Rational molecular design of a reversible BODIPY-Based fluorescent probe for real-time imaging of GSH dynamics in living cells

Zhang, Yushi; Zhang, Junqing; Su, Meihui; Li, Changhua

doi:10.1016/j.bios.2020.112866

Cited by 33 publications

(13 citation statements)

References 60 publications

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“…另外, 使用 BODIPY α 位醛基做 Knoevenagel 反应的例子也很少见. 李昌华课题组 [55] 利用该方法合成出来了一个可以实时监测活细胞 [56] . Dehaen 等 [57]…”

Section: α 位酰化的 Bodipy 的反应unclassified

Progress in the Synthesis of Boron Dipyrromethene (BODIPY) Fluorescent Dyes

Liu¹,

Teng²,

Niu³

et al. 2022

Chinese Journal of Organic Chemistry

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Boron dipyrromethene (BODIPY) dyes are widely used in the fields of life sciences, chemical analysis and optoelectronic materials due to its excellent photophysical properties, favorable biocompatibility, facile synthesis and modification etc. The synthesis and derivative strategies of BODIPY provide the basis for its wide application and have attracted great attention from researchers. In this review, the modification strategies for different reaction positions of BODIPY have been discussed, and Pd-catalyzed cross-coupling reactions and oxidative coupling reactions about BODIPY are discussed individually. Finallly, the development of this field is prospected. Keywords boron dipyrromethene (BODIPY); fluorescent dyes; synthesis; functional modification 有机荧光染料在电致发光、荧光探针、生物成像、防伪等领域有着广泛的应用. 常见的有机荧光染料包括氟硼二吡咯(BODIPY) [1][2] 、荧光素 [3][4] 、香豆素 [5] 、罗丹明 [6] 、菁染料 [7] 、酰亚胺类 [8][9][10] 和硝基苯并恶二唑(NBD) 类 [11] 等. 其中, BODIPY 类有机荧光染料具有优异的光物理性质, 如摩尔消光系数大、荧光量子产率高、吸收和发射半峰宽窄、光物理性能受外界环境(比如溶剂、 pH 等)影响小等. 更重要的是, BODIPY 具有良好的生物

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Section: α 位酰化的 Bodipy 的反应unclassified

Progress in the Synthesis of Boron Dipyrromethene (BODIPY) Fluorescent Dyes

Liu¹,

Teng²,

Niu³

et al. 2022

Chinese Journal of Organic Chemistry

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“…Fluorescence imaging, which takes advantage of the visible or near-infrared (NIR) signal of a fluorescent probe to visualize a specific biological target, has played an important role in preclinical diagnosis, clinical monitoring, and treatment [13][14][15][16][17][18][19]. Compared with traditional imaging modalities such as X-ray computed tomography (CT), nuclear magnetic resonance imaging (NMRI), and positron emission tomography (PET), NIR fluorescence imaging has demonstrated advantages, such as high spatiotemporal resolution, real-time visualization, noninvasiveness, and a low cost [20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

“…AALI induced by alcohol to cause liver inflammation results in an imbalance of ROS and antioxidants in the liver, such as GSH-PX and GSH. Therefore, it is closely related to the concentration of GSH [16,[46][47][48][49]. When AALI is improved by an antioxidant drug, the GSH level is enhanced accordingly [8,12,[49][50][51].…”

Section: Introductionmentioning

confidence: 99%

Dynamic evaluation of the protective effect of Dendrobium officinale polysaccharide on acute alcoholic liver injury mice in vitro and in vivo by NIR fluorescence imaging

Nie

Zhou

et al. 2021

Anal Bioanal Chem

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Acute alcoholic liver injury (AALI) is a threat to human health. Dendrobium officinale polysaccharide (DOP) has the potential to protect the liver by enhancing the anti-oxidative system to maintain the relative balance of ROS (active oxygen species) and antioxidants in AALI mice. However, the dynamic improvement effect of DOP on AALI is still not clear and accurate medication guidance is not available, which limits the clinical application of DOP. Because of the advantages of high sensitivity, noninvasiveness, and visualization, near-infrared (NIR) fluorescence imaging has been widely studied in biochemistry and biomedicine. As the glutathione (GSH) level in the liver is closely related to the progression of AALI, herein, an NIR fluorescent probe for GSH, HCG was used to dynamically evaluate the effect of DOP on AALI mice. In this study, DOP was proven to maintain the relative balance of GSH content in the liver to protect it from damage. To the best of our knowledge, it is the first time to assess the effect of DOP on AALI mice through a NIR fluorescence imaging technique. This study may also provide a potential NIR imaging agent for the clinical research to improve the management of liver injury-related diseases.

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“…Using fluorescent probes for long-term monitoring of live cells is the key to understanding and modulating molecular events happening within organelles, unraveling the physiological dynamics. Recently reported fluorogenic probes involve the D-A (donor–acceptor) type platforms such as substituted acetylnaphthalene derivatives ( Tang and Jiang, 2017 ; Zhang et al, 2021a ; Gao et al, 2021 ), BODIPYs ( Tian et al, 2018 ; Bai et al, 2019 ; Liu et al, 2019 ; Zhang et al, 2021b ; Li et al, 2021 ), AIEgens ( Shi et al, 2019 ; Xu et al, 2021 ; Zheng et al, 2021 ), and organometallic compounds ( Jin et al, 2021 ; Zhu et al, 2021 ; Ünlüer, 2021 ). However, tuning the bandgaps for predictable photophysical properties of D-A type molecules was limited by synthetic approaches.…”

Section: Introductionmentioning

confidence: 99%

Novel Pyrazine-Bridged D-A-D Type Charge Neutral Probe for Membrane Permeable Long-Term Live Cell Imaging

et al. 2021

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A novel donor–acceptor–donor (D-A-D) type compound containing pyrazine as the acceptor and triphenylamine as the donor has been designed and synthesized. The photophysical properties and biocompatibility of this probe, namely (OMeTPA)2-Pyr for live cell imaging were systematically investigated, with observed large Stokes shifts, high photostability, and low cytotoxicity. Furthermore, we demonstrated that (OMeTPA)2-Pyr could permeate live cell membranes for labeling. The proposed mechanism of this probe was the binding and shafting through membrane integral transport proteins by electrostatic and hydrophobic interactions. These salient and novel findings can facilitate the strategic design of new pyrazine-fused charge-neutral molecular platforms as fluorescent probes, for long-term in situ dynamic monitoring in live cells.

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Rational molecular design of a reversible BODIPY-Based fluorescent probe for real-time imaging of GSH dynamics in living cells

Cited by 33 publications

References 60 publications

Progress in the Synthesis of Boron Dipyrromethene (BODIPY) Fluorescent Dyes

Progress in the Synthesis of Boron Dipyrromethene (BODIPY) Fluorescent Dyes

Dynamic evaluation of the protective effect of Dendrobium officinale polysaccharide on acute alcoholic liver injury mice in vitro and in vivo by NIR fluorescence imaging

Novel Pyrazine-Bridged D-A-D Type Charge Neutral Probe for Membrane Permeable Long-Term Live Cell Imaging

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