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AIE
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES · 2018 ·Vol. 34 ·期 3 ·363-368 · IF 1.248

A Label-free Fluorescent Aptasensor for Turn-on Monitoring Ochratoxin A Based on AIE-active Probe and Graphene Oxide

Ma Lian,Xu Bin,Liu Leijing,Tian Wenjing

A label-free fluorescent aptasensor for specific and ultrasensitive monitoring ochratoxin A(OTA) was developed using the specific aptamer of OTA(OSA) as recognition element, an aggregation-induced emission(AIE) molecule(a 9,10-distyrylanthracene with two ammonium groups, DSAI) as a fluorescent probe, and graphene oxide(GO) as a quencher. In the absence of OTA, the AIE probe DSAI and OSA complex(DSAI/OSA) is adsorbed on the GO surface, and the fluorescence of DSAI will be quenched efficiently via the fluorescence resonance energy transfer(FRET) from DSAI to GO. Upon the OTA addition, a more stable complex(OSA-OTA) is formed and released from GO. Meanwhile, DSAI and OSA-OTA can form a new complex(DSAI/OSA-OTA), then the fluorescent signal of DSAI recovers gradually. Therefore, by introducing GO and DSAI, the fluorescence signal of DSAI can be easily turned from “off” to “on” after the addition of OTA, and the ultrasensitive detection of OTA by monitoring the change of the fluorescence signal of DSAI can be readily realized. The detection limit of the assay can reach 0.324 nmol/L with a linear detection range of 10—200 nmol/L. And the aptasensor exhibits high selectivity for OTA against other analogues. Moreover, it has been successfully applied for the detection of OTA in red wine samples.

CAS / MDL: 303-47-9
研究领域: 分析化学 · 食品安全 · 毒理学 · 生物化学
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SENSORS AND ACTUATORS B-CHEMICAL · 2023 · IF 8.4

Debut of a novel AIE-based fluorescent probe as tyrosinase tracer to image skin pigmentary disorders

Xueyan Huang,Lan Zhang,Fan Zheng,Yanpeng Fang,Feng Gao,Qian Chen,Qinghai Zeng,Wenbin Zeng

Tyrosinase (TYR) functions as the critical enzyme in biosynthesis of melanin , and its abnormality is an important hallmark for skin pigmentary disorders. This renders the visualization of tyrosinase dynamics a strategically vital way to facilitate clinical diagnostic and monitoring. However, the use of small molecule fluorescent probes to assess tyrosinase levels and evaluate related therapeutics and drugs has been limited. This is mainly due to the aggregation-induced quenching (ACQ) effects of existing fluorescent probes. In this study, we introduce the first aggregation-induced emission (AIE) small molecule fluorescent probe , BTFTYR , for simple, highly sensitive, and effective detection of tyrosinase activity. The specific fluorescence signal generated by tyrosinase catalytic reaction enables the imaging of pigment cells. We demonstrate its application in visualizing tyrosinase with high contrast in living vertebrates, benefiting from the inherent photobleaching resistance of AIE materials, large Stokes shift , and considerable tissue permeability. We also show the outstanding skin penetration capability of BTFTYR in a skin model. Moreover, we present the first comprehensive evaluation of relevant clinical therapeutic approaches or drugs, including ultraviolet B (UVB) irradiation, kojic acid , and α-MSH, by interpreting the tyrosinase variation with BTFTYR . Finally, our studies confirm that BTFTYR neither causes skin inflammation nor produces visceral toxicity, making it a promising chemical tool for medical diagnosis and drug screening. This tool may further help elucidate the pathomechanisms associated with tyrosinase.

研究领域: 生物化学 · 药学 · 材料科学 · 医学成像
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BIOSENSORS & BIOELECTRONICS · 2024 · IF 10.7

Ratiometric fluorescence sensing NADH using AIE-dots transducers at the point of care

Sile Deng,Xiaoju Men,Muhua Hu,Xiao Liang,Yujuan Dai,Zhengkun Zhan,Zhongchao Huang,Haobin Chen,Zhuxin Dong

Reduced nicotinamide adenine dinucleotide (NADH) has a strong impact on physiological metabolism, and its concentration is related to metabolic and neurodegenerative diseases. A more reliable and accurate detection method for NADH quantitation is needed for early disease diagnosis and point-of-care testing. Aggregation-induced emission (AIE) materials are widely used to improve the sensitivity in analytes assays due to their anti-aggregation-caused quenching property. Here we developed TPA-BQD-Py AIE-dots transducers and evaluated its performance in NADH detection. The NADH concentration-dependent ratiometric sensing was based on electron transfer from TPA-BQD-Py AIE-dots to NADH with variable fluorescence intensity at 584 nm and 470 nm, resulting in high sensitivity (limit of detection at 110 nM), photostability, selectivity, and a rapid and reversible response. We further developed the application of TPA-BQD-Py AIE-dots transducers in in vivo NADH imaging using a smartphone and digital camera, respectively, demonstrating the potential for NADH point-of-care testing.

