某些超分子主体与药物相互作用的光谱特性及色谱行为研究
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摘要
环糊精、葫芦脲作为第二代和第四代超分子主体化合物,由于它们对客体分子的良好包合性能,使其在催化、生化、医药、分离材料和污水处理等领域有很好的应用前景。近几年来,葫芦脲对药物分子的包合性能成为研究的热点,也成为某些药物新分析方法建立的重要有效手段。建立简单、准确、可靠、灵敏和可重复的药物分析方法,是控制药品质量的有效途径,一直是药物分析工作者的主要任务之一。环糊精在药物分析上的应用已相当广泛,作为药物分离材料特别是手性分离材料也有较广的应用。近20年来深入研究的桥联环糊精,在分子识别和分子自组装中表现了良好的特性,但作为手性分离材料的应用较少。鉴于这些主要特性,本论文主要做了以下几方面的研究工作：
第一部分综述了葫芦脲在分子识别、分子组装、分子器件和主要应用方面的研究进展,并对环糊精手性固定相的发展和桥联环糊精的主要特点和研究成果做了简要概括,提出本论文的主要研究内容。
第二部分建立了一种简单、灵敏、有效的测定雷尼替丁、尼扎替丁和西咪替丁的荧光测定法。该方法是基于某些药物和巴马汀探针对葫芦[7]脲空腔的竞争反应。葫芦[7]脲能与巴马汀相互作用形成稳定的包合物而使溶液的荧光显著增强。然而,当加入被测药物时溶液的荧光剧烈淬灭。考察了不同实验因素对荧光猝灭的影响。在最佳的实验条件下,以343nm为激发波长,在495nm发射波长处测定荧光强度,荧光猝灭值(ΔF)和药物浓度在0.04-1.9μg·mL-1呈线性关系。检测限为0.013-0.030μg·mL-1。所建立的方法可以同时用于原料药、药物制剂和生物样品的测定。该方法的灵敏度比一般的光谱法高两个数量级。
第三部分建立了一种简单、灵敏的高效液相色谱荧光检测法(HPLC-FLD),可以同时测定巴马汀和小檗碱。该方法是基于在葫芦[7]脲的存在下,巴马汀和小檗碱水溶液的荧光显著增强。色谱条件是：在商品C18柱上,以葫芦[7]脲为液相色谱流动相添加剂,以(50/50,v/v)的甲醇/0.05%醋酸三乙胺缓冲溶液水(pH4.1)为流动相,并在缓冲溶液中加入1.25×10-4mo1·L-1葫芦[7]脲。以343nm为激发波长,在495nm发射波长处测定荧光强度,巴马汀和小檗碱的线性范围分别为3-230ng-mL-1和2-220ng.mL-,线性回归方程分别为Y=594248+7.56×104X(R=0.9993)和Y=811028+6.32×104X(R=0.9995)。巴马汀和小檗碱的检测限分别为1.0ng·mL-1和0.7ng-mL-。本方法的灵敏度几乎与液质联用方法的灵敏度相当。同时可用于中药金鸡胶囊和血浆中巴马汀和小檗碱的测定。该HPLC-FLD法方便快捷、灵敏、重现性好。
第四部分制备了一种新型羟基葫芦[7]脲键合固定相,并用作液相色谱固定相,在高效液相色谱上对一些原小檗碱类生物碱(如：黄连碱、小檗碱、药根碱)和鸦片生物碱(如可待因、罂粟碱、蒂巴因、单乙酰吗啡)进行了测定。考察了流动相的组成对分离的影响,如乙腈含量、缓冲溶液的浓度、pH值等。结果表明：羟基葫芦[7]脲固定相相比羟基葫芦[6]脲固定相,对这些原小檗碱类生物碱具有更好的选择性,这些鸦片类生物碱在两种色谱固定相上均能得到基线分离。相比C18柱,此固定相对这些原小檗碱类生物碱在等度洗脱下进行分离,无需梯度洗脱,具有操作简单,性能稳定的优点。
第五部分合成了三种芳香二胺桥联-β-环糊精,它们分别是：3-氨甲基-苄胺-桥联(6-氨基-6-脱氧-β-环糊精)(1),4,4'-二胺二苯基-亚甲基-桥联(6-氨基-6-脱氧-β-环糊精)(2),1,2-双(4-氨苯基)-乙基-桥联(6-氨基-6-脱氧-β-环糊精)(3)。将这三种芳香二胺桥联-β-环糊精分别键合到色谱硅胶上制成手性色谱固定相(CSPs),并用于液相色谱拆分手性化合物。用甲醇和醋酸三乙基胺缓冲溶液作流动相,对11种手性化合物进行了拆分。结果显示：三种手性色谱固定相相比β-环糊精固定相,对测定的这些手性化合物有更强的拆分能力。可以看出两个环糊精单元之间桥基的长度对对映体选择性有较大的影响,随着桥基的增长手性识别能力下降,具有最短桥基的CSP1分离能力最强。这和文献报道的分子识别规律是一致的。
第六部分将单壁碳纳米管(SWCNT)和羟丙基-β-环糊精(HP-β-CD)衍生化制成液相色谱固定相,在高效液相色谱上对多种多环芳烃和结构类似物进行了分析。实验结果表明：在单壁碳纳米管羟丙基-β=环糊精固定相上,以水/甲醇(5：5,v/v)为流动相,八种多环芳烃能够分离；以(3：7,v/v)甲醇/醋酸三乙基胺缓冲液为流动相,其中醋酸三乙基胺的体积百分比浓度为0.1%且pH为4.1,结构相似的六种地平类药物能得到分离。与羟丙基-β-环糊精固定相相比,此单壁碳纳米管固定相对这些多环芳烃和地平类药物显示出更强的分离能力。此方法可以用来提高环糊精固定相的分离效率。
