本文選題：花菁染料　切入點(diǎn)：氟離子　出處：《海南大學(xué)》2017年碩士論文

【摘要】：氟離子屬于人體必需的微量元素之一,它對(duì)人體健康起著至關(guān)重要的作用。在各種氟離子檢測(cè)的分析方法中,熒光傳感被認(rèn)為是一種操作簡(jiǎn)單,專一性好和靈敏度高的理想技術(shù)。本文以具有近紅外(Near-Infrared,簡(jiǎn)稱NIR)光譜特征,光穩(wěn)定性好以及水溶性好等優(yōu)點(diǎn)的部花菁骨架1作為熒光發(fā)色團(tuán),以Si-O鍵為反應(yīng)位點(diǎn),設(shè)計(jì)合成了 OFF-ON型的具有NIR激發(fā)和發(fā)射波長(zhǎng)的熒光探針CyR-Si(3a,3b和3c)。完成的主要工作包括:1、以環(huán)己酮為原料合成了部花菁骨架1,再通過(guò)與間苯二酚等發(fā)生消除、retro-Knoevenagel、環(huán)化及脫水反應(yīng)得到一種帶有羥基的熒光物質(zhì)。隨后在羥基鄰位構(gòu)建出含有H,C1和F取代基的探針3a,3b和3c,其結(jié)構(gòu)通過(guò)HRMS,1HNMR和13CNMR等測(cè)試手段得到驗(yàn)證。此外,對(duì)探針的光物理數(shù)據(jù)的計(jì)算方法以及其他操作步驟做了簡(jiǎn)要說(shuō)明,如熒光量子產(chǎn)率,pKa,檢測(cè)限等。2、考察了探針 3a,3b 和 3c 在 DMSO/PBS=7:3(v/v,0.01M,pH = 7.4)體系中分別對(duì)氟離子的響應(yīng)情況。其中熒光選擇實(shí)驗(yàn)和競(jìng)爭(zhēng)實(shí)驗(yàn)表明探針3a-c對(duì)氟離子都具有專一選擇性和很好的抗干擾能力。熒光滴定實(shí)驗(yàn)表明探針的熒光強(qiáng)度和氟離子濃度在0～100mM(探針3a),0～70mM(探針3b)和0～70mM(探針3c)范圍內(nèi)具有很好的線性關(guān)系,由此計(jì)算出探針3a-c對(duì)F-的檢測(cè)限分別為:0.116MM,0.061μM和0.152 μM,說(shuō)明探針對(duì)氟離子的檢測(cè)具有很高的靈敏度。探針對(duì)氟離子的響應(yīng)機(jī)理通過(guò)高效液相色譜(HPLC)得到了驗(yàn)證。由MTT實(shí)驗(yàn)可知探針3a-c在20μM時(shí)都具有良好的生物相容性,且在HepG2細(xì)胞內(nèi)對(duì)氟離子的成像檢測(cè)均取得了顯著的效果。另外,光譜數(shù)據(jù)表明探針3c具有更快的響應(yīng)速率和更強(qiáng)的熒光信號(hào)等優(yōu)點(diǎn),因此被用在小鼠體內(nèi)對(duì)氟離子進(jìn)行成像檢測(cè),且在活體內(nèi)檢測(cè)到的最低氟離子的量為1 mgF/Kg。
[Abstract]:Fluorine ion is one of the essential trace elements in human body, and it plays an important role in human health. In all kinds of analytical methods of fluorine ion detection, fluorescence sensing is considered to be a simple operation. An ideal technique with good specificity and high sensitivity. In this paper, the part cyanine skeleton 1, which has the advantages of near infrared Near-Infrared (NIR) spectral characteristics, good light stability and good water solubility, is used as the fluorescence chromophore, and the Si-O bond is used as the reaction site. The fluorescence probes CyR-Si3aO3b with NIR excitation and emission wavelengths of OFF-ON type were designed and synthesized. The main work accomplished included: 1: 1, the cyclization, cyclization, cyclization and cyclization of cyclization and cyclization by using cyclohexanone as raw material to synthesize part cyanine skeleton 1, and to eliminate retro-Knoevenagel1 with resorcinol and so on. In the dehydration reaction, a fluorescent substance with hydroxyl group was obtained. The probes 3aF3b and 3ccontaining HNC1 and F substituents were constructed at the hydroxyl ortho site. The structures of the probes were confirmed by HRMS 1H NMR and 13CNMR. The calculation method and other operation steps of the photophysical data of the probe are briefly described. For example, fluorescence quantum yield and detection limit. 2. The response of probe 3ah3b and 3c to fluorine ions in DMSO / PBS7: 3 / V / V / V / V = 0.01Mg pH = 7.4) system was investigated. The fluorescence selection experiment and competitive experiment showed that the probe 3a-c had a special effect on fluorine ions. The fluorescence titration experiments show that the fluorescence intensity and the concentration of fluorine ion are linear in the range of 0 ~ 100mM (probe 3b) and 0 ~ 70mM (probe 3c). The detection limits of F- for probe 3a-c were calculated to be respectively 0. 116 and 0. 061 渭 M and 0.152 渭 M, respectively, indicating that the probe has a high sensitivity to fluorine ion detection. The response mechanism of probe to fluorine ion is verified by high performance liquid chromatography (HPLC). The results showed that the probe 3a-c had good biocompatibility at 20 渭 M. In addition, the spectral data show that the probe 3c has the advantages of faster response rate and stronger fluorescence signal. Therefore, fluorine ion was detected by imaging in mice, and the lowest fluorine ion was detected in vivo with a dose of 1 mg F / K g.
【學(xué)位授予單位】：海南大學(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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