本文選題：吲哚菁染料 + 非離子水溶性樹(shù)權(quán)PEG醚鏈�。� 參考：《河南大學(xué)》2014年碩士論文

【摘要】：目的：吲哚菁染料具有光譜范圍廣(550nm-1200nm)、熒光量子產(chǎn)率高和檢測(cè)靈敏度高等特點(diǎn),現(xiàn)已被廣泛應(yīng)用于熒光探針、蛋白質(zhì)標(biāo)示、DNA測(cè)序和細(xì)胞染色等方面。我們?cè)O(shè)計(jì)在吲哚“N”位引入非離子型水溶性樹(shù)杈PEG醚鏈,得到擁有產(chǎn)率更高、水溶性更好、光學(xué)性質(zhì)更加優(yōu)良等特點(diǎn)的新型水溶性不對(duì)稱吲哚菁染料。 方法：吲哚菁染料一般通過(guò)三個(gè)步驟合成得到,首先：通過(guò)Fisher反應(yīng)得到堿性雜環(huán)；其次：堿性雜環(huán)與烷基化試劑反應(yīng)得到季銨鹽；最后：縮合劑與帶有活性甲基的季銨鹽反應(yīng)得到目標(biāo)產(chǎn)物�；撬峄诫隆�(duì)甲苯磺酰氯和聚三乙二醇等為原料合成得到一種新型水溶性不對(duì)稱吲哚五甲川菁染料Cy5-671和一種新型水溶性不對(duì)稱吲哚三甲川菁染料Cy3-567。由磺酸基苯肼和對(duì)溴甲基苯甲酸等為原料合成得到一種吲哚五甲川菁染料Cy5-668。利用紫外可見(jiàn)分光光度計(jì)和熒光分光光度計(jì)測(cè)定了產(chǎn)物的光學(xué)性質(zhì)；吲哚菁染料經(jīng)過(guò)琥珀酰亞胺酯活化后與牛血清白蛋白或羊抗小鼠IGg進(jìn)行了標(biāo)示實(shí)驗(yàn)；同時(shí)把Cy5-671和Cy5-668的性質(zhì)進(jìn)行了對(duì)比。 結(jié)果：我們總共合成十余種中間產(chǎn)物,最終得到了三種水溶性不對(duì)稱吲哚菁染料,其結(jié)構(gòu)都經(jīng)'HNMR和MS確認(rèn)。Cy5-671的最大吸收波長(zhǎng)為657nm,消光系數(shù)為1.6×105／M-1cm-1,最大熒光發(fā)射波長(zhǎng)671nm,熒光量子產(chǎn)率為0.24；Cy5-668的最大吸收波長(zhǎng)為650nm,消光系數(shù)為1.4×105/M-1cm-1,最大熒光發(fā)射波長(zhǎng)668nm,熒光量子產(chǎn)率為0.10；Cy3-567的最大吸收波長(zhǎng)為559nm,消光系數(shù)為0.8×105/M-lcm-1,最大熒光發(fā)射波長(zhǎng)567nm,熒光量子產(chǎn)率為0.06；Cy5-671在水中的光穩(wěn)定明顯高于Cy5-668；Cy5-671標(biāo)記牛血清白蛋白的D/P值1.96,Cy5-668標(biāo)記牛血清白蛋白的D/P值1.57,Cy3-567標(biāo)記牛血清白蛋白的D/P值1.59。 結(jié)論：新型水溶性不對(duì)稱吲哚五甲川吲哚菁染料Cy5-671在吲哚“N”位引入非離子型水溶性樹(shù)權(quán)PEG醚鏈,與Cy5-668相比較,Cy5-671擁有較好的水溶性,并且容易分離提純,產(chǎn)率也較高；擁有較好的光譜性質(zhì)和較高的熒光量子產(chǎn)率并且標(biāo)示蛋白質(zhì)能獲得比較好的有利于實(shí)際應(yīng)用的D/P值。
[Abstract]:Objective: indocyanine dyes have been widely used in fluorescent probes, protein-labeled DNA sequencing and cell staining for their high fluorescence quantum yield and high detection sensitivity, with a wide spectrum range of 550 nm ~ 1 200 nm.We designed a new water-soluble asymmetric indocyanine dye with higher yield, better water solubility and better optical properties by introducing non-ionic water soluble branch PEG ether chain into indole "N" site.Methods: indocyanine dyes were synthesized in three steps: first, basic heterocycles were obtained by Fisher reaction, secondly, quaternary ammonium salts were obtained by the reaction of basic heterocycles with alkylation reagents.Finally, the reagents reacted with quaternary ammonium salts with active methyl to obtain the target product.A new water-soluble asymmetric indolepentacyanine dye Cy5-671 and a new water-soluble asymmetric indoletrimethylcyanine dye Cy3-567 were synthesized from sulfonated phenylhydrazine, p-toluenesulfonyl chloride and polyethylene glycol.An indole-pentamethylcyanine dye Cy5-668 was synthesized from sulfonated phenylhydrazine and p-bromomethyl benzoic acid.The optical properties of the product were determined by UV-Vis spectrophotometer and fluorescence spectrophotometer, and the indocyanine dyes were labeled with bovine serum albumin (BSA) or sheep anti-mouse IGg after the activation of succinimide.At the same time, the properties of Cy5-671 and Cy5-668 are compared.Results: we synthesized more than ten intermediate products and finally got three water-soluble asymmetric indocyanine dyes.The D / P value of bovine serum albumin labeled with D- P value of 1.57 Cy3-567 was 1.59.Conclusion: the new water-soluble asymmetric indole-pentacanine indoline cyanine dye (Cy5-671) was introduced into the indole-" N "site with a non-ionic water-soluble tree weight PEG ether chain. Compared with Cy5-668, Cy5-671 has better water solubility, easy separation and purification, and higher yield.It has better spectral properties, higher fluorescence quantum yield and better D / P value for practical application.
【學(xué)位授予單位】：河南大學(xué)
【學(xué)位級(jí)別】：碩士
【學(xué)位授予年份】：2014
【分類(lèi)號(hào)】：R914.5

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