碱基修饰核苷与血清白蛋白的相互作用研究
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摘要
核苷类化合物具有广泛的生物活性,是一类重要的药物及药物中间体,在抗肿瘤、抗病毒和抗艾滋病药物中占有重要的地位,是目前公认的最有抗病毒潜能的一类药物。对天然核苷的修饰和改造可以极大地增强药物的活性,有关研究已成为当今药物化学、分子生物学和制药学的热点课题之一。
血清白蛋白是动物和人体血浆中重要的存储和转运蛋白,也是血浆中含量最丰富的蛋白质。血清白蛋白可与许多药物广泛结合,药物与蛋白质的作用机制是描述药物动力学性质的一项重要参数。建立药物与蛋白质结合的体外模型,了解二者的结合机理、结合常数、结合部位、结合力、结合距离等问题,对于揭示体内的药物动力学问题、指导合理用药具有一定意义,同时对于进行药物分子设计,新药开发,也具有重要的指导意义。药物与蛋白质的相互作用在药物动力学及临床药理学上的重要意义,使得这一研究领域十分活跃。本文在前人工作的基础上,综合多种实验方法,研究了模拟生理条件下(pH 7.40,离子强度0.10 mol/L),七种碱基修饰核苷:碘苷(IDUR)、5-I-尿苷(5-IUR)、6-巯基嘌呤(6-MP)、巯基鸟嘌呤(6-TG)、氰基乙基-5-氯-尿嘧啶(CECU)、氰基乙基-尿嘧啶(CEU)和5-I-尿嘧啶(5-IU)与血清白蛋白的相互作用,研究内容共分为七部分:
第一章:简要介绍了核苷及其碱基修饰作用、蛋白质的结构、性质和生理功能;概述了荧光光谱及计算机模拟分子对接模型在小分子和蛋白质相互作用研究中的应用原理和方法。
第二章:在模拟生理条件下,运用荧光光谱和紫外吸收光谱研究了七种碱基修饰核苷与血清白蛋白的相互作用,确定了碱基修饰核苷对血清白蛋白内源荧光的猝灭机制并计算了不同温度下的猝灭常数。
第三章:在确定了碱基修饰核苷与血清白蛋白相互作用机理的基础上,运用Lineweaver-Burk方程求出了七种碱基修饰核苷与血清白蛋白在不同温度下的结合常数,根据热力学方程计算出了部分热力学参数,确定了七种碱基修饰核苷与血清白蛋白间的主要作用力类型。
第四章:基于F?ster能量转移理论和血清白蛋白的荧光光谱与碱基修饰核苷的吸收光谱的重叠光谱积分,计算了碱基修饰核苷在蛋白质上的结合位置即与色氨酸残基之间的距离r。
第五章:根据光谱研究所得实验结果和数据,运用计算机模拟技术对碱基修饰核苷与人血清白蛋白的相互作用进行了研究,建立了碱基修饰核苷与蛋白质结合的体外模型。
第六章:讨论了常见离子的存在对结合作用的影响。结果表明:常见离子的存在将导致碱基修饰核苷与血清白蛋白间的结合发生改变。
第七章:总结了本论文研究得到的创新性研究成果,并对本研究领域的工作进行了展望。
Nucleosides and their derivatives exhibit significant biological activities such as antitumor, antiviral and antibacterial activities. They are a sort of important drugs and pharmaceutic intermediates. It is recognized that nucleosides have the most potential function to restrain virus. Drug activity could be greatly enhanced when the natural nucleoside have been modified and embellished, thus, the study in this field has become a focus in modern medicinal chemistry, molecular biology and medicament subject in recent years.
Serum albumin, the most abundant protein constituent of blood plasma and serves as a protein storage component, has many important physiological functions. Serum albumin can interact with many endogenous and exogenous substances including many drugs. It is important to study the interaction of drug with the protein because protein-drug binding plays an important role in pharmacology and pharmacodynamics. the study of interaction mechanism between small molecules and protein have very important significance for the pharmacokinetic behavior and the exploitations of new drugs. Establishing the binding model of the drug with serum albumin and investigating the binding mechanism, binding constants, binding sites, binding mode and binding distance, is significant to reveal Pharmacokinetics problems and guide for design and exploit new drugs. The significance of interaction between drugs and serum albumin in the pharmacokinetics and clinical pharmacology lead the study of this aspect to an active study field.
