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AIE
TALANTA · 2023 · IF 6.1

A GSH-activated AIE-based polymer photosensitizer for killing cancer cells

Wei Lang,Li-Zhen Chen,Yong Chen,Qian-Yong Cao

Developing efficient photosensitizers which are sensitive to therapeutic tumor signals, but non-toxic to normal cells has always been a tremendous challenge in photodynamic therapy (PDT) process. Herein, a novel copolymer P1 was developed by ring-opening metathesis polymerization (ROMP) with disulfide bond linked ferrocene-norbornene dyad NB-SS-PyFc and the aggregation-induced emission (AIE) fluorephore anchored norbornene NB-TPE , and its nanoparticles (NPs) were obtained by using the amphiphilic Pluronic F-127 as the surfactant via a nanoprecipitation method. The P1 NPs show a weak emission and a low 1 O 2 generation for the quenching effect from the ferrocene moiety to the AIE group. However, the addition of GSH can recover the AIE fluorephore emission and 1 O 2 generation for cleavage the disulfide bond. Importantly, P1 NPs have been used for image-guided cancer cells apoptosis for the GSH activated 1 O 2 generation.

研究领域: 生物医学工程 · 肿瘤学 · 材料科学
✓ 已验证 DOI PubMed 高影响因子
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Materials Chemistry Frontiers · 2020 ·Vol. 4 ·期 11 ·3201-3208 · IF 6.788

Mitochondria-anchoring and AIE-active photosensitizer for self-monitored cholangiocarcinoma therapy

Tao Zhou,Jianfang Zhu,Dan Shang,Chuxing Chai,Youzhen Li,Haiying Sun,Yongqin Li,Meng Gao,Min Li

The morbidity of extrahepatic cholangiocarcinoma (CCA) has increased markedly in the past few decades. However, most patients with extrahepatic CCA are diagnosed at an advanced stage and thus cannot receive curative resection in time. To increase the long-term survival probability of nonresectable extrahepatic CCA patients, it is highly desirable to develop alternative treatment strategies. Photodynamic therapy is a highly efficient method for the ablation of cancer cells, but the conventional photosensitizers (PSs) suffer from self-quenching after local accumulation in organelles. To tackle this challenge, we herein develop a mitochondria-anchoring photosensitizer, TTVPHE, with aggregation-induced emission (AIE) characteristics for efficient ablation of extrahepatic CCA cells through the mitochondrial injury pathway. The TTVPHE probe shows significant advantages in terms of fast cell penetration ability, selective mitochondria-targeting ability, and excellent ROS generation ability under white light irradiation. Moreover, the probe can in situ monitor the mitochondrial injury process by translocation from mitochondria to the nuclear membrane. The ultrastructural changes in the morphology of mitochondria under PDT were also characterized using high resolution TEM. This AIE-active probe is promising for the treatment of advanced stage CCA.

CAS / MDL: 25542-62-5 108-89-4
研究领域: 肿瘤学 · 药学 · 生物医学工程
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SENSORS AND ACTUATORS B-CHEMICAL · 2018 · IF 5.667

A facile four-armed AIE fluorescent sensor for heparin and protamine

Yuxia Gao,Kailun Wei,Jianzuo Li,Ying Li,Jun Hu

In this research a four-armed amino-tailored tetraphenylethene TPE-NH 2 was synthesized, and it could detect heparin (Hep) quantitatively, primarily promoted by the electrostatic interactions between its positively charged amino groups and the sulfates, carboxylates of heparin. On account of the aggregation-induced emission (AIE) nature of tetraphenylethene backbone, the aggregation restricted the rotation of C C single bond through rigidifying the conformation of TPE-NH 2 , thus making it display intense fluorescence with a broad working range (≤2.0 μg/mL) and a low detection limit (down to 35.89 ng/mL) for heparin. Meanwhile, the TPE-NH 2 /Hep complex can be further disaggregated by protamine due to the stronger affinity between heparin and protamine, consequently leading to the highly sensitive detection of protamine. What’s more, the low toxicity of TPE-NH 2 makes it a potential functional sensor for detecting heparin in the matrix of human serum.

研究领域: 生物化学 · 医学检测 · 材料科学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2021 · IF 4.098

AIE-based fluorescent boronate probe and its application in peroxynitrite imaging

Minglu Li,Hui Han,Shengmei Song,Shaomin Shuang,Chuan Dong

Fluorescent probes have contributed greatly to our understanding of the biological role of peroxynitrite (ONOO – ). The ONOO – fluorescence probe characterized by the arlyboronate received a moderate opening fluorescence response, and the borate-masked probe significantly increased the sensitivity of ONOO – . Thus, two simple fluorescent probes ( ADB and ANB ) with the recognition receptor of phenyl boronate moiety were constructed for the detection of ONOO – . The change of emission spectrum was affected differently by the electron donating (or withdrawing) of the substituents. ANB was shown to have a low sensitivity and quantum yield towards ONOO – in aqueous solution, whereas ADB with aggregation-induced emission (AIE) process exhibited not only good sensitivity for ONOO – with a detection limit of 75 nM, but also ADB could be used to quantitative detecting ONOO – in response to concentrations of ONOO – within 20 s. Importantly, ADB had good performance for the detection of exogenous ONOO – in the RAW 264.7 cells.

