喜树碱与生物大分子相互作用的光谱研究
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摘要
蛋白质是生命物质的基础和遗传性状的直接表达者,可参与DNA的复制、生物体细胞骨架的构成,具有多种生理功能,在生物体内起重要的作用。核酸是携带和传递遗传信息的载体,在生物的生长、发育、遗传和变异等生命过程中具有重要作用。从分子水平研究药物小分子与蛋白质、核酸的作用机理对于阐明药物在生物体内的药效发挥和代谢过程,新药的设计与开发,促进生命科学的发展等具有重要的意义。
喜树碱(CPT)属于天然的生物碱类化合物,具有广泛的生理活性,如抗炎、抗病毒、抗癌作用,因此,近年来一直受到人们的关注。本文对喜树碱、小分子与生物大分子相互作用的研究背景、现状、意义及其主要研究方法进行了综述；运用荧光光谱、紫外-可见光谱和红外光谱等手段系统研究了喜树碱与牛血清白蛋白(BSA)、溶菌酶(LYSO)、过氧化氢酶(CAT)、肌红蛋白(MB)、细胞色素C (CYT)及DNA的相互作用情况,研究结果对于进一步开展喜树碱及其衍生物的研究具有一定的指导作用。本论文的具体研究内容如下：
1、喜树碱的荧光光谱研究。以硫酸奎宁激发波长313 nm的荧光量子产率0.55为标准,在pH=7.40和20℃的条件下,测定CPT在不同激发波长下的荧光量子产率,在激发波长为365 nm的荧光量子产率为0.9977,结果证实喜树碱是一种强荧光化合物。
2、喜树碱与五种蛋白质的相互作用及分析研究。(1)利用荧光光谱研究了CPT与三种蛋白质(BSA、LYSO和CAT)的相互作用情况。计算出其结合常数,CPT与三者的作用力类型,且作用力大小为CAT>LYSO>BSA；结合紫外和同步荧光光谱讨论了CPT对蛋白构象的影响；(2)采用改进的荧光光谱法、紫外-可见光谱法和红外光谱法研究CPT与BSA、CAT、LYSO、MB和CYT五种蛋白的相互作用,结果显示：CPT-LYSO之间的作用力是静电作用力,其它均为疏水作用力,其作用力大小为CYT>MB>CAT>LYSO>BSA,与常规荧光光谱法一致。红外光谱法定性说明CPT对蛋白构象的影响。(3)根据研究喜树碱与五种蛋白的相互作用情况,研究了测定CPT的最佳条件,在生理条件下,初步建立一种CPT的测定方法,成功的消除蛋白的影响,并通过实际样品分析验证了方法的可靠性。
3、CPT与多种氨基酸生物小分子的相互作用研究。采用荧光光谱法研究了CPT与色氨酸(TRP)、酪氨酸(TYR)和苯丙氨酸(PHE)的作用机理,实验结果发现CPT与TRP的结合能力最强,CPT与TYR的结合能力最弱；采用改进的荧光光谱法考察了蛋白中常见氨基酸中的十三个氨基酸对CPT的荧光光谱的影响,结果发现CPT以形成分子间氢键的形式与十三种氨基酸分别作用。
4、喜树碱与鲑鱼精DNA分子的相互作用。采用改进荧光光谱法研究了CPT与鲑鱼精DNA的相互作用,探讨了其作用机理,并获得二者的结合位点数、结合常数、热力学参数等数据信息。在pH=7.40的条件下,20℃时,λex=252 nm和λex=222 nm时,结合常数KA分别为4.18×104 L·mol-1、2.36×104L·mol-1,结合位点数n分别为0.85、1.12；热力学参数△S0>0与△H0<0,证明CPT与DNA的作用力类型以疏水作用力为主；紫外-可见分光光度法结果证明CPT以嵌插结合模式与DNA发生作用,根据碱基和磷酸基红外光谱峰的变化,碱基1693 cm-1处和磷酸基1063 cm-1、1230 cm-1处的特征谱带分别移至1631cm-1、1058 cm-1和1289 cm-1,结果表明CPT与DNA的碱基和磷酸基团作用且改变DNA的B构型。
5、以吖啶橙作为荧光探针研究CPT与DNA的相互作用。在模拟生理条件下,以吖啶橙(AO)为荧光探针对CPT与DNA的相互作用进行了研究,通过变性实验、盐效应、阴离子猝灭剂KI、磷酸盐、竞争实验、粘度实验及抑制率等,结果表明CPT与DNA分子间的结合模式包括嵌插作用模式和沟槽作用模式,以嵌插作用模式为主。
Protein is the important matter of life and the direct expression of genetic traits. It can participate inDNA replication and the constitution of the frame of biological cells, and has various physiological functions, and takes an important role in life. The nucleic acid is the carrier of carrying and transferring the genetic information, and important for the growth, development of biological and genetic variation and life process. The interaction between small molecules and protein or nucleic acid is studied from molecular level, which has an important significance on drugs in the biological effects, and metabolic process of drugs, and the design of new drugs, and the development of the life information science.
