咔唑及咪唑类荧光标记试剂的合成及其在高效液相色谱—质谱中的研究应用
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摘要
高效液相色谱是目前对复杂混合物分离能力最强有利的手段之一,已经广泛应用于许多研究领域和工业体系,如临床医学、生物化工、食品卫生、环境监测和质量检测等。尽管如此,由于高效液相色谱目前所使用的检测器中,还没有一种同气相色谱的氢火焰离子化检测器的灵敏度相比拟的通用型检测器,因此当样品中被测组分的含量低或受其本身性质的限定时,很多化合物不能直接被应用于高效液相色谱的分析,大大降低了检测的灵敏度。近年来许多研究人员将化学衍生法应用于高效液相色谱中,试图提高检测灵敏度和改善分离效果。目前,该方法中使用的衍生化试剂种类繁多,用途广泛,但在实际应用中都存在着这样或那样的缺点。因此,开发能够满足实际高效液相色谱分析需要的高灵敏荧光试剂有着非常重要的意义。本论文以设计制备新型荧光衍生试剂以期提高检测灵敏度和改进现有试剂在实际分析过程中的缺陷为主导思想,从新型标记试剂的设计制备、光谱性质的鉴定、新衍生反应的开发、衍生反应条件的优化、色谱分离条件研究、质谱定量定性研究、实际样品测定等方面开展研究工作。具体工作内容如下：
第一章：综述了高效液相色谱和高效液相色谱-质谱联用技术的发展及其理论知识,介绍了荧光衍生法的原理和发展,列举了近年来广泛应用的荧光衍生试剂。
第二章：设计合成了两类新型荧光标记试剂：2-[2-(4-二甲氨基)苯基-1-氢-菲[9,10-d]咪唑]-乙酸(DMAPPIA),2-[2-(7H-二苯并[a,g]咔唑-乙氧基)]-乙基氯甲酸酯(DBCEC-C1)并对这两种化合物的结构和光谱性质进行表征和研究。
第三章：荧光标记试剂2-[2-(4-二甲氨基)苯基-1-氢-菲[9,10-d]咪唑]-乙酸(DMAPPIA)用于脂肪胺的高效液相色谱-质谱分析,通过对衍生化反应条件和色谱条件的优化,建立了脂肪胺的柱前衍生高效液相色谱荧光检测法,并将该方法用于腐鱼和虾酱样品的测定,结果表明所建立的方法具有很大的可行性。
第四章：荧光标记试剂2-[2-(7H-二苯并[a,g]咔唑-乙氧基)]-乙基氯甲酸酯(DBCEC-Cl)作为柱前衍生试剂,用于酚类化合物、芳香胺和20种氨基酸的高效液相色谱-质谱检测,通过对衍生化反应条件和色谱条件的优化,建立了酚类化合物、芳香胺和氨基酸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。
High performance liquid chromatography(HPLC) is one of the most capable methods of separating complex mixture due to its powerful capacity. It has been enthusiastically and widely used in many research fields and industrial systems, such as clinical medicane, biochemistry, food hygiene, environmental monitoring and quality control. However, not all compounds are accessible to directly analysis by HPLC when the contents of the samples are less or limited by its nature, as they reduced the detection sensitivity significantly. In recent years, many researchers have used chemical derivatization in HPLC in attempt to improve detection sensitivity and separation efficiency. Although a number of different types of fluorescent tagging reagents have been developed, many reports have described various shortcomings in application. Therefore, it is highly significant to develop high sensitivity fluorescent regents to meet the actual needs of HPLC. The dominant ideology of this paper is to design a new fluorescent derivatization reagent to enhance detection sensitivity and overcome the shortcomings of existing reagents in actually analysis process. It is detailed as follows:design and syntheses of new tagging reagents, identification of spectral properties, development of new derivatization reaction, optimization of the chromatographic separation conditions, research of mass spectrometry quantitative and qualitative, analysis of real sample and so on. Specific works are as follows:
Chapter one:The development and basic theory of high performance liquid chromatography and high performance liquid chromatography coupled with mass spectrometry technique were systematically reviewed. The principles and development of fluorescent derivatization were simply introduced. At last, the derivative reagents widely used in recent years were cited.
Chapter two:Two novel fluorescent lableling reagents were synthesized: 2-[2-(4-dimethylamino)phenyl-l-hydrogen-philippine[9,10-d]imidazole]-acetic acid(DMAPPIA), 2-[2-(7H-dibenzo[a,g]carbazole-ethoxy)]-ethyl chloroformate (DBCEC-C1). Then, their structure and spectroscopic properties were characterized.
Chapter there:Pre-column derivatization methods for the sensitive determination of aliphatic amines with 2-[2-(4-dimethylamino)-phenyl-l-hydrogen-philippine [9,10-d]imidazole]-acetic acid (DMAPPIA) as labeling reagents followed by HPLC-MS analysis have been developed. The optimization of derivatization and chromatographic separation conditions using DMAPPIA as labeling reagent were evaluated. Then, the established method has applied to analyze Rotten fish and Shrimp paste samples, the results showed that the method had great feasibility.