In this dissertation, fluorescence quenching method in combination with UV and molecular modeling were firstly used to investigate the interaction of seven nucleobase-modified nucleosides with serum albumin under simulated physiological conditions (pH 7.40, ionic strength 0.10 mol/L), they are 5-Iodo-deoxyuridine (IDUR), 5-iodouridine (5-IUR), 6-Mercaptopurine (6-MP), Thioguanine (6-TG), Cyanogen-ethylic-5-chlorinuracil uracil (CECU), Cyanogen-ethylic uracil (CEU), 5-Iodouracil (5-IU) . This dissertation consists of seven chapters.
Chapter 1: In this chapter, the function of nucleobase-modified nucleoside, the structures, properties and functions of proteins were briefly introduced. The principle and methods of fluorescence techniques and molecular modeling for study the interaction of small molecules with proteins were described.
Chapter 2: Under the simulated physiological conditions, the interactions were investigated between the seven nucleobase-modified nucleosides and serum albumin utilizing fluorescence quenching method in combination with UV spectrum. The quenching mechanisms of nucleobase-modified nucleosides to serum albumin were determined and the quenching constants at different temperatures were calculated.
Chapter 3: On the basis of interaction mechanism, the binding constants at the different temperatures were calculated between the seven nucleobase-modified nucleosides and serum albumin by using Lineweaver-Burk equation. The partial thermodynamic parameters were obtained according to thermodynamic equations, and the main acting forces were determined.
Chapter 4: According to the F?rster energy transfer theory and the integral of the overlap spectra between the fluorescence spectra of serum albumin and the ultra-visible absorption spectra of the nucleobase-modified nucleoside, the binding distances between nucleobase-modified nucleoside and tryptophan residue of serum albumin were calculated.
Chapter 5: Based on the data and the results of spectroscopic study, the interaction between nucleobase-modified nucleoside and human serum albumin were studied by using molecular modeling technique. The molecular modeling between nucleobase-modified nucleosides and serum albumin were established.
Chapter 6: The effect of common ions on binding constants was discussed. The results indicated that the binding constants between nucleobase-modified nucleosides and serum albumin were changed in the presence of common ions.
Chapter 7: The main innovations of this paper were summarized, and the prospects were suggested.
血清白蛋白是动物和人体血浆中重要的存储和转运蛋白,也是血浆中含量最丰富的蛋白质。血清白蛋白可与许多药物广泛结合,药物与蛋白质的作用机制是描述药物动力学性质的一项重要参数。建立药物与蛋白质结合的体外模型,了解二者的结合机理、结合常数、结合部位、结合力、结合距离等问题,对于揭示体内的药物动力学问题、指导合理用药具有一定意义,同时对于进行药物分子设计,新药开发,也具有重要的指导意义。药物与蛋白质的相互作用在药物动力学及临床药理学上的重要意义,使得这一研究领域十分活跃。本文在前人工作的基础上,综合多种实验方法,研究了模拟生理条件下(pH 7.40,离子强度0.10 mol/L),七种碱基修饰核苷:碘苷(IDUR)、5-I-尿苷(5-IUR)、6-巯基嘌呤(6-MP)、巯基鸟嘌呤(6-TG)、氰基乙基-5-氯-尿嘧啶(CECU)、氰基乙基-尿嘧啶(CEU)和5-I-尿嘧啶(5-IU)与血清白蛋白的相互作用,研究内容共分为七部分:
第一章:简要介绍了核苷及其碱基修饰作用、蛋白质的结构、性质和生理功能;概述了荧光光谱及计算机模拟分子对接模型在小分子和蛋白质相互作用研究中的应用原理和方法。
第二章:在模拟生理条件下,运用荧光光谱和紫外吸收光谱研究了七种碱基修饰核苷与血清白蛋白的相互作用,确定了碱基修饰核苷对血清白蛋白内源荧光的猝灭机制并计算了不同温度下的猝灭常数。
第三章:在确定了碱基修饰核苷与血清白蛋白相互作用机理的基础上,运用Lineweaver-Burk方程求出了七种碱基修饰核苷与血清白蛋白在不同温度下的结合常数,根据热力学方程计算出了部分热力学参数,确定了七种碱基修饰核苷与血清白蛋白间的主要作用力类型。
第四章:基于F?ster能量转移理论和血清白蛋白的荧光光谱与碱基修饰核苷的吸收光谱的重叠光谱积分,计算了碱基修饰核苷在蛋白质上的结合位置即与色氨酸残基之间的距离r。
第五章:根据光谱研究所得实验结果和数据,运用计算机模拟技术对碱基修饰核苷与人血清白蛋白的相互作用进行了研究,建立了碱基修饰核苷与蛋白质结合的体外模型。
第六章:讨论了常见离子的存在对结合作用的影响。结果表明:常见离子的存在将导致碱基修饰核苷与血清白蛋白间的结合发生改变。
第七章:总结了本论文研究得到的创新性研究成果,并对本研究领域的工作进行了展望。
Nucleosides and their derivatives exhibit significant biological activities such as antitumor, antiviral and antibacterial activities. They are a sort of important drugs and pharmaceutic intermediates. It is recognized that nucleosides have the most potential function to restrain virus. Drug activity could be greatly enhanced when the natural nucleoside have been modified and embellished, thus, the study in this field has become a focus in modern medicinal chemistry, molecular biology and medicament subject in recent years.