CPT is a plant anti-cancer drug, with anti-inflammatory and antiviral effect. But it has the strong toxic and side-effect, and its derivatives have become a hot point of research. The research status and the significance and the main methods of the interaction between CPT and biomacromolecules have been mainly introduced. This paper, the fluorescence spectrometry, the improvement of fluorescence spectrometry, uv-vis spectrophotometry and infrared spectrum method were used to nvestigate CPT interact with cow serum albumin, lysozyme, catalase, muscle protein and cytochrome C and DNA. Results have certain guiding role on the further development of research on CPT and its derivatives. The thesis is divided into the following several parts:
1. The research on the fluorescence spectrum and analysis of CPT。By the standard of the fluorescence quantity irradiation 0.55 of quinine sulfate with excitation wavelength at 313 nm, in the determination conditions that pH was 7.40 and 20 degrees celsius, the fluorescence quantity irradiation of CPT were determined under different excitation wavelength, the quantum yield of fluorescence excitation wavelength at 365 nm is 0.9977. The results proved that CPT is a strong fluorescence compound.
2. The research of interaction between CPT and five proteins and analysis. (1) The interaction between CPT and three kinds of protein molecules were reseached by the methord of fluorescence spectrum. LYSO, CAT and BSA are the research objects. The quenching mechanism of the three kinds protein with endogenous fluorescent by CPT was investigated, the combination constant are also found, and the ability of CPT interacts with three kinds of protein were compared according to the combination constants, and the acting force form were discussed through the thermodynamic parameters. Results show that, the forces of CPT with protein is CAT> LYSO> BSA. The affection of CPT on protein conformations were discussed by uv and synchronous fluorescence spectroscopy; (2) The interaction between CPT and BSA, CAT, LYSO, CYT, MB and CYT were studyed by fluorescence spectrometry, ultraviolet-visible spectroscopy and infrared spectrum, and CPT was the subject and five kinds of protein molecules was the object. Main reaction type:the force of LYSO-CPT is the electrostatic force, and other forces are hydrophobic force.The ability of interaction was compared and analysised by the binding constant of the systems, and the influence of CPT on protein conformation was explained through the data. Results show that, the forces of CPT with protein is CYT> MB> CAT> LYSO> BSA, which were same as the conventional fluorescence spectrometry, under the condition of in vitro experiments. (3) The methods of measurement CPT were established in the system containing these five kinds of protein, and the reliability of the method was validated by the analysis in the actual samples.
3. The study of the interaction between CPT and kinds of amino acid small biomolecules. The reaction mechanism of CPT with amino acid (TRP、TYR and PHE) was studied by fluorescence spectrometry. Experimental results showed that the combination of CPT and TRP was the strongest, and the try was the weakest through comparison of the binding constants. The affection of thirteen amino acids on the fluorescence spectrometry of CPT was investigated, the results showed that CPT was held together by hydrogen bonds with these 13 kinds of amino acids, but because of the limitation of the method, the forces can't be compared.
4. The study of the improved fluorescence spectroscopy on the interaction between CPT and salmon sperm DNA.The interaction between CPT and salmon sperm DNA was investigated by means of the improved fluorescence spectrometry, and the mechanism of action was discussed, and the date information of the binding constant and number of binding sites for the CPT and DNA were obtained. In conditions that pH was 7.40 and 20 degrees celsius, the binding constant at the fluorescence excitation wavelength was 252 nm and 222 nm is 4.18×104L·mol-1 and 2.36×104 L·mol-1 and the number of binding sites at the fluorescence excitation wavelength was 252 nm and 222 nm is 0.85 and 1.12; The type of interaction force of intermolecular interaction was mainly hydrophobic force, according to△S0>0 and△H0<0. The results of Uv-Vis spectrophotometry and sychronous fluorescence spectrometry indicated that CPT interacted with DNA by intercalation. According to IR of the base and phosphoric acid:the IR peak of base at 1693 cm-1 and phosphoric acid at 1063 cm-1,1230 cm-1 moved to 1631 cm-1,1058 cm-1 and 1289 cm-1, the experimental results showed that the interaction of CPT with the bases and phosphate groups of DNA changed the B configurations of DNA.
