Emerging designs of aggregation-induced emission luminogens for lipid droplets imaging

Zhang, Fei; Wu, Xiaoxiao; Liu, Bin; Han, Ting; Yan, Dingyuan; Wang, Dong; Tang, Ben Zhong

doi:10.1016/j.ccr.2023.215337

Cited by 16 publications

(3 citation statements)

References 154 publications

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“…The exceptional luminescence characteristics of the AIE-active 2-Pyr-ROF and 2-Pip-ROF provide them with prospective opportunities for live cell imaging applications. [48] The cytotoxicity of two luminogens was initially assessed in MCF7 and Hela cells (see Supporting Information, Figure S8). Their low biological toxicity was demonstrated by the uniform 96 % and 91 % cell viability that was obtained at a high concentration of 50 μM in aqueous solution.…”

Section: Lipid Droplets Imagingmentioning

confidence: 99%

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Effects of a Larger N‐Heterocyclic Ring in Rofecoxib Analogues on AIE Activity and Multifunctional Applications

Liu,

Yao,

et al. 2024

Eur J Org Chem

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Two analogues of rofecoxib, 2‐Pyr‐ROF and 2‐Pip‐ROF, were designed according to the strategy of heterocyclic ring enlargement and facilely synthesized in a facile manner by Knoevenagel reactions. The first compound, 2‐Pyr‐ROF, had low quantum yields (QY) of 3.0% in the solid states. After replacing the pyrrolidinyl with piperidinyl, the resulting 2‐Pip‐ROF had a significantly increased QY, with a value of 28%. The root‐mean‐square deviation (RMSD) values between S0 and S1 of 2‐Pyr‐ROF and 2‐Pip‐ROF in tetrahydrofuran were 0.51, 0.35 Å, respectively. As compared with 2‐Pyr‐ROF, compound 2‐Pip‐ROF exhibits a smaller RMSD, which indicates a lower non‐radiative transition rate. A single‐crystal X‐ray diffraction study and Hirshfeld surfaces analysis revealed that 2‐Pip‐ROF had a more nonplanar molecule structure and a weaker π‐π interaction, which might result in a higher fluorescence intensity and QY. Owing to its better aggregation‐induced emission (AIE) behavior, compound 2‐Pip‐ROF showed more multi‐functional applications, including mechanochromism, acidochromism, and lipid droplets imaging ability. These results imply that the strategy of heterocyclic ring enlargement provides a new paradigm for the design of new luminogens with AIE properties.

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Section: Lipid Droplets Imagingmentioning

confidence: 99%

“…[51] These results reveal that two luminogens, particularly 2-Pip-ROF, could image cells efficiently at low concentrations, suggesting that they are a useful instrument for fluorescence imaging of LDs in living cells. [48]…”

Section: Lipid Droplets Imagingmentioning

confidence: 99%

Effects of a Larger N‐Heterocyclic Ring in Rofecoxib Analogues on AIE Activity and Multifunctional Applications

Liu,

Yao,

et al. 2024

Eur J Org Chem

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“…Lipid droplets (LDs), which serve as the primary storage sites for intracellular neutral lipids, are complex, active, and highly dynamic multifunctional organelles. They play important roles in intracellular energy storage and metabolism, membrane transport, protein degradation, and signaling. − A variety of metabolic diseases, including nonalcoholic fatty liver disease, cardiovascular disease, and type II diabetes, are often accompanied by the dysregulation of intracellular lipid homeostasis. − The nuclear membrane (NM) is a bilayered structure enveloping the cell nucleus that is composed of lipids, proteins, and small amounts of sugars and is involved in many key biological processes in cells, including gene regulation, DNA replication, and RNA transport . Similarly, the NM plays a vital role in the formation of LDs.…”

Section: Introductionmentioning

confidence: 99%

3D Imaging of Lipid Droplet–Nuclear Membrane Contact Sites and Cirrhotic Lipid Droplet Overexpression

Ma,

Huang,

Long

et al. 2024

Anal. Chem.

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To coordinate cellular physiology, cells rely on the rapid exchange of molecules at specialized organelle–organelle contact sites. Lipid droplets (LDs) and nuclear membrane (NM) contact sites are particularly vital communication hubs, playing key roles in the exchange of signaling molecules, lipids, and metabolites. However, there is still a lack of understanding of the specific morphology of the contact sites. Here, we combine advanced three-dimensional (3D) imaging with a high-brightness fluorescent probe specifically targeting LDs to map the structural landscape of LD–NM contact sites. The probe exhibits exceptional photophysical properties, making it highly suitable for visualizing the changes occurring in LDs during the apoptosis process. In addition, we utilize the advantages of the probe to accurately monitor the overexpression of abnormal LDs in cirrhosis by 3D imaging for the first time. The outcomes of this investigation highlight that the probe has potential as a robust imaging tool to investigate intricate biological functions of LDs and their implications in related diseases.

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Near infrared aggregation‐induced emission fluorescent materials for lipid droplets testing and photodynamic therapy

Wu,

Zhang,

et al. 2024

Luminescence

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Near‐infrared (NIR) fluorescent probes with aggregation‐induced emission (AIE) properties are of great significance in cell imaging and cancer therapy. However, the complexity of its synthesis, poor photostabilities, and expensive raw materials still pose some obstacles to their practical application. This study reported an AIE luminescent material with red emission and its application in in vitro imaging and photodynamic therapy (PDT) study. This material has the characteristics of simple synthesis, large Stokes shift, good photostabilities, and excellent lipid droplets‐specific testing ability. Interestingly, this red‐emitting material can effectively produce reactive oxygen species (ROS) under white light irradiation, further achieving PDT‐mediated killing of cancer cells. In conclusion, this study demonstrates a simple approach to synthesize NIR AIE probes with both imaging and therapeutic effects, providing an ideal architecture for constructing long‐wavelength emission AIE materials.

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Emerging designs of aggregation-induced emission luminogens for lipid droplets imaging

Cited by 16 publications

References 154 publications

Effects of a Larger N‐Heterocyclic Ring in Rofecoxib Analogues on AIE Activity and Multifunctional Applications

Effects of a Larger N‐Heterocyclic Ring in Rofecoxib Analogues on AIE Activity and Multifunctional Applications

3D Imaging of Lipid Droplet–Nuclear Membrane Contact Sites and Cirrhotic Lipid Droplet Overexpression

Near infrared aggregation‐induced emission fluorescent materials for lipid droplets testing and photodynamic therapy

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