毛细管电泳法用于药材有效成分和体液内药物的分析研究
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摘要
药物分析研究的主要内容包括中药有效成分分析、体内药物活性成分监测、手性药物拆分、药物与生物大分子的相互作用等。毛细管电泳技术是正在迅速发展的一种高效液相分离分析技术，具有分辨率高、分析速度快、分析成本低、应用范围广等优点，在药物分析中得到了广泛应用。本文基于高效毛细管电泳技术，采取毛细管区带电泳（CZE）、非水毛细管电泳(NACE)、亲和毛细管电泳(ACE)等三种分离模式，以气相色谱-质谱法（GC-MS）、化学发光法（CL）、三维荧光光谱作为补充方法，重点对药物分析的中药有效成分分析、体内药物活性成分分析、药物与人血清白蛋白相互作用等方面开展应用研究，建立了多种药物的简便、灵敏的分离检测方法，将ACE用于抗癌药物与人血清白蛋白的相互作用机理研究，获得满意结果。
第一章绪论部分简要阐述了毛细管电泳的基本原理，对毛细管电泳的不同分离模式及其在药物分析中的应用进行了综述。
第二章对中药材决明子的有效成分蒽醌和脂肪酸类化合物进行分析研究。采用非水毛细管电泳对决明子中的蒽醌化合物进行分离，研究了不同缓冲液、非水介质和添加剂对分离的影响，对多种蒽醌化合物实现了有效分离；通过电泳条件优化，提出了NACE测定大黄素和橙黄决明素的新方法，两种组分的标准曲线线性范围分别为2.04—204μg/mL和3.32--332μg/mL，检出限分别为0.61和1.0μg/mL。另外，采用超声辅助-石油醚提取决明子中脂肪酸类成分，并以GC-MS法进行了分析测定。研究表明，以石油醚为提取剂，不饱和脂肪酸的提取率高于传统回流方法。提取物中共检测出7种脂肪酸，其中亚油酸含量丰富，其质量分数为44.45%。
第三章采用毛细管电泳法对人体液中的头孢类抗生素及其配伍药物进行分析研究。首先，采用毛细管区带电泳法同时分离测定了人血清和尿液液中的头孢孟多和丙磺舒。在优化条件下，被测药物在6min内实现有效分离。以水杨酸为内标物，头孢孟多和丙磺舒的标准曲线分别在10～200和5～110mg/L范围内具有良好线性关系（r＞0.999）。其次，采用毛细管区带电泳分离模式，建立了一种快速、灵敏的同时测定头孢哌酮、舒巴坦和丙磺舒的新方法。实验结果表明三种药物的标准曲线均具有良好线性，检出限(S/N=3)分别为3.2、15和1.6μg/mL。
第四章采用毛细管电泳-电化学发光法和流动注射化学发光法对人体液和药物制剂中氟喹诺酮药物进行分析研究。将毛细管电泳分离技术与电化学发光法检测方法结合，建立了毛细管电泳-电化学发光法同时测定人尿液中氟罗沙星和脯氨酸，两种药物的检出限分别为0.06和0.02μg/mL，线性范围分别为0.4～80和0.1～60μg/mL。本文还以流动注射化学发光法对喹诺酮类药物依诺沙星的在不同发光体系中的独特作用进行了研究，建立了高灵敏的化学发光测定依诺沙星的新方法，检出限达到10-10g/mL数量级，灵敏度远高于CE-ECL法（10-8g/mL）和CE法（10-6g/mL）。
第五章采用亲和毛细管电泳法对抗癌药物5-氟尿嘧啶与人血清白蛋白的相互作用进行研究，对FU与HSA在接近生理条件下的缔合作用进行分析，结果表明FU与HSA亲和力较低，结合常数为9.19×104M-1。实验测得缔合过程的焓变（H）和熵变（S）均为正值，说明FU与HSA缔合是一个吸热的熵驱动过程，疏水作用在缔合过程中发挥着主要作用。法华林和酮洛芬对FU的竞争性置换试验表明，FU与蛋白质HSA的结合部位是位点Ⅰ。三维荧光光谱研究证实5-氟尿嘧啶在与血清蛋白的结合过程中能够改变血清蛋白的构象。
第六章总结了本文研究工作主要内容、成果及创新点，对毛细管电泳及其在药物分析中的应用研究发展趋势进行了展望。
The major research field of pharmaceutical analysis involves the analysis of effectivecomponents in Chinese medicine, the monitoring of active ingredient of drugs in the body,chiral drugs separation, the interaction between drug molecule and biomacromolecule and soon. Due to the superior seperation efficiency, fast speed, low cost, and wide application,capillary electrophoresis (CE) is becoming a rapid development technique for pharmaceuticalanalysis. In this paper, based on three separation modes including capillary zoneelectrophoresis (CZE), non-aqueous capillary electrophoresis (NACE), and affinity capillaryelectrophoresis (ACE), coupled with gas chromatography-mass spectrometry (GC-MS),chemiluminescence (CL), and three-dimensional fluorescence spectra, several simple andsensitive analysis methods for the determination of some drugs were developed. The proposedmethods had been successfully applied for the dermination of various drugs such as effectivecomponents in Chinese medicine, the monitoring of active ingredient of drugs in the body.Moreover, the interaction mechanism between an antitumor drug and human serum albuminwas investigated by ACE, and satisfactory results were obtained.