5. The interaction between CPT and DNA was studied by the fluorescent probe of acetamiprid orange. The interaction between CPT and DNA was investigated using the fluorescence probe of acetamiprid orange (AO) under the physiological conditions, as well as the absorption spectra of DAN. The results of salteffectanion, luminescence quenchers KI, phosphate, competition tests, viscosity tests, inhibitory rate and denatured tests have indicated that CPT was bound to DNA by the mode of intercalation or the mode of groove binding, and the mode of intercalation was the mainly of intercalation mode.
喜树碱(CPT)属于天然的生物碱类化合物,具有广泛的生理活性,如抗炎、抗病毒、抗癌作用,因此,近年来一直受到人们的关注。本文对喜树碱、小分子与生物大分子相互作用的研究背景、现状、意义及其主要研究方法进行了综述；运用荧光光谱、紫外-可见光谱和红外光谱等手段系统研究了喜树碱与牛血清白蛋白(BSA)、溶菌酶(LYSO)、过氧化氢酶(CAT)、肌红蛋白(MB)、细胞色素C (CYT)及DNA的相互作用情况,研究结果对于进一步开展喜树碱及其衍生物的研究具有一定的指导作用。本论文的具体研究内容如下：
1、喜树碱的荧光光谱研究。以硫酸奎宁激发波长313 nm的荧光量子产率0.55为标准,在pH=7.40和20℃的条件下,测定CPT在不同激发波长下的荧光量子产率,在激发波长为365 nm的荧光量子产率为0.9977,结果证实喜树碱是一种强荧光化合物。
2、喜树碱与五种蛋白质的相互作用及分析研究。(1)利用荧光光谱研究了CPT与三种蛋白质(BSA、LYSO和CAT)的相互作用情况。计算出其结合常数,CPT与三者的作用力类型,且作用力大小为CAT>LYSO>BSA；结合紫外和同步荧光光谱讨论了CPT对蛋白构象的影响；(2)采用改进的荧光光谱法、紫外-可见光谱法和红外光谱法研究CPT与BSA、CAT、LYSO、MB和CYT五种蛋白的相互作用,结果显示：CPT-LYSO之间的作用力是静电作用力,其它均为疏水作用力,其作用力大小为CYT>MB>CAT>LYSO>BSA,与常规荧光光谱法一致。红外光谱法定性说明CPT对蛋白构象的影响。(3)根据研究喜树碱与五种蛋白的相互作用情况,研究了测定CPT的最佳条件,在生理条件下,初步建立一种CPT的测定方法,成功的消除蛋白的影响,并通过实际样品分析验证了方法的可靠性。
3、CPT与多种氨基酸生物小分子的相互作用研究。采用荧光光谱法研究了CPT与色氨酸(TRP)、酪氨酸(TYR)和苯丙氨酸(PHE)的作用机理,实验结果发现CPT与TRP的结合能力最强,CPT与TYR的结合能力最弱；采用改进的荧光光谱法考察了蛋白中常见氨基酸中的十三个氨基酸对CPT的荧光光谱的影响,结果发现CPT以形成分子间氢键的形式与十三种氨基酸分别作用。
4、喜树碱与鲑鱼精DNA分子的相互作用。采用改进荧光光谱法研究了CPT与鲑鱼精DNA的相互作用,探讨了其作用机理,并获得二者的结合位点数、结合常数、热力学参数等数据信息。在pH=7.40的条件下,20℃时,λex=252 nm和λex=222 nm时,结合常数KA分别为4.18×104 L·mol-1、2.36×104L·mol-1,结合位点数n分别为0.85、1.12；热力学参数△S0>0与△H0<0,证明CPT与DNA的作用力类型以疏水作用力为主；紫外-可见分光光度法结果证明CPT以嵌插结合模式与DNA发生作用,根据碱基和磷酸基红外光谱峰的变化,碱基1693 cm-1处和磷酸基1063 cm-1、1230 cm-1处的特征谱带分别移至1631cm-1、1058 cm-1和1289 cm-1,结果表明CPT与DNA的碱基和磷酸基团作用且改变DNA的B构型。
5、以吖啶橙作为荧光探针研究CPT与DNA的相互作用。在模拟生理条件下,以吖啶橙(AO)为荧光探针对CPT与DNA的相互作用进行了研究,通过变性实验、盐效应、阴离子猝灭剂KI、磷酸盐、竞争实验、粘度实验及抑制率等,结果表明CPT与DNA分子间的结合模式包括嵌插作用模式和沟槽作用模式,以嵌插作用模式为主。
Protein is the important matter of life and the direct expression of genetic traits. It can participate inDNA replication and the constitution of the frame of biological cells, and has various physiological functions, and takes an important role in life. The nucleic acid is the carrier of carrying and transferring the genetic information, and important for the growth, development of biological and genetic variation and life process. The interaction between small molecules and protein or nucleic acid is studied from molecular level, which has an important significance on drugs in the biological effects, and metabolic process of drugs, and the design of new drugs, and the development of the life information science.
