【摘要】：熒光光譜和熒光成像是當(dāng)今科學(xué)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(chǎn)率等優(yōu)點(diǎn),已被廣泛應(yīng)用于蛋白質(zhì)標(biāo)記、DNA檢測和環(huán)境檢測等領(lǐng)域。N-羥基琥珀酰亞胺活性酯(NHS活性酯)被應(yīng)用于腫瘤診斷、免疫分析、親合色譜、抗原分離等領(lǐng)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(yàn)證其反應(yīng)活性,與甘氨酸甲酯反應(yīng),得到了含有BODIPY熒光團(tuán)的氨基酸甲酯。本文共計(jì)合成了7個(gè)BODIPY熒光染料,均未見文獻(xiàn)報(bào)道。通過核磁、質(zhì)譜、紅外光譜等進(jìn)行了表征分析。在實(shí)驗(yàn)過程中,有如下探索和結(jié)論:1、三聚氯氰母體上引入對(duì)羥基苯甲酸苯甲酯后由于電子效應(yīng)的影響,其反應(yīng)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(yīng)需要關(guān)注化合物的穩(wěn)定性,25℃,反應(yīng)時(shí)間不超過3 h;反應(yīng)溶劑對(duì)反應(yīng)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(dāng)連有對(duì)氯酚時(shí),以親核性的DMAP做堿會(huì)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(chǎn)物進(jìn)行了測試。最大吸收波長都在502 nm左右,熒光量子產(chǎn)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(hào)：2370564