In Chapter1, after demonstration the basic principle of CE, different seperation modesand their application in drugs analysis were reviewed.
In Chapter2, the analytical methods for the determination of anthraquinones and fattyacids in Semen Cassiae were studied. Several anthraquinone compounds in Semen Cassiaewere successfully seperated by NACE, and the influence factors including the types ofbuffer, non-aqueous media and additive were investigated in detail. Under the optimizedconditions, a new method for simultaneous determination of emodin and aurantio-obtusinwas established. The linear ranges were2.04—204and3.32—332μg/mL, respectively,with the limit of detection (LOD)0.61μg/mL for emodin and1.0μg/mL foraurantio-obtusin. Furthermore, fatty acids were extracted from cassiae seed by usingultrasonic-assisted method with petroleum ether as solvent, and the extracts were analyzedby GC-MS. The results showed that ultrasonic-assisted extraction was more effective forunsaturated fatty acid than conventional refluxing method. There were seven fatty acidswere characterized and determined. Unsaturated fatty acids especially linoleic acid are richin the extracts with a content of mass fraction44.45%.
Chapter3described the establishment of novel methods for the determination of cephalosporins and medicines combined with them in the body fluids by CE. Firstly, theapplicability of capillary zone electrophoresis for simultaneous determination ofcefamandole and probenecid in human serum and urine samples has been studied. Underthe optimized conditions, the analytes can be separated in6min effectively. When salicylicacid was chosen as the internal standard，the standard curves of cefamandole andprobenecid showed good linearity between10～200and5～110mg/L respectively with thecorrelation coefficients r＞0.999. Secondly, a rapid and sensitive method for simultaneousdetermination of cefoperazone, sulbactam and probenecid by CZE was also proposed. Theexperiment results showed that the standard curves for three drugs had good linearity，andthe LODs were3.2,15and1.6μg/mL(S/N=3), respectively.
Chapter4presented the development of methods for the determination offluoroquinolones in pharmaceutical preparation and biological fluids withCE-electrochemiluminescence(CE-ECL) and flow injection chemiluminescence(FI-CL). First,fleroxacin and proline in urine were simultaneously determined by CE coupled withelectrochemiluminescence. The linear ranges were0.4～80and0.1～60μg/mL, respectively,with the LOD of0.06μg/mL for fleroxacin and0.02μg/mL for proline. Moreover, the uniquebehaviors of enoxacin belongs to quinolones drugs in different chemiluminescence systemswere investigated by flow injection chemiluminescence. Based on it, a new sensitive methodof CL was proposed for determination of enoxacin. The LOD was as low as10-10g/mL,which is more sensitive than CE-ECL（10-8g/mL）and CE（10-6g/mL）.