CAS / MDL: 146-14-5
研究领域: 分析化学 · 生物医学工程 · 即时诊断 · 荧光传感 · 代谢组学
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MACROMOLECULAR CHEMISTRY AND PHYSICS · 2021 ·Vol. 222 ·期 23 ·2100284 · IF 2.527

Polyurea Modified with 4-Dihydropyrimidone-2-ketone Rings by Biginelli Reaction and its Boostered AIE Characteristic

Da Zhang,Jinxin Zheng,Pengfei Zhang,Ronghui Zhao,Zhuo Chen,Meng Wang,Kuilin Deng

In the synthesis of traditional AIE-active polymers with conjugate or multi-benzene system, the troublesome process is still faced such as consuming time, high temperature, catalysis, no water or vacuum, and so on. In this study, the polydihydropyrimidone derivatives (PDPMDs) with AIE properties are facilely synthesized by the introduction of 4-dihydropyrimidone rings onto non-AIE-active intermediate polyureas (PUs) in Biginelli reaction. It is found that the unsymmetrical L- lysine ethyl diisocyanate and butylenediamine played a very important role in the smooth preparation and fluorescence enhancement of PDPMDs. Compared with the intermediate PUs, the fluorescence of PDPMDs is significantly enhanced (35-fold increase), which is mainly due to the intramolecular aggregation of dihydropyrimidone rings on PUs chains. At the same time, with the increase of the content of dihydropyrimidone rings, the fluorescence intensity of PDPMDs also increases, and the emission wavelength shows an obvious red shift. The fluorescence of PDPMDs also showed obvious dependence on excitation wavelength, which further reveals the clusterization-triggering emission (CTE) mechanism. In summary, the strategy of endowing AIE properties to non-AIE active polymer by introducing heterocycles into the backbone through multi-component reaction provides useful guidance for AIE functionalization of other non-AIE materials.

研究领域: 材料科学 · 化学 · 高分子科学
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ANALYTICAL LETTERS · 2023 · IF 2

Fluorescent Determination of Esterase in Living Cells by A Low-Dosage, Ultra-Sensitive Probe Based on Aggregation Induced Emission (AIE)

Xiaoye Wen,Fang Li

Esterase is an essential hydrolase in organisms. Many severe diseases are caused by its abnormal expression. Sensitive probes for the esterase activity need to be developed. However, the currently reported fluorescence probes for esterase have drawbacks, such as long response times, low sensitivity, and high dosages. In this work, three fluorophores with the cyano group were designed and synthesized. The optical properties of these fluorophores were measured. A turn-on fluorescence detector for the determination of esterase with a fast response speed and high sensitivity at low doses was developed that was based upon aggregation-induced emission (AIE). The mechanism was studied by high-resolution mass spectrometry (HRMS), dynamic light scattering (DLS), and high-performance liquid chromatography (HPLC). In addition, the probe had excellent stability and biocompatibility and specifically recognized esterase with a short response time (less than 5 min) and ultra-high sensitivity. The detection limit was 1.03 × 10−4 U/mL, with a linear range from 1.03 × 10−4 to 0.05 U/mL. Furthermore, the probe had low cytotoxicity, and cellular imaging of exogenous esterase was achieved. This probe is anticipated to offer many applications in biomedical science.

研究领域: 生物化学 · 分析化学 · 生物医学科学 · 分子生物学
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JOURNAL OF NANOBIOTECHNOLOGY · 2021 ·Vol. 19 ·期 1 ·1-13 · IF 10.435

Multifunctional AIE iridium (III) photosensitizer nanoparticles for two-photon-activated imaging and mitochondria targeting photodynamic therapy

Cai Xuzi,Wang Kang-Nan,Ma Wen,Yang Yuanyuan,Chen Gui,Fu Huijiao,Cui Chunhui,Yu Zhiqiang,Wang Xuefeng

Developing novel photosensitizers for deep tissue imaging and efficient photodynamic therapy (PDT) remains a challenge because of the poor water solubility, low reactive oxygen species (ROS) generation efficiency, serve dark cytotoxicity, and weak absorption in the NIR region of conventional photosensitizers. Herein, cyclometalated iridium (III) complexes (Ir) with aggregation-induced emission (AIE) feature, high photoinduced ROS generation efficiency, two-photon excitation, and mitochondria-targeting capability were designed and further encapsulated into biocompatible nanoparticles (NPs). The Ir-NPs can be used to disturb redox homeostasis in vitro, result in mitochondrial dysfunction and cell apoptosis. Importantly, in vivo experiments demonstrated that the Ir-NPs presented obviously tumor-targeting ability, excellent antitumor effect, and low systematic dark-toxicity. Moreover, the Ir-NPs could serve as a two-photon imaging agent for deep tissue bioimaging with a penetration depth of up to 300 μm. This work presents a promising strategy for designing a clinical application of multifunctional Ir-NPs toward bioimaging and PDT.

