某些天然产物和喹啉醛希夫碱配体及稀土金属配合物与生物大分子相互作用机理研究
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摘要
本论文分为三个部分。
第一部分概述了DNA和免疫球蛋白(Ig)的生物学基础、DNA和蛋白质与药物小分子相互作用的研究方法和技术以及喹啉化合物生物活性研究进展。
第二部分利用8-羟基喹啉-2-醛和4个芳香酰肼合成了4个新的Schiff-base配体,包括8-羟基喹啉-2-醛-苯甲酰腙、8-羟基喹啉-2-醛-2′-羟基苯甲酰腙、8-羟基喹啉-2-醛-4′-羟基苯甲酰腙和8-羟基喹啉-2-醛-异烟酰腙,并合成了它们的40个稀土金属配合物。利用红外光谱、~1H核磁波谱、质谱、元素分析、摩尔电导和晶体结构解析等实验方法确定了它们的结构,结果表明,从La(Ⅲ)到Er(Ⅲ),其金属配合物粉末样品的结构为[LnL~(1-4)(NO_3)(OH_2)_2]_2,而从DMF中析出的配合物晶体都具有[LnL~(1-4)(NO_3)(DMF)_2]_2的骨架结构:Yb(Ⅲ)配合物粉末样品的结构为[YbL~(1-4)(NO_3)(OH_2)]_2,而从DMF中析出的配合物晶体的骨架结构为[YbL~(1-4)(NO_3)(DMF)]_2。其中,配体的芳香酰肼侧链均发生了烯醇化而为二价负离子四齿配体,通过酚氧负离子、甲亚胺氮原子、喹啉环吡啶氮原子和烯醇式氧负离子与中心离子配位。配合物在DMF溶液中均为非电解质。在从La(Ⅲ)到Er(Ⅲ)的配合物中,这类通过酚羟基氧负离子联结形成的二聚体配合物均为9配位形式,而且存在一个(LnO)_2平面,整个分子的两个配体处于两个平行平面。单体结构中,一个DMF/H_2O分子从(LnO)_2平面的一侧与中心离子配位,另一个DMF/H_2O分子和一个NO_3~-(双齿配位)从平面的另一侧与中心离子配位。而Yb(Ⅲ)配合物为8配位形式,在其单体结构中,一个DMF/H_2O分子从(YbO)_2平面的一侧与中心离子配位,一个NO_3~-(双齿配位)从平面的另一侧与中心离子配位。
配体及配合物与小牛胸腺DNA的相互作用实验结果表明,这些物质都能与DNA以插入模式结合,而且配合物与DNA的结合强度大于配体,尤其是含有羟基基团的配合物表现出与DNA较强的结合能力。溴化乙锭荧光示踪法实验结果表明,这些物质都可以作为潜在的抗肿瘤药物,而且配合物比配体的抗肿瘤活性要高,但是它们的药理学、药效学和毒理学性质还需进一步进行体内研究。抗氧化活性实验结果表明,这些物质都具有较强的清除羟基自由基和超氧负离子自由基的能力。含有羟基取代基的配体及其配合物表现出较强的清除羟基自由基的能力,而含有N原子杂环的配合物表现出较强的清除超氧负离子自由基的能力。实验结果表明清除羟基自由基和清除超氧负离子自由基的作用机理不同。赋予这些DNA结合试剂抗氧化性质,它们可能会有效地抑制DNA/TBP(结合蛋白)或者异构酶(topoisomerases)的形成。
第三部分利用荧光淬灭、傅里叶变换红外(FT-IR)光谱、圆二色性(circulardichroism,CD)光谱、透射电镜(transmission electron microscopy,TEM),分子模型(molecular modeling)以及其它实验方法研究了4种植物药有效成分包括紫杉醇、姜黄素、山奈酚和槲皮素与静注免疫球蛋白(IVIG)的相互作用。
实验结果表明,当药物与IVIG发生作用后,尽管蛋白的多聚肽链发生了部分的去折叠,但是蛋白的β构型依然保持,即其生理学和免疫学功能可能依然保持,而且这类结合都是非特异性的弱结合,所以IVIG能作为它们的体内转运蛋白。另外,紫杉醇与IVIG的结合作用在一定浓度比范围内(C_(Taxol)/C_(IVIG)＜15:1)能抑制紫杉醇在水体系中的聚合或结晶。槲皮素相对于山奈酚因为3′-OH的存在,其与IVIG的结合强度高于山奈酚,同时能稳定蛋白的二级结构并能抑制蛋白的无序化。但是需要引起注意的是,这些药物与IVIG的结合强度都略小于它们与人血清白蛋白(HSA)的结合强度,在体内可能存在一定的竞争反应。该研究将为临床医师建立全新的免疫辅助疗法提供一定的理论依据,同时对于药物分子设计也能提供一定的参考。另外,该研究建立起了比较完善的药物分子与蛋白相互作用的研究方法,将为其它药物尤其是配合物药物与蛋白的相互作用研究提供一定的指导意义。
This dissertation comprises of three chapters.