本论文的主要特点和创新点：
1.葫芦[7]脲运用于雷尼替丁、尼扎替丁和西咪替丁三种H2组胺受体药物的测定,实现了三种H2组胺受体无荧光药物的荧光测定,该荧光测定法比一般的光谱方法灵敏度高,灵敏的测定方法可以用于生物体液中药物的测定。
2.葫芦[7]脲用作液相色谱流动相添加剂,实现了两种结构非常相似的异喹啉药物巴马汀和小檗碱的高效液相色谱分离和测定,该方法与已报道的液相色谱法相比具有高灵敏度,其检测限可与价格昂贵的液质联用法相媲美。该方法简单易行,也可以用于其他生物样品的测定。
3.合成了几种新的色谱固定相,并对其各自的分离特性进行了评价。羟基葫芦[7]脲键合固定相对分离生物碱类药物有一定的优势；桥基短的芳香二胺桥联-β-环糊精手性固定相对手性化合物的拆分比普通β-环糊精手性固定相好很多；单壁碳纳米管单独用于固定相分离效果较差,但如与羟丙基-β-环糊精结合制作色谱固定相,其协同作用显示了对环境污染物多环芳烃和结构相似物良好的分离能力,单壁碳纳米管在改善环糊精固定相分离能力上具有一定的应用潜力。
As the second and fourth generation of supramolecular host compounds, cyclodextrin and cucurbit[n]urils have a promising application prospect in the fields of catalysts, biochemistry, medicine, separating materials and sewage treatment, due to their good inclusion properties. In recent years, the inclusion of cucurbit[n]urils with drug molecules become a hot research, also become an important and effective means of new analytical methods for certain drugs to be established. A simple, accurate, reliable, sensitive, and repeatable analytical method of drugs is an effective way to control the drugs quality. The analytical method of drugs to be established is one of the main task of the analyst. Cyclodextrin has a wide range of applications in pharmaceutical analysis, which also has a broader application as materials for drug separation, especially chiral separation materials. Through depth study of the past20years, bridged cyclodextrin showed good characteristics in molecular recognition and molecular self-assembly, but has little application in chiral separation materials. In view of these essential characteristics above, the following aspects are researched in this paper:
In the first part of this paper, research progress of cucurbit[n]urils in the fields of molecular recognition, molecular assembly, molecular device was summarized. The progress of cyclodextrin as chiral stationary phase, the chief characteristics and research results of bridged cyclodextrin were summarized in brief. Main contents of research in this paper was proposed.
