苯并吖啶酮类双敏感探针制备及其在反相高效液相色谱—质谱中应用
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摘要
反相高效液相色谱(RP-HPLC)因其强大的分离分析能力而成为许多研究领域广泛采用的一种有效分离手段,如生物学、化学、毒物学、临床医学、食品卫生及环境科学等。该方法也是分析化学中发展最快,应用最广的方法之一,然而由于样品中待测组分含量低或其本身性质以及高效液相色谱检测器的限制,并非所有化合物都可直接用于色谱分析。因此,开发具有高灵敏度的检测方法具有重要意义。近年来,研究者利用荧光标记试剂与本身不发荧光的化合物(如脂肪胺、脂肪醇等)发生衍生化反应,转变为发射荧光的衍生物,从而可以进行荧光检测,大大提高了检测灵敏度。本论文主要设计合成了三种质谱和荧光双敏感的苯并吖啶酮类探针分子,并研究了各探针分子的光谱性质。通过优化衍生、色谱和质谱条件,建立了高效、灵敏的反相高效液相色谱方法,并应用于有意义的实际样品分析。具体工作如下：
第一章：简述了高效液相色谱和高效液相色谱-质谱联用的研究进展和基本理论；介绍了荧光原理和化学衍生化；总结了广泛使用的荧光衍生试剂。
第二章：三种荧光探针：2-(苯并吖啶酮)-乙基咪唑酸酯(BAEIC)、5-羰基咪唑苯并吖啶酮(IEBA)和苯并[b]吖啶酮-5-乙基对甲苯磺酸酯(BAETS)的设计合成及结构表征。
第三章：利用双敏感探针2-(苯并吖啶酮)-乙基咪唑酸酯(BAEIC)作为柱前衍生标记试剂,用于脂肪胺的高效液相色谱分析,通过对衍生化条件的优化,建立了脂肪胺的柱前衍生高效液相色谱荧光检测法,并将该方法用于实际样品的测定。结果表明,建立的方法具有线性范围宽、重现性好、操作简单等特性,适用于实际样品的分析测定。
第四章：利用5-羰基咪唑苯并吖啶酮(IEBA)作为荧光标记试剂,用于脂肪胺、芳香胺短链脂肪醇和长链脂肪醇的高效液相色谱-质谱检测,通过对衍生化反应条件和色谱条件的优化,建立了脂肪胺、芳香胺和脂肪醇类化合物的柱前衍生高效液相色谱荧光检测法,并将该方法应用于相关实际样品的测定,结果表明所建立的方法具有很大的可行性。
第五章：利用苯并[b]吖啶酮-5-乙基对甲苯磺酸酯(BAETS)作为荧光标记试剂,用于胆汁酸的高效液相色谱-质谱检测。通过对衍生化反应条件和色谱条件的优化,建立了胆汁酸类化合物的柱前衍生高效液相色谱荧光检测法,并将该方法应用于相关实际样品的测定,结果表明所建立的方法具有很大的可行性。
For the powerful separation and analytical capacities, reversed-phase high performance liquid chromatographic method has been widely used in many fields of scientific research and application, such as biology, chemistry, toxicology, clinical medicine, food hygiene and environmental monitoring. It is also one of the fastest developing and the most widely used methods in analytical chemistry. However, not all compounds are accessible to be analyzed by chromatography due to the limitation of the compounds'properties and the low content of detected components. Therefore, developing testing methods with high sensitivity has very important significance. In recent years, derivatization of analytes with fluorescent labeling reagent has been widely adopted by many researchers. This derivatization method which adopt fluorescence detection can enhance detective sensitivity in a large extent. In this paper, three dual-sensitive benzoacridinone probes which were sensitive not only to fluorescence but also to MS ionizable potential were designed, prepared and characterized. The spectral properties, optimal derivatization conditions, chromatographic separation conditions and MS conditions were investigated. Pre-column derivatization methods based on reversed-phase high-performance liquid chromatography were established and evaluated for the analysis of real samples.
Chapter One:The developing progress and basic theory about high performance liquid chromatography and high performance liquid chromatography coupled with mass spectrometry were simply presented. The principles of fluorescence and chemical derivatization were introduced. The widely used fluorescence derivatization reagents were summarized.
Chapter Two:The syntheses of three fluorescent probes: 2-(benzoacridin)ethyl-imidazole-1-carboxylate(BAEIC), 5-(2-(1H-imidazol-1-yl)-2-oxoethyl)benzo[b]acridin-12(5H)-one(IEBA)and 2-(12-oxobenzo[b]acridin-5(12H)-yl)ethyl 4-methylbenzenesulfonate(BAETS) were described followed with their structural characterization.
Chapter Three:Pre-column derivatization method for the sensitive determination of amine compounds using BAEIC as labeling reagent followed by HPLC-MS analysis has been developed. The optimal derivatization was evaluated. The proposed method showed wide linear range, excellent reproducibility, and simple derivatization for the determination of aliphatic amines. The suitability of the developed method for the analysis of real sample was satisfactory.
Chapter Four:Pre-column derivatization methods for the sensitive determination of aliphatic amine, aromatic amines, short-chain aliphatic alcohols and policosanol with 5-(2-(1H-imidazol-1-yl)-2-oxoethyl)benzo[b]acridin-12(5H)-one (IEBA) as labeling reagent followed by HPLC-MS analysis have been developed. The optimization of derivatization and chromatographic separation conditions using IEBA as labeling reagent was evaluated. Then, this method was applied to the determination of different real samples, the results suggested that the established methods have great feasibility.