The molecular biological foundation of DNA and Ig(Immunoglobulin),the research technology and methods of DNA and protein with drugs as well as the research and advance in quinoline derivatives with biological activities are summarized in chapter 1.
In the chapter 2,four new Schiff-base ligands,8-hydroxyquinoline-2-carbaldehyde-(benzoyl)hydrazone,8-hydroxyquinoline-2-carbaldehyde-(2'-hydroxybenzoyl) hydrazone,8-hydroxyquinoline-2-carbaldehyde-(4'-hydroxybenzoyl)hydrazone and 8-hydroxyquinoline-2-carbaldehyde-(isonicotinyl)hydrazone,are synthesized,respectively,from 8-hydroxy-quinoline-2-carbaldehyde and four aroylhydrazides.Moreover,their 40 lanthanide complexes are synthesized.The structrues of these ligands and rare-earth metal complexes are determined by FT-IR spectra,~1H NMR,ESI-Trap/Mass,Elemental analyses,Molar conductance and X-crystallogrphy.Experimental results indicate that all the powder metal complexes are of[LnL~(1-4)(NO_3)(OH_2)_2]_2 from La(Ⅲ) to Er(Ⅲ) complexes while their crystals have the framework of[LnL~(1-4)(NO_3)(DMF)_2]_2,where one H_2O/DMF molecule is binding orthogonally to the ligand-plane from one side to the metal ion,while another H_2O/DMF and a nitrate anion(bidentate) are binding from the other.However, powder Yb(Ⅲ) complexes and crystals have the frameworks of[YbL~(1-4)(NO_3)(OH_2)]_2 and[YbL~(1-4)(NO_3)(DMF)]_2,respectively,where one H_2O/DMF molecule is binding orthogonally to the ligand-plane from one side to the metal ion,while a nitrate anion (bidentate) are binding from the other.For all these metal complexes,every ligand acts as a dibasic tetradentate ligand,binding to metal ion through the phenolate oxygen atom,nitrogen atom of quinolinato unit,C=N group,and ~-O-C=N- group (enolized and deprotonated from O=C-NH-) of the aroylhydrazine side chain. Dimerization of the monomeric unit occurs through the phenolate oxygen atoms leading to a central planar four-membered(LnO)_2 ring.
