含N-羟基琥珀酰亚胺酯的三枝BODIPY染料的合成
发布时间：2018-12-10 12:28
【摘要】：荧光光谱和荧光成像是当今科学研究必不可少的工具。荧光分析法具有高选择性、高灵敏度、高荧光量子产率等优点,已被广泛应用于蛋白质标记、DNA检测和环境检测等领域。N-羟基琥珀酰亚胺活性酯(NHS活性酯)被应用于肿瘤诊断、免疫分析、亲合色谱、抗原分离等领域。本文得到含有NHS活性酯的氟硼二吡咯类(BODIPY)荧光化合物。验证其反应活性,与甘氨酸甲酯反应,得到了含有BODIPY荧光团的氨基酸甲酯。本文共计合成了7个BODIPY荧光染料,均未见文献报道。通过核磁、质谱、红外光谱等进行了表征分析。在实验过程中,有如下探索和结论:1、三聚氯氰母体上引入对羟基苯甲酸苯甲酯后由于电子效应的影响,其反应活性与其他BODIPY荧光化合物相比低很多。2、文中涉及的三枝BODIPY苄基酯在钯碳、氢气环境中的氢解反应需要关注化合物的稳定性,25℃,反应时间不超过3 h;反应溶剂对反应影响不大。3、以N,N'-二琥珀酰亚胺基碳酸酯(DSC)制备NHS活性酯,当连有对氯酚时,以亲核性的DMAP做碱会催化三VA嗪环发生亲核取代,造成三枝化合物的断裂。改用N,N-二异丙基乙胺(DIEA)可避免此过程。4、荧光产物进行了测试。最大吸收波长都在502 nm左右,荧光量子产率37.41%-63.41%。
[Abstract]:Fluorescence spectroscopy and fluorescence imaging are essential tools for scientific research today. Fluorescence analysis has been widely used in protein labeling for its advantages of high selectivity, high sensitivity and high fluorescence quantum yield. N-hydroxysuccinimide (NHS) has been used in tumor diagnosis, immunoassay, affinity chromatography, antigen separation and so on. In this paper, fluorinated boron dipyrrole (BODIPY) fluorescent compounds containing NHS active esters were obtained. The amino acid methyl ester containing BODIPY fluorescence group was obtained by reaction with methyl glycine. In this paper, seven BODIPY fluorescent dyes have been synthesized, which have not been reported in literature. It was characterized by NMR, MS and IR spectra. In the course of the experiment, the following conclusions were made: 1. The activity of methyl p-hydroxybenzoate was much lower than that of other BODIPY fluorescent compounds due to the effect of electron effect. The hydrogenolysis reaction of three BODIPY benzyl esters in palladium and carbon and hydrogen environment needs to pay attention to the stability of the compounds. The reaction time is less than 3 h at 25 鈩，
本文编号：2370564
[Abstract]:Fluorescence spectroscopy and fluorescence imaging are essential tools for scientific research today. Fluorescence analysis has been widely used in protein labeling for its advantages of high selectivity, high sensitivity and high fluorescence quantum yield. N-hydroxysuccinimide (NHS) has been used in tumor diagnosis, immunoassay, affinity chromatography, antigen separation and so on. In this paper, fluorinated boron dipyrrole (BODIPY) fluorescent compounds containing NHS active esters were obtained. The amino acid methyl ester containing BODIPY fluorescence group was obtained by reaction with methyl glycine. In this paper, seven BODIPY fluorescent dyes have been synthesized, which have not been reported in literature. It was characterized by NMR, MS and IR spectra. In the course of the experiment, the following conclusions were made: 1. The activity of methyl p-hydroxybenzoate was much lower than that of other BODIPY fluorescent compounds due to the effect of electron effect. The hydrogenolysis reaction of three BODIPY benzyl esters in palladium and carbon and hydrogen environment needs to pay attention to the stability of the compounds. The reaction time is less than 3 h at 25 鈩，
本文编号：2370564
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