研究领域: 生物医学工程 · 纳米技术 · 癌症治疗 · 光学成像
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FARADAY DISCUSSIONS · 2016 ·Vol. 196 ·335-350 · IF 3.544

AIE fluorophore with enhanced cellular uptake for tracking esterase-activated release of taurine and ROS scavenging

Jun Wang,Yinglong Wu,Fang Zeng,Shuailing Huang,Shuizhu Wu

Fluorophores with aggregation-induced emission (AIE) characteristics are attractive and versatile tools for both chemical sensing and biological imaging. Herein, we designed and synthesized a fluorescent light-up system CTPE-Tau with enhanced cellular uptake ability. The system possesses several advantages, such as a large Stokes shift, low cytotoxicity, and good photostability. Also, it has been successfully utilized to track esterase-activated release of taurine and to scavenge intracellular ROS, and shows great potential for trackable visualized therapy.

研究领域: 化学传感 · 生物成像 · 诊疗学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2022 · IF 4.831

Preparation of temperature-responsive nanomicelles with AIE property as fluorescence probe for detection of Fe3+ and Fe2+

Xinhui Hou,Yifan Song,Yupeng Lv,Peiyao Wang,Kun Chen,Guiying Li,Lei Guo

Temperature-responsive nanomicelles with aggregation induced emission (AIE) property were prepared by the host–guest complexation of ferrocene functionalized tetraphenyl (TPE-Fc) and β-cyclodextrin-poly ( N -isopropylacrylamide) (β-CD-(PNIPAM) 7 ). The AIE chromophore TPE-Fc bound to the hydrophobic cavity of cyclodextrin serves as the core of micelles, and temperature sensitive PNIPAM serves as the shell to give the micelles good solubility. The size of the nanomicelles is about 100 nm. At the excitation wavelength of 340 nm, the strongest fluorescent emission peak was 421 nm. The introduction of cyclodextrin star polymer increased the fluorescence intensity of nanomicelles, thus improving the recognition of probe to Fe 3+ and Fe 2+ . The fluorescent probe can quickly detect Fe 3+ and Fe 2+ in water within 5 min even in the presence of various interfering ions. The detection limits of Fe 3+ and Fe 2+ were 1.04 μM and 0.78 μM, respectively in the range of 10–90 μM. The formation of complex between the probe and Fe 3+ /Fe 2+ was supported by Job’s plot. The probe was successfully applied to the detection of Fe 3+ and Fe 2+ in actual water sample with a good recovery. In addition, a possible sensing mechanism for the interaction of iron ions with amide bond groups of nanomicelles was proposed.

CAS / MDL: 77-86-1
研究领域: 材料科学 · 分析化学 · 纳米技术
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DYES AND PIGMENTS · 2017 · IF 3.473

Novel fluorescent perylene liquid crystal with diphenylacrylonitrile groups: Observation of a large pseudo stokes shift based on AIE and FRET effects

Mingguang Zhu,Youzhen Zhuo,Kaicong Cai,Hongyu Guo,Fafu Yang

A novel perylene liquid crystal with diphenylacrylonitrile groups on 1,7-bay positions was synthesized in high yield. This highly decorated perylene bisimide showed the ordered hexagonal columnar liquid crystalline behaviour between 124.9 and 189.5 °C. Upon excitation of 480 nm, an attenuation of fluorescent intensity was observed with the increase of water fraction in THF/H 2 O mixtures. However, the fluorescence intensity enhanced dramatically and attained a maximum value at water fraction of 40% in THF/H 2 O systems when excited at 330 nm. The fluorescence intensity increased by 10 times and the pseudo Stokes shift achieved 251 nm. These phenomena were well elucidated by the AIE and FRET effect, which were supported by the investigation of fluorescence quantum yield and fluorescence lifetime .