CPT is a plant anti-cancer drug, with anti-inflammatory and antiviral effect. But it has the strong toxic and side-effect, and its derivatives have become a hot point of research. The research status and the significance and the main methods of the interaction between CPT and biomacromolecules have been mainly introduced. This paper, the fluorescence spectrometry, the improvement of fluorescence spectrometry, uv-vis spectrophotometry and infrared spectrum method were used to nvestigate CPT interact with cow serum albumin, lysozyme, catalase, muscle protein and cytochrome C and DNA. Results have certain guiding role on the further development of research on CPT and its derivatives. The thesis is divided into the following several parts:
1. The research on the fluorescence spectrum and analysis of CPT。By the standard of the fluorescence quantity irradiation 0.55 of quinine sulfate with excitation wavelength at 313 nm, in the determination conditions that pH was 7.40 and 20 degrees celsius, the fluorescence quantity irradiation of CPT were determined under different excitation wavelength, the quantum yield of fluorescence excitation wavelength at 365 nm is 0.9977. The results proved that CPT is a strong fluorescence compound.
2. The research of interaction between CPT and five proteins and analysis. (1) The interaction between CPT and three kinds of protein molecules were reseached by the methord of fluorescence spectrum. LYSO, CAT and BSA are the research objects. The quenching mechanism of the three kinds protein with endogenous fluorescent by CPT was investigated, the combination constant are also found, and the ability of CPT interacts with three kinds of protein were compared according to the combination constants, and the acting force form were discussed through the thermodynamic parameters. Results show that, the forces of CPT with protein is CAT> LYSO> BSA. The affection of CPT on protein conformations were discussed by uv and synchronous fluorescence spectroscopy; (2) The interaction between CPT and BSA, CAT, LYSO, CYT, MB and CYT were studyed by fluorescence spectrometry, ultraviolet-visible spectroscopy and infrared spectrum, and CPT was the subject and five kinds of protein molecules was the object. Main reaction type:the force of LYSO-CPT is the electrostatic force, and other forces are hydrophobic force.The ability of interaction was compared and analysised by the binding constant of the systems, and the influence of CPT on protein conformation was explained through the data. Results show that, the forces of CPT with protein is CYT> MB> CAT> LYSO> BSA, which were same as the conventional fluorescence spectrometry, under the condition of in vitro experiments. (3) The methods of measurement CPT were established in the system containing these five kinds of protein, and the reliability of the method was validated by the analysis in the actual samples.
3. The study of the interaction between CPT and kinds of amino acid small biomolecules. The reaction mechanism of CPT with amino acid (TRP、TYR and PHE) was studied by fluorescence spectrometry. Experimental results showed that the combination of CPT and TRP was the strongest, and the try was the weakest through comparison of the binding constants. The affection of thirteen amino acids on the fluorescence spectrometry of CPT was investigated, the results showed that CPT was held together by hydrogen bonds with these 13 kinds of amino acids, but because of the limitation of the method, the forces can't be compared.
4. The study of the improved fluorescence spectroscopy on the interaction between CPT and salmon sperm DNA.The interaction between CPT and salmon sperm DNA was investigated by means of the improved fluorescence spectrometry, and the mechanism of action was discussed, and the date information of the binding constant and number of binding sites for the CPT and DNA were obtained. In conditions that pH was 7.40 and 20 degrees celsius, the binding constant at the fluorescence excitation wavelength was 252 nm and 222 nm is 4.18×104L·mol-1 and 2.36×104 L·mol-1 and the number of binding sites at the fluorescence excitation wavelength was 252 nm and 222 nm is 0.85 and 1.12; The type of interaction force of intermolecular interaction was mainly hydrophobic force, according to△S0>0 and△H0<0. The results of Uv-Vis spectrophotometry and sychronous fluorescence spectrometry indicated that CPT interacted with DNA by intercalation. According to IR of the base and phosphoric acid:the IR peak of base at 1693 cm-1 and phosphoric acid at 1063 cm-1,1230 cm-1 moved to 1631 cm-1,1058 cm-1 and 1289 cm-1, the experimental results showed that the interaction of CPT with the bases and phosphate groups of DNA changed the B configurations of DNA.
5. The interaction between CPT and DNA was studied by the fluorescent probe of acetamiprid orange. The interaction between CPT and DNA was investigated using the fluorescence probe of acetamiprid orange (AO) under the physiological conditions, as well as the absorption spectra of DAN. The results of salteffectanion, luminescence quenchers KI, phosphate, competition tests, viscosity tests, inhibitory rate and denatured tests have indicated that CPT was bound to DNA by the mode of intercalation or the mode of groove binding, and the mode of intercalation was the mainly of intercalation mode.
引文
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