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Facile synthesis of green-light and large Stokes-shift emitting coumarins for bioconjugation
Dyes and Pigments ( IF 4.5 ) Pub Date : 2018-01-11 , DOI: 10.1016/j.dyepig.2018.01.016
Jiayuan Li , Changyu Zhang , Shuai Wu , Xin Wen , Zhen Xi , Long Yi

Bright and hydrosoluble fluorescent dyes with large Stokes shifts are widely used as molecular probes and light-emitting markers in chemistry and biology. In this report, one-step synthesis of a bright green-emitting coumarin (Φ = 0.52, λem = 505 nm) was achieved from available reagents under neat conditions. The novel dye 1 showed very large Stokes shift (Δλ = 138 nm) due to strong intramolecular charge transfer (ICT) effect, which was confirmed by density functional theory (DFT) calculations. Dye 1 was hydrosoluble and displayed strong emission at a wide range of pH from 3 to 8. Importantly, the secondary amine in 1 made it extremely convenient for futher bioconjugation. Representative derivatives were showcased for various successful applications of fluorogenic enzyme assay, biolabelling and mitochondrial staining.



中文翻译:

易于合成绿光和大斯托克斯位移发射香豆素以进行生物缀合

具有大斯托克斯位移的明亮的水溶性荧光染料被广泛用作化学和生物学中的分子探针和发光标记。在这份报告中,明亮的绿色发光香豆素(一步法合成Φ  = 0.52,λ EM  = 505纳米)从纯的条件下可得的试剂来实现的。该新型染料1显示出非常大的斯托克斯频移(Δ λ  = 138纳米),由于强的分子内电荷转移(ICT)效应,其通过密度泛函理论(DFT)计算证实。染料1为水溶性,在宽范围的pH值至8中显示重要的强发射从图3中,仲胺1使进一步的生物共轭极为方便。展示了代表性的衍生物,用于荧光酶测定,生物标记和线粒体染色的各种成功应用。

更新日期:2018-01-11
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