Studies on the interaction of ligands and metal complexes and Calf thymus DNA (CT-DNA) indicate that all the investigated compounds can bind to CT-DNA through intercalative modes,but the bindings of metal complexes to CT-DNA are more efficient than those of ligands.Fluorescent trace methods by ethidium bromide(EtBr) indicate that all the investigated compounds may have potential anti-tumor activities but the anti-tumor activities metal complexes may be better than those of ligands, however,their pharmacodynamical,pharmacological and toxicological properties should be further studied in vivo.Anti-oxidation experimental results indicate that all the investigated compounds have strong anti-oxidation activities including scavenging hydroxyl radicals and superoxide radicals.However,ligands and metal complexes containing active phenolic hydroxyl groups show stronger scavenging effects for hydroxyl radicals,and metal complexes containing N-heteroaromatic substituents show stronger scavenging effects for superoxide radicals.This indicates that there are different mechamisms between scavenging hydroxyl radicals and superoxide radicals. Adding a reactive entity endowed with oxidative properties should improve the efficiency of inhibition of the formation of a DNA/TBP complex or topoisomerases.
In the chapter 3,the interactions of intravenous immunoglobulin(IVIG) with four plant active components including Taxol,Curcumin,Kaempferol and Quercetin are investigated through fluorescence quening,FT-IR spectra,CD(circular dichroism) spectra,TEM(transmission electron microscopy),molecular modeling and other experimental methods,etc.
The experimental results indicate that a partial unfolding of the protein structure take place after addition of every drug,but the typicalβstructural conformation of IVIG is retentive,that is,the biological and immunological functions of IVIG may retentive.The interactions of drugs and IVIG are all non-specific and weak,so IVIG can be used as transfer protein for these drugs in vivo.In addition,the interaction of Taxol and IVIG can inhibit Taxol from crystallizing in aqueous solution when the molar concentration ratio of Taxol to IVIG does not exceed 15:1.Moreover,Quercetin containing 3'-OH has higher binding constant than Kaempferol,and may be more efficient agent to stable the secondary structure and inhibit the random of protein in comparison with Kaempferol.However,the interactions of these drugs and IVIG are slightly weaker than their binding to