新型N-取代吡啶酰胺和其稀土配合物的合成及与DNA作用模式的研究
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摘要
癌症己成为世界性严重危害人类健康和生命安全的常见病之一。化疗是治疗癌症的重要手段,但是其毒副作用较大,于是,开展高效、广谱、低毒的抗癌药物的合成及其抗癌活性研究业已成为当今新药开发的战略性课题。目前人们的研究大多集中在过渡或主族金属元素上,如铂系类抗癌药物,金属茂钛类抗癌药物,有机锡类抗癌药物和钴、铜等元素与惰性配体形成的低氧选择性抗癌药物。稀土离子及其配合物能够更加高效的通过氢键和水解模式与DNA作用,因而作为核酸断裂剂其效果优于过渡金属离子及其配合物。吡啶酰胺分子中既含有亲脂性的吡啶基,又具备亲水性的酰胺基团,因而其配合物具备易于穿透细胞膜,与靶分子DNA结合能力强的优点。同时又因其水溶性而降低了对人体的肾毒性。为此,本论文设计合成了新型N-取代吡啶酰胺及其稀土配合物并采用多种方法研究了它们与DNA作用的强度和模式,以期筛选出高效、低毒的抗肿瘤新药。
本论文合成了五种新型N-取代吡啶酰胺类化合物:N-苯基-吡啶-2-甲酰胺(L~1),N-2-氯苯基-吡啶-2-甲酰胺(L~2),N-2-硝基苯基-吡啶-2-甲酰胺(L~3),N-2-吡啶基-吡啶-2-甲酰胺(L~4),N,N'-双(2-吡啶甲酰胺)-1,4-二乙烯三胺(L~5)。核磁共振、红外光谱、元素分析的结果确认了其结构的正确性。采用紫外可见光谱,荧光光谱,表面增强拉曼光谱,粘度法,琼脂糖凝胶电泳等方法和手段研究了它们与DNA作用的情况。研究结果表明,配体L~1,L~2,L~3,L~4和L~5能与DNA发生不同程度的作用,作用的强度依照如下顺序递减:L~3,L~1,L~4,L~2和L~5。配体L~1,L~2,L~3和L~4分子较小,平面性好,易于插入DNA分子的碱基对中,因而其与DNA`作用的模式为插入作用。配体L~5分子两端的酰胺基团具有亲水性好的特点,而分子的中间部分为柔韧性好的脂肪链,两端的酰胺基团易与DNA分子发生沟面结合,因而其与DNA作用的模式主要为沟面结合。适中的刚性芳香环,较小的空间位阻,更利于配体与DNA分子发生插入作用。在芳香环上引入吸电子基团将不利于芳香环与DNA的碱基的芳香环之间的耦合,从而降低药物分子的活性。反之,在芳香环上引入给电子基或者发色基团将更利于芳香环与DNA的碱基的芳香环之间的耦合,从而增加药物分子的活性。
合成了N-苯基-吡啶-2-甲酰胺(L~1)的12种稀土配合物,经元素分析、摩尔电导、红外光谱、热重分析等手段确认其组成为:[Ln(L~1)_3(H_2O)_2](NO_3)_3·2H_2O,Ln=La(Ⅲ)和Ce(Ⅲ);[Ln(L~1)_2(H_2O)(NO_3)](NO_3)_2·3H_2O,Ln=Nd(Ⅲ)、Sm(Ⅲ)、Eu(Ⅲ)、Gd(Ⅲ)、Dy(Ⅲ)、Ho(Ⅲ)、Er(Ⅲ)、Tm(Ⅲ)、Yb(Ⅲ)和Lu(Ⅲ)。我们将配合物分为三个系列,即La(Ⅲ)系列(包含La(Ⅲ)和Ce(Ⅲ)配合物)、Eu(Ⅲ)系列(包含Sm(Ⅲ)、Eu(Ⅲ)、Gd(Ⅲ)和Dy(Ⅲ)配合物)和Ho(Ⅲ)系列(包含Ho(Ⅲ)、Er(Ⅲ)、Tm(Ⅲ)、Yb(Ⅲ)和Lu(Ⅲ)配合物)。对以上三个系列配合物分别采用紫外可见光谱、荧光光谱、表面增强拉曼光谱、粘度法、琼脂糖凝胶电泳和原子力显微镜研究了它们与DNA作用的强度和模式。结果表明,系列配合物与DNA均能发生较强的作用。Eu(Ⅲ)系列配合物与DNA作用的能力最强,次之为La(Ⅲ)系列配合物,Ho(Ⅲ)系列最弱。系列配合物与DNA分子作用的方式可能为配体L~1分子的芳香平面插入DNA分子的双螺旋碱基对之间。系列配合物与DNA作用的能力均强于配体L~1,其原因可能在于:与Ln(Ⅲ)配位后,配体L~1的π体系得到扩展,导致配位后的配体L~1能更深的插入DNA分子的双螺旋碱基对之间。
合成并表征了N,N'-双(2-吡啶甲酰胺)-1,4-二乙烯三胺(L~5)的11种稀土配合物。经元素分析、摩尔电导、红外光谱、热重分析等手段确认其组成为:[La(H_3L~5)(NO_3)_2]NO_3Cl_3·3H_2O,Ln=La(Ⅲ)、Nd(Ⅲ)、Sm(Ⅲ)、Eu(Ⅲ)、Gd(Ⅲ)、Dy(Ⅲ)、Ho(Ⅲ)、Er(Ⅲ)、Tm(Ⅲ)、Yb(Ⅲ)和Lu(Ⅲ)。采用紫外可见光谱,荧光光谱,表面增强拉曼光谱,粘度法等方法和手段研究了它们与DNA作用的情况。研究结果表明,系列配合物与DNA之间没有明显的插入作用,其作用模式可能为沟面结合和静电作用。
Cancer has become a worldwide disease that creates serious threat to humanity health and life safety.Chemotherapy is an important treatment method but with obvious toxic effects.So to synthesize high efficient, broad-Spectrum,low toxic anticarcinogen and study their anticancer activity is becoming a strategic task of new drug development.Nowadays,the study on this topic is mostly concentrated on main group and transition metals, such as Platinum group anticarcinogen,metallocene