新型荧光标记试剂的合成及其在高效液相色谱—质谱中的应用
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摘要
高效液相色谱因其强大的分离分析能力已被广泛应用于许多研究和工业领域如生物化学、毒物学、化学化工、临床医学、神经生物学、食品卫生、环保检测和质量控制等。该法也是分析化学中发展最快、应用最广泛的领域之一。然而,由于样品中被测组分本身性质及其低含量的限制,并非所有化合物都可直接用于液相色谱分析。因此提高方法的检测灵敏度具有非常重要的意义。荧光检测具有很高的灵敏度,利用荧光标记技术使本身不发荧光或者荧光量子产率低的化合物(如脂肪胺、芳香胺,雌醇等)转化成发射荧光的衍生物,能够实现高灵敏荧光检测。本文重点研究了几种新型荧光标记试剂的合成和表征,考察了荧光标记试剂的光谱性质,优化了衍生反应条件、色谱分离条件,并将建立的方法应用于不同实际样品的分析。具体工作如下:
第一章:介绍了荧光原理及荧光标记法。简述了高效液相色谱的发展及其基础知识。综述了荧光标记试剂在胺类和羟基化合物的高效液相色谱分析中的应用。
第二章:四种荧光标记试剂:2-(11H-苯[a]咔唑)一乙酸(BCA)、2-(11H-苯[a]咔唑)异丙基氯甲酸酯(BCPC-Cl)、2-(11H-苯[a]咔唑)乙基氯甲酸酯(BCEC-C1)和2-(2-苯基-1-氢-菲[9,10-d]咪唑)-乙酸(PPIA)的设计合成、结构表征、光谱性质研究。
第三章:荧光标记试剂BCA用于脂肪胺的高效液相色谱.质谱分析。通过对衍生化条件和色谱分离条件的优化,建立了脂肪胺的柱前衍生高效液相色谱荧光检测法,并将该方法用于土壤和污水样品的测定,检验了所建立的分析方法的可行性。
第四章:荧光标记试剂BCPC-C1用于芳香胺的高效液相色谱-质谱分析。通过对衍生化条件和色谱分离条件的优化,建立了芳香胺的柱前衍生高效液相色谱荧光检测法,并将该方法用于污水样品的测定,检验了所建立的分析方法的可行性。
第五章:荧光标记试剂BCEC-Cl用于雌二醇和雌三醇的高效液相色谱-质谱分析。通过对衍生化条件和色谱分离条件的优化,建立了雌醇的柱前衍生高效液相色谱荧光检测法,并将该方法用于藏羚羊粪样品的测定,检验了所建立的分析方法的可行性。
第六章:荧光标记试剂PPIA用于芳香胺的高效液相色谱-质谱分析。通过对衍生化条件和色谱分离条件的优化,建立了芳香胺的柱前衍生高效液相色谱荧光检测法,并将该方法用于污水样品的测定,检验了所建立的分析方法的可行性。
High performance liquid chromatography(HPLC),due to its powerful separation capacity, has been enthusiastically and widely adopted in many fields of scientific research and industry, such as biochemistry,toxicology,clinical sciences,chemical industry,clinical medicine, neurobiology,food hygiene,environmental science and quality control.It is also one of the fastest developing and the most widely used methods in analytical chemistry.However,not all compounds are suitable to be directly analyzed by HPLC because of the limitation of the compound properties and the very low contents of the corresponding compounds.So it is important to enhance the sensitivity of detection.Currently,fluorescence detection is still recognized to be one of the most sensitive detection technologies.Therefore,derivatization of analytes with fluorescence labeling reagents has been widely adopted.It can alter the chemical and physical properties of target compounds and make them easier to analyze.In this paper,we designed and synthesized four novel fluorescence labeling reagents.The optimal derivatization and chromatographic separation conditions were investigated.At the same time,fluorescence and UV-Vis spectra of labeling reagents and the suitability of the developed method for the analysis of real samples were evaluated.
