本文關(guān)鍵詞： 熒光探針 Rhodol熒光團 次氯酸 硫化氫 生物成像　出處：《西北大學》2017年碩士論文　論文類型：學位論文

【摘要】：近年來熒光成像技術(shù)因其時間和空間分辨率好,操作安全、簡便?經(jīng)發(fā)展成為監(jiān)測各種生理過程中生物分子變化最重要的手段之一,而選擇光譜性能優(yōu)良的熒光分子對成像分析至關(guān)重要。本文從熒光分子結(jié)構(gòu)改進入手,首次設(shè)計并合成了一種新型的Rhodol類熒光染料ROA,并以此為熒光團設(shè)計合成了三種不同類型的熒光探針。研究內(nèi)容如下:(1)以ROA為熒光骨架,設(shè)計合成了一種高選擇性次氯酸根熒光探針RO610。該探針分子由于碳氮雙鍵的異構(gòu)化作用熒光被猝滅,而與次氯酸反應之后,碳氮雙鍵被氧化、水解為甲酰基,異構(gòu)化作用消失,分子熒光顯著增強。利用這種熒光信號的變化,我們已將RO610成功應用于活細胞及小鼠體內(nèi)外源性次氯酸根的檢測。(2)首次用肼基修飾ROA上的甲酰基,合成了一種同時具有C=N雙鍵和聯(lián)氨基的氧雜蒽類次氯酸根熒光探針R0585。此探針實現(xiàn)了緩沖溶液測試體系中次氯酸的實時檢測,且不受其它活性氧類物質(zhì)的干擾。對其檢測機理進行研究發(fā)現(xiàn)次氯酸首先作用于此分子的聯(lián)氨基團,將其氧化為重氮基后經(jīng)過分子內(nèi)質(zhì)子轉(zhuǎn)移形成一種穩(wěn)定的結(jié)構(gòu)RON,并已經(jīng)通過核磁滴定與質(zhì)譜分析驗證了此機理。這一設(shè)計策略也為次氯酸熒光探針的設(shè)計提供了一種新思路。(3)以化合物ROA為母體,設(shè)計、合成了一種H2S熒光探針R0587。我們將Cu2+與RO587絡(luò)合得到RO587-Cu2+,因Cu2+的順磁性效應,R0587的熒光信號被猝滅。因為Cu2+與S2-之間具有更強的親和作用,所以我們利用S2-將配合物的Cu2+奪出,使得RO587熒光得到恢復,從而實現(xiàn)對S2-的檢測。此方法具有反應迅速,靈敏度高等優(yōu)點并能選擇性地檢測硫化氫而不受其他陰離子及含巰基的生物小分子的影響,為專一性檢測硫化氫提供了一種新的思路和方法。
[Abstract]:In recent years, fluorescence imaging technology because of its time and space resolution, safe operation, convenient? Become changes in various physiological processes in molecular biological monitoring is one of the most important means and the choice of fluorescent molecular spectra with excellent performance is of vital importance to image analysis. This paper starts from the fluorescence molecular structure is improved, and a new design for the first time in Rhodol type of fluorescent dye ROA was synthesized, and then three different types of fluorescent probes were synthesized fluorophore design. The contents are as follows: (1) using the ROA fluorescent skeleton, a highly selective fluorescent probe for hypochlorite RO610. the probe molecule due to isomerization of carbon and nitrogen double bonds were designed and synthesized. The fluorescence quenching, and with hypochlorous acid after the reaction, the carbon nitrogen double oxidation, hydrolysis of formyl, isomerization disappeared, molecular fluorescence was significantly enhanced. The change of the fluorescence signal, we have RO6 Detection of 10 successful application in living cells and in mice with exogenous hypochlorite. (2) for the first time with hydrazide modified ROA formyl, and has a C=N double bond and amino xanthene fluorescent hypochlorite probe R0585. the probe was synthesized to achieve the real-time detection of buffer solution test system in hypochlorous acid, and is not interfered by other reactive oxygen species. The study found that hypochlorite in the role of the first combination of this molecular amino group on the detection mechanism of the oxidation of diazo after intramolecular proton transfer to form a stable structure of RON, and has been through the analysis of NMR titration and mass spectrometry to verify the mechanism. This design strategy also provides a new idea for the design of hypochlorous acid fluorescent probe. (3) design to compound ROA as the matrix, a H2S fluorescent probe R0587. was synthesized by complexation with RO587 Cu2+ we will get RO587-Cu2+ for Paramagnetic effects of Cu2+, R0587 fluorescence was quenched. Because the affinity has a stronger effect between Cu2+ and S2-, so we will use S2- complexes of Cu2+ took out, makes the RO587 fluorescence recovery, so as to realize the detection of S2-. This method has the advantages of rapid response, high sensitivity and selective detection of hydrogen sulfide not affected by other anions and sulfhydryl molecules, provides a new idea and method for the specific detection of hydrogen sulfide.

【學位授予單位】：西北大學
【學位級別】：碩士
【學位授予年份】：2017
【分類號】：O657.3

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本文編號：1502408