结果表明配合物以插入方式与DNA结合。
The current situation, the theoretical foundation and research methods of ruthehium polypyridine complexes with DNA were summarized. Five series of novel ligands and their ruthenium(II) complexes were synthesized and characterized. The effect of different complexes on DNA-binding properties was investigated by electronic absorption titration, viscosity measurements, DNA thermal denaturation and photoactivated cleavage experiment. The in vitro cytotoxic activity and the values of IC_(50) of some complexes were eluvateded by the method of MTT. Besides, the apoptosis activity and hydroxyl radical scavenging activity of ligand and their complexes were investigated. This dissertation concretely consists of the following five chapters.
In chapter 1, the structural character of ruthenium polypyridyl complexes, the interaction modes, study methods and current study situations were summarized. The trend of the research in this field and the significance of these researches dissertation were put forward.
In chapter 2, a ligand, Fpp (2-(3',3'-difluoro-3,4-methylenedioxyphenyl)imidazo [4,5-f][1,10]phenanthroline) which contains elements of fluorin and oxygen and its ruthenium(II) polypyridyl complexes [Ru(dmb)_2(Fpp)]~(2+) and [Ru(bpy)_2(Fpp)]~(2+) were synthesized and characterized by elemental analysis, ES-MS and ~1H NMR and ~(13)C NMR, their electrochemical behaviors were studied by cyclic voltammetry. DNA-binding properties were investigated by electronic absorption titration, viscosity measurements, DNA thermal denaturation and photoactivated cleavage experiment. The results show that the two complexes combine with DNA in the mode of intercalation, the DNA-binding affinity of the two complexes is [Ru(bpy)_2(Fpp)]~(2+) > [Ru(dmb)_2(Fpp)]~(2+), which implies the effect of the ancillary ligand has an on going trend from dmb→bpy. This may be due to他the difference in hydrophobicity of these ancillary ligands. And the electrochemical behaviors of these complexes were analyzed.
In chapter 3, two new ligands maip (2-(3-nitrophenyl)imidazo[4,5-f][1,10] phenanthroline) and paip (2-(4-nitrophenyl)imidazo[4,5-f][1,10] phenanthroline) containing amino and their ruthenium(II) polypyridyl complexes ([Ru(bpy)2(maip)]~(2+), [Ru(bpy)_2(paip)]~(2+), [Ru(dmb)_2(maip)]~(2+), [Ru(dmb)_2(paip)]~(2+), [Ru(dmp)_2(maip)]~(2+), [Ru(dmp)_2(paip)]~(2+), [Ru(phen)_2(maip)]~(2+) and [Ru(phen)_2(paip)]~(2+)) were synthesized and characterized by elemental analysis, ES-MS and 1H NMR. The interaction of these complexes with DNA was investigated by electronic absorption titration, viscosity measurements, DNA thermal denaturation and photoactivated cleavage experiment. Results show that intercalative ligand paip has larger DNA binding affinity than maip, this may ascribe to that paip has richer electron than maip. The cell viability of these complexes was investigated by the method of MTT. The hydroxyl radical scavenging activity was also studied.
In chapter 4, a novel symmetric ligand DBHIP (2-(3,5-dibromo-4-hydroxyphenyl) imidazo[4,5-f][1,10]phenanthroline) and its ruthenium(II) polypyridyl complexes ([Ru(bpy)_2DBHIP](ClO_4)_2 and [Ru(phen)_2DBHIP](ClO_4)_2) were synthesized and characterized by elemental analysis, ES-MS, 1HNMR and 13C NMR. The DNA-binding properties were studied by electronic absorption titration, viscosity measurements, DNA thermal denaturation and photoactivated cleavage. The results show complex [Ru(phen)_2(DBHIP)]~(2+) has larger DNA affinity than complex [Ru(bpy)_2(DBHIP)]~(2+). Their electrochemical behaviors were also studied by cyclic voltammetry. The cytotoxicity in vitro and the values of IC_(50) of these complexes were obtained by the MTT method. The cytotoxicity of ligand was slightly weakened when the ligand bonded to the metal atom Ru to form complexes. The antioxidant activity of ligang and its complexes against hydroxyl radical scavenging activity was also explored.
In chapter 5, Ru (II) polypyridyl complex [Ru(dmb)_2ITAP](ClO_4)_2 (ITAP = isatino [1,2-b]-1,4,8,9-tetraazatriphenylene, dmb = 4,4'-dimethyl-2,2'-bipyridine) was synthesized and characterized by elemental analysis, ES-MS and 1H NMR. The electrochemical behaviors of this complex were studied by cyclic voltammetry. The DNA-binding properties were studied by electronic absorption titration, viscosity measurements, DNA thermal denaturation and photoactivated cleavage experiment. The results indicate that [Ru(dmb)_2ITAP](ClO_4)_2 interacts with DNA through intercalation mode.
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