Chapter one:The fluorescence theory and fluorescence labeling technology were introduced systematically.The history and basic theory about HPLC were simply introduced.The applications of fluorescence labeling reagents for the labeling of amino and hydroxy by HPLC were summarized.
Chapter two:The syntheses of four fluorescence labeling reagents 2-(11H-benzo[a]carbazo-1-11-yl) acetic acid(BCA),2-(11H-benzo[a]carbazol-11-yl)isopropyl chloroformate(BCPC-Cl), 2-(11H-benzo[a]carbazol-11-yl)ethyl carbonochloridate(BCEC-Cl)and 2-(2-phenyl-1H-phena-nthro-[9,10-d]imidazole-1-yl)-acetic acid(PPIA)were described,and followed by their structural characterization and spectral properties.
Chapter three:Pre-column derivatization methods for the sensitive determination of aliphatic amines using 2-(11H-benzo[a]carbazol-11-yl)acetic acid(BCA)as labeling reagents followed by HPLC-MS analysis have been developed.The optimal derivatization and chromatographic separation conditions using BCA as labeling reagent were evaluated.And the feasibility of this method has been identified by analyzing soil and waste water sample.
Chapter four:Pre-column derivatization methods for the sensitive determination of aromatic amines using 2-(11H-benzo[a]carbazol-11-yl)isopropyl chloroformate(BCPC-Cl)as labeling reagents followed by HPLC-MS analysis have been developed.The optimal derivatization and chromatographic separation conditions using BCPC-Cl as labeling reagent were evaluated.And the feasibility of this method has been identified by analyzing waste water sample.
Chapter five:Pre-column derivatization methods for the sensitive determination of estrones using 2-(11H-benzo[a]carbazol-11-yl)ethyl carbonochloridate(BCEC-Cl)as labeling reagent followed by HPLC-MS analysis have been developed.The optimal derivatization and chromatographic separation conditions using BCEC-Cl as labeling reagent were evaluated.And the feasibility of this method has been identified by analyzing Tibetan antelope feces sample.
Chapter six:Pre-column derivatization methods for the sensitive determination of aromatic amines using 2-(2-phenyl-1H-phenanthro-[9,10-d]imidazole-1-yl)-acetic acid(PPIA)as labeling reagents followed by HPLC-MS analysis have been developed.The optimal derivatization and chromatographic separation conditions using PPIA as labeling reagent were evaluated.And the feasibility of this method has been identified by analyzing waste water sample.
第一章:介绍了荧光原理及荧光标记法。简述了高效液相色谱的发展及其基础知识。综述了荧光标记试剂在胺类和羟基化合物的高效液相色谱分析中的应用。
第二章:四种荧光标记试剂:2-(11H-苯[a]咔唑)一乙酸(BCA)、2-(11H-苯[a]咔唑)异丙基氯甲酸酯(BCPC-Cl)、2-(11H-苯[a]咔唑)乙基氯甲酸酯(BCEC-C1)和2-(2-苯基-1-氢-菲[9,10-d]咪唑)-乙酸(PPIA)的设计合成、结构表征、光谱性质研究。
第三章:荧光标记试剂BCA用于脂肪胺的高效液相色谱.质谱分析。通过对衍生化条件和色谱分离条件的优化,建立了脂肪胺的柱前衍生高效液相色谱荧光检测法,并将该方法用于土壤和污水样品的测定,检验了所建立的分析方法的可行性。
第四章:荧光标记试剂BCPC-C1用于芳香胺的高效液相色谱-质谱分析。通过对衍生化条件和色谱分离条件的优化,建立了芳香胺的柱前衍生高效液相色谱荧光检测法,并将该方法用于污水样品的测定,检验了所建立的分析方法的可行性。
第五章:荧光标记试剂BCEC-Cl用于雌二醇和雌三醇的高效液相色谱-质谱分析。通过对衍生化条件和色谱分离条件的优化,建立了雌醇的柱前衍生高效液相色谱荧光检测法,并将该方法用于藏羚羊粪样品的测定,检验了所建立的分析方法的可行性。
第六章:荧光标记试剂PPIA用于芳香胺的高效液相色谱-质谱分析。通过对衍生化条件和色谱分离条件的优化,建立了芳香胺的柱前衍生高效液相色谱荧光检测法,并将该方法用于污水样品的测定,检验了所建立的分析方法的可行性。
