Light-controlled fluorescent probes for precisely monitoring brain amyloid-β aggregates in Alzheimer's disease

Gu, Yinhui; Ding, Zhonglong; Cheng, Zheng; Xu, Yanqi; Liu, Tianguang; Mao, Chuanyu; Ran, Chongzhao; Yang, Jing; Wang, Peng

doi:10.1016/j.cej.2022.137385

Cited by 16 publications

(8 citation statements)

References 52 publications

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“…It is well-known that coumarin has been widely used as chromosphere for fluorescent probes due to its high fluorescence intensity, good photostability, large molar absorption coefficient, and high quantum efficiency. − In addition, coumarin derivatives often possess advantages of good biocompatibility, low toxicity to humans and the environment. Remarkably, several coumarin derivatives have been developed as fluorescent probes for Aβ detection in recent years. − Thus, we envisioned that incorporation of an aromatic coumarin framework into the π bridge between the donor and acceptor groups might lead to new specific fluorescent probes for Aβ (Figure c). First, we propose to construct a simple molecule by combining the coumarin moiety with conjugated double bonds, while maintaining dimethylamino group as the electron donor and dicyanomethylene group as the acceptor (Figure c, XCYC-1 ).…”

Section: Resultsmentioning

confidence: 99%

Design of a Coumarin-Based Fluorescent Probe for Efficient In Vivo Imaging of Amyloid-β Plaques

Cao

Liu

Zhang

et al. 2023

ACS Chem. Neurosci.

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Amyloid-β (Aβ) is the core constituent protein of senile plaques, which is one of the key pathological hallmarks of Alzheimer’s disease (AD). Here we describe the design, synthesis, and evaluation of coumarin-derived small molecule fluorophores for Aβ imaging. By embedding the aromatic coumarin framework into π bridge of a push–pull chromophore, a novel fluorescence probe XCYC-3 applicable to efficient Aβ recognition was discovered. XCYC-3 displays higher fluorescent enhancement for aggregated Aβ than monomeric Aβ, and possesses good blood-brain barrier permeability. In vitro staining and in vivo imaging studies demonstrated that XCYC-3 could efficiently recognize Aβ plaques in the brain of AD transgenic mice. These results suggest that XCYC-3 is a promising fluorescence imaging agent for Aβ, which might provide important clues for the future development of potent NIR fluorescent probes for Aβ diagnosis.

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Section: Resultsmentioning

confidence: 99%

Design of a Coumarin-Based Fluorescent Probe for Efficient In Vivo Imaging of Amyloid-β Plaques

Cao

Liu

Zhang

et al. 2023

ACS Chem. Neurosci.

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“…Herein, we engineered the fluorescent probe FAS1 targeting macrophages to monitor ferroptosis and atherosclerotic plaques. As shown in Scheme , FAS1 contains a typical AIEgen unit of quinoline malononitrile (electron acceptor) and hydrophobic LD fluorophore of coumarin moiety (electron donor) connected by a rotatable vinyl bond to form a D-π- A structure. ,− The AIE characteristic greatly compensates for the decrease of fluorescence intensity caused by the intramolecular torsional charge transfer (TICT) effect, so the probe exhibited large stokes displacement and good light bleaching resistance . Laser confocal imaging confirmed that the designed FAS1 can co-locate well with BODIPY 493/503 (a commercial probe for LDs imaging) at the organelles of lipid droplets after being treated with ferroptosis inducer erastin.…”

Section: Introductionmentioning

confidence: 94%

“…41 Fluorescence imaging has become an indispensable modality that features inherent superiorities including high temporalspatial resolution, high sensitivity and specificity, simple operation, and fast acquisition. 42,43 To date, numerous fluorescent probes have been developed to detect lipid droplets (LDs) for studying the process of ferroptosis. Liu and coworkers designed a dual-functional fluorescence probe to monitor polarity change in the cellular microenvironment during ferroptosis.…”