CAS / MDL: 10026-22-9
研究领域: 材料科学 · 化学 · 光学
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JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY · 2022 · IF 6.814

Enhanced photo-hypoxia-activated combination therapy traced by AIE photosensitizer and targeted by hyaluronic acid: Disulphide bond interference of detoxification barrier

Feng Ouyang,Xiaoli Zhang,Li Zhang,Yu Liu,Qi Shuai

The treatment efficacy of anticancer drugs in complex physiological environments is still restricted by multi-drug resistance. To overcome this issue, a nanodrug system of HA-SS@CuS@ZIF-8@TPZ&TBMACN (HSCZTT) that breaks through the detoxification barrier for tirapazamine (TPZ) delivery was developed in this manuscript. In addition to the photothermal effect aroused by CuS in HSCZTT, which can damage tumour cells, TBMACN with photostable fluorescence in the aggregate state can also generate sufficient reactive oxygen species (ROS) to destroy tumour cells. The continuous consumption of oxygen in PDT aggravates the hypoxic environment of tumours, which further activates the TPZ released in the acidic microenvironment of the tumour to achieve apoptosis of the tumour cells. The HSCZTT can not only target the CD44 receptor overexpressed on the surface of the cancer cell , but can also effectively consume a large amount of glutathione (GSH) through the disulphide bond-modified hyaluronic acid, which serves as a targeted disulphide bond, interfering with the detoxification barrier. Our finding presents a rational strategy to overcome multidrug resistance for the improved efficacy of anticancer drugs by the targeting of Hyaluronic acid (HA), release of the drug by the acid response of ZIF-8, breakthrough of the detoxification barrier, precise positioning of the drug release and combined treatment with phototherapy and hypoxia-activated chemotherapy.

CAS / MDL: 1313-84-4 298-93-1
研究领域: 癌症治疗 · 纳米医学 · 药物科学 · 生物医学工程
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Frontiers in Bioengineering and Biotechnology · 2024 · IF 4.3

Antimicrobial peptide-modified AIE visual composite wound dressing for promoting rapid healing of infected wounds

Yi Chen,Hongjin Qian,Dandan Peng,Yan Jiang,Qiaolin Liu,Yan Tan,Longbao Feng,Biao Cheng,Guilan Li

Wound infection is a major problem faced during wound healing. Therefore, it is necessary to develop wound dressings with excellent antimicrobial properties. Here, a smart response system of PVA-TPE/HA-AMP/SF/ALG wound dressing was prepared by a combination of chemical cross-linking and freeze-drying methods. We grafted AMP onto HA to endow the wound dressing with bacterial resistance and slow release of AMP. At the same time, the system detects bacterial activity in real time for precise antimicrobial activity (through the use of PVA-TPE) and modulates inflammation to reduce bacterial infection (through the use of AMP). In addition, the PVA-TPE/HA-AMP/SF/ALG wound dressing has a good three-dimensional mesh structure, which promotes cell proliferation, enhances collagen deposition and angiogenesis, and thus effectively promotes rapid healing of infected wounds. Moreover, it can induce the expression of inflammatory factors such as VEGF, TNF-α, IFN-γ, IL-4 and TGF-β1 in infected wounds through the Wnt/CAMK/p-PKC signaling pathway, inhibit inflammatory responses, promote wound healing and reduce scar formation. Therefore, the PVA-TPE/HA-AMP/SF/ALG wound dressing smart response system shows great promise in infected wound healing.

CAS / MDL: 100-36-7 9002-89-5
研究领域: 材料科学 · 生物医学工程 · 伤口愈合 · 药学
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DALTON TRANSACTIONS · 2022 ·Vol. 51 ·期 42 ·16119-16125 · IF 4.569

AIE-active Ir(III) complexes functionalised with a cationic Schiff base ligand: synthesis, photophysical properties and applications in photodynamic therapy

Shengnan Liu,Jiahong Han,Weijin Wang,Yulei Chang,Runlin Wang,Ziwei Wang,Guangzhe Li,Dongxia Zhu,Martin R. Bryce

Photodynamic therapy (PDT) is a promising cancer treatment method. Traditional small-molecule photosensitizers (PSs) suffer from low intersystem crossing (ISC) ability and aggregation-caused quenching (ACQ), which adversely affects the luminous efficiency and singlet oxygen (1O2) yield of PSs in the aggregated state. Ir(III) complexes are promising PSs with long excited-state lifetime, good photophysical and photochemical properties and large Stokes shifts. Aggregation-induced emission (AIE) characteristics could reduce the nonradiative recombination and improve the ISC ability of excited states through the restriction of the intramolecular motions in aggregated states. Accordingly, two AIE-active Ir(III) complexes Ir-1-N+ and Ir-2-N+ were successfully designed and obtained based on Schiff base ligands. Experimental results showed that Ir-1-N+ and Ir-2-N+ have good photophysical properties and the corresponding nanoparticles (NPs) have good water solubility and 1O2 generation ability. Notably, Ir-2-N+ NPs can be efficiently taken up by mouse breast cancer cells (4T1 cells) with good biocompatibility, low dark toxicity and excellent phototoxicity. This work demonstrates a versatile strategy for exploiting efficient transition metal PSs with a cationic ligand in PDT.

CAS / MDL: 298-93-1
研究领域: 化学 · 材料科学 · 生物医学工程 · 癌症研究
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