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DYES AND PIGMENTS · 2024 · IF 4.1

Electronic structure modulation in quinoline derivatives through substituent-mediated effects: Development of AIE fluorescent probes for Fe3+ detection in water samples

Longjie Wang,Yuchen Zhang,Yibo Chen,Xiangdi Huang,Mingxia Feng,Zhigang Ma,Yanxiong Liu,Linlin Chen,Liyan Zheng,Qiue Cao

Iron (Fe 3+ ) is an essential trace element in biological organisms. Abnormal concentrations of Fe 3+ in aquatic possess the potential to disrupt normal physiological and metabolic processes in living organisms. Consequently, the pursuit of developing fluorescent probes for detecting Fe 3+ concentrations in water samples is highly significant. The lone electron pair on the nitrogen atom of quinoline demonstrates outstanding coordination capabilities, enabling the selective detection of metal ions through coordination. Nevertheless, the interaction between metal ions and quinoline-based fluorescent probes tends to lead to nanoparticle aggregation, causing aggregation-caused quenching (ACQ) phenomena. This severely restricts the practical application of these probes. To address this challenge, the study utilizes quinoline as the foundational framework and modulates the excited-state electronic structure of quinoline derivatives through substituent effects . This facilitates the transition from ACQ to aggregation-induced emission (AIE). By integrating theoretical calculations, the paper proposes a comprehensive strategy for designing AIE molecules based on quinoline. This contribution provides innovative perspectives on AIE molecule design. Ultimately, the AIE property of the 8-MQB molecule is harnessed to develop a fluorescent probe capable of detecting Fe 3+ in water samples. The fluorescence intensity exhibits a robust linear correlation with Fe 3+ concentrations within the range of 5.0 μM to 0.3 mM. Moreover, the probe demonstrates exceptional resistance to interference from other metal ions. In conclusion, this research presents a universal strategy for designing AIE molecules and introduces an AIE probe for the rapid detection of Fe 3+ concentrations in water samples.

研究领域: 化学 · 材料科学 · 分析化学 · 环境科学
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Polymer Chemistry · 2015 ·Vol. 6 ·期 47 ·8214-8221 · IF 5.52

Stimulus responsive cross-linked AIE-active polymeric nanoprobes: fabrication and biological imaging application

Qing Wan,Ke Wang,Chengbin He,Meiying Liu,Guangjian Zeng,Hongye Huang,Fengjie Deng,Xiaoyong Zhang,Yen Wei

The combination of functional polymers and hydrophobic AIE dyes to prepare luminescent organic nanoparticles (LONs) with strong fluorescence, great water dispersibility and desirable biocompatibility has received a lot of attention for potential applications in cell imaging and theranostics. Although great effort has been devoted to preparing AIE dye based LONs through both covalent and noncovalent strategies, the fabrication of cross-linked AIE dye based LONs with stimulus responsive behavior has not been reported previously. In this work, the AIE dye based LONs were constructed via cross-linking aldehyde-containing polymers and AIE dye (2,2′-diaminotetraphenyl ethylene) with two amino groups through formation of a Schiff base, which is a well-known dynamic bond with pH responsiveness. After successful incorporation of the hydrophobic AIE dye into the copolymers, cross-linked core–shell luminescent nanoparticles can be formed. The obtained AIE dye based LONs exhibited strong fluorescence and high water dispersibility because the AIE dye aggregated in the core and the hydrophilic polymers were covered on the shell. Biological evaluation results demonstrated that the AIE dye based LONs exhibited excellent biocompatibility and biological imaging properties. More importantly, these AIE dye based LONs exhibited desirable pH responsiveness, implying that these polymeric LONs can be potentially utilized for pH sensors and controlled drug delivery. With the combination of dynamic crosslinking and pH responsiveness, the obtained AIE dye based LONs should be of great significance for biomedical applications.

研究领域: 材料科学 · 生物医学工程 · 细胞生物学
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JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY · 2020 · IF 3.306

Multi-responsive fluorescent probe based on AIE for the determination of Fe3+, total inorganic iron, and CN- in aqueous medium and its application in logic gates

Xiaoye Wen,Li Yan,Zhefeng Fan

A novel and simple probe (denoted LN-1) with AIE property based on malononitrile and 4-diethylaminobenzaldehyde was designed and synthesized. The use of two different mechanisms for the independent detection of Fe 3+ and CN − is more convenient and efficient than the continuous detection of anions and cations. The detection mechanism was verified by mass spectrometry (MS), nuclear magnetic resonance (NMR) spectrum, and particle size distribution. Under optimized experimental conditions, excellent calibration curves were obtained for the LN-1-Fe 3+ and the LN-1-CN − with detection limits of 0.17 and 0.39 μM, respectively. This method was successfully applied to detect the content of Fe 3+ and total inorganic iron in actual samples. Owing to its low cytotoxicity, good biocompatibility, and enhanced orange emission in aqueous solution, the LN-1 was successfully applied for CN − imaging in live cells. In addition, Fe 3+ and EDTA incorporation into the LN-1 changed the fluorescent intensity, which is beneficial in constructing ultrasensitive INHIBIT logic gate.