The second chapter describes a validated, simple, and sensitive fluorescence quenching method for the determination of ranitidine, nizatidine, and cimetidine in tablets and biological fluids. This is the first single fluorescence method reported for the analysis of all three H2antagonists. The competitive reaction between the investigated drug and the palmatine probe for the occupancy of the cucurbit[7]uril (CB[7]) cavity was studied using spectrofluorometry. CB[7] was found to react with the probe to form a stable complex. The fluorescence intensity of the complex was also enhanced greatly. However, the addition of the drug dramatically quenched the fluorescence intensity of the complex. Accordingly, a new fluorescence quenching method for the determination of the studied drugs was established. The different experimental parameters affecting the fluorescence quenching intensity were studied carefully. At optimum reaction conditions, the rectilinear calibration graphs between the fluorescence quenching values (ΔF) and the medicament concentration were obtained in the concentration range of0.04-1.9μg mL-1for the investigated drugs. The limits of detection ranged from0.013to0.030μg mL-1at495nm using an excitation wavelength of343nm. The proposed method can be used for the determination of the three H2antagonists in raw materials, dosage forms and biological fluids.
The third chapter describes a simple and sensitive high performance liquid chromatography-fluorescence detector (HPLC-FLD) method which was developed for simultaneous determination of palmatine (PAL) and berberine (BRH). The method is based on the enhancement of the fluorescence of PAL and BRH in aqueous solution in the presence of cucurbit[7]uril (CB[7]). The chromatographic resolution of PAL and BRH was performed on SymmetryShieldTM RP18column with CB[7] as the mobile phase additive. The composition of the mobile phase was (50/50, v/v) absolute methanol/0.05%(v/v) triethylammonium acetate buffer (pH4.1) with1.25×10-4M CB[7]. The linear ranges of PAL and BRH were3-230and2-220ng mL-1, with the regression equations of
Y-594248+7.56x104×(R=0.9993),Y=811028+6.32×104×(R=0.9995), respectively. The limits of detection for PAL and BRH were1and0.7ng·mL-1, respectively, with fluorescence detection at an excitation wavelength of347nm and an emission wavelength of495nm. The sensitivity of the proposed method was almost equal to previous liquid chromatography-mass spectroscopy method. The proposed method was applied to determine PAL and BRH in human plasma and Jinji capsules. The HPLC-FLD method was sensitive, and convenient.
In the fourth chapter, a novel perhydroxyl-cucurbit[7]uril bonded stationary phase was prepared and used to separated protoberberine alkaloids (coptisine, berberine and jatrorrhizine) and opium alkaloids (narceine, codeine, thebaine, and monoacetylmorphine) by high-performance liquid chromatography (HPLC). The influence of mobile phase variation such as acetonitrile content, buffer concentration and pH to the chromatographic behavior was studied. The results showed that perhydroxyl-cucurbit[7]uril stationary phase had better selectivity for these protoberberine alkaloids than perhydroxyl-cucurbit[6]uril stationary phase and these opium alkaloids were obtained baseline separation in the two columns.
In the fifth chapter, three diamino-bridged bis(β-cyclodextrin)s, namely1,3-(aminomethyl)-benzylamine-bridged bis(6-amino-6-deoxy-β-cyclodextrin)(1),4,4-diaminodiphenyl methano-bridged bis(6-amino-6-deoxy-β-cyclodextrin)(2), and4,4-ethylenedianiline-bridged bis(6-amino-6-deoxy-β-cyclodextrin)(3), were prepared and used in the novel application as chiral stationary phases (CSPs) in HPLC. Their ability to separate11enantiomers was investigated using triethylammonium acetate buffer containing methanol as the mobile phase. All three CSPs, particularly CSP1, have better enantiomer separation efficiencies than the parent β-cyclodextrin. Therefore, the linker length between two cyclodextrin units is effective to enantioselectivity, and the resolution ability decreases with increased linker length, which conforms with the molecular recognition ability.