In chapter5, the characterization of interaction between antitumor drug5-fluorouracil(FU) and human serum albumin (HSA) was studied by affinity capillary electrophoresis(ACE). The binding of FU drug to HSA at near-physiological conditions was evaluated. FUwas found to show low affinity toward HSA, with binding constant of9.19×104M-1. Thepositive H and S values obtained by ACE showed that the binding reaction was anendothermic process, the entropy drived the binding, and hydrophobic interaction playedmajor roles in the binding of FU to HSA. The replacement test with warfarin and ketoprofenshowed that binding site of FU at the protein HSA is believed to be site I. Three-dimensionalfluorescence studies showed that the presence of FU could change the conformation of BSAduring the binding process.
In chapter6, the main work, findings and innovation of this thesis were illustrated. At theend, the development trend of CE in the application of drugs analysis was presented.
第一章绪论部分简要阐述了毛细管电泳的基本原理，对毛细管电泳的不同分离模式及其在药物分析中的应用进行了综述。
第二章对中药材决明子的有效成分蒽醌和脂肪酸类化合物进行分析研究。采用非水毛细管电泳对决明子中的蒽醌化合物进行分离，研究了不同缓冲液、非水介质和添加剂对分离的影响，对多种蒽醌化合物实现了有效分离；通过电泳条件优化，提出了NACE测定大黄素和橙黄决明素的新方法，两种组分的标准曲线线性范围分别为2.04—204μg/mL和3.32--332μg/mL，检出限分别为0.61和1.0μg/mL。另外，采用超声辅助-石油醚提取决明子中脂肪酸类成分，并以GC-MS法进行了分析测定。研究表明，以石油醚为提取剂，不饱和脂肪酸的提取率高于传统回流方法。提取物中共检测出7种脂肪酸，其中亚油酸含量丰富，其质量分数为44.45%。
第三章采用毛细管电泳法对人体液中的头孢类抗生素及其配伍药物进行分析研究。首先，采用毛细管区带电泳法同时分离测定了人血清和尿液液中的头孢孟多和丙磺舒。在优化条件下，被测药物在6min内实现有效分离。以水杨酸为内标物，头孢孟多和丙磺舒的标准曲线分别在10～200和5～110mg/L范围内具有良好线性关系（r＞0.999）。其次，采用毛细管区带电泳分离模式，建立了一种快速、灵敏的同时测定头孢哌酮、舒巴坦和丙磺舒的新方法。实验结果表明三种药物的标准曲线均具有良好线性，检出限(S/N=3)分别为3.2、15和1.6μg/mL。
第四章采用毛细管电泳-电化学发光法和流动注射化学发光法对人体液和药物制剂中氟喹诺酮药物进行分析研究。将毛细管电泳分离技术与电化学发光法检测方法结合，建立了毛细管电泳-电化学发光法同时测定人尿液中氟罗沙星和脯氨酸，两种药物的检出限分别为0.06和0.02μg/mL，线性范围分别为0.4～80和0.1～60μg/mL。本文还以流动注射化学发光法对喹诺酮类药物依诺沙星的在不同发光体系中的独特作用进行了研究，建立了高灵敏的化学发光测定依诺沙星的新方法，检出限达到10-10g/mL数量级，灵敏度远高于CE-ECL法（10-8g/mL）和CE法（10-6g/mL）。
第五章采用亲和毛细管电泳法对抗癌药物5-氟尿嘧啶与人血清白蛋白的相互作用进行研究，对FU与HSA在接近生理条件下的缔合作用进行分析，结果表明FU与HSA亲和力较低，结合常数为9.19×104M-1。实验测得缔合过程的焓变（H）和熵变（S）均为正值，说明FU与HSA缔合是一个吸热的熵驱动过程，疏水作用在缔合过程中发挥着主要作用。法华林和酮洛芬对FU的竞争性置换试验表明，FU与蛋白质HSA的结合部位是位点Ⅰ。三维荧光光谱研究证实5-氟尿嘧啶在与血清蛋白的结合过程中能够改变血清蛋白的构象。
第六章总结了本文研究工作主要内容、成果及创新点，对毛细管电泳及其在药物分析中的应用研究发展趋势进行了展望。
The major research field of pharmaceutical analysis involves the analysis of effectivecomponents in Chinese medicine, the monitoring of active ingredient of drugs in the body,chiral drugs separation, the interaction between drug molecule and biomacromolecule and soon. Due to the superior seperation efficiency, fast speed, low cost, and wide application,capillary electrophoresis (CE) is becoming a rapid development technique for pharmaceuticalanalysis. In this paper, based on three separation modes including capillary zoneelectrophoresis (CZE), non-aqueous capillary electrophoresis (NACE), and affinity capillaryelectrophoresis (ACE), coupled with gas chromatography-mass spectrometry (GC-MS),chemiluminescence (CL), and three-dimensional fluorescence spectra, several simple andsensitive analysis methods for the determination of some drugs were developed. The proposedmethods had been successfully applied for the dermination of various drugs such as effectivecomponents in Chinese medicine, the monitoring of active ingredient of drugs in the body.Moreover, the interaction mechanism between an antitumor drug and human serum albuminwas investigated by ACE, and satisfactory results were obtained.