anticarcinogen, organotin anticarcinogen and copper complex anticarcinogen,etc.Rare earthsions and their complexes as chemical nucleases are superior to transition metal and their complexes because they can bind to nucleic acid more efficiently by hydrogen bonding and hydrolyzed mode,as a result,it has gained prominence.Pyridinecarboxamide contains lipophilic group of pyridine,which can make the drugs more capable of penetrating through cell membrane to bind to the target DNA.More importantly,hydrophilic group of carboxamide can reduce toxicity brought by the drugs to the kidney.In this paper,we design and synthesize novel acylamide derivatives and their rare earth complexes.In order to screening high efficient,broad-Spectrum,low toxic anticancer drugs,design,synthesis and DNA-binding mode of novel acylamide derivatives and their rare earth complexes are discussed in this paper.
We synthesized five novel N-substituted pyridinecarboxamide: N-phenyl-2-pyridinecarboxamide(L~1),N-2-chlorine phenyl-2-pyridinecarboxamide(L~2),N-2-nitro phenyl-2-pyridinecarboxamide(L~3),N-pyridyl-2-pyridinecarboxamide(L~4),N, N'-bis(2-pyridine carboxamide)-1,4-diethylenetriamine(L~5).They were characterized by NMR spectrum,IR spectrum and elemental analysis.The interaction between the compounds and DNA was studied by means of UV-visible spectra,fluorescence spectra,surface enhanced raman spectroscopic,viscometric titration and agarose gel electrophoresis.The results showed that compounds can bind to DNA in different degree.The binding ability followed the trend from high to low:L~3,L~1,L~4,L~2 and L~5. Because the molecules of L~1,L~2,L~3 and L~4 have the advantage of small size and appropriate planarity,they are easy to insert their aromatic ring to the base pairs of DNA.The acylamide groups of two terminal in L~5 have the advantage of hydrophilicity,and the middle long fatly chain in L~5 is of good flexibility.So the interaction modes between DNA and L~5 are mainly in groove binding.In conclusion,appropriate planarity and lesser steric hindrance make the ligands prone to insert their aromatic ring to the base pairs of DNA.The introduction of absorbing electronic group in aromatic ring will go against coupling effect between the ligands' aromatic ring and DNA,Which will decreased the pharmacodynamic effect.On the contrary, the introduction of electron-donating groups will enhance the effectiveness of medicine.