Section: ■ Introductionmentioning

confidence: 99%

“…X-ray computed tomography (CT), positron emission tomography (PET), ultrasonography (US), and magnetic resonance imaging (MRI) are applied for the identification of AS plaques in the clinic. − However, neither of these imaging techniques allows early-stage AS detection with the restriction of long scanning and postprocessing times . Fluorescence imaging has become an indispensable modality that features inherent superiorities including high temporal-spatial resolution, high sensitivity and specificity, simple operation, and fast acquisition. , To date, numerous fluorescent probes have been developed to detect lipid droplets (LDs) for studying the process of ferroptosis. Liu and co-workers designed a dual-functional fluorescence probe to monitor polarity change in the cellular microenvironment during ferroptosis .…”

Section: Introductionmentioning

confidence: 99%

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Visualization of the Ferroptosis in Atherosclerotic Plaques with Nanoprobe Engineered by Macrophage Cell Membranes

Gu,

Cui,

Wang

et al. 2023

Anal. Chem.

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Atherosclerosis (AS) is the root cause of cardiovascular diseases. Ferroptosis is characterized by highly irondependent lipid peroxidation and has been reported to play an important role in the pathogenesis of AS. Visualization of the ferroptosis process in atherosclerotic plaques is of great importance for diagnosing and treating AS. In this work, the rationally designed fluorescent probe FAS1 exhibited excellent advantages including large Stokes shift, sensitivity to environmental viscosity, good photostability, and improved water solubility. It also could co-locate with commercial lipid droplets (LDs) probes (BODIPY 493/503) well in RAW264.7 cells treated by the ferroptosis inducer. After self-assembly into nanoparticles and then encapsulation with macrophage membranes, the engineered FAS1@MM NPs could successfully target the atherosclerotic plaques in Western dietinduced apolipoprotein E knockout (ApoE −/− ) mice and reveal the association of ferroptosis with AS through fluorescence imaging in vivo. This study may provide additional insights into the roles of ferroptosis in the diagnosis and treatment of AS.

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“…Wang and colleagues designed and synthesized a new series of photo-triggered fluorescent probes for Aβ detection. [70] Under the light irradiation, these probes were transformed to weak fluorescent benzothiazole-coumarin structure through releasing the protecting group and cyclization reaction. Subsequently, the benzothiazole-coumarin could bind with Aβ fibrils to generate strong fluorescence complex.…”

Section: Chemistry-a European Journalmentioning

confidence: 99%

Small Molecular Fluorescent Probes for Alzheimer's Disease Associated Active Species

Tang

Wang

Liu

et al. 2023

Chemistry A European J

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Alzheimer's disease (AD) is a progressive neurodegenerative disorder and is the main cause of dementia worldwide. As the pathogenesis of AD is quite complicated, there is continuous attention to AD‐associated active species, such as amyloid‐β plaques, neurofibrillary tangles, metal ions, reactive oxygen/nitrogen/sulphur species, cholinesterase, viscosity, formaldehyde and so on. To this end, a series of small molecular fluorescent probes for these active species have been explored for early diagnosis and even remedy of AD. Herein, we systematacially summarize the versatile fluorescent probes mainly in recent three years, including the relationship between the structure and properties as well as the targeted diagnosis and imaging application of all these fluorescent probes. Moreover, the challenges and perspectives of the AD‐related fluorescent probes are briefly explicated. We firmly expect this review may provide guidance for constructing new AD‐relevant fluorescent probes and promote the clinical study of AD.

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Light-controlled fluorescent probes for precisely monitoring brain amyloid-β aggregates in Alzheimer's disease

Cited by 16 publications

References 52 publications

Design of a Coumarin-Based Fluorescent Probe for Efficient In Vivo Imaging of Amyloid-β Plaques

Design of a Coumarin-Based Fluorescent Probe for Efficient In Vivo Imaging of Amyloid-β Plaques

Visualization of the Ferroptosis in Atherosclerotic Plaques with Nanoprobe Engineered by Macrophage Cell Membranes

Small Molecular Fluorescent Probes for Alzheimer's Disease Associated Active Species

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