基于氧杂蒽—香豆素和尼罗红的荧光探针的合成与性能研究

发布时间：2018-06-07 22:03

本文选题：荧光染料 + 氧杂蒽　；参考：《郑州大学》2017年硕士论文

【摘要】：近年来,荧光探针的研究备受关注。由于其具有选择性好、灵敏度高、操作简便快速、毒性小、易实现实时原位检测和观察等优点,已被广泛用于活细胞与活体组织中生物分子的检测。其中,氧杂蒽荧光团因其光稳定好、摩尔消光系数高、Stokes位移大及相对较长的发射波长等优点而被广泛用于荧光探针构建。尼罗红染料因为具有高的荧光量子产率,最大发射位于红光区(500-700 nm),受样品背景干扰相对较少等优点,在荧光探针构建方面有较大应用潜力。本文主要设计合成了三个基于氧杂蒽-香豆素的荧光探针(L1-L3)和一个基于尼罗红的荧光探针L4,对它们的识别性能进行了研究,并应用于细胞成像和环境的检测;目标化合物(L1-L4)的结构均经过1H NMR,13C NMR,HR-MS的确证。具体内容如下:1、基于氧杂蒽-香豆素的ClO~-荧光探针L1和L2的合成及其应用。这两个探针能够在乙醇/PB的缓冲体系中选择性识别ClO~-,识别前后有明显的颜色变化,可实现对ClO~-裸眼识别,具有良好的生物相容性,能够用于活细胞内Cl O~-的细胞荧光成像,除此之外,我们也做了相关的试纸实验,应用效果良好。2、基于氧杂蒽-香豆素的HSO_3~-荧光探针L3的合成及其应用。该探针能够在纯的Tris-HCl缓冲体系选择性识别HSO_3~-,识别前后颜色变化明显,可用于裸眼识别,生物相容性好,并成功应用于活细胞内HSO_3~-的荧光成像。3、基于尼罗红-NBD的荧光探针L4的合成及其应用。该探针能够用于识别小分子的生物硫醇(半胱氨酸和谷胱甘肽)和HS-。探针在荧光发射543 nm处可以专一性识别半胱氨酸,在荧光发射636 nm处的可依据动力学选择性识别HS-,识别前后有显著颜色变化,并成功应用于活细胞成像。
[Abstract]:In recent years, the study of fluorescent probes has attracted much attention. It has been widely used in the detection of biomolecules in living cells and living tissues because of its advantages of good selectivity, high sensitivity, simple and rapid operation, low toxicity and easy to realize real-time in situ detection and observation. Among them, oxyanthracene fluorescence group is widely used in fluorescent probe construction because of its advantages of good light stability, high molar extinction coefficient, large Stokes shift and relatively long emission wavelength. Because of its high fluorescence quantum yield and its maximum emission in the red region of 500-700 nm, the Nile red dye has the advantages of relatively little interference from the background of the sample, so it has great application potential in the construction of fluorescent probe. In this paper, three fluorescent probes L1-L3 based on oxyanthracene-coumarin and a fluorescent probe L4 based on Nile red were designed and synthesized. Their recognition properties were studied and applied to cell imaging and environmental detection. The structure of the target compound L1-L4 was confirmed by 1H-NMR-13C NMR-HR-MS. The main contents are as follows: 1. Synthesis and application of ClON-fluorogenic probes L1 and L2 based on oxyanthracene-coumarin. These two probes can selectively recognize ClO- in the buffer system of ethanol / PB, and have obvious color changes before and after recognition. They can realize the recognition of ClO- by naked eye, have good biocompatibility, and can be used in the fluorescence imaging of living cells. In addition, we have also done the relevant test paper experiments, the application effect is good. 2. The synthesis and application of HSO _ 3C _ 3 fluorescence probe L3 based on oxyanthracene-coumarin. The probe can selectively recognize HSOs 3s in the pure Tris-HCl buffer system, and the color changes are obvious before and after recognition. The probe can be used for naked eye recognition and has good biocompatibility. It has been successfully applied to the fluorescence imaging of HSO _ 3- in living cells, and to the synthesis and application of the fluorescence probe L4 based on Nile red -NBD. The probe can be used to recognize biological mercaptan (cysteine and glutathione) and HS-. The probe can specifically recognize cysteine at 543 nm of fluorescence emission and HS-selective recognition at 636 nm of fluorescence emission. It has significant color changes before and after recognition and has been successfully used in living cell imaging.
【学位授予单位】：郑州大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O657.3

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