human serum albumin(HSA).These studies will provide fundamental data for clinicians who may construct new protocols for patients by using the high-safety profile of drug-protein conjugates and provide some references in drug research.Additionally,these studies have established a nearly integrated experimental method,which will be a guide and meaningful for the subsequent interactions of drugs and proteins,especially for metal complex drugs.
第一部分概述了DNA和免疫球蛋白(Ig)的生物学基础、DNA和蛋白质与药物小分子相互作用的研究方法和技术以及喹啉化合物生物活性研究进展。
第二部分利用8-羟基喹啉-2-醛和4个芳香酰肼合成了4个新的Schiff-base配体,包括8-羟基喹啉-2-醛-苯甲酰腙、8-羟基喹啉-2-醛-2′-羟基苯甲酰腙、8-羟基喹啉-2-醛-4′-羟基苯甲酰腙和8-羟基喹啉-2-醛-异烟酰腙,并合成了它们的40个稀土金属配合物。利用红外光谱、~1H核磁波谱、质谱、元素分析、摩尔电导和晶体结构解析等实验方法确定了它们的结构,结果表明,从La(Ⅲ)到Er(Ⅲ),其金属配合物粉末样品的结构为[LnL~(1-4)(NO_3)(OH_2)_2]_2,而从DMF中析出的配合物晶体都具有[LnL~(1-4)(NO_3)(DMF)_2]_2的骨架结构:Yb(Ⅲ)配合物粉末样品的结构为[YbL~(1-4)(NO_3)(OH_2)]_2,而从DMF中析出的配合物晶体的骨架结构为[YbL~(1-4)(NO_3)(DMF)]_2。其中,配体的芳香酰肼侧链均发生了烯醇化而为二价负离子四齿配体,通过酚氧负离子、甲亚胺氮原子、喹啉环吡啶氮原子和烯醇式氧负离子与中心离子配位。配合物在DMF溶液中均为非电解质。在从La(Ⅲ)到Er(Ⅲ)的配合物中,这类通过酚羟基氧负离子联结形成的二聚体配合物均为9配位形式,而且存在一个(LnO)_2平面,整个分子的两个配体处于两个平行平面。单体结构中,一个DMF/H_2O分子从(LnO)_2平面的一侧与中心离子配位,另一个DMF/H_2O分子和一个NO_3~-(双齿配位)从平面的另一侧与中心离子配位。而Yb(Ⅲ)配合物为8配位形式,在其单体结构中,一个DMF/H_2O分子从(YbO)_2平面的一侧与中心离子配位,一个NO_3~-(双齿配位)从平面的另一侧与中心离子配位。
配体及配合物与小牛胸腺DNA的相互作用实验结果表明,这些物质都能与DNA以插入模式结合,而且配合物与DNA的结合强度大于配体,尤其是含有羟基基团的配合物表现出与DNA较强的结合能力。溴化乙锭荧光示踪法实验结果表明,这些物质都可以作为潜在的抗肿瘤药物,而且配合物比配体的抗肿瘤活性要高,但是它们的药理学、药效学和毒理学性质还需进一步进行体内研究。抗氧化活性实验结果表明,这些物质都具有较强的清除羟基自由基和超氧负离子自由基的能力。含有羟基取代基的配体及其配合物表现出较强的清除羟基自由基的能力,而含有N原子杂环的配合物表现出较强的清除超氧负离子自由基的能力。实验结果表明清除羟基自由基和清除超氧负离子自由基的作用机理不同。赋予这些DNA结合试剂抗氧化性质,它们可能会有效地抑制DNA/TBP(结合蛋白)或者异构酶(topoisomerases)的形成。
第三部分利用荧光淬灭、傅里叶变换红外(FT-IR)光谱、圆二色性(circulardichroism,CD)光谱、透射电镜(transmission electron microscopy,TEM),分子模型(molecular modeling)以及其它实验方法研究了4种植物药有效成分包括紫杉醇、姜黄素、山奈酚和槲皮素与静注免疫球蛋白(IVIG)的相互作用。
实验结果表明,当药物与IVIG发生作用后,尽管蛋白的多聚肽链发生了部分的去折叠,但是蛋白的β构型依然保持,即其生理学和免疫学功能可能依然保持,而且这类结合都是非特异性的弱结合,所以IVIG能作为它们的体内转运蛋白。另外,紫杉醇与IVIG的结合作用在一定浓度比范围内(C_(Taxol)/C_(IVIG)＜15:1)能抑制紫杉醇在水体系中的聚合或结晶。槲皮素相对于山奈酚因为3′-OH的存在,其与IVIG的结合强度高于山奈酚,同时能稳定蛋白的二级结构并能抑制蛋白的无序化。但是需要引起注意的是,这些药物与IVIG的结合强度都略小于它们与人血清白蛋白(HSA)的结合强度,在体内可能存在一定的竞争反应。该研究将为临床医师建立全新的免疫辅助疗法提供一定的理论依据,同时对于药物分子设计也能提供一定的参考。另外,该研究建立起了比较完善的药物分子与蛋白相互作用的研究方法,将为其它药物尤其是配合物药物与蛋白的相互作用研究提供一定的指导意义。
This dissertation comprises of three chapters.
The molecular biological foundation of DNA and Ig(Immunoglobulin),the research technology and methods of DNA and protein with drugs as well as the research and advance in quinoline derivatives with biological activities are summarized in chapter 1.