Then we synthesized twelve rare earth complexes containing ligand of N-phenyl-2-pyridinecarboxamide.The results of elemental analysis, conductivity measurement,IR spectra and thermal analysis confirmed their chemical composition were:[Ln(L~1)_3(H_2O)_2](NO_3)_3·2H_2O,Ln=La(Ⅲ)and Ce(Ⅲ);[Ln(L~1)_2(H_2O)(NO_3)](NO_3)_2·3H_2O,Ln=Nd(Ⅲ),Sm(Ⅲ),Eu(Ⅲ), Gd(Ⅲ),Dy(Ⅲ),Ho(Ⅲ),Er(Ⅲ),Tm(Ⅲ),Yb(Ⅲ)and Lu(Ⅲ).To make convenient discussion,the twelve rare earth complexes could be divided into three series.La(Ⅲ)series contained La(Ⅲ)and Ce(Ⅲ)complexes;Eu(Ⅲ) series were Sm(Ⅲ),Eu(Ⅲ),Gd(Ⅲ)and Dy(Ⅲ)complexes;Ho(Ⅲ)series were Ho(Ⅲ),Er(Ⅲ),Tm(Ⅲ),Yb(Ⅲ)and Lu(Ⅲ)complexes.The interaction between the three series and DNA was studied by means of UV-visible spectra,fluorescence spectra,SERS spectra,viscometric titration,agarose gel electrophoresis and atomic force microscopy.The results showed that all complexes can bind to DNA strongly.The binding ability of the three series followed the trend from high to low:Eu(Ⅲ)series,La(Ⅲ)series and Ho(Ⅲ) series.Series complexes bound to DNA probably by inserting their L~1 molecule to the base pairs of DNA.Series complexes bound to DNA stronger than free L~1.The results are probably attributed to the extension of theπsystem of the intercalated ligand due to the coordination of Ln(Ⅲ),which also leads to a planar area greater than that of the free ligand,which leads to the coordinated ligand penetrating more deeply into,and stacking more strongly with the base pairs of the DNA.
In addition,we synthesized and characterized eleven rare earth complexes containing ligand of N,N'-bis(2-pyridinecarboxamide)-1, 4-diethylenetriamine.The results of elemental analysis,conductivity measurement,IR spectra,thermal analysis and NMR spectrum confirmed their chemical composition were:[La(H_3L~5)(NO_3)_2]NO_3Cl_3·3H_2O,Ln= La(Ⅲ),Nd(Ⅲ),Sm(Ⅲ),Eu(Ⅲ),Gd(Ⅲ),Dy(Ⅲ),Ho(Ⅲ),Er(Ⅲ),Tm(Ⅲ), Yb(Ⅲ)and Lu(Ⅲ).And also,the interaction between series complexes and DNA was studied by means of UV-visible spectra,fluorescence spectra, SERS spectra and viscometric titration.From the results,there were not evident insertion action between series complexes and DNA.Their interaction modes were probably in groove binding and electrostatic effect.
本论文合成了五种新型N-取代吡啶酰胺类化合物:N-苯基-吡啶-2-甲酰胺(L~1),N-2-氯苯基-吡啶-2-甲酰胺(L~2),N-2-硝基苯基-吡啶-2-甲酰胺(L~3),N-2-吡啶基-吡啶-2-甲酰胺(L~4),N,N'-双(2-吡啶甲酰胺)-1,4-二乙烯三胺(L~5)。核磁共振、红外光谱、元素分析的结果确认了其结构的正确性。采用紫外可见光谱,荧光光谱,表面增强拉曼光谱,粘度法,琼脂糖凝胶电泳等方法和手段研究了它们与DNA作用的情况。研究结果表明,配体L~1,L~2,L~3,L~4和L~5能与DNA发生不同程度的作用,作用的强度依照如下顺序递减:L~3,L~1,L~4,L~2和L~5。配体L~1,L~2,L~3和L~4分子较小,平面性好,易于插入DNA分子的碱基对中,因而其与DNA`作用的模式为插入作用。配体L~5分子两端的酰胺基团具有亲水性好的特点,而分子的中间部分为柔韧性好的脂肪链,两端的酰胺基团易与DNA分子发生沟面结合,因而其与DNA作用的模式主要为沟面结合。适中的刚性芳香环,较小的空间位阻,更利于配体与DNA分子发生插入作用。在芳香环上引入吸电子基团将不利于芳香环与DNA的碱基的芳香环之间的耦合,从而降低药物分子的活性。反之,在芳香环上引入给电子基或者发色基团将更利于芳香环与DNA的碱基的芳香环之间的耦合,从而增加药物分子的活性。
