本文選題：熒光探針 + 小分子��； 參考：《濟(jì)南大學(xué)》2017年碩士論文

【摘要】：熒光探針的合成與應(yīng)用作為各學(xué)科領(lǐng)域交叉的前沿學(xué)科,正在得到科研工作者的廣泛關(guān)注。其工作原理是將肉眼無(wú)法觀察到的分子間的作用以光信號(hào)的形式表現(xiàn)出來(lái)。熒光探針存在的典型的特點(diǎn)是穩(wěn)定性好,操作簡(jiǎn)單易行,檢測(cè)時(shí)間短,生物毒性低。將熒光探針與生物成像結(jié)合,可以用于示蹤生物體內(nèi)的某種物質(zhì),實(shí)現(xiàn)對(duì)物質(zhì)的實(shí)時(shí)原位檢測(cè),甚至是監(jiān)測(cè)生理過(guò)程。因此對(duì)熒光探針的研究具有十分重要的意義。本文以希夫堿類化合物設(shè)計(jì)了一種檢測(cè)鋅離子的探針,以花菁類染料為熒光團(tuán)設(shè)計(jì)了一種檢測(cè)肼的探針,以BODIPY為熒光團(tuán)設(shè)計(jì)了一種檢測(cè)氯磷酸二乙酯(DCP)的探針。在第一部分,基于鋅離子對(duì)腦功能、基因轉(zhuǎn)移、免疫功能起著非常重要的作用。實(shí)驗(yàn)設(shè)計(jì)合成了一種基于希夫堿的檢測(cè)鋅離子的熒光探針。該探針以肼為橋,將2-位醛基取代的氰基聯(lián)苯酚的醛基與氨茴酸甲酯的酯基連接得到探針化合物。鋅離子具有強(qiáng)的配位能力,會(huì)與探針形成比較穩(wěn)定的配合物。探針的共軛程度變大,剛性平面更加穩(wěn)定,發(fā)射波長(zhǎng)紅移。此探針的響應(yīng)時(shí)間為17 s,檢測(cè)限為1.3×10~(-8) mol/L。探針被成功的應(yīng)用于細(xì)胞中鋅離子的識(shí)別。在第二部分,由于肼的濃度過(guò)高的時(shí)候會(huì)引起人體的一些病變,像頭暈眼花、惡心、昏迷肺部水腫的癥狀并且皮膚接長(zhǎng)時(shí)間的暴露在肼含量高的環(huán)境中會(huì)引起皮炎等皮膚中毒現(xiàn)象。因此我們以花菁類染料為熒光團(tuán),以4-溴丁酸為識(shí)別基團(tuán)合成了一種檢測(cè)肼的熒光探針。肼的強(qiáng)的親核作用會(huì)與溴發(fā)生取代反應(yīng),中間產(chǎn)物中游離的氨基進(jìn)攻酯基,釋放出熒光團(tuán)中的羥基,探針的熒光恢復(fù),是一個(gè)比率型的近紅外熒光探針。其響應(yīng)時(shí)間為18 min,檢測(cè)限為1.19×10~(-8) mol/L。探針被成功的用于細(xì)胞和生物活體內(nèi)肼的檢測(cè)。在第三部分,基于DCP是一種結(jié)構(gòu)與神經(jīng)毒劑沙林相似的神經(jīng)毒劑模擬分子,當(dāng)環(huán)境中DCP的含量過(guò)高時(shí)會(huì)危及生命。我們以BODIPY為熒光團(tuán),以氰基聯(lián)苯酚的羥基作為識(shí)別基團(tuán)合成了一種檢測(cè)DCP的熒光探針。DCP是一種強(qiáng)的親電試劑,探針化合物中加入的DCP會(huì)與包含的羥基發(fā)生親電取代反應(yīng),導(dǎo)致探針?lè)肿觾?nèi)的PET被禁阻,同時(shí)由于位阻的原因探針含有羥基的供電部分旋轉(zhuǎn)受阻,探針表現(xiàn)出熒光。是一種熒光增強(qiáng)型的檢測(cè)DCP的探針。探針的響應(yīng)時(shí)間為9 min,檢測(cè)限為1.3×10~(-8) mol/L。探針?lè)肿颖怀晒Φ脑O(shè)計(jì)成試紙,用于環(huán)境中DCP的檢測(cè)。
[Abstract]:The synthesis and application of fluorescent probes, as a frontier subject in various disciplines, are receiving extensive attention from researchers. The principle is that the interaction between molecules can not be observed by the naked eye in the form of light signals. The typical characteristics of fluorescent probe are good stability, simple operation, short detection time and low biotoxicity. The combination of fluorescent probe and biological imaging can be used to trace a certain substance in the organism and realize the real-time in-situ detection of the substance, and even monitor the physiological process. Therefore, the study of fluorescent probe is of great significance. In this paper, we designed a probe for the detection of zinc ion with Schiff base compounds, a probe for the detection of hydrazine with cyanine dyes as fluorescence group, and a probe for the detection of diethyl chlorophosphate with BODIPY as fluorescence group. In the first part, zinc ion plays a very important role in brain function, gene transfer and immune function. A fluorescence probe for zinc ion detection based on Schiff base was designed and synthesized. Using hydrazine as a bridge, the probe compound was obtained by connecting the aldehyde group of 2-position substituted cyano-biphenol with the ester group of methyl anethanilate. Zinc ions have strong coordination ability and form stable complexes with the probe. The conjugation degree of the probe becomes larger, the rigid plane is more stable, and the emission wavelength is redshift. The response time of the probe is 17 s and the detection limit is 1.3 脳 10 ~ (-8) mol / L. The probe has been successfully applied to the recognition of zinc ions in cells. In the second part, when the concentration of hydrazine is too high, it can cause some pathological changes in the human body, such as dizziness, nausea, Symptoms of pulmonary edema in coma and prolonged skin exposure to high levels of hydrazine can lead to dermatitis and other skin poisoning. Therefore, we synthesized a fluorescence probe for hydrazine with cyanine dyes as fluorescence group and 4-bromobutyric acid as recognition group. The strong nucleophilic effect of hydrazine can replace bromine. The free amino attack ester group in the intermediate product releases the hydroxyl in the fluorescence group and the fluorescence of the probe recovers. It is a ratio type near infrared fluorescence probe. The response time was 18 min and the detection limit was 1.19 脳 10 ~ (-8) mol 路L ~ (-1) 路L ~ (-1) 路L ~ (-1) 路min. The probe was successfully used for the detection of hydrazine in cells and living organisms. In the third part, DCP is a mimic molecule of nerve agent similar to the nerve agent sarin. When the content of DCP in environment is too high, it will be life-threatening. Using BODIPY as fluorescence group and hydroxyl group of cyano-biphenol as recognition group, we synthesized a fluorescent probe. DCP is a strong electrophilic reagent for the detection of DCP. The DCP added in the probe compound can take place in the electrophilic substitution reaction with the containing hydroxyl group. As a result, the PET in the probe molecule is blocked, and the probe exhibits fluorescence due to the hindrance of the rotation of the power supply part containing hydroxyl groups in the probe due to the steric resistance. It is a fluorescent enhanced probe for detecting DCP. The response time of the probe was 9 min and the detection limit was 1.3 脳 10 ~ (-8) mol 路L ~ (-1) 路L ~ (-1) 路L ~ (-1). Probe molecules were successfully designed as test papers for the detection of DCP in the environment.
【學(xué)位授予單位】：濟(jì)南大學(xué)
【學(xué)位級(jí)別】：碩士
【學(xué)位授予年份】：2017
【分類號(hào)】：O657.3

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