A NIR fluorescence probe having significant fluorescence turn-on signal at 700 nm and large Stokes shift for rapid detection of HOCl in vivo

Zhang, Haiyan; Yin, Xinyu; Hong, Jiaxin; Deng, Yingzhen; Feng, Guoqiang

doi:10.1016/j.talanta.2020.121768

Cited by 51 publications

(9 citation statements)

References 56 publications

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“…Fluorophores based on dicyanoisophorone (DCI) are well-known for their easy preparation, good photostability, and strong fluorescence with large Stokes shift in the far-red to near-infrared (NIR) window . These attractive features make them widely used for designing NIR fluorescent probes to image various biological species in living systems. − However, whether DCI fluorophores can be used for high-fidelity tracking of lysosomal dynamics is unknown. Herein, we report that DCIP , a readily available DCI fluorophore containing a piperazine group (Scheme ), can be used as a high-performance lysosomal probe for labeling and imaging lysosomes.…”

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confidence: 99%

Real-Time and High-Fidelity Tracking of Lysosomal Dynamics with a Dicyanoisophorone-Based Fluorescent Probe

Hong

Xia

2021

Anal. Chem.

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The development of high-performance probes that can visualize and track the dynamic changes of lysosomes is very important for the in-depth study of lysosomes. Herein, we report that a dicyanoisophorone-based probe (named DCIP) can be used for high-fidelity imaging of lysosomes and lysosomal dynamics. DCIP can be easily prepared and shows strong far-red to near-infrared emissions centered at 653 nm in water with a huge Stokes shift (224 nm), high quantum yield (Φ = 0.15), high pKa value (∼8.79), and good biocompatibility. DCIP also shows good cell permeability and can label lysosomes rapidly with bright fluorescence without a time-consuming washing process before imaging. DCIP also possesses good photostability and negligible background, making it effective for long-term and high spatiotemporal resolution (0.44 s of exposure) imaging of lysosomes. Moreover, DCIP achieved high-fidelity tracking of lysosomal dynamics at an extremely low concentration (1 nM). Finally, we also demonstrated that DCIP could real-time track the interactions of lysosomes with other organelles (damaged mitochondria as a model) and image the drug-escape processes from lysosomes. All of the results show that DCIP holds broad prospects in lysosome-related research.

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confidence: 99%

Real-Time and High-Fidelity Tracking of Lysosomal Dynamics with a Dicyanoisophorone-Based Fluorescent Probe

Hong

Xia

2021

Anal. Chem.

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“…Practically, the Stokes shift is crucial to any use of fluorescence-based methods because it allows the easy separation of emitted fluorescence from excitation light by using appropriate optical filters. [44][45][46] Taking a comparison between the different electron distribution systems, it is found that TPAs-SCH 3 -2CN is of 140 nm Stokes shift, which is larger than that of TPAs-SCH 3 (100 nm) (Figure 2). Additionally, TPAs-SCH 3 , TPAs-2SCH 3 , TPAs-3SCH 3 are highly emissive in the both of solvents, such as THF and Water, or their random mixtures, exhibiting the less sensitivity to the environment changes; However, TPAs-SCH 3 -2CN is non-emissive in the good solvent of THF, and highly emissive in the aggregation state as using the less good solvent of water, supplying numerous opportunities to itself with versatile applications as probes (Figure 3).…”

Section: Synthesis and Spectroscopic Studiesmentioning

confidence: 95%

A New Lipid‐Droplets‐Targeted Fluorescence Probe with Dual‐Reactive Sites for Specific Detection of ClO⁻ in Living Cells

Yuan

Yin

et al. 2022

ChemistrySelect

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Lipid droplets (LDs) are organelles composed of a lipid core surrounded by a phospholipid monolayer, plays an important role in a variety of physiological processes as well as diseases. In this work, TPAs-SCH 3 -2CN with an enhanced electron D-π-A system, is synthesized, which makes itself as an orange emission compound (E m = 590 nm) and also have high polarity.It is verified that TPAs-SCH 3 -2CN is an excellent LDs-targeted probe, and it also sensitive to the ClO À detection in vitro and in cells. Impressively, due to the high lipophilicity, TPAs-SCH 3 -2CN is able to stain the yolk lipids in zebrafish, exhibiting the potential for monitoring lipid transport and metabolism processes.

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“…It provides a potential tool for the detection of HClO in environmental systems and biological systems in the future. In addition, Zhang and his colleagues synthesized a new near-infrared fluorescent probe 23 [ 50 ] with large Stokes shift, with coumarin-dicyanoisophorone as the fluorescence response group, and dimethyl thioaminomethyl acid ester response site. It is a turn-on probe.…”

Section: Classification Of Small Molecule Fluorescent Probes For Detecting Hypochlorous Acid/hypochloritementioning

confidence: 99%

Research Progress of Small Molecule Fluorescent Probes for Detecting Hypochlorite

Song

Yuan

et al. 2021

Sensors

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Hypochlorous acid (HOCl) generates from the reaction between hydrogen peroxide and chloride ions via myeloperoxidase (MPO)-mediated in vivo. As very important reactive oxygen species (ROS), hypochlorous acid (HOCl)/hypochlorite (OCl−) play a crucial role in a variety of physiological and pathological processes. However, excessive or misplaced production of HOCl/OCl− can cause variety of tissue damage and human diseases. Therefore, rapid, sensitive, and selective detection of OCl− is very important. In recent years, the fluorescent probe method for detecting hypochlorous acid has been developed rapidly due to its simple operation, low toxicity, high sensitivity, and high selectivity. In this review, the progress of recently discovered fluorescent probes for the detection of hypochlorous acid was summarized with the aim to provide useful information for further design of better fluorescent probes.

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A NIR fluorescence probe having significant fluorescence turn-on signal at 700 nm and large Stokes shift for rapid detection of HOCl in vivo

Cited by 51 publications

References 56 publications

Real-Time and High-Fidelity Tracking of Lysosomal Dynamics with a Dicyanoisophorone-Based Fluorescent Probe

Real-Time and High-Fidelity Tracking of Lysosomal Dynamics with a Dicyanoisophorone-Based Fluorescent Probe

A New Lipid‐Droplets‐Targeted Fluorescence Probe with Dual‐Reactive Sites for Specific Detection of ClO⁻ in Living Cells

Research Progress of Small Molecule Fluorescent Probes for Detecting Hypochlorite

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A NIR fluorescence probe having significant fluorescence turn-on signal at 700 nm and large Stokes shift for rapid detection of HOCl in vivo

Cited by 51 publications

References 56 publications

Real-Time and High-Fidelity Tracking of Lysosomal Dynamics with a Dicyanoisophorone-Based Fluorescent Probe

Real-Time and High-Fidelity Tracking of Lysosomal Dynamics with a Dicyanoisophorone-Based Fluorescent Probe

A New Lipid‐Droplets‐Targeted Fluorescence Probe with Dual‐Reactive Sites for Specific Detection of ClO− in Living Cells

Research Progress of Small Molecule Fluorescent Probes for Detecting Hypochlorite

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A New Lipid‐Droplets‐Targeted Fluorescence Probe with Dual‐Reactive Sites for Specific Detection of ClO⁻ in Living Cells