本文選題：香豆素　切入點：萘　出處：《江蘇大學》2017年碩士論文　論文類型：學位論文

【摘要】：自然界中有各種各樣的金屬,包括堿金屬和堿土金屬,過渡金屬和重金屬,這些金屬在生物體中扮演著重要的角色。攝入過多或攝入不足會導致生理功能障礙,甚至導致疾病。因此,設計和合成一種可用于金屬離子檢測的熒光探針是非常重要的。本文設計合成了一系列新型小分子熒光探針分別用于Fe~(3+),Al~(3+),Zn~(2+)等離子的識別與檢測。(1)設計合成了一種基于香豆素衍生物的Fe~(3+)熒光猝滅性小分子熒光探針7-二乙氨基香豆素-3-醛。當pH=7時,探針溶液本身熒光較強,考察一系列金屬離子Pb~(2+),Ni~(2+),Mg~(2+),Cd~(2+),Co~(2+),Cu~(2+),Mg~(2+),Fe~(2+),Zn~(2+),K~+,Li~+,Na~+,Al~(3+),Fe~(3+),Cr~(3+)對探針的影響,發(fā)現(xiàn)僅僅與Fe~(3+)結(jié)合后熒光淬滅,由此建立了Fe~(3+)測定的新方法。本方法具有水溶性好、靈敏度高、選擇性好等優(yōu)點,檢出限低至2.5×10-2μM。同時,本熒光探針可實現(xiàn)生物細胞Ramos內(nèi)Fe~(3+)的檢測,證明其在化學傳感以及生物成像領(lǐng)域具有潛在的應用價值。(2)通過將D-葡萄糖胺鹽酸鹽與2-羥基-1-萘甲醛反應合成了新的萘席夫堿基熒光探針,即1-(C2-葡糖基-亞氨基-甲基)-萘-2-醇。它自身沒有熒光,但是對Al~(3+)具有極強的熒光響應,而且在Pb~(2+),Mg~(2+),Cd~(2+),Co~(2+),Cu~(2+),Ni~(2+),Fe~(2+),Mn~(2+),Hg~(2+),K~+,Li~+,Na~+,Fe~(3+),Cr~(3+)和Zn~(2+)等15種乙醇溶液中僅對Al~(3+)具有極強的選擇性。隨著Al~(3+)的加入,在激發(fā)波長為427 nm處的熒光強度會增強50倍,這是由于Al~(3+)和探針之間的螯合增強(CHEF)作用。由Job曲線可以知道探針與Al~(3+)是1:1結(jié)合的,而且經(jīng)計算得出探針與Al~(3+)的締合常數(shù)為5.748×103 M-1。在0~25μM線性區(qū)間內(nèi),計算得到探針L2對Al~(3+)的檢出限為2.83×10-3μM。此外,研究發(fā)現(xiàn)L-Al~(3+)絡合物的熒光可以在相同體系中添加F-時猝滅,考察其它陰離子,包括Cl~-,Br~-,I~-,NO_2~-,NO_3~-,ClO_4~-,CO_3~(2-),HCO_3~-,SO_4~(2-),HSO_4~-,CH_3COO-等均無此現(xiàn)象。[L Al~(3+)]絡合物與F-陰離子的結(jié)合通過不同的熒光滴定研究建立,在乙醇中的檢測限為3.2 nM。本熒光探針能夠?qū)崿F(xiàn)細胞內(nèi)Al~(3+)和F-的檢測,在傳感及生物成像領(lǐng)域具有潛在的實際應用價值。(3)設計合成了一種新穎的基于香豆素的熒光探針((4E-4-((7-羥基-4-甲基-2-氧代-2H-色烯-8-基亞甲基)肼基硫代酰胺)L3,可以在水環(huán)境中作為比色傳感器來檢測Fe~(3+),其通過在水環(huán)境中從無色到棕色的顏色變化來表現(xiàn)出對于Fe~(3+)的高選擇性和靈敏性的識別。同時,探針L3也可以作為熒光探針在乙醇:水(8:2,v/v)的混合溶劑中顯示出對Zn~(2+)的顯著的熒光增強效應。Fe~(3+)或Zn~(2+)的選擇性識別不受其它競爭性金屬離子例如Pb~(2+),Cd~(2+),Mg~(2+),Fe~(2+),Co~(2+),Ni~(2+),Cu~(2+),Mn~(2+),Hg~(2+),K~+,Li~+,Na~+,Al~(3+),Cr~(3+)和Sr~(2+)等離子存在的干擾。此外,在這項研究中,細胞成像的結(jié)果表明這種新的探針可以用在生物體系中的Zn~(2+)檢測。
[Abstract]:There are a variety of metals in nature, including alkali and alkaline earth metals, transition metals and heavy metals, which play an important role in organisms. And even cause disease. It is very important to design and synthesize a fluorescent probe which can be used for metal ion detection. In this paper, a series of novel small molecular fluorescent probes have been designed and synthesized for the identification and detection of Fe~(3 (Fe~(3). A Fe~(3 based on coumarin derivatives) fluorescence quenching small molecular fluorescence probe 7-diethylaminocoumarin -3-aldehyde. At pH = 7:00, The fluorescence of the probe solution itself is stronger. The effect of a series of metal ions, Pb~(2, Pb~(2, Pb~(2 and Pb~(2, on the probe is investigated. It is found that the probe is quenched only after it is combined with Fe~(3. A new method for the determination of Fe~(3 was established. The method has the advantages of good water solubility, high sensitivity and good selectivity. The detection limit is as low as 2.5 脳 10 ~ (-2) 渭 M. at the same time, the