应用化学

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新型水溶性不对称五甲川吲哚菁染料的合成、荧光性能及荧光标记

汤昆1,邱娜1,吴品3,贾春辉1,2,王升2,张付利1*   

  1. (1.河南大学医学院环境医学研究所 开封 475004;2.河南大学药学院 开封 475004;
    3河南晋开化工投资控股集团有限责任公司二分公司 开封 475100)
  • 收稿日期:2013-12-26 修回日期:2014-03-18 出版日期:2014-10-09 发布日期:2014-10-09
  • 通讯作者: 张付利,教授; Tel/Fax:0371-23880585; E-mail:hdzfl508@163.com; 研究方向:有机合成
  • 基金资助:
    国家自然科学基金(21202036)资助项目

Novel Water-soluble Asymmetric Pentamethine Cyanine Dyes:Synthesis, Fluorescent Properties and Fluorescent Labeling

JIA Chunhui1,2, QIU Na1, WU Pin3, WANG Sheng2, TANG Kun1, ZHANG Fuli1*   

  1. (1.Research Institute of Environmental Medicine,Medical College of Henan University,Kaifeng 475004,China;
    2.Pharmaceutical College of Henan University,Kaifeng 475004,China;
    3.Second Branch of Henan Jinkai Investment Holding Group,Kaifeng 475100,China)
  • Received:2013-12-26 Revised:2014-03-18 Published:2014-10-09 Online:2014-10-09

摘要: 合成了枝状聚乙二醇醚链取代的新型不对称五甲川吲哚菁荧光染料,利用1H NMR、HRMS等技术手段表征了化合物的结构,并测定了染料的荧光性能、光稳定性,标示了牛血清白蛋白。 结果表明,该染料的最大吸收波长为657 nm,最大荧光发射波长为671 nm,荧光量子产率为0.24,经过8 h的光照反应,染料有4.4%产生光降解,溶于水,n(染料)∶n(牛血清白蛋白)=2∶1时,标记蛋白质的染料/蛋白质(D/P)值达1.57。

关键词: 吲哚菁染料, 五甲川, 荧光标记, 枝状化合物, 牛血清白蛋白, 荧光量子产率

Abstract: Novel asymmetric pentamethine cyanine(Cy5) dye with a branched ether chain(polyethylene glycol) was synthesized.The structure of the product was identified by 1H NMR and HRMS. The fluorescence properties and light stability of this Cy5 were investigated. Then albumin bovine serum(BSA) was labeled with this Cy5. The maximum absorption and emission wavelengths of the dye in water were 657 nm and 671 nm. The fluorescence quantum yield(Ф) was 0.24 in water. After irradiated for 8 h, the 4.4% of the aqueous soluble dye was photodegradated. The dye-to-protein(D/P) value of fluorescent labeling reached 1.57 when the molar ratio of dye and BSA was 2∶1.

Key words: indocyanine dyes, pentamethine, fluorescent labeling, branched compounds, albumin bovine serum, fluorescence quantum yield

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