本文選題：吲哚菁染料 + 非離子水溶性樹權PEG醚鏈　； 參考：《河南大學》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)率高和檢測靈敏度高等特點,現(xiàn)已被廣泛應用于熒光探針、蛋白質標示、DNA測序和細胞染色等方面。我們設計在吲哚“N”位引入非離子型水溶性樹杈PEG醚鏈,得到擁有產(chǎn)率更高、水溶性更好、光學性質更加優(yōu)良等特點的新型水溶性不對稱吲哚菁染料。 方法：吲哚菁染料一般通過三個步驟合成得到,首先：通過Fisher反應得到堿性雜環(huán)；其次：堿性雜環(huán)與烷基化試劑反應得到季銨鹽；最后：縮合劑與帶有活性甲基的季銨鹽反應得到目標產(chǎn)物�；撬峄诫�、對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稱吲哚五甲川菁染料Cy5-671和一種新型水溶性不對稱吲哚三甲川菁染料Cy3-567。由磺酸基苯肼和對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。利用紫外可見分光光度計和熒光分光光度計測定了產(chǎn)物的光學性質；吲哚菁染料經(jīng)過琥珀酰亞胺酯活化后與牛血清白蛋白或羊抗小鼠IGg進行了標示實驗；同時把Cy5-671和Cy5-668的性質進行了對比。 結果：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稱吲哚菁染料,其結構都經(jīng)'HNMR和MS確認。Cy5-671的最大吸收波長為657nm,消光系數(shù)為1.6×105／M-1cm-1,最大熒光發(fā)射波長671nm,熒光量子產(chǎn)率為0.24；Cy5-668的最大吸收波長為650nm,消光系數(shù)為1.4×105/M-1cm-1,最大熒光發(fā)射波長668nm,熒光量子產(chǎn)率為0.10；Cy3-567的最大吸收波長為559nm,消光系數(shù)為0.8×105/M-lcm-1,最大熒光發(fā)射波長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標記牛血清白蛋白的D/P值1.96,Cy5-668標記牛血清白蛋白的D/P值1.57,Cy3-567標記牛血清白蛋白的D/P值1.59。 結論：新型水溶性不對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權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和較高的熒光量子產(chǎn)率并且標示蛋白質能獲得比較好的有利于實際應用的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.
【學位授予單位】：河南大學
【學位級別】：碩士
【學位授予年份】：2014
【分類號】：R914.5

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