高等学校化学学报 ›› 2009, Vol. 30 ›› Issue (11): 2146.

• 研究论文 • 上一篇    下一篇

荧光探针5-羰基咪唑苯并吖啶酮的合成及其LC-APCI-MS法测定胺

付艳艳2, 孙志伟1,3, 赵怀鑫2, 白新伟2, 索有瑞1, 李玉林1, 尤进茂1,2   

  1. 1. 中国科学院西北高原生物研究所, 西宁 810001;
    2. 曲阜师范大学化学与化工学院, 生命有机分析重点实验室, 曲阜 273165;
    3. 中国科学院研究生院, 北京 100049
  • 收稿日期:2009-06-24 出版日期:2009-11-10 发布日期:2009-11-10
  • 通讯作者: 尤进茂, 男, 博士, 教授, 主要从事新型荧光材料的开发及在分析中的应用研究. E-mail: jmyou6304@163.com
  • 基金资助:

    国家自然科学基金(批准号: 20075016)和中国科学院“百人计划”项目(批准号: 328)资助.

Syntheses of Fluorescence Probe 5-[2-(1H-imidazol-1-yl)-2-oxoethyl]benzo[b]acridin-12(5H)-one and Its Application for the Determination of Aliphatic Amines with LC-APCI-MS

FU Yan-Yan2 , SUN Zhi-Wei1,3, ZHAO Huai-Xin2, BAI Xin-Wei2 , SUO You-Rui1 , LI Yu-Lin1, YOU Jin-Mao1,2*   

  1. 1. Northwest Plateau Institute of Biology, Chinese Academy of Sciences, Xining 810001, China;
    2. Key Laboratory of Life-Organic Analysis, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, China;
    3. Graduate School of the Chinese Academy of Sciences, Beijing 100049, China
  • Received:2009-06-24 Online:2009-11-10 Published:2009-11-10
  • Contact: YOU Jin-Mao. E-mail: jmyou6304@163.com
  • Supported by:

    国家自然科学基金(批准号: 20075016)和中国科学院“百人计划”项目(批准号: 328)资助.

摘要:

在不加任何催化剂条件下, 2-(12-苯并吖啶酮)-乙酸(BAAA)与N,N′-羰基双咪唑(CDI)缩合生成新型荧光探针5-羰基咪唑苯并吖啶酮(IEBA). IEBA在DMF溶剂中与胺类化合物形成的酰胺类衍生物不仅可发出强烈的荧光, 还具有较高的质谱离子化能力. 该衍生物在乙腈和甲醇-水溶液中的百分离子化δ值分别在0~57.32% 和0~62.14%范围内. 最大激发和发射波长λex/λem=272 nm/505 nm. 12种胺类衍生物的荧光检出限范围为0.15~0.50 ng/mL, 在线APCI-MS检出限范围为1.43~8.51 ng/mL.

关键词: 液相色谱-离子阱质谱; 百分离子化; 2-(苯并吖啶酮)-乙酸; 5-羰基咪唑苯并吖啶酮

Abstract:

2-{12-Oxobenzo[b]acridin-5(12H)-yl}-acetic acid(BAAA) reacted with coupling agent N,N′-carbonyldiimidazole(CDI) to form an activated amide intermediate 5-[2-(1H-imidazol-1-yl)-2-oxoethyl]benzo[b]acridin-12(5H)-one(IEBA), which was a novel fluorescence probe. The amide intermediate(IEBA) reacted preferably with amines in DMF solvent in the absence of catalysts to give the high yields of derivatives, which not only have high fluorescence sensitivity but also have strong ionizable ability. The optimum excitation and emission wavelengths were at λex/λem=272 nm/505 nm. The percent ionization δ values in aqueous acetonitrile and aqueous methanol were in the range of 0—57.32% and 0—62.14%, respectively. The fluorescence detection limits of twelve amine derivatives(at a signal-to-noise ratio of 3) were in the range of 0.15—0.50 ng/mL. The online APCI-MS detection limits were at levels of 1.43—8.51 ng/mL(S/N=3).

Key words: High performance liquid chromatography/ion-trap mass spectrometry; Percent ionization; 2-{12-Oxobenzo[b]acridin-5(12H)-yl}-acetic acid; 5-[2-(1H-imidazol-1-yl)-2-oxoethyl]benzo[b]acridin-12(5H)-one

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