多种天然化合物的模式识别及双通道传感器的设计与合成
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摘要
摘要
本论文基于超分子化学领域经典的指示剂置换法,设计合成了一系列带有多个硼酸结合位点的受体,并筛选了多种指示剂组成指示剂对。受体与指示剂对结合起来,组成了动力学三组分检测体系。该检测体系应用于传感阵列对多种天然化合物进行了模式识别与分类。另外基于汞离子诱导醛基脱保护机理,设计合成了一种以BODIPY为荧光团的双通道化学传感器。
第一部分研究了传感阵列对人参皂苷和人参提取物的模式识别与分类。与传统的硼酸受体不同之处在于受体中引入了多个硼酸结合位点,并引入了各种各样长度与结构不同的连接臂,进而增强受体与客体之间的交互作用。对多种指示剂进行了筛选,得到了两组能产生理想光信号的指示剂对。受体与指示剂对结合起来组成了动力学三组分检测体系,并最终建立了传感阵列。通过传感阵列,成功地对人参皂苷和人参提取物进行了模式识别与分类。
第二部分研究了传感阵列对黄酮类化合物和红茶提取物的模式识别与分类。大部分黄酮类化合物带有邻苯二酚基团,这一基团可以与芳香基硼酸可逆结合,形成环状的硼酸酯。利用硼酸类受体和指示剂对组成的动力学检测体系对黄酮类化合物具有差异响应,并由此建立相应的传感阵列。模式识别分析结果表明该传感阵列对黄酮类化合物和红茶提取物有着出色的区分和分类能力。
第三部分基于汞离子诱导的硫缩醛脱保护反应,设计、合成和表征了一个基于1,3-二噻烷修饰的BODIPY化学传感器,能对汞离子和银离子产生不同的信号模式。
In the dissertation, a library of simple multi-boronic acid-based receptors with various spacers was synthesized for the sensing of saccharide-based natural products. Based on indicator displacement assay, a cross-reactive sensing array was constructed using the receptors in conjunction with different pairs of indicators. Pattern recognition analysis created from the colorimetric response of the hosts and indicator pairs reveal excellent classification of natural products. Moreover, based on the concept of aldehyde group protection/deprotection, a new BODIPY based dual-channel chemodosimeter for Hg2+ and Ag+ has been developed.
The first section studied on the pattern recognition of ginsenosides and ginseng extracts. A library of simple bis-boronic acid based receptors for ginsenosides were designed and synthesized. Multiple boronic acids were incorporated for simultaneous binding of saccharides on two ends of ginsenosides while some of the spacers were used to target hydrophobic steroids. A suite of indicators were screened, and the pairing of indicators (ML-PV or ARS-PV) provided greater absorbance signal modulation. Pattern recognition analysis indicated excellent separation and classification of individual ginsenosides and ginseng extracts with high accuracy.
The second section focused on the discrimination of vicinal-diol-containing flavonoids and black tea extracts. Boronic acids are suitable for binding flavonoids because most flavonoids contain catechol groups which can reversibly associate with phenyl boronic acids to form cyclic boronic esters. The resulting dynamic three-component sensing ensembles (H-ML-PV, H-ARS-PV) are capable of responding differently to flavonoids, providing the basis for array sensing. Sensing arrays in 96-well plates were constructed and successfully employed to discriminate both vicinal-diol-containing flavonoids and black tea extracts.
The third section described the design, synthesis and spectral characterization of BODIPY-1,3-dithiane-based chemodosimeter, which yields distinctive signal patterns towards Hg2+ and Ag+.
本论文基于超分子化学领域经典的指示剂置换法,设计合成了一系列带有多个硼酸结合位点的受体,并筛选了多种指示剂组成指示剂对。受体与指示剂对结合起来,组成了动力学三组分检测体系。该检测体系应用于传感阵列对多种天然化合物进行了模式识别与分类。另外基于汞离子诱导醛基脱保护机理,设计合成了一种以BODIPY为荧光团的双通道化学传感器。
第一部分研究了传感阵列对人参皂苷和人参提取物的模式识别与分类。与传统的硼酸受体不同之处在于受体中引入了多个硼酸结合位点,并引入了各种各样长度与结构不同的连接臂,进而增强受体与客体之间的交互作用。对多种指示剂进行了筛选,得到了两组能产生理想光信号的指示剂对。受体与指示剂对结合起来组成了动力学三组分检测体系,并最终建立了传感阵列。通过传感阵列,成功地对人参皂苷和人参提取物进行了模式识别与分类。
第二部分研究了传感阵列对黄酮类化合物和红茶提取物的模式识别与分类。大部分黄酮类化合物带有邻苯二酚基团,这一基团可以与芳香基硼酸可逆结合,形成环状的硼酸酯。利用硼酸类受体和指示剂对组成的动力学检测体系对黄酮类化合物具有差异响应,并由此建立相应的传感阵列。模式识别分析结果表明该传感阵列对黄酮类化合物和红茶提取物有着出色的区分和分类能力。
第三部分基于汞离子诱导的硫缩醛脱保护反应,设计、合成和表征了一个基于1,3-二噻烷修饰的BODIPY化学传感器,能对汞离子和银离子产生不同的信号模式。
In the dissertation, a library of simple multi-boronic acid-based receptors with various spacers was synthesized for the sensing of saccharide-based natural products. Based on indicator displacement assay, a cross-reactive sensing array was constructed using the receptors in conjunction with different pairs of indicators. Pattern recognition analysis created from the colorimetric response of the hosts and indicator pairs reveal excellent classification of natural products. Moreover, based on the concept of aldehyde group protection/deprotection, a new BODIPY based dual-channel chemodosimeter for Hg2+ and Ag+ has been developed.
The first section studied on the pattern recognition of ginsenosides and ginseng extracts. A library of simple bis-boronic acid based receptors for ginsenosides were designed and synthesized. Multiple boronic acids were incorporated for simultaneous binding of saccharides on two ends of ginsenosides while some of the spacers were used to target hydrophobic steroids. A suite of indicators were screened, and the pairing of indicators (ML-PV or ARS-PV) provided greater absorbance signal modulation. Pattern recognition analysis indicated excellent separation and classification of individual ginsenosides and ginseng extracts with high accuracy.
The second section focused on the discrimination of vicinal-diol-containing flavonoids and black tea extracts. Boronic acids are suitable for binding flavonoids because most flavonoids contain catechol groups which can reversibly associate with phenyl boronic acids to form cyclic boronic esters. The resulting dynamic three-component sensing ensembles (H-ML-PV, H-ARS-PV) are capable of responding differently to flavonoids, providing the basis for array sensing. Sensing arrays in 96-well plates were constructed and successfully employed to discriminate both vicinal-diol-containing flavonoids and black tea extracts.
The third section described the design, synthesis and spectral characterization of BODIPY-1,3-dithiane-based chemodosimeter, which yields distinctive signal patterns towards Hg2+ and Ag+.
引文
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