Highly selective colorimetric and fluorescent BODIPY dyes for sensing of cysteine and/or homocysteine
Highly selective colorimetric and fluorescent BODIPY dyes for sensing of cysteine and/or homocysteine
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用于检测半胱氨酸和/或同型半胱氨酸的高选择性比色和荧光 BODIPY 染料
DOI：
10.1039/c5nj02346g
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发表时间：
2016
影响因子：
3.3
通讯作者：
Jiao Lijuan
中科院分区：
文献类型：
--
作者：
Wu Qinghua;Zhou Jinyuan;Wu Yangchun;Yu Changjiang;Hao Erhong;Jiao Lijuan
利用可见光可激发的BODIPY的“关闭”或“打开”荧光，在甲醇-HEPES缓冲液中选择性地荧光和比色“裸眼”感测半胱氨酸（Cys）和/或同型半胱氨酸（Hcy），（45 mM，pH = 7.2，v/v = 1/1）溶液中的各种常见氨基酸和相关的硫醇-基于α-和β-甲酰基BODIPY 1和3上的甲酰基与Cys/Hcy的反应，获得了含有化合物的化合物。β-FormylBODIPY 1对Cys和Hcy的选择性响应优于其他分析物，由于荧光强度的急剧淬灭，颜色从绿色明显变为浅棕色。相比之下，α-甲酰基BODIPY 3给出Cys和Hcy之间的“肉眼”区分，具有从浅橙子到黄绿色的显著颜色变化，因为加入Cys后绿色荧光强度显著增加。通过NMR、HRMS和DFT计算研究了BODIPYs 1和3对半胱氨酸和/或同型半胱氨酸的敏感机理。α-FormylBODIPY 3已应用于活细胞中Cys的生物成像。
By taking advantage of “turn off” or “turn on” fluorescence of visible light excitable BODIPYs, a selective fluorescent and colorimetric “naked eye” sensing of cysteine (Cys) and/or homocysteine (Hcy) in methanol-HEPES buffer (45 mM, pH = 7.2, v/v = 1/1) solution over various common amino acids and related thiol-containing compounds has been achieved based on the reaction of the formyl groups on α- and β-formyl BODIPYs 1 and 3 with Cys/Hcy. β-FormylBODIPY 1 showed a selective response for both Cys and Hcy over the other analytes, with an apparent color change from green to light brown due to a dramatic quenching of the fluorescence intensity. In contrast, α-formylBODIPY 3 gave “naked eye” discrimination between Cys and Hcy, with a dramatic color change from light orange to yellowish green because of a significant increase of the green fluorescence intensity with the addition of Cys. The possible mechanism for sensing of Cys and/or Hcy by BODIPYs 1 and 3 was studied by NMR, HRMS and DFT calculations. α-FormylBODIPY 3 has been applied to the biological imaging of Cys in living cells.