本文選題：熒光素　切入點(diǎn)：熒光探針　出處：《蘭州大學(xué)》2017年博士論文

【摘要】：熒光素作為一種染料,在水中具有較高的量子產(chǎn)率、高的消光系數(shù)以及在可見光區(qū)的激發(fā)和發(fā)射波長等優(yōu)點(diǎn),在熒光探針領(lǐng)域中備受科學(xué)家們的親睞。本論文選用熒光素骨架作為熒光團(tuán),利用有機(jī)合成化學(xué)方法,設(shè)計(jì)合成一系列熒光素衍生物,并對其性質(zhì)做了詳細(xì)研究。本文中完成的主要工作如下:(1)利用甘氨酸、苯丙氨酸以及天冬酰胺修飾熒光素設(shè)計(jì)出一系列熒光探針類L~1、L~2、L~3。該類探針基于熒光“on-off-on”接力策略在100%HEPES(p H=7.0)水溶液中識(shí)別Cu~(2+)和硫醇氨基酸分子。實(shí)驗(yàn)結(jié)果表明,探針與Cu~(2+)之間結(jié)合引起體系中探針熒光猝滅,接著加入硫醇氨基酸置換出探針分子,體系熒光恢復(fù)。且被成功應(yīng)用在IMPLICATION邏輯門模擬和細(xì)胞成像中。(2)我們在探針結(jié)構(gòu)設(shè)計(jì)中集成了熒光素和香豆素結(jié)構(gòu),提出一種雙模式熒光探針L~4和L~5,從生物硫醇中選擇性識(shí)別半胱氨酸,這種熒光探針能在5分鐘內(nèi)與半胱氨酸完成相互作用,在450 nm激發(fā)下發(fā)生熒光打開模式,有趣的是在短波長332 nm下,該探針對半胱氨酸表現(xiàn)出比率型熒光模式。所有實(shí)驗(yàn)結(jié)果表明在其他氨基酸、陰離子、陽離子存在的條件下,探針對半胱氨酸具有專一選擇性,檢測限達(dá)0.084μM,遠(yuǎn)低于細(xì)胞間半胱氨酸濃度,并且在Hep G2細(xì)胞中選擇性檢測了半胱氨酸,目前尚無此類熒光素衍生物識(shí)別半胱氨酸的報(bào)道。(3)利用熒光素單雙醛分子與異煙酰肼反應(yīng),制備出異煙酰腙類熒光探針L~6和L~7,分別在純乙醇和HEPES(p H=7.0)緩沖溶液中對苦味酸進(jìn)行紫外光譜和熒光光譜響應(yīng),實(shí)驗(yàn)結(jié)果表明了苦味酸(TNP)的強(qiáng)吸電子能力誘導(dǎo)探針中電子云發(fā)生轉(zhuǎn)移,導(dǎo)致熒光猝滅。最后,我們將探針吸附在試紙上,成功對不同濃度的TNP溶液進(jìn)行了定量檢測。
[Abstract]:As a kind of dye, fluorescein has the advantages of high quantum yield, high extinction coefficient, excitation and emission wavelength in visible region, etc. In this paper, a series of fluorescein derivatives were designed and synthesized by organic synthetic chemistry. The main work done in this paper is as follows: 1) using glycine. Phenylalanine and asparagine modified fluorescein have designed a series of fluorescent probes, such as L _ (1) and L _ (2) O _ (2) L _ (3), which recognize Cu~(2) and mercaptan amino acid molecules in aqueous solution of 100%HEPES(p H _ (7. 0) based on fluorescent "on-off-on" relay strategy. The fluorescence quenching of the probe was induced by the binding between the probe and Cu~(2, and the thiol amino acid was added to replace the probe molecule. We have integrated the fluorescein and coumarin structures in the probe structure design, and have been successfully used in IMPLICATION logic gate simulation and cell imaging. A double mode fluorescence probe, Ln4 and L5, was proposed to selectively recognize cysteine from biological mercaptan. The fluorescence probe could interact with cysteine in 5 minutes and produce fluorescence open mode at 450 nm excitation. Interestingly, the probe exhibited a ratio fluorescence pattern to cysteine at a short wavelength of 332 nm. All the experimental results showed that the probe was specific to cysteine in the presence of other amino acids, anions and cations. The detection limit was 0.084 渭 m, which was much lower than the concentration of cysteine between cells. Cysteine was selectively detected in Hep G2 cells. There was no report of the recognition of cysteine by this kind of fluorescein derivative. Isoniacyl Hydrazone fluorescent probes Ln6 and L7 were prepared, and the UV and fluorescence spectra of picric acid in pure ethanol and HEPES(p H7. 0 buffer solution were investigated. The experimental results show that the strong electron absorption ability of picrate can induce electron cloud transfer in the probe, which leads to fluorescence quenching. Finally, the probe is adsorbed on the test paper and the different concentrations of TNP solution are detected quantitatively.
【學(xué)位授予單位】：蘭州大學(xué)
【學(xué)位級(jí)別】：博士
【學(xué)位授予年份】：2017
【分類號(hào)】：O657.3

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本文編號(hào)：1655885