合成了N-苯基-吡啶-2-甲酰胺(L~1)的12种稀土配合物,经元素分析、摩尔电导、红外光谱、热重分析等手段确认其组成为:[Ln(L~1)_3(H_2O)_2](NO_3)_3·2H_2O,Ln=La(Ⅲ)和Ce(Ⅲ);[Ln(L~1)_2(H_2O)(NO_3)](NO_3)_2·3H_2O,Ln=Nd(Ⅲ)、Sm(Ⅲ)、Eu(Ⅲ)、Gd(Ⅲ)、Dy(Ⅲ)、Ho(Ⅲ)、Er(Ⅲ)、Tm(Ⅲ)、Yb(Ⅲ)和Lu(Ⅲ)。我们将配合物分为三个系列,即La(Ⅲ)系列(包含La(Ⅲ)和Ce(Ⅲ)配合物)、Eu(Ⅲ)系列(包含Sm(Ⅲ)、Eu(Ⅲ)、Gd(Ⅲ)和Dy(Ⅲ)配合物)和Ho(Ⅲ)系列(包含Ho(Ⅲ)、Er(Ⅲ)、Tm(Ⅲ)、Yb(Ⅲ)和Lu(Ⅲ)配合物)。对以上三个系列配合物分别采用紫外可见光谱、荧光光谱、表面增强拉曼光谱、粘度法、琼脂糖凝胶电泳和原子力显微镜研究了它们与DNA作用的强度和模式。结果表明,系列配合物与DNA均能发生较强的作用。Eu(Ⅲ)系列配合物与DNA作用的能力最强,次之为La(Ⅲ)系列配合物,Ho(Ⅲ)系列最弱。系列配合物与DNA分子作用的方式可能为配体L~1分子的芳香平面插入DNA分子的双螺旋碱基对之间。系列配合物与DNA作用的能力均强于配体L~1,其原因可能在于:与Ln(Ⅲ)配位后,配体L~1的π体系得到扩展,导致配位后的配体L~1能更深的插入DNA分子的双螺旋碱基对之间。
合成并表征了N,N'-双(2-吡啶甲酰胺)-1,4-二乙烯三胺(L~5)的11种稀土配合物。经元素分析、摩尔电导、红外光谱、热重分析等手段确认其组成为:[La(H_3L~5)(NO_3)_2]NO_3Cl_3·3H_2O,Ln=La(Ⅲ)、Nd(Ⅲ)、Sm(Ⅲ)、Eu(Ⅲ)、Gd(Ⅲ)、Dy(Ⅲ)、Ho(Ⅲ)、Er(Ⅲ)、Tm(Ⅲ)、Yb(Ⅲ)和Lu(Ⅲ)。采用紫外可见光谱,荧光光谱,表面增强拉曼光谱,粘度法等方法和手段研究了它们与DNA作用的情况。研究结果表明,系列配合物与DNA之间没有明显的插入作用,其作用模式可能为沟面结合和静电作用。
Cancer has become a worldwide disease that creates serious threat to humanity health and life safety.Chemotherapy is an important treatment method but with obvious toxic effects.So to synthesize high efficient, broad-Spectrum,low toxic anticarcinogen and study their anticancer activity is becoming a strategic task of new drug development.Nowadays,the study on this topic is mostly concentrated on main group and transition metals, such as Platinum group anticarcinogen,metallocene anticarcinogen, organotin anticarcinogen and copper complex anticarcinogen,etc.Rare earthsions and their complexes as chemical nucleases are superior to transition metal and their complexes because they can bind to nucleic acid more efficiently by hydrogen bonding and hydrolyzed mode,as a result,it has gained prominence.Pyridinecarboxamide contains lipophilic group of pyridine,which can make the drugs more capable of penetrating through cell membrane to bind to the target DNA.More importantly,hydrophilic group of carboxamide can reduce toxicity brought by the drugs to the kidney.In this paper,we design and synthesize novel acylamide derivatives and their rare earth complexes.In order to screening high efficient,broad-Spectrum,low toxic anticancer drugs,design,synthesis and DNA-binding mode of novel acylamide derivatives and their rare earth complexes are discussed in this paper.
