【摘要】：熒光光譜和熒光成像是當今科學研究必不可少的工具。熒光分析法具有高選擇性、高靈敏度、高熒光量子產率等優(yōu)點,已被廣泛應用于蛋白質標記、DNA檢測和環(huán)境檢測等領域。N-羥基琥珀酰亞胺活性酯(NHS活性酯)被應用于腫瘤診斷、免疫分析、親合色譜、抗原分離等領域。本文得到含有NHS活性酯的氟硼二吡咯類(BODIPY)熒光化合物。驗證其反應活性,與甘氨酸甲酯反應,得到了含有BODIPY熒光團的氨基酸甲酯。本文共計合成了7個BODIPY熒光染料,均未見文獻報道。通過核磁、質譜、紅外光譜等進行了表征分析。在實驗過程中,有如下探索和結論:1、三聚氯氰母體上引入對羥基苯甲酸苯甲酯后由于電子效應的影響,其反應活性與其他BODIPY熒光化合物相比低很多。2、文中涉及的三枝BODIPY芐基酯在鈀碳、氫氣環(huán)境中的氫解反應需要關注化合物的穩(wěn)定性,25℃,反應時間不超過3 h;反應溶劑對反應影響不大。3、以N,N'-二琥珀酰亞胺基碳酸酯(DSC)制備NHS活性酯,當連有對氯酚時,以親核性的DMAP做堿會催化三VA嗪環(huán)發(fā)生親核取代,造成三枝化合物的斷裂。改用N,N-二異丙基乙胺(DIEA)可避免此過程。4、熒光產物進行了測試。最大吸收波長都在502 nm左右,熒光量子產率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，

本文編號：2370564