大Stokes位移的近红外氟硼二吡咯(BODIPY)荧光探针应用于生物体中Na2S2O4的检测

doi:10.6023/cjoc202210011

摘要/Abstract

基于氟硼二吡咯(BODIPY)的骨架结构, 设计合成了两种近红外荧光探针Azo-BDP1和Azo-BDP2, 其Stokes位移分别为217和224 nm. 作为Na₂S₂O₄的两个可视化探针, Azo-BDP1和Azo-BDP2具有高灵敏度和高选择性. 机理研究方面, 采用质谱分析证实了识别机制. 除此之外, 探索了Azo-BDP1在生物体中Na₂S₂O₄的荧光成像.

关键词: 氟硼二吡咯(BODIPY), 大斯托克斯位移, 可视化, 近红外

Based on the main skeleton of fluoroboron dipyrrole (BODIPY), two near-infrared fluorescent probes Azo-BDP1 and Azo-BDP2 were rationally designed and synthesized with large Stokes shift of 217 and 224 nm, respectively. As two visualized probes for Na₂S₂O₄, Azo-BDP1 and Azo-BDP2 exhibited high sensitivity and selectivity. The reaction-based recognition mechanism was confirmed by mass spectral analysis, in addition, fluorescence imaging studies in zebrafish embryos and zebrafish proved that the probe Azo-BDP1 is suitable for the detection of Na₂S₂O₄ in vivo.

Key words: fluoroboron dipyrrole (BODIPY), large Stokes shift, visualization, near-infrared

引用此文

赵小龙, 郭亮武, 李宇晴, 冉启元, 吴会慧, 张祯, 苏瀛鹏, 周鹏鑫, 燕娜. 大Stokes位移的近红外氟硼二吡咯(BODIPY)荧光探针应用于生物体中Na₂S₂O₄的检测[J]. 有机化学, 2023, 43(7): 2484-2491.

Xiaolong Zhao, Liangwu Guo, Yuqing Li, Qiyuan Ran, Huihui Wu, Zhen Zhang, Yingpeng Su, Pengxin Zhou, Na Yan. Near-Infrared Visualization Fluoroboron Dipyrrole (BODIPY) Fluore-scent Probe with Large Stokes Shift for Detecting Na₂S₂O₄ in vivo[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2484-2491.

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图/表 6

Scheme 1. Synthesis route of Azo-BDP1 and Azo-BDP2

Figure 1. (a) Fluorescence emission spectra of 10 μmol/L Azo-BDP1 upon additional different concentrations of Na2S2O4 (0~130 μmol/L) in dimethyl sulfoxide (DMSO) solution (inset: color change of Azo-BDP1 in the absence (left) or presence (right) of 100 μmol/L Na2S2O4 under irradiation at 365 nm); (b) UV-vis absorption of Azo-BDP1 upon additional different concentrations of Na2S2O4 (0~130 μmol/L) in DMSO solution (inset: images of Azo-BDP1 in the absence (left) or presence (right) of 100 μmol/L Na2S2O4 under naked eye colorimetric changes); (c) Fluorescence emission spectra of 10 μmol/L Azo-BDP1 upon additional different concentrations of Na2S2O4 (0~130 μmol/L) in DMSO solution (inset: color change of Azo-BDP2 in the absence (left) or presence (right) of 100 μmol/L Na2S2O4 under irradiation at 365 nm); (d) UV-vis absorption of Azo-BDP2 upon additional different concentrations of Na2S2O4 (0~130 μmol/L) in DMSO solution (inset: images of Azo-BDP2 in the absence (left) or presence (right) of 100 μmol/L Na2S2O4 under naked eye colorimetric changes) Error bars represent standard deviations (n=3), λex=468 nm

Figure 2. Time-dependent fluorescence spectra (a) and fluorescence intensity at 685 nm (b) of 10 μmol/L Azo-BDP1 treated with 100 μmol/L Na2S2O4 in DMSO solution; Time-dependent fluorescence spectra (c) and fluorescence intensity at 692 nm (d) of 10 μmol/L Azo-BDP2 treated with 100 μmol/L Na2S2O4 in DMSO solution λex=468 nm. Error bars represent standard deviations (n=3)

Figure 3. Fluorescence spectra (a) and fluorescence intensity (F－F0) at 685 nm (b) of 10 μmol/L Azo-BDPP1 treated with various species (inset: under irradiation at 365 nm of the probe Azo-BDP1 with different compound); Fluorescence spectra (c) and fluorescence intensity (F－F0) at 692 nm (d) of 10 μmol/L Azo-BDP2 treated with various species (inset: under irradiation at 365 nm color change of the probe Azo-BDP2 with different compound Na2S2O4, NaCl, FeCl2, NaNO2, NaBr, CaCl2, CuCl2, KI, Na2S2O3, Na2SO3, FeCl3, Vc, Na2S, Na2SO4, Hcy, Cys, GSH, LT, L-Ser. λex=468 nm

Figure 4. Images of live zebrafish embryos (a) Fluorescent images of live zebrafish incubated with Azo-BDP1 (10.0 μmol/L) for 10 min, (b) bright field, (c) merged images; (d) fluorescence image of living cells pretreated with Azo-BDP1 (10.0 μmol/L) for 10 min and further incubated with Na2S2O4 (100 μmol/L) for 10 min, (e) bright field, (f) merged images, λex=525 nm

Figure 5. Images of live zebrafish (a) Fluorescent images of live zebrafish incubated with Azo-BDP1 (10.0 μmol/L) for 10 min, (b) bright field, (c) merged images; (d) fuorescence image of living cells pretreated with Azo-BDP1 (10.0 μmol/L) for 10 min and further incubated with Na2S2O4 (100 μmol/L) for 10 min, (e) bright field, (f) merged images, λex=525 nm

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大Stokes位移的近红外氟硼二吡咯(BODIPY)荧光探针应用于生物体中Na₂S₂O₄的检测

Near-Infrared Visualization Fluoroboron Dipyrrole (BODIPY) Fluore-scent Probe with Large Stokes Shift for Detecting Na₂S₂O₄ in vivo

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