Chapter four:Pre-column derivatization methods for the sensitive determination of aromatic amines, phenolic compounds and 20 kinds of amino acids with 2-[2-(7H-dibenzo[a,g]carbazole-ethoxy)]-ethyl chloroformate (DBCEC-C1) as labeling reagents followed by HPLC-MS analysis have been developed. The optimization of derivatization and chromatographic separation conditions using DBCEC-C1 as labeling reagent were evaluated. Then, the established method has applied to analyze the real samples, the results showed that the method had great feasibility.
第一章：综述了高效液相色谱和高效液相色谱-质谱联用技术的发展及其理论知识,介绍了荧光衍生法的原理和发展,列举了近年来广泛应用的荧光衍生试剂。
第二章：设计合成了两类新型荧光标记试剂：2-[2-(4-二甲氨基)苯基-1-氢-菲[9,10-d]咪唑]-乙酸(DMAPPIA),2-[2-(7H-二苯并[a,g]咔唑-乙氧基)]-乙基氯甲酸酯(DBCEC-C1)并对这两种化合物的结构和光谱性质进行表征和研究。
第三章：荧光标记试剂2-[2-(4-二甲氨基)苯基-1-氢-菲[9,10-d]咪唑]-乙酸(DMAPPIA)用于脂肪胺的高效液相色谱-质谱分析,通过对衍生化反应条件和色谱条件的优化,建立了脂肪胺的柱前衍生高效液相色谱荧光检测法,并将该方法用于腐鱼和虾酱样品的测定,结果表明所建立的方法具有很大的可行性。
第四章：荧光标记试剂2-[2-(7H-二苯并[a,g]咔唑-乙氧基)]-乙基氯甲酸酯(DBCEC-Cl)作为柱前衍生试剂,用于酚类化合物、芳香胺和20种氨基酸的高效液相色谱-质谱检测,通过对衍生化反应条件和色谱条件的优化,建立了酚类化合物、芳香胺和氨基酸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。
High performance liquid chromatography(HPLC) is one of the most capable methods of separating complex mixture due to its powerful capacity. It has been enthusiastically and widely used in many research fields and industrial systems, such as clinical medicane, biochemistry, food hygiene, environmental monitoring and quality control. However, not all compounds are accessible to directly analysis by HPLC when the contents of the samples are less or limited by its nature, as they reduced the detection sensitivity significantly. In recent years, many researchers have used chemical derivatization in HPLC in attempt to improve detection sensitivity and separation efficiency. Although a number of different types of fluorescent tagging reagents have been developed, many reports have described various shortcomings in application. Therefore, it is highly significant to develop high sensitivity fluorescent regents to meet the actual needs of HPLC. The dominant ideology of this paper is to design a new fluorescent derivatization reagent to enhance detection sensitivity and overcome the shortcomings of existing reagents in actually analysis process. It is detailed as follows:design and syntheses of new tagging reagents, identification of spectral properties, development of new derivatization reaction, optimization of the chromatographic separation conditions, research of mass spectrometry quantitative and qualitative, analysis of real sample and so on. Specific works are as follows:
Chapter one:The development and basic theory of high performance liquid chromatography and high performance liquid chromatography coupled with mass spectrometry technique were systematically reviewed. The principles and development of fluorescent derivatization were simply introduced. At last, the derivative reagents widely used in recent years were cited.
Chapter two:Two novel fluorescent lableling reagents were synthesized: 2-[2-(4-dimethylamino)phenyl-l-hydrogen-philippine[9,10-d]imidazole]-acetic acid(DMAPPIA), 2-[2-(7H-dibenzo[a,g]carbazole-ethoxy)]-ethyl chloroformate (DBCEC-C1). Then, their structure and spectroscopic properties were characterized.
Chapter there:Pre-column derivatization methods for the sensitive determination of aliphatic amines with 2-[2-(4-dimethylamino)-phenyl-l-hydrogen-philippine [9,10-d]imidazole]-acetic acid (DMAPPIA) as labeling reagents followed by HPLC-MS analysis have been developed. The optimization of derivatization and chromatographic separation conditions using DMAPPIA as labeling reagent were evaluated. Then, the established method has applied to analyze Rotten fish and Shrimp paste samples, the results showed that the method had great feasibility.
Chapter four:Pre-column derivatization methods for the sensitive determination of aromatic amines, phenolic compounds and 20 kinds of amino acids with 2-[2-(7H-dibenzo[a,g]carbazole-ethoxy)]-ethyl chloroformate (DBCEC-C1) as labeling reagents followed by HPLC-MS analysis have been developed. The optimization of derivatization and chromatographic separation conditions using DBCEC-C1 as labeling reagent were evaluated. Then, the established method has applied to analyze the real samples, the results showed that the method had great feasibility.
引文
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