研究领域: 分析化学 · 生物医学
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Polymer Chemistry · 2017 ·Vol. 8 ·期 48 ·7486-7498 · IF 5.375

Self-assembled core–shell-corona multifunctional non-viral vector with AIE property for efficient hepatocyte-targeting gene delivery

Bing Wang,Ping Chen,Ji Zhang,Xiao-Chuan Chen,Yan-Hong Liu,Zheng Huang,Qing-Ying Yu,Ju-Hui Zhang,Wei Zhang,Xi Wei,Xiao-Qi Yu

With the aim to develop a novel multifunctional gene delivery system that may overcome the common barriers of gene transfection, two amphiphilic molecules with tetraphenyl ethylene (TPE) as a hydrophobic moiety and linear PEI-galactose as a hydrophilic part were elaborately designed and synthesized. The molecules could self-assemble to form micelles and exhibited aggregation-induced emission (AIE) property, which may be used for cell imaging. Several assays revealed that the disulfide bond in TSPG may facilitate vector decomposition and DNA release, resulting in higher transfection efficiency and lower cytotoxicity than TCPG and PEI 25 kDa. These vectors showed excellent serum tolerance, and even higher efficiency could be obtained in transfection with the presence of serum. Moreover, the transfection in different cell lines showed that TSPG complex could induce higher gene expression in asialoglycoprotein receptor-rich HepG2 cells than in HeLa cells, which lack such receptors. Galactose competition assay also demonstrated that the galactose moiety could afford the vector with targeting ability toward hepatoma cells. Cellular uptake inhibition assay indicated that the DNA complex entered the cell mainly via caveolae-mediated endocytosis. Results showed that TSPG may serve as a promising reagent for simultaneous gene transfection and imaging with good biocompatibility and cell targeting ability.

研究领域: 生物医学工程 · 分子生物学 · 药剂学
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Frontiers in Bioengineering and Biotechnology · 2021 · IF 5.89

A Multifunctional AIE Nanoprobe as a Drug Delivery Bioimaging and Cancer Treatment System

Hu Keqi,Zhou Daquan,Rao Linlin,Wang Peng,Xiang Chunxiang,Chen Feng

Of all malignant brain tumors, glioma is the deadliest and most common, with a poor prognosis. Drug therapy is considered as a promising way to stop the progression of disease and even cure tumors. However, the presence of blood brain barrier (BBB) and blood tumor barrier (BTB) limits the delivery of these therapeutic genes. In this work, an intelligent cell imaging and cancer therapy drug delivery system targeting the blood-brain barrier and the highly expressed transferrin receptors (TfR) in gliomas has been successfully constructed, and an amphiphilic polymer (PLA-PEG-T7/TPE) with aggregation-induced emission (AIE) properties has been designed and successfully synthesized. PLA-PEG-T7/TPE self-assembled polymer micelles showed significant AIE effect in aqueous solution with good biocompatibility. Therefore, it can be used for potential biological imaging applications. In addition, drug-carrying micelles showed typical behavior of regulating drug release. Inhibition of cell proliferation in vitro showed that the drug-loaded micelles had dose-dependent cytotoxicity to LN229 cells. In the in vivo anti-tumor experiment, PLA-PEG-T7/TPE/TMZ had the best therapeutic effect. These results indicated that T7 functionalized PLA-PEG was a promising platform for nasopharyngeal cancer drug combination therapy.

CAS / MDL: 85622-93-1
研究领域: 肿瘤学 · 生物材料学 · 药理学
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CHINESE JOURNAL OF POLYMER SCIENCE · 2023 · IF 4.3

pH Induced Self-assembly of AIE Fluorescent Probe for Tumor Imaging

Xiang Jing-Yuan,Zhang Wen-Long,Li He-Ting,He Ya-Ning

This work reported an AIE fluorescent probe for tumor imaging based on the pH induced self-assembly strategy. The fluorescent probe was composed of an acid-responsive soluble copolymer PEG- b -PAMA-DMMA with a maleic acid amide group and an anionic soluble aggregation-induced emission fluorogen (AIEgen) TPE-2SO 3 − . The polymer could be transformed into a protonated amine-containing polymer after the hydrolysis of maleic acid amide in acidic tumor microenvironment, which would be further self-assembled with TPE-2SO 3 − to form aggregated nanoparticles. The transition of TPE-2SO 3 − from dispersed state to aggregated state led to an obvious increase in fluorescence intensity due to its AIE characteristics.