研究领域: 生物化学 · 医学影像学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Polymer Chemistry · 2015 ·Vol. 6 ·期 29 ·5288-5294 · IF 5.52

A rather facile strategy for the fabrication of PEGylated AIE nanoprobes

Qing Wan,Ke Wang,Huilin Du,Hongye Huang,Meiying Liu,Fengjie Deng,Yanfeng Dai,Xiaoyong Zhang,Yen Wei

Fluorescent organic nanoparticles (FNPs) have attracted great research interest for biological sensors, biological imaging and disease treatment. However, the preparation of ultrabright FNPs using conventional organic dyes is still a challenge for their aggregation caused quenching effect. In this work, we reported for the first time that polyethylene glycol (PEG) and an aggregation induced emission (AIE) dye, 2,2′-diaminotetraphenyl ethylene (DATPE), can be facilely conjugated by trimellitic anhydride chloride. Taking advantage of the different reaction activities of anhydride and chloride, anhydride-terminated PEG (ADPEG) was first synthesized through the reaction between hydroxyl groups and benzoyl chloride. Then ADPEG could further react with the amino groups of DATPE. Because of the AIE properties of DATPE, these amphiphilic triblock copolymers can self-assemble into FNPs (PEG-TPE FNPs) and emit strong blue-green fluorescence in aqueous solution. Cell uptake behavior and cytotoxicity evaluation suggested that PEG-TPE FNPs possessed excellent cytocompatibility and could be facilely taken up by cells, implying that PEG-TPE FNPs are promising for biomedical applications. More importantly, the method described in this work is rather simple and effective and, more importantly, can be extended to fabricate many other multifunctional FNPs on a large scale for various biomedical applications.

CAS / MDL: 25322-68-3 1204-28-0
研究领域: 材料科学 · 生物医学工程 · 化学
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DYES AND PIGMENTS · 2021 · IF 4.889

Cucurbituril-mediated AIE: An unconventional indicator displacement assay for ketamine detection

Kun Yan,Lancheng Wang,Huimin Zhou,Zhendong Hua,Peng Xu,Hui Xu,Youmei Wang,Bin Di,Chi Hu

Typical AIE luminogens with extensive π-electron conjugation are limited in use on account of their complex synthesis, high cost and environmental concerns. To this end, we report here a novel host-guest inclusion complex that is assembled from nonemissive ligands, and surprisingly exhibits notable AIE features in aqueous solution while maintaining good sensitivity for ketamine (KET) detection. Isothermal titration studies confirm that palmatine (PAL) binds to cucurbit[8]uril (Q8) in a 2:1 ratio with an equilibrium association constant of 1.75 × 10 11  M −2 , suggesting that the unconventional AIE effects can be attributed to the stacking of two PAL moieties inside a single Q8 cavity. Geometric constraints of the macrocycle result in dimeric coupling of PAL in the ground state with significant bathochromic shifts in absorption and emission, which can be readily excited to exhibit enhanced photoluminescence . The unusual upfield perturbation and broadening of Q8 signals in the 1 H NMR spectrum upon binding with PAL convey decisive information that Q8 not only serves as a molecular container, but also participates in the electron delocalization during the AIE events. Upon addition of KET, fluorescence was switched off through guest exchange to generate [email protected] as well as free PAL. The significant AIE characteristics of 2* [email protected] in combination with its specific molecular recognition towards KET gives rise to 5.0 ng/mL limit of detection with linear range from 16.8 to 500 ng/mL, and a pronounced selectivity over possible interfering substances in biological matrices. We demonstrate the first example of Q8-mediated AIE effects, where the photoluminescence of virtually nonemissive or feebly emissive ligands is remarkably intensified through clustering inside a macrocyclic host molecule, therefore offering great promise for further development into dedicated AIE-based sensors.