We synthesized five novel N-substituted pyridinecarboxamide: N-phenyl-2-pyridinecarboxamide(L~1),N-2-chlorine phenyl-2-pyridinecarboxamide(L~2),N-2-nitro phenyl-2-pyridinecarboxamide(L~3),N-pyridyl-2-pyridinecarboxamide(L~4),N, N'-bis(2-pyridine carboxamide)-1,4-diethylenetriamine(L~5).They were characterized by NMR spectrum,IR spectrum and elemental analysis.The interaction between the compounds and DNA was studied by means of UV-visible spectra,fluorescence spectra,surface enhanced raman spectroscopic,viscometric titration and agarose gel electrophoresis.The results showed that compounds can bind to DNA in different degree.The binding ability followed the trend from high to low:L~3,L~1,L~4,L~2 and L~5. Because the molecules of L~1,L~2,L~3 and L~4 have the advantage of small size and appropriate planarity,they are easy to insert their aromatic ring to the base pairs of DNA.The acylamide groups of two terminal in L~5 have the advantage of hydrophilicity,and the middle long fatly chain in L~5 is of good flexibility.So the interaction modes between DNA and L~5 are mainly in groove binding.In conclusion,appropriate planarity and lesser steric hindrance make the ligands prone to insert their aromatic ring to the base pairs of DNA.The introduction of absorbing electronic group in aromatic ring will go against coupling effect between the ligands' aromatic ring and DNA,Which will decreased the pharmacodynamic effect.On the contrary, the introduction of electron-donating groups will enhance the effectiveness of medicine.
Then we synthesized twelve rare earth complexes containing ligand of N-phenyl-2-pyridinecarboxamide.The results of elemental analysis, conductivity measurement,IR spectra and thermal analysis confirmed their chemical composition were:[Ln(L~1)_3(H_2O)_2](NO_3)_3·2H_2O,Ln=La(Ⅲ)and Ce(Ⅲ);[Ln(L~1)_2(H_2O)(NO_3)](NO_3)_2·3H_2O,Ln=Nd(Ⅲ),Sm(Ⅲ),Eu(Ⅲ), Gd(Ⅲ),Dy(Ⅲ),Ho(Ⅲ),Er(Ⅲ),Tm(Ⅲ),Yb(Ⅲ)and Lu(Ⅲ).To make convenient discussion,the twelve rare earth complexes could be divided into three series.La(Ⅲ)series contained La(Ⅲ)and Ce(Ⅲ)complexes;Eu(Ⅲ) series were Sm(Ⅲ),Eu(Ⅲ),Gd(Ⅲ)and Dy(Ⅲ)complexes;Ho(Ⅲ)series were Ho(Ⅲ),Er(Ⅲ),Tm(Ⅲ),Yb(Ⅲ)and Lu(Ⅲ)complexes.The interaction between the three series and DNA was studied by means of UV-visible spectra,fluorescence spectra,SERS spectra,viscometric titration,agarose gel electrophoresis and atomic force microscopy.The results showed that all complexes can bind to DNA strongly.The binding ability of the three series followed the trend from high to low:Eu(Ⅲ)series,La(Ⅲ)series and Ho(Ⅲ) series.Series complexes bound to DNA probably by inserting their L~1 molecule to the base pairs of DNA.Series complexes bound to DNA stronger than free L~1.The results are probably attributed to the extension of theπsystem of the intercalated ligand due to the coordination of Ln(Ⅲ),which also leads to a planar area greater than that of the free ligand,which leads to the coordinated ligand penetrating more deeply into,and stacking more strongly with the base pairs of the DNA.
In addition,we synthesized and characterized eleven rare earth complexes containing ligand of N,N'-bis(2-pyridinecarboxamide)-1, 4-diethylenetriamine.The results of elemental analysis,conductivity measurement,IR spectra,thermal analysis and NMR spectrum confirmed their chemical composition were:[La(H_3L~5)(NO_3)_2]NO_3Cl_3·3H_2O,Ln= La(Ⅲ),Nd(Ⅲ),Sm(Ⅲ),Eu(Ⅲ),Gd(Ⅲ),Dy(Ⅲ),Ho(Ⅲ),Er(Ⅲ),Tm(Ⅲ), Yb(Ⅲ)and Lu(Ⅲ).And also,the interaction between series complexes and DNA was studied by means of UV-visible spectra,fluorescence spectra, SERS spectra and viscometric titration.From the results,there were not evident insertion action between series complexes and DNA.Their interaction modes were probably in groove binding and electrostatic effect.
引文
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