CAS / MDL: 2002-24-6
研究领域: 材料科学 · 生物医学工程 · 癌症研究 · 纳米技术
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NEW JOURNAL OF CHEMISTRY · 2023 ·Vol. 47 ·期 14 ·6916-6923 · IF 3.3

An “AIE + ESIPT” mechanism-based benzothiazole-derived fluorescent probe for the detection of Hg2+ and its applications

Yanru Huang,Ying Li,Yang Li,Keli Zhong,Lijun Tang

Mercury ion (Hg2+) contamination is very hazardous and harmful to the natural environment and human health. The development of small molecule fluorescent probes for the rapid detection of Hg2+ is of great significance. In the present work, an “AIE + ESIPT” mechanism-based benzothiazole derived fluorescent probe was applied to Hg2+ detection and displayed excellent selectivity, good anti-interference ability, low detection limit (2.85 × 10−9 M), and a large Stokes shift (170 nm) in the DMF/H2O mixture solution with fw = 60% H2O volume fraction. The fluorescence response mechanism, involving the desulfurization reaction of O-(2-(benzo[d]thiazol-2-yl)-6-formyl-4-methylphenyl)dimethylcarbamothioate (probe L) with Hg2+ to release the “AIE + ESIPT” fluorophore, was well established based on the UV-vis, 1H NMR, and HRMS spectral analyses. The practical application evaluation indicates that probe L could be used to precisely determine Hg2+ in live cell imaging, natural water, and seafood samples.

研究领域: 分析化学 · 环境科学 · 生物医学
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RSC Advances · 2016 ·Vol. 6 ·期 68 ·63874-63879 · IF 3.289

Synthesis and optical properties of aggregation-induced emission (AIE) molecules based on the ESIPT mechanism as pH- and Zn2+-responsive fluorescent sensors

Liqiang Yan,Tingting Qing,Renjie Li,Zhongwei Wang,Zhengjian Qi

A series of schiff base derivatives with salicylaldehyde moieties were designed and synthesized. These materials exhibit typical AIE properties and high fluorescence quantum yields in an aggregated state based on the excited-state intramolecular proton transfer (ESIPT) mechanism. Then, the effect of substituted group types and positions on the fluorescence of these novel compounds was investigated through fluorescence spectra analysis and theoretical calculations. And it was found that the salicylaldehyde derivatives can be used as potential pH and Zn2+ sensors.

研究领域: 化学 · 材料科学 · 分析化学
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DYES AND PIGMENTS · 2022 · IF 5.122

Synthesis of amphiphilic AIE fluorescent nanoparticles via CO2 involved multicomponent reaction and its biological imaging potential

Juan Fu,Ziyang He,Xin Hu,Teng Guo,Ye Liang,Fengjie Deng,Meiying Liu,Yuanqing Wen,Xiaoyong Zhang,Yen Wei

Fluorescent materials with aggregation-induced emission (AIE) have standout as one of the most interesting candidates for biomedical applications. The development of new methods for fabrication of AIE-active materials will surely advance their applications in related fields. In this work, we reported a novel method for preparation of AIE-active luminescent polymer (Lys-PEG-TPE) through a three-component reaction involving carbon dioxide (CO 2 ) using lysine, Polyethylene glycol (PEG) and AIEgen as the reactants. On account of the introduction of PEG , Lys-PEG-TPE could well disperse in aqueous solution, while hydrophobic TPE will aggregate in the core of self-assembled nanoparticles , endowing the obvious enhancement of fluorescence intensity. Results from biological assays suggested that Lys-PEG-TPE exhibits almost no toxicity after incubation with HepG2 cells and its fluorescence can be clearly observed in cytoplasm after cell internalization. More importantly, the AIE feature of Lys-PEG-TPE could not only effectively solve the aggregation-induced quenching effect of traditional fluorescent molecules, the carboxyl groups of lysine could also be used for loading functional cationic ions (e.g., anticancer drugs or imaging agents) to fabricate multifunctional theranostic and imaging composites. Considering the benign reaction conditions, high atom economy, and well tunability of reactants of multicomponent reactions, this strategy should be of broad interesting for fabrication of multifunctional AIE-active materials for biomedical applications.