Chapter Five:Pre-column derivatization method for the sensitive determination of bile acids with 2-(12-oxobenzo[b]acridin-5(12H)-yl)ethyl 4-methylbenzenesulfonate(BAETS) as derivative reagents followed by HPLC-MS analysis has been developed. The optimization of derivatization and chromatographic separation conditions using BAETS as labeling reagent was evaluated. Then, this method was applied to the determination of actual sample, the results suggested that the established method has great feasibility.
第一章：简述了高效液相色谱和高效液相色谱-质谱联用的研究进展和基本理论；介绍了荧光原理和化学衍生化；总结了广泛使用的荧光衍生试剂。
第二章：三种荧光探针：2-(苯并吖啶酮)-乙基咪唑酸酯(BAEIC)、5-羰基咪唑苯并吖啶酮(IEBA)和苯并[b]吖啶酮-5-乙基对甲苯磺酸酯(BAETS)的设计合成及结构表征。
第三章：利用双敏感探针2-(苯并吖啶酮)-乙基咪唑酸酯(BAEIC)作为柱前衍生标记试剂,用于脂肪胺的高效液相色谱分析,通过对衍生化条件的优化,建立了脂肪胺的柱前衍生高效液相色谱荧光检测法,并将该方法用于实际样品的测定。结果表明,建立的方法具有线性范围宽、重现性好、操作简单等特性,适用于实际样品的分析测定。
第四章：利用5-羰基咪唑苯并吖啶酮(IEBA)作为荧光标记试剂,用于脂肪胺、芳香胺短链脂肪醇和长链脂肪醇的高效液相色谱-质谱检测,通过对衍生化反应条件和色谱条件的优化,建立了脂肪胺、芳香胺和脂肪醇类化合物的柱前衍生高效液相色谱荧光检测法,并将该方法应用于相关实际样品的测定,结果表明所建立的方法具有很大的可行性。
第五章：利用苯并[b]吖啶酮-5-乙基对甲苯磺酸酯(BAETS)作为荧光标记试剂,用于胆汁酸的高效液相色谱-质谱检测。通过对衍生化反应条件和色谱条件的优化,建立了胆汁酸类化合物的柱前衍生高效液相色谱荧光检测法,并将该方法应用于相关实际样品的测定,结果表明所建立的方法具有很大的可行性。
For the powerful separation and analytical capacities, reversed-phase high performance liquid chromatographic method has been widely used in many fields of scientific research and application, such as biology, chemistry, toxicology, clinical medicine, food hygiene and environmental monitoring. It is also one of the fastest developing and the most widely used methods in analytical chemistry. However, not all compounds are accessible to be analyzed by chromatography due to the limitation of the compounds'properties and the low content of detected components. Therefore, developing testing methods with high sensitivity has very important significance. In recent years, derivatization of analytes with fluorescent labeling reagent has been widely adopted by many researchers. This derivatization method which adopt fluorescence detection can enhance detective sensitivity in a large extent. In this paper, three dual-sensitive benzoacridinone probes which were sensitive not only to fluorescence but also to MS ionizable potential were designed, prepared and characterized. The spectral properties, optimal derivatization conditions, chromatographic separation conditions and MS conditions were investigated. Pre-column derivatization methods based on reversed-phase high-performance liquid chromatography were established and evaluated for the analysis of real samples.
Chapter One:The developing progress and basic theory about high performance liquid chromatography and high performance liquid chromatography coupled with mass spectrometry were simply presented. The principles of fluorescence and chemical derivatization were introduced. The widely used fluorescence derivatization reagents were summarized.
Chapter Two:The syntheses of three fluorescent probes: 2-(benzoacridin)ethyl-imidazole-1-carboxylate(BAEIC), 5-(2-(1H-imidazol-1-yl)-2-oxoethyl)benzo[b]acridin-12(5H)-one(IEBA)and 2-(12-oxobenzo[b]acridin-5(12H)-yl)ethyl 4-methylbenzenesulfonate(BAETS) were described followed with their structural characterization.
Chapter Three:Pre-column derivatization method for the sensitive determination of amine compounds using BAEIC as labeling reagent followed by HPLC-MS analysis has been developed. The optimal derivatization was evaluated. The proposed method showed wide linear range, excellent reproducibility, and simple derivatization for the determination of aliphatic amines. The suitability of the developed method for the analysis of real sample was satisfactory.
Chapter Four:Pre-column derivatization methods for the sensitive determination of aliphatic amine, aromatic amines, short-chain aliphatic alcohols and policosanol with 5-(2-(1H-imidazol-1-yl)-2-oxoethyl)benzo[b]acridin-12(5H)-one (IEBA) as labeling reagent followed by HPLC-MS analysis have been developed. The optimization of derivatization and chromatographic separation conditions using IEBA as labeling reagent was evaluated. Then, this method was applied to the determination of different real samples, the results suggested that the established methods have great feasibility.
Chapter Five:Pre-column derivatization method for the sensitive determination of bile acids with 2-(12-oxobenzo[b]acridin-5(12H)-yl)ethyl 4-methylbenzenesulfonate(BAETS) as derivative reagents followed by HPLC-MS analysis has been developed. The optimization of derivatization and chromatographic separation conditions using BAETS as labeling reagent was evaluated. Then, this method was applied to the determination of actual sample, the results suggested that the established method has great feasibility.
引文
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