研究领域: 分析化学 · 超分子化学 · 材料科学 · 传感器与执行器
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Small · 2022 ·Vol. 18 ·期 24 ·2201117 · IF 15.153

Janus-Structural AIE Nanofiber with White Light Emission and Stimuli-Response

Shikun Zhao,Jiangman Sun,Zhen Qin,Yufeng Li,Hao Yu,Guan Wang,Xinggui Gu,Kai Pan

White-light emitting elastomers (WLEEs) based on stimuli-responsive aggregation-induced emission (AIE) and regulated Förster resonance energy transfer (FRET) have aroused increasing attention due to the demands for wearable optoelectronic devices. Herein, the blue and orange AIEgens with different environmental sensitivities are synthesized and then encapsulated on both sides of nanofibers via side-by-side electrospinning aiming to achieve the Janus WLEEs. After regulating the blue-orange AIEgens ratio, efficient and stable white light emission with a CIE coordinate of about (0.33, 0.31) is achieved at a blue-orange AIEgens mass ratio of 3:1. Besides, the Janus nanofibers (Janus-NFs) also present super stretchability with elongation at the break over 150% and tensile strength close to 7 MPa. The sensitivity of fluorescence for Janus-NFs to its stretching deformation is used to visualize the evolution of the microstructure of nanofibers during stretching. Moreover, the Janus-NFs are also sensitive to HCl and NH 3 , of which the fluorescence color would change under HCl and NH 3 fuming above 2 and 57 ppm in air, respectively. The promising applications of the white light Janus-NFs in smart fabrics, warning sensors, and anti-counterfeiting packaging are demonstrated. This finding provides an efficient strategy for achieving wearable WLEEs with multiple functionalities, promoting the development of wearable devices.

CAS / MDL: 68-12-2
研究领域: 材料科学 · 光学 · 纳米技术
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ANALYTICAL CHEMISTRY · 2022 · IF 8.008

Mitochondria MicroRNA Spatial Imaging via pH-Responsive Exonuclease-Assisted AIE Nanoreporter

Jinya Du,Yuchun Qiao,Xiangdan Meng,Wei Wei,Wenhao Dai,Lingzhi Yang,Changying Yang,Haifeng Dong

Mitochondrial microRNAs (mitomiRs) critically orchestrate mitochondrial functions. Spatial imaging of mitomiRs is essential to understand its clinical value in diagnosis and prognosis. However, the direct monitoring of mitomiRs in living cells remains a key challenge. Herein, we report an AIE nanoreporter strategy for mitomiRs imaging in living cells through pH-controlled exonuclease (Exo)-assisted target cycle signal amplification. The AIE-labeled DNA detection probes are conjugated on Exo III encapsulated polymeric nanoparticles (NPs) via consecutive adenines (polyA). The amplified sensing functions are off during the cytoplasm delivery process, and it can be spatially switched from off to on when in the alkaline mitochondria (about pH 8) after triphenylphosphonium (TPP)-mediated mitochondrial targeting. Where the NPs degraded to release Exo III and cancer-specific mitomiRs hybridize with AIE-labeled DNA detection probes to expose the cleavage site of released Exo III, enabling spatially restricted mitomiRs imaging. The mitomiRs expression fluctuation was also realized. This study contributes to a facile strategy that could easily extend to a broad application for the understanding of mitomiRs-related pathological processes.

CAS / MDL: 7758-99-8 134-03-2
研究领域: 生物学 · 生物化学 · 分子生物学 · 癌症研究 · 纳米技术
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CHINESE JOURNAL OF CHEMISTRY · 2023 ·Vol. 41 ·期 23 ·3245-3252 · IF 5.4

Emission Properties of Individual AIE-Luminogens in Solution at Room Temperature†

Yuehua Zhao,Hongbo Chen,Shaojie Geng,Shunjie Liu,Dapeng Wang

Comprehensive Summary Here, we combined the photon antibunching analysis, fluorescence correlation spectroscopy, and time-domain fluorescence lifetime imaging microscopy (TD-FLIM) to study the emission properties of a representative AIE-luminogen—4,4’-(benzo[ c ][1,2,5] thiadiazole-4,7-diyl)bis( N , N -diphenylaniline) (TPA-BT) at the single emitter level in a tetrahydrofuran (THF)/water solution where water is a non-solvent for TPA-BT. Our findings suggest that, at a constant water fraction in the solution, the size of TPA-BT aggregates increases with the TPA-BT concentration; TPA-BT aggregates are not a quantum emitter at room temperature in the solution. Moreover, utilizing TD-FLIM and a gel trapping technique allowed us to study the fluorescence lifetime of individual TPA-BT aggregates. Adding a polar solvent like water does not result in an overall decrease in fluorescence lifetime. Rather, it causes the fluorescence lifetime distribution to become wider, and only some molecules experience a decrease in their fluorescence lifetime. These results could represent a step forward in further understanding the photophysics of AIE-luminogens.