The sixth chapter describes a novel application of functionalized single-walled carbon nanotubes (SWCNTs) as a stationary phase for the liquid chromatographic separation of polycyclic aromatic hydrocarbons and structurally similar analogues. The SWCNTs were first oxidized to give carboxylic derivatives (SWCNT-COOH), afterwards these were covalently derivatized with hydroxypropyl-β-cyclodextrin (HP-β-CD). Then, the HP-β-CD-SWCNTs were bonded to silica gel with3-(triethoxysilyl) propyl isocyanate, which were used as a stationary phase to separate the investigated substances by HPLC. Eight polycyclic aromatic hydrocarbons were separated using water/methanol(5:5, v/v) as the mobile phase, and six structurally similar dipine drugs were separated using (3:7, v/v) methanol/triethylammonium acetate buffer (0.1%, v/v, pH4.1) as the mobile phase on this stationary phase. The results showed that the HP-β-CD-SWCNTs stationary phase had stronger separation ability for aromatic hydrocarbons and analogues compared with the HP-β-CD stationary phase. This method can be used to improve the separation efficiency of the β-CD stationary phases.
The chief characteristics and innovations of this thesis are as follows:
1. Cucurbit[7]uril was used for the determination of three H2antagonists ranitidine, nizatidine and cimetidine. Therefore, the three H2antagonists which have no fluorescence can be determined by fluoremetry. The fluoremetry is more sensitive than the normal spectroscopic method, so can be used to determine the three H2antagonists in biological fluids.
2. A simple and sensitive high performance liquid chromatography-fluorescence detector (HPLC-FLD) method was developed for simultaneous determination of palmatine (PAL) and berberine (BRH) using CB[7] as the mobile phase additive. The method was more sensitive than the normal chromatographic method, almost equal to expensive liquid chromatography-mass spectroscopy method. The proposed method can be applied to determine PAL and BRH in biological fluids. The above HPLC-FLD method was sensitive and convenient.
3. Several novel chromatography stationary phases were prepared and their respective separation advantages were also evaluated. Perhydroxyl-cucurbit[7]uril bonded stationary phase have certain advantages in separating alkaloids drugs. Diamino-bridged bis(β-cyclodextrin)s with short bridged group had better enantiomer separation efficiencies than the parent β-cyclodextrin. Single-walled carbon nanotubes (SWCNTs) alone used in the stationary phase had poor separation effect. However, SWCNTs, derivatized with hydroxypropyl-β-cyclodextrin (HP-β-CD) as a stationary phase showed good separative capability of environmental pollutants polycyclic aromatic hydrocarbons and structurally similar analogues. SWCNTs had certain potential application in the improvement of the separation efficiency of the β-CD stationary phases.
第一部分综述了葫芦脲在分子识别、分子组装、分子器件和主要应用方面的研究进展,并对环糊精手性固定相的发展和桥联环糊精的主要特点和研究成果做了简要概括,提出本论文的主要研究内容。