研究领域: 材料科学 · 生物医学工程 · 化学
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Small · 2019 ·Vol. 15 ·期 50 ·1905080 · IF 10.856

Stereotactic Photodynamic Therapy Using a Two-Photon AIE Photosensitizer

Xiaojing He,Bo Situ,Meng Gao,Shujuan Guan,Bairong He,Xiaoxue Ge,Shiwu Li,Maliang Tao,Hang Zou,Ben Zhong Tang,Lei Zheng

Two-photon photodynamic therapy (TP-PDT) is emerging as a powerful strategy for stereotactic targeting of diseased areas, but ideal photosensitizers (PSs) are currently lacking. This work reports a smart PS with aggregation-induced emission (AIE) feature, namely DPASP, for TP-PDT with excellent performances. DPASP exhibits high affinity to mitochondria, superior photostability, large two-photon absorption cross section as well as efficient reactive oxygen species generation, enabling it to achieve photosensitization both in vitro and in vivo under two-photon excitation. Moreover, its capability of stereotactic ablation of targeted cells with high-precision is also successfully demonstrated. All these merits make DPASP a promising TP-PDT candidate for accurate ablation of abnormal tissues with minimal damages to surrounding areas in the treatment of various diseases.

研究领域: 诊疗学 · 生物医学工程 · 分子影像 · 癌症治疗
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DYES AND PIGMENTS · 2019 · IF 4.018

An AIE dye based smartphone and LDA integrated portable, intelligent and rapid detection system as trace water indicator and cyanide detector

Linfeng Chen,Xike Tian,Yong Li,Chao Yang,Liqiang Lu,Zhaoxin Zhou,Yulun Nie

Portable, rapid, accurate and on-site detection of analysis target has always been the goal of continuous efforts in the field of analysis. In this work, a novel intelligent and rapid detection system based on an AIE dye (TPA-DCV) was established for portable and on-site detection of trace water in organic solvents and CN − in water by integrating the smartphone and linear discriminant analysis (LDA). The TPA-DCV displayed remarkable solvatochromism effect and showed different fluorescence colors to different water contents of different solvents, with the minimum detection limit of 54 ppm. In addition, TPA-DCV also exhibited specific response to CN − , and showed significant fluorescence changes to different amounts of CN − . With the assist of this detection system, these different fluorescence color signals could be accurately classified in canonical score plot. What's more, the classification and distribution of fluorescence color in canonical score plot showed regular change with the target concentration, which could be used to quantify the trace water and CN − . The rationality and practicability of this detection system were preliminary verified by a large number of real sample analyses. This detection system greatly simplifies the analysis process, which is in the proof of intelligent and rapid detection just using a simple color analysis without any instrument test, which may be a big step forward.

研究领域: 分析化学 · 环境科学 · 生物医学工程
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ACS Applied Materials & Interfaces · 2024 · IF 8.3

Multiple Applications of Chiral Self-Assembled H8–BINOL Nanoprobes with AIE-ESIPT Characteristics: Chiral Switching and pH Visualization Detection

Rong Wang,Kaiyue Song,Lixue Yang,Yue Sun,Xiaoxia Sun,Yu Hu

R-BTOBD exhibited significant aggregation-induced Emission (AIE) characteristics, including high brightness (αAIE ≈ 40), robust light stability, a substantial Stokes shift (128 nm), and a high signal-to-noise ratio, effectively overcoming aggregation-caused quenching (ACQ). Derived from the axially chiral R-H8–BINOL, R-BTOBD was synthesized via nucleophilic cyclization and exhibited pronounced self-assembly properties. Through robust intra- and intermolecular hydrogen bonding interactions, R-BTOBD formed diverse supramolecular structures, including spherical flower-like aggregates, hollow-core triangular tubules, hexagonal tubules, and irregular white block-like stacks. The specific morphology was influenced by factors such as solvent and pH. For fluorescence applications, R-BTOBD can be employed as an effective visual pH detector through an AIE-enhanced excited-state intramolecular proton transfer (AIE-ESIPT) mechanism. When incorporated into pH paper, it exhibited a bright yellow fluorescence across a wide pH range (pH 1–11), transitioning to an intense bright blue fluorescence under strongly basic conditions (pH 12–14). In chiral applications, R-BTOBD demonstrated potential as a chiral switching agent, leveraging the pronounced changes and inversions in its circular dichroism (CD) signals under varying aggregation states and pH conditions. Additionally, it serves as a specific chiral enantioselective fluorescence probe for l-lysine, demonstrating high efficiency and a low detection limit. Given its exceptional fluorescence and chiral properties, this fluorescent material has significant potential for diverse applications in fluorescence, chirality, and visual inspection.

研究领域: 材料科学 · 分析化学 · 生物化学
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