研究领域: 光学 · 化学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2019 · IF 2.931

Double-detecting fluorescent sensor for ATP based on Cu2+ and Zn2+ response of hydrazono-bis-tetraphenylethylene

Shengjie Jiang,Jiabin Qiu,Shibing Chen,Hongyu Guo,Fafu Yang

Although all kinds of sensors with unique detecting ability for one guest were reported, the fluorescence sensor with multiple detecting abilities was seldom presented. This work designed and synthesized a novel AIE fluorescence probe bearing double detecting for ATP based on Cu 2+ and Zn 2+ response of hydrazono-bis-tetraphenylethylene ( Bis-TPE ). Bis-TPE was prepared in 82% yield with simple procedure. It exhibited strong red AIE fluorescence based on the large conjugated electron effect in aqueous media. It showed outstanding selective sensing abilities for Cu 2+ by strong fluorescence quenching and for Zn 2+ by red-orange fluorescence change. The sensing mechanism of 1:1 stoichiometric ratios was confirmed by 1 H NMR and MS study. The strong red fluorescence of Bis-TPE  + Cu 2+ system could be recovered by adding ATP. The orange fluorescence of Bis-TPE  + Zn 2+ system could be quenched by adding Cu 2+ and then was recovered by adding ATP. These double detecting abilities for ATP with the “off-on” red fluorescence in Bis-TPE  + Cu 2+ system and “allochroic-off-on” orange fluorescence in Bis-TPE  + Zn 2+ +Cu 2+ system were successfully applied to test Cu 2+ , Zn 2+ and ATP in test paper and living cell imaging, displaying the good application prospects for sensing Cu 2+ , Zn 2+ and double detecting ATP in the complicated environment.

研究领域: 分析化学 · 生物化学 · 材料科学 · 生物成像
✓ 已验证 DOI PubMed 高影响因子
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BIOCONJUGATE CHEMISTRY · 2025 · IF 3.9

AIE Photosensitizer with Tuned Membrane Interactions for Effective-Gram-Negative Bacteria Elimination

Edward Kamya,Shangzhao Yi,Zhongzhong Lu,Jincong Yan,Hewan Dawit,Shah Mehmood,Yi Cao,Renjun Pei

Photodynamic antimicrobial therapy (PDAT) for efficient bacterial infection eradication critically relies on photosensitizers (PSs) that can specifically target and disrupt bacterial membranes. However, the complex membrane architecture of Gram-negative bacteria poses a significant challenge to the efficacy of most aggregation-induced emission (AIE) PSs. Herein, we introduce TPQ, an AIE PS meticulously designed to overcome this challenge by incorporating an outer membrane disruption ability, thereby boosting PDAT efficacy against Gram-negative bacteria. TPQ demonstrated excellent microbial imaging and potent PDAT activity against both Gram-positive and Gram-negative bacteria, attributed to its inherent fluorescence, high singlet oxygen generation, and balanced electrostatic and hydrophobic interactions with bacterial membranes. Notably, TPQ achieved exceptional PDAT activity (>97% efficacy) against Gram-negative bacteria while exhibiting minimal cytotoxicity to mammalian cells. Furthermore, TPQ-mediated PDAT effectively healed Escherichia coli-infected wounds on mice models with assured biosafety. This work provides valuable insights into the rational design of AIE PSs and highlights the synergistic effect of membrane disruption for advancing PDAT applications, particularly against recalcitrant Gram-negative bacterial infections.

研究领域: 微生物学 · 医学 · 生物材料学
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JOURNAL OF POLYMER RESEARCH · 2022 ·Vol. 29 ·期 4 ·1-9 · IF 3.061

In situ monitoring of photo-PISA via aggregation-induced emission (AIE) technology

Zhang Andong,Hao Jingyi,Hou Sen,Shi Ge,He Yanjie,Cui Zhe,Liu Minying,Qiao Xiaoguang,Fu Peng,Pang Xinchang

Aggregation-induced emission (AIE) has already been applied for in-situ monitoring living radical polymerization process. Here we utilized functionalized monomer TPEE as fluoresce probes for the in-situ monitoring of photo-induced RAFT-PISA process. Hydrophilic POEGA macro chain transfer agent (Macro-CTA) was first prepared with light sensitive CTA 4-Cyanopentanoic acid dithiobenzoate, and (2-(4-vinylphenyl)ethene-1,1,2-triyl)tribenzene (TPEE) was copolymerized with styrene to form the hydrophobic block under UV irradiation. The growth of hydrophobic block induced the self-assembly of polymer chains and the emission signal could be observed by naked eyes afterwards. The PL intensity increased with the increase of particle size, as well as the monomer conversion and molecular weight, owing to the enhancement of AIE monomer in the self-assembly latex particles. This no-invasive and facile approach to in-situ visualization and continuously monitoring of the photo-induced RAFT-PISA process might be helpful for both scientific research and commercial application.

研究领域: 高分子化学 · 材料科学
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