第二部分建立了一种简单、灵敏、有效的测定雷尼替丁、尼扎替丁和西咪替丁的荧光测定法。该方法是基于某些药物和巴马汀探针对葫芦[7]脲空腔的竞争反应。葫芦[7]脲能与巴马汀相互作用形成稳定的包合物而使溶液的荧光显著增强。然而,当加入被测药物时溶液的荧光剧烈淬灭。考察了不同实验因素对荧光猝灭的影响。在最佳的实验条件下,以343nm为激发波长,在495nm发射波长处测定荧光强度,荧光猝灭值(ΔF)和药物浓度在0.04-1.9μg·mL-1呈线性关系。检测限为0.013-0.030μg·mL-1。所建立的方法可以同时用于原料药、药物制剂和生物样品的测定。该方法的灵敏度比一般的光谱法高两个数量级。
第三部分建立了一种简单、灵敏的高效液相色谱荧光检测法(HPLC-FLD),可以同时测定巴马汀和小檗碱。该方法是基于在葫芦[7]脲的存在下,巴马汀和小檗碱水溶液的荧光显著增强。色谱条件是：在商品C18柱上,以葫芦[7]脲为液相色谱流动相添加剂,以(50/50,v/v)的甲醇/0.05%醋酸三乙胺缓冲溶液水(pH4.1)为流动相,并在缓冲溶液中加入1.25×10-4mo1·L-1葫芦[7]脲。以343nm为激发波长,在495nm发射波长处测定荧光强度,巴马汀和小檗碱的线性范围分别为3-230ng-mL-1和2-220ng.mL-,线性回归方程分别为Y=594248+7.56×104X(R=0.9993)和Y=811028+6.32×104X(R=0.9995)。巴马汀和小檗碱的检测限分别为1.0ng·mL-1和0.7ng-mL-。本方法的灵敏度几乎与液质联用方法的灵敏度相当。同时可用于中药金鸡胶囊和血浆中巴马汀和小檗碱的测定。该HPLC-FLD法方便快捷、灵敏、重现性好。
第四部分制备了一种新型羟基葫芦[7]脲键合固定相,并用作液相色谱固定相,在高效液相色谱上对一些原小檗碱类生物碱(如：黄连碱、小檗碱、药根碱)和鸦片生物碱(如可待因、罂粟碱、蒂巴因、单乙酰吗啡)进行了测定。考察了流动相的组成对分离的影响,如乙腈含量、缓冲溶液的浓度、pH值等。结果表明：羟基葫芦[7]脲固定相相比羟基葫芦[6]脲固定相,对这些原小檗碱类生物碱具有更好的选择性,这些鸦片类生物碱在两种色谱固定相上均能得到基线分离。相比C18柱,此固定相对这些原小檗碱类生物碱在等度洗脱下进行分离,无需梯度洗脱,具有操作简单,性能稳定的优点。
第五部分合成了三种芳香二胺桥联-β-环糊精,它们分别是：3-氨甲基-苄胺-桥联(6-氨基-6-脱氧-β-环糊精)(1),4,4'-二胺二苯基-亚甲基-桥联(6-氨基-6-脱氧-β-环糊精)(2),1,2-双(4-氨苯基)-乙基-桥联(6-氨基-6-脱氧-β-环糊精)(3)。将这三种芳香二胺桥联-β-环糊精分别键合到色谱硅胶上制成手性色谱固定相(CSPs),并用于液相色谱拆分手性化合物。用甲醇和醋酸三乙基胺缓冲溶液作流动相,对11种手性化合物进行了拆分。结果显示：三种手性色谱固定相相比β-环糊精固定相,对测定的这些手性化合物有更强的拆分能力。可以看出两个环糊精单元之间桥基的长度对对映体选择性有较大的影响,随着桥基的增长手性识别能力下降,具有最短桥基的CSP1分离能力最强。这和文献报道的分子识别规律是一致的。
第六部分将单壁碳纳米管(SWCNT)和羟丙基-β-环糊精(HP-β-CD)衍生化制成液相色谱固定相,在高效液相色谱上对多种多环芳烃和结构类似物进行了分析。实验结果表明：在单壁碳纳米管羟丙基-β=环糊精固定相上,以水/甲醇(5：5,v/v)为流动相,八种多环芳烃能够分离；以(3：7,v/v)甲醇/醋酸三乙基胺缓冲液为流动相,其中醋酸三乙基胺的体积百分比浓度为0.1%且pH为4.1,结构相似的六种地平类药物能得到分离。与羟丙基-β-环糊精固定相相比,此单壁碳纳米管固定相对这些多环芳烃和地平类药物显示出更强的分离能力。此方法可以用来提高环糊精固定相的分离效率。
本论文的主要特点和创新点：
1.葫芦[7]脲运用于雷尼替丁、尼扎替丁和西咪替丁三种H2组胺受体药物的测定,实现了三种H2组胺受体无荧光药物的荧光测定,该荧光测定法比一般的光谱方法灵敏度高,灵敏的测定方法可以用于生物体液中药物的测定。
2.葫芦[7]脲用作液相色谱流动相添加剂,实现了两种结构非常相似的异喹啉药物巴马汀和小檗碱的高效液相色谱分离和测定,该方法与已报道的液相色谱法相比具有高灵敏度,其检测限可与价格昂贵的液质联用法相媲美。该方法简单易行,也可以用于其他生物样品的测定。
3.合成了几种新的色谱固定相,并对其各自的分离特性进行了评价。羟基葫芦[7]脲键合固定相对分离生物碱类药物有一定的优势；桥基短的芳香二胺桥联-β-环糊精手性固定相对手性化合物的拆分比普通β-环糊精手性固定相好很多；单壁碳纳米管单独用于固定相分离效果较差,但如与羟丙基-β-环糊精结合制作色谱固定相,其协同作用显示了对环境污染物多环芳烃和结构相似物良好的分离能力,单壁碳纳米管在改善环糊精固定相分离能力上具有一定的应用潜力。
As the second and fourth generation of supramolecular host compounds, cyclodextrin and cucurbit[n]urils have a promising application prospect in the fields of catalysts, biochemistry, medicine, separating materials and sewage treatment, due to their good inclusion properties. In recent years, the inclusion of cucurbit[n]urils with drug molecules become a hot research, also become an important and effective means of new analytical methods for certain drugs to be established. A simple, accurate, reliable, sensitive, and repeatable analytical method of drugs is an effective way to control the drugs quality. The analytical method of drugs to be established is one of the main task of the analyst. Cyclodextrin has a wide range of applications in pharmaceutical analysis, which also has a broader application as materials for drug separation, especially chiral separation materials. Through depth study of the past20years, bridged cyclodextrin showed good characteristics in molecular recognition and molecular self-assembly, but has little application in chiral separation materials. In view of these essential characteristics above, the following aspects are researched in this paper:
In the first part of this paper, research progress of cucurbit[n]urils in the fields of molecular recognition, molecular assembly, molecular device was summarized. The progress of cyclodextrin as chiral stationary phase, the chief characteristics and research results of bridged cyclodextrin were summarized in brief. Main contents of research in this paper was proposed.
The second chapter describes a validated, simple, and sensitive fluorescence quenching method for the determination of ranitidine, nizatidine, and cimetidine in tablets and biological fluids. This is the first single fluorescence method reported for the analysis of all three H2antagonists. The competitive reaction between the investigated drug and the palmatine probe for the occupancy of the cucurbit[7]uril (CB[7]) cavity was studied using spectrofluorometry. CB[7] was found to react with the probe to form a stable complex. The fluorescence intensity of the complex was also enhanced greatly. However, the addition of the drug dramatically quenched the fluorescence intensity of the complex. Accordingly, a new fluorescence quenching method for the determination of the studied drugs was established. The different experimental parameters affecting the fluorescence quenching intensity were studied carefully. At optimum reaction conditions, the rectilinear calibration graphs between the fluorescence quenching values (ΔF) and the medicament concentration were obtained in the concentration range of0.04-1.9μg mL-1for the investigated drugs. The limits of detection ranged from0.013to0.030μg mL-1at495nm using an excitation wavelength of343nm. The proposed method can be used for the determination of the three H2antagonists in raw materials, dosage forms and biological fluids.
The third chapter describes a simple and sensitive high performance liquid chromatography-fluorescence detector (HPLC-FLD) method which was developed for simultaneous determination of palmatine (PAL) and berberine (BRH). The method is based on the enhancement of the fluorescence of PAL and BRH in aqueous solution in the presence of cucurbit[7]uril (CB[7]). The chromatographic resolution of PAL and BRH was performed on SymmetryShieldTM RP18column with CB[7] as the mobile phase additive. The composition of the mobile phase was (50/50, v/v) absolute methanol/0.05%(v/v) triethylammonium acetate buffer (pH4.1) with1.25×10-4M CB[7]. The linear ranges of PAL and BRH were3-230and2-220ng mL-1, with the regression equations of
Y-594248+7.56x104×(R=0.9993),Y=811028+6.32×104×(R=0.9995), respectively. The limits of detection for PAL and BRH were1and0.7ng·mL-1, respectively, with fluorescence detection at an excitation wavelength of347nm and an emission wavelength of495nm. The sensitivity of the proposed method was almost equal to previous liquid chromatography-mass spectroscopy method. The proposed method was applied to determine PAL and BRH in human plasma and Jinji capsules. The HPLC-FLD method was sensitive, and convenient.
