新型次氯酸荧光探针的合成与性能研究

发布时间：2018-04-05 11:14

本文选题：荧光探针　切入点：次氯酸　出处：《济南大学》2017年硕士论文

【摘要】：次氯酸在日常生活和工业生产中应用十分广泛,然而残留在水体中的次氯酸会引起水体污染,对人体健康存在潜在的危害。生物体内的次氯酸具有重要的生理功能,一旦其含量超出正常的生理水平范围,会引起一系列疾病。对于环境样品及生物体内次氯酸的检测已成为一个重要课题,发展新型的快速、灵敏、高选择性次氯酸荧光探针具有重要意义和应用价值。本论文充分运用分子内电荷转移机制,设计合成了五例新型次氯酸荧光探针,并分别在环境样品和生物体系中对次氯酸进行检测。以4-羟基萘酰亚胺作为荧光团,硫代氨基甲酸酯作为识别受体,合成了两例超灵敏次氯酸荧光探针NDMTC和Lyso-NDMTC。探针NDMTC对次氯酸具有高的灵敏度和选择性,能在较宽的pH范围内快速识别次氯酸,可用于环境样品中次氯酸的检测,实现了对细胞和小鼠体内内源性次氯酸的双光子荧光成像,并可以区分乳腺细胞和乳腺癌细胞。溶酶体靶向探针Lyso-NDMTC实现了对肝癌细胞溶酶体内次氯酸的检测和荧光成像分析。以三氰基呋喃为母体,修饰上对甲酰基苯硼酸频哪醇酯合成了一例长波长次氯酸荧光探针TCF-OCl。探针具有良好的选择性和水溶性,反应前后出现了明显的颜色变化(由浅黄色到红色),可以通过吸收光谱法和荧光光谱法快速检测次氯酸。探针TCF-OCl成功应用于环境水体中次氯酸的检测;探针最大发射波长在610 nm,实现了巨噬细胞内次氯酸的灵敏成像分析。以4-氨基萘酰亚胺作为荧光团,氨乙基硫脲为识别受体,合成了一例比率型次氯酸荧光探针AETU-HOCl。探针的发射峰在533 nm,加入次氯酸之后发射峰蓝移至473 nm。探针拥有高选择性,在其它高浓度分析物存在时依然稳定,可以在较宽的pH范围内快速识别次氯酸。探针可用于环境样品中次氯酸的检测分析,并实现了细胞外源性和内源性次氯酸的比率荧光成像分析。以苯硼酸为识别受体合成一例次氯酸荧光探针BTAT。探针具有好的选择性和水溶性。可通过吸收光谱法和荧光光谱法快速检测次氯酸。并实现了环境样品和细胞核内次氯酸的检测分析。综上,本文合成的五例新型次氯酸荧光探针,不仅为水环境和生物体系中次氯酸的检测提供了新的方法,而且还为次氯酸荧光探针以及其他环境污染物荧光探针的发展奠定了理论基础。
[Abstract]:Hypochlorite is widely used in daily life and industrial production. However, hypochlorite residues in water can cause water pollution and have potential harm to human health.Hypochloric acid has important physiological function, once its content exceeds the normal physiological level, it will cause a series of diseases.It has become an important subject for the detection of hypochloric acid in environmental samples and organisms. It is of great significance and application value to develop new fast, sensitive and highly selective hypochloric acid fluorescent probes.In this paper, five novel hypochlorite fluorescent probes were designed and synthesized by using intramolecular charge transfer mechanism, and the hypochloric acid was detected in environmental samples and biological systems.Using 4-hydroxynaphthalimide as fluorescence group and thiocarbamate as recognition receptor, two highly sensitive fluorescent probes of hypochloric acid (NDMTC and Lyso-NDMTC) were synthesized.The probe NDMTC has high sensitivity and selectivity to hypochloric acid and can quickly recognize hypochloric acid in a wide pH range. It can be used to detect hypochloric acid in environmental samples and realize two-photon fluorescence imaging of endogenous hypochloric acid in cells and mice.And can distinguish between breast cells and breast cancer cells.Lysosomal targeted probe Lyso-NDMTC was used to detect hypochloric acid in lysosome of hepatoma cells.A long wavelength fluorescence probe TCF-OCl was synthesized with tricyanofuran as the parent and modified with p-formyl phenoborborate.The probe has good selectivity and water solubility, and there are obvious color changes (from light yellow to red) before and after the reaction. Hypochloric acid can be detected quickly by absorption spectrometry and fluorescence spectrometry.The probe TCF-OCl has been successfully applied to the detection of hypochloric acid in environmental water, and the maximum emission wavelength of the probe is 610nm.The sensitive imaging of hypochloric acid in macrophages has been realized.Using 4-aminonaphthalimide as fluorescence group and aminoethyl thiourea as recognition receptor, a fluorescent probe AETU-HOCl was synthesized.The emission peak of the probe was 533 nm, and the emission peak blue shifted to 473 nm after hypochloric acid was added.The probe has high selectivity and remains stable in the presence of other high concentrations of analytes. It can quickly recognize hypochloric acid in a wide pH range.The probe can be used for the detection and analysis of hypochloric acid in environmental samples and the ratio fluorescence imaging analysis of exogenous and endogenous hypochloric acid in cells has been realized.A fluorescent probe BTAT was synthesized by using phenylboric acid as the recognition receptor.The probe has good selectivity and water solubility.Hypochloric acid can be detected quickly by absorption spectrometry and fluorescence spectrometry.The detection and analysis of hypochloric acid in environmental samples and nuclei were carried out.In summary, five new hypochlorite fluorescent probes synthesized in this paper not only provide a new method for the detection of hypochloric acid in water environment and biological system, but also provide a new method for the detection of hypochloric acid in water environment and biological system.It also lays a theoretical foundation for the development of hypochloric acid fluorescent probes and other environmental pollutants fluorescent probes.
【学位授予单位】：济南大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O657.3;X830

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