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

doi:10.6023/cjoc202210011

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (7): 2484-2491.DOI: 10.6023/cjoc202210011 Previous Articles Next Articles

Special Issue: 有机氟化学虚拟合辑

ARTICLES

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

赵小龙^a^,^*(), 郭亮武^a, 李宇晴^a, 冉启元^a, 吴会慧^a, 张祯^a, 苏瀛鹏^a, 周鹏鑫^a, 燕娜^b

^a西北师范大学化学化工学院教育部生态环境相关高分子重点实验室兰州 730070
^b兰州大学药学院兰州 730000

收稿日期:2022-10-14 修回日期:2023-03-10 发布日期:2023-03-23
通讯作者: 赵小龙
基金资助:
甘肃省高等学校产业支撑计划(2021CYZC-17); 甘肃省自然科学基金(21JR1RA227); 国家自然科学基金(21462039)

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

Xiaolong Zhao^a(), Liangwu Guo^a, Yuqing Li^a, Qiyuan Ran^a, Huihui Wu^a, Zhen Zhang^a, Yingpeng Su^a, Pengxin Zhou^a, Na Yan^b

^aLaboratory of Eco-Environment-Related Polymer Materials, Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070
^bSchool of Pharmacy, Lanzhou University, Lanzhou 730000

Received:2022-10-14 Revised:2023-03-10 Published:2023-03-23
Contact: Xiaolong Zhao
Supported by:
Gansu Province Industrial Support Program for Colleges(2021CYZC-17); Natural Science Foundation of Gansu Province(21JR1RA227); National Natural Science Foundation of China(21462039)

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Abstract

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

Cite this article

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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Fig. & Tab. 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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