In the chapter 2,four new Schiff-base ligands,8-hydroxyquinoline-2-carbaldehyde-(benzoyl)hydrazone,8-hydroxyquinoline-2-carbaldehyde-(2'-hydroxybenzoyl) hydrazone,8-hydroxyquinoline-2-carbaldehyde-(4'-hydroxybenzoyl)hydrazone and 8-hydroxyquinoline-2-carbaldehyde-(isonicotinyl)hydrazone,are synthesized,respectively,from 8-hydroxy-quinoline-2-carbaldehyde and four aroylhydrazides.Moreover,their 40 lanthanide complexes are synthesized.The structrues of these ligands and rare-earth metal complexes are determined by FT-IR spectra,~1H NMR,ESI-Trap/Mass,Elemental analyses,Molar conductance and X-crystallogrphy.Experimental results indicate that all the powder metal complexes are of[LnL~(1-4)(NO_3)(OH_2)_2]_2 from La(Ⅲ) to Er(Ⅲ) complexes while their crystals have the framework of[LnL~(1-4)(NO_3)(DMF)_2]_2,where one H_2O/DMF molecule is binding orthogonally to the ligand-plane from one side to the metal ion,while another H_2O/DMF and a nitrate anion(bidentate) are binding from the other.However, powder Yb(Ⅲ) complexes and crystals have the frameworks of[YbL~(1-4)(NO_3)(OH_2)]_2 and[YbL~(1-4)(NO_3)(DMF)]_2,respectively,where one H_2O/DMF molecule is binding orthogonally to the ligand-plane from one side to the metal ion,while a nitrate anion (bidentate) are binding from the other.For all these metal complexes,every ligand acts as a dibasic tetradentate ligand,binding to metal ion through the phenolate oxygen atom,nitrogen atom of quinolinato unit,C=N group,and ~-O-C=N- group (enolized and deprotonated from O=C-NH-) of the aroylhydrazine side chain. Dimerization of the monomeric unit occurs through the phenolate oxygen atoms leading to a central planar four-membered(LnO)_2 ring.
Studies on the interaction of ligands and metal complexes and Calf thymus DNA (CT-DNA) indicate that all the investigated compounds can bind to CT-DNA through intercalative modes,but the bindings of metal complexes to CT-DNA are more efficient than those of ligands.Fluorescent trace methods by ethidium bromide(EtBr) indicate that all the investigated compounds may have potential anti-tumor activities but the anti-tumor activities metal complexes may be better than those of ligands, however,their pharmacodynamical,pharmacological and toxicological properties should be further studied in vivo.Anti-oxidation experimental results indicate that all the investigated compounds have strong anti-oxidation activities including scavenging hydroxyl radicals and superoxide radicals.However,ligands and metal complexes containing active phenolic hydroxyl groups show stronger scavenging effects for hydroxyl radicals,and metal complexes containing N-heteroaromatic substituents show stronger scavenging effects for superoxide radicals.This indicates that there are different mechamisms between scavenging hydroxyl radicals and superoxide radicals. Adding a reactive entity endowed with oxidative properties should improve the efficiency of inhibition of the formation of a DNA/TBP complex or topoisomerases.
In the chapter 3,the interactions of intravenous immunoglobulin(IVIG) with four plant active components including Taxol,Curcumin,Kaempferol and Quercetin are investigated through fluorescence quening,FT-IR spectra,CD(circular dichroism) spectra,TEM(transmission electron microscopy),molecular modeling and other experimental methods,etc.
The experimental results indicate that a partial unfolding of the protein structure take place after addition of every drug,but the typicalβstructural conformation of IVIG is retentive,that is,the biological and immunological functions of IVIG may retentive.The interactions of drugs and IVIG are all non-specific and weak,so IVIG can be used as transfer protein for these drugs in vivo.In addition,the interaction of Taxol and IVIG can inhibit Taxol from crystallizing in aqueous solution when the molar concentration ratio of Taxol to IVIG does not exceed 15:1.Moreover,Quercetin containing 3'-OH has higher binding constant than Kaempferol,and may be more efficient agent to stable the secondary structure and inhibit the random of protein in comparison with Kaempferol.However,the interactions of these drugs and IVIG are slightly weaker than their binding to human serum albumin(HSA).These studies will provide fundamental data for clinicians who may construct new protocols for patients by using the high-safety profile of drug-protein conjugates and provide some references in drug research.Additionally,these studies have established a nearly integrated experimental method,which will be a guide and meaningful for the subsequent interactions of drugs and proteins,especially for metal complex drugs.
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