fluorescence probe can be used to detect Fe~(3 in the Ramos of biological cells. It is proved that it has potential application value in the field of chemical sensing and biological imaging. A new fluorescence probe of naphthalene Schiff base was synthesized by the reaction of D-glucosamine hydrochloride with 2-hydroxy-1-naphthalene formaldehyde. It has no fluorescence on its own, but it has a very strong fluorescence response to Al~(3. Moreover, in 15 kinds of ethanol solutions, such as Pb~(2, Al~(3, Al~(3, Al~(3), the fluorescence intensity at 427nm can be enhanced by 50 times with the addition of Al~(3. The fluorescence intensity at 427nm is increased by 50 times with the addition of the Al~(3, the fluorescence intensity is increased by 50 times at 427nm, and the fluorescence intensity at 427nm can be increased by 50 times with the addition of the Al~(3, and the fluorescence intensity is increased by 50 times in the 15 kinds of ethanol solutions, such as Pb~(2, Al~(3, and Zn~(2), and the fluorescence intensity at 427nm is enhanced by 50 times with the addition of Al~(3, and the fluorescence intensity is increased by 50 times at the excitation wavelength of 427nm, and the fluorescence intensity can be increased by 50 times at the excitation wavelength of 427nm. This is due to the chelation enhancement between Al~(3) and the probe. From the Job curve, we can know that the probe and Al~(3) are 1: 1 bound, and the association constant of the probe and Al~(3) is calculated to be 5.748 脳 103M-1.In the linear range of 0 ~ 25 渭 M, The detection limit of probe L2 for Al~(3 was calculated to be 2.83 脳 10-3 渭 M. in addition, it was found that the fluorescence of L-Alb3) complex could be quenched by adding F- in the same system, and other anions were investigated. There is no such phenomenon, including the Cl-OBr-Br-ti-tip-no _ 2- no _ 3- _ _ _. A novel coumarin-based fluorescence probe 4e-4-dihydroxy-4-methyl-2-oxo-2H-2-chromene-8-methylenehydrazide) thioamides L3 has been designed and synthesized in the field of sensing and biometric imaging. A colorimetric sensor used as a colorimetric sensor in water to detect Fe~(3, which exhibits a highly selective and sensitive recognition of Fe~(3 by changing its color from colorless to brown in the water environment. Probe L3 can also be used as a fluorescence probe in ethanol: water 8: 2 v / v) to show a significant fluorescence enhancement effect on Zn~(2) or selective recognition of Zn~(2) from other competitive metal ions such as Pb~(2. In addition, the presence of plasma in the presence of K and Sr~(2. In this study, cell imaging results suggest that the new probe can be used for Zn~(2 detection in biological systems.
【學位授予單位】：江蘇大學
【學位級別】：碩士
【學位授予年份】：2017
【分類號】：O657.3

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