In the fourth chapter, a novel perhydroxyl-cucurbit[7]uril bonded stationary phase was prepared and used to separated protoberberine alkaloids (coptisine, berberine and jatrorrhizine) and opium alkaloids (narceine, codeine, thebaine, and monoacetylmorphine) by high-performance liquid chromatography (HPLC). The influence of mobile phase variation such as acetonitrile content, buffer concentration and pH to the chromatographic behavior was studied. The results showed that perhydroxyl-cucurbit[7]uril stationary phase had better selectivity for these protoberberine alkaloids than perhydroxyl-cucurbit[6]uril stationary phase and these opium alkaloids were obtained baseline separation in the two columns.
In the fifth chapter, three diamino-bridged bis(β-cyclodextrin)s, namely1,3-(aminomethyl)-benzylamine-bridged bis(6-amino-6-deoxy-β-cyclodextrin)(1),4,4-diaminodiphenyl methano-bridged bis(6-amino-6-deoxy-β-cyclodextrin)(2), and4,4-ethylenedianiline-bridged bis(6-amino-6-deoxy-β-cyclodextrin)(3), were prepared and used in the novel application as chiral stationary phases (CSPs) in HPLC. Their ability to separate11enantiomers was investigated using triethylammonium acetate buffer containing methanol as the mobile phase. All three CSPs, particularly CSP1, have better enantiomer separation efficiencies than the parent β-cyclodextrin. Therefore, the linker length between two cyclodextrin units is effective to enantioselectivity, and the resolution ability decreases with increased linker length, which conforms with the molecular recognition ability.
The sixth chapter describes a novel application of functionalized single-walled carbon nanotubes (SWCNTs) as a stationary phase for the liquid chromatographic separation of polycyclic aromatic hydrocarbons and structurally similar analogues. The SWCNTs were first oxidized to give carboxylic derivatives (SWCNT-COOH), afterwards these were covalently derivatized with hydroxypropyl-β-cyclodextrin (HP-β-CD). Then, the HP-β-CD-SWCNTs were bonded to silica gel with3-(triethoxysilyl) propyl isocyanate, which were used as a stationary phase to separate the investigated substances by HPLC. Eight polycyclic aromatic hydrocarbons were separated using water/methanol(5:5, v/v) as the mobile phase, and six structurally similar dipine drugs were separated using (3:7, v/v) methanol/triethylammonium acetate buffer (0.1%, v/v, pH4.1) as the mobile phase on this stationary phase. The results showed that the HP-β-CD-SWCNTs stationary phase had stronger separation ability for aromatic hydrocarbons and analogues compared with the HP-β-CD stationary phase. This method can be used to improve the separation efficiency of the β-CD stationary phases.
The chief characteristics and innovations of this thesis are as follows:
1. Cucurbit[7]uril was used for the determination of three H2antagonists ranitidine, nizatidine and cimetidine. Therefore, the three H2antagonists which have no fluorescence can be determined by fluoremetry. The fluoremetry is more sensitive than the normal spectroscopic method, so can be used to determine the three H2antagonists in biological fluids.
2. A simple and sensitive high performance liquid chromatography-fluorescence detector (HPLC-FLD) method was developed for simultaneous determination of palmatine (PAL) and berberine (BRH) using CB[7] as the mobile phase additive. The method was more sensitive than the normal chromatographic method, almost equal to expensive liquid chromatography-mass spectroscopy method. The proposed method can be applied to determine PAL and BRH in biological fluids. The above HPLC-FLD method was sensitive and convenient.
3. Several novel chromatography stationary phases were prepared and their respective separation advantages were also evaluated. Perhydroxyl-cucurbit[7]uril bonded stationary phase have certain advantages in separating alkaloids drugs. Diamino-bridged bis(β-cyclodextrin)s with short bridged group had better enantiomer separation efficiencies than the parent β-cyclodextrin. Single-walled carbon nanotubes (SWCNTs) alone used in the stationary phase had poor separation effect. However, SWCNTs, derivatized with hydroxypropyl-β-cyclodextrin (HP-β-CD) as a stationary phase showed good separative capability of environmental pollutants polycyclic aromatic hydrocarbons and structurally similar analogues. SWCNTs had certain potential application in the improvement of the separation efficiency of the β-CD stationary phases.
引文
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