High performance liquid chromatography(HPLC),due to its powerful separation capacity, has been enthusiastically and widely adopted in many fields of scientific research and industry, such as biochemistry,toxicology,clinical sciences,chemical industry,clinical medicine, neurobiology,food hygiene,environmental science and quality control.It is also one of the fastest developing and the most widely used methods in analytical chemistry.However,not all compounds are suitable to be directly analyzed by HPLC because of the limitation of the compound properties and the very low contents of the corresponding compounds.So it is important to enhance the sensitivity of detection.Currently,fluorescence detection is still recognized to be one of the most sensitive detection technologies.Therefore,derivatization of analytes with fluorescence labeling reagents has been widely adopted.It can alter the chemical and physical properties of target compounds and make them easier to analyze.In this paper,we designed and synthesized four novel fluorescence labeling reagents.The optimal derivatization and chromatographic separation conditions were investigated.At the same time,fluorescence and UV-Vis spectra of labeling reagents and the suitability of the developed method for the analysis of real samples were evaluated.
Chapter one:The fluorescence theory and fluorescence labeling technology were introduced systematically.The history and basic theory about HPLC were simply introduced.The applications of fluorescence labeling reagents for the labeling of amino and hydroxy by HPLC were summarized.
Chapter two:The syntheses of four fluorescence labeling reagents 2-(11H-benzo[a]carbazo-1-11-yl) acetic acid(BCA),2-(11H-benzo[a]carbazol-11-yl)isopropyl chloroformate(BCPC-Cl), 2-(11H-benzo[a]carbazol-11-yl)ethyl carbonochloridate(BCEC-Cl)and 2-(2-phenyl-1H-phena-nthro-[9,10-d]imidazole-1-yl)-acetic acid(PPIA)were described,and followed by their structural characterization and spectral properties.
Chapter three:Pre-column derivatization methods for the sensitive determination of aliphatic amines using 2-(11H-benzo[a]carbazol-11-yl)acetic acid(BCA)as labeling reagents followed by HPLC-MS analysis have been developed.The optimal derivatization and chromatographic separation conditions using BCA as labeling reagent were evaluated.And the feasibility of this method has been identified by analyzing soil and waste water sample.
Chapter four:Pre-column derivatization methods for the sensitive determination of aromatic amines using 2-(11H-benzo[a]carbazol-11-yl)isopropyl chloroformate(BCPC-Cl)as labeling reagents followed by HPLC-MS analysis have been developed.The optimal derivatization and chromatographic separation conditions using BCPC-Cl as labeling reagent were evaluated.And the feasibility of this method has been identified by analyzing waste water sample.
Chapter five:Pre-column derivatization methods for the sensitive determination of estrones using 2-(11H-benzo[a]carbazol-11-yl)ethyl carbonochloridate(BCEC-Cl)as labeling reagent followed by HPLC-MS analysis have been developed.The optimal derivatization and chromatographic separation conditions using BCEC-Cl as labeling reagent were evaluated.And the feasibility of this method has been identified by analyzing Tibetan antelope feces sample.
Chapter six:Pre-column derivatization methods for the sensitive determination of aromatic amines using 2-(2-phenyl-1H-phenanthro-[9,10-d]imidazole-1-yl)-acetic acid(PPIA)as labeling reagents followed by HPLC-MS analysis have been developed.The optimal derivatization and chromatographic separation conditions using PPIA as labeling reagent were evaluated.And the feasibility of this method has been identified by analyzing waste water sample.
引文
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