Serum albumin, the most abundant protein constituent of blood plasma and serves as a protein storage component, has many important physiological functions. Serum albumin can interact with many endogenous and exogenous substances including many drugs. It is important to study the interaction of drug with the protein because protein-drug binding plays an important role in pharmacology and pharmacodynamics. the study of interaction mechanism between small molecules and protein have very important significance for the pharmacokinetic behavior and the exploitations of new drugs. Establishing the binding model of the drug with serum albumin and investigating the binding mechanism, binding constants, binding sites, binding mode and binding distance, is significant to reveal Pharmacokinetics problems and guide for design and exploit new drugs. The significance of interaction between drugs and serum albumin in the pharmacokinetics and clinical pharmacology lead the study of this aspect to an active study field.
In this dissertation, fluorescence quenching method in combination with UV and molecular modeling were firstly used to investigate the interaction of seven nucleobase-modified nucleosides with serum albumin under simulated physiological conditions (pH 7.40, ionic strength 0.10 mol/L), they are 5-Iodo-deoxyuridine (IDUR), 5-iodouridine (5-IUR), 6-Mercaptopurine (6-MP), Thioguanine (6-TG), Cyanogen-ethylic-5-chlorinuracil uracil (CECU), Cyanogen-ethylic uracil (CEU), 5-Iodouracil (5-IU) . This dissertation consists of seven chapters.
Chapter 1: In this chapter, the function of nucleobase-modified nucleoside, the structures, properties and functions of proteins were briefly introduced. The principle and methods of fluorescence techniques and molecular modeling for study the interaction of small molecules with proteins were described.
Chapter 2: Under the simulated physiological conditions, the interactions were investigated between the seven nucleobase-modified nucleosides and serum albumin utilizing fluorescence quenching method in combination with UV spectrum. The quenching mechanisms of nucleobase-modified nucleosides to serum albumin were determined and the quenching constants at different temperatures were calculated.
Chapter 3: On the basis of interaction mechanism, the binding constants at the different temperatures were calculated between the seven nucleobase-modified nucleosides and serum albumin by using Lineweaver-Burk equation. The partial thermodynamic parameters were obtained according to thermodynamic equations, and the main acting forces were determined.
Chapter 4: According to the F?rster energy transfer theory and the integral of the overlap spectra between the fluorescence spectra of serum albumin and the ultra-visible absorption spectra of the nucleobase-modified nucleoside, the binding distances between nucleobase-modified nucleoside and tryptophan residue of serum albumin were calculated.
Chapter 5: Based on the data and the results of spectroscopic study, the interaction between nucleobase-modified nucleoside and human serum albumin were studied by using molecular modeling technique. The molecular modeling between nucleobase-modified nucleosides and serum albumin were established.
Chapter 6: The effect of common ions on binding constants was discussed. The results indicated that the binding constants between nucleobase-modified nucleosides and serum albumin were changed in the presence of common ions.
Chapter 7: The main innovations of this paper were summarized, and the prospects were suggested.
引文
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