In Chapter1, after demonstration the basic principle of CE, different seperation modesand their application in drugs analysis were reviewed.
In Chapter2, the analytical methods for the determination of anthraquinones and fattyacids in Semen Cassiae were studied. Several anthraquinone compounds in Semen Cassiaewere successfully seperated by NACE, and the influence factors including the types ofbuffer, non-aqueous media and additive were investigated in detail. Under the optimizedconditions, a new method for simultaneous determination of emodin and aurantio-obtusinwas established. The linear ranges were2.04—204and3.32—332μg/mL, respectively,with the limit of detection (LOD)0.61μg/mL for emodin and1.0μg/mL foraurantio-obtusin. Furthermore, fatty acids were extracted from cassiae seed by usingultrasonic-assisted method with petroleum ether as solvent, and the extracts were analyzedby GC-MS. The results showed that ultrasonic-assisted extraction was more effective forunsaturated fatty acid than conventional refluxing method. There were seven fatty acidswere characterized and determined. Unsaturated fatty acids especially linoleic acid are richin the extracts with a content of mass fraction44.45%.
Chapter3described the establishment of novel methods for the determination of cephalosporins and medicines combined with them in the body fluids by CE. Firstly, theapplicability of capillary zone electrophoresis for simultaneous determination ofcefamandole and probenecid in human serum and urine samples has been studied. Underthe optimized conditions, the analytes can be separated in6min effectively. When salicylicacid was chosen as the internal standard，the standard curves of cefamandole andprobenecid showed good linearity between10～200and5～110mg/L respectively with thecorrelation coefficients r＞0.999. Secondly, a rapid and sensitive method for simultaneousdetermination of cefoperazone, sulbactam and probenecid by CZE was also proposed. Theexperiment results showed that the standard curves for three drugs had good linearity，andthe LODs were3.2,15and1.6μg/mL(S/N=3), respectively.
Chapter4presented the development of methods for the determination offluoroquinolones in pharmaceutical preparation and biological fluids withCE-electrochemiluminescence(CE-ECL) and flow injection chemiluminescence(FI-CL). First,fleroxacin and proline in urine were simultaneously determined by CE coupled withelectrochemiluminescence. The linear ranges were0.4～80and0.1～60μg/mL, respectively,with the LOD of0.06μg/mL for fleroxacin and0.02μg/mL for proline. Moreover, the uniquebehaviors of enoxacin belongs to quinolones drugs in different chemiluminescence systemswere investigated by flow injection chemiluminescence. Based on it, a new sensitive methodof CL was proposed for determination of enoxacin. The LOD was as low as10-10g/mL,which is more sensitive than CE-ECL（10-8g/mL）and CE（10-6g/mL）.
In chapter5, the characterization of interaction between antitumor drug5-fluorouracil(FU) and human serum albumin (HSA) was studied by affinity capillary electrophoresis(ACE). The binding of FU drug to HSA at near-physiological conditions was evaluated. FUwas found to show low affinity toward HSA, with binding constant of9.19×104M-1. Thepositive H and S values obtained by ACE showed that the binding reaction was anendothermic process, the entropy drived the binding, and hydrophobic interaction playedmajor roles in the binding of FU to HSA. The replacement test with warfarin and ketoprofenshowed that binding site of FU at the protein HSA is believed to be site I. Three-dimensionalfluorescence studies showed that the presence of FU could change the conformation of BSAduring the binding process.
In chapter6, the main work, findings and innovation of this thesis were illustrated. At theend, the development trend of CE in the application of drugs analysis was presented.
引文
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