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COLLOID AND POLYMER SCIENCE · 2020 ·Vol. 298 ·期 8 ·1119-1128 · IF 1.536

Redox-responsive AIE micelles for intracellular paclitaxel delivery

Wang Qiang,Gao Feng,Zhou Xianyong

Compared with conventional drug nanocarriers, multifunctional drug delivery systems exhibited characteristic advantages. In this study, we developed a multifunctional drug delivery system possessing stimuli-responsive drug release and cellular imaging. Amphiphilic polymers, methoxypolyethylene glycol-cystamine-tetraphenylethene (mPEG 1k -SS-TPE), were synthesized by combining methoxypolyethylene glycol (mPEG 1k ) and tetraphenylethene (TPE) using reduction-sensitive disulfide bonds that can be disconnected by high level of inherent glutathione (GSH). Size distribution and morphology of mPEG 1k -SS-TPE micelles were evaluated. Meanwhile, the reduction-sensitivity of mPEG 1k -SS-TPE micelles was surveyed compared with that of mPEG 1k -TPE micelles. Nile Red was encapsulated into mPEG 1k -SS-TPE micelles to visually observe intracellular drug delivery against SW480 cells. Paclitaxel (PTX) was chosen to be loaded into micelles to evaluate the cytotoxicity against HCT116, HT-29, and SW480. Graphical Abstract

研究领域: 生物材料 · 药物化学 · 肿瘤学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2024 · IF 7.7

Chitosan based fluorescent probe with AIE property for detection of Fe3+ and bacteria

Peiyao Wang,Yupeng Lv,Xinhui Hou,Xiaoluan Yang,Qian Tao,Guiying Li

Fluorescent probe with aggregation-induced emission (AIE) property has been widely used because of the advantages of high sensitivity, good selectivity and non-destructive testing. The development of fluorescent probe with good biocompatibility, photostability and biodegradability is of great significance in biomedicine and environmental detection. Herein, a novel type of fluorophore CS-TPE for detection of Fe 3+ and bacteria was prepared by the Schiff base reaction of chitosan (CS) and 4-(1,2,2-triphenylethenyl) benzaldehyde (TPE-CHO). The fluorescence response mechanism of CS-TPE system was investigated by various characterization techniques. CS-TPE had an obvious AIE behavior with strong blue-green emissions at 473 nm and reaches the highest photoluminescence (PL) emission in 90 % H 2 O/ethanol mixtures. CS-TPE fluorescent probe exhibited sensitive quenching response to Fe 3+ , which can be used as a biosensor for detecting the concentration of Fe 3+ with short response time (5 min), low detection limit (0.998 μM) and wide detection range (10–300 μM). Meanwhile, CS-TPE exhibited good antibacterial performance for S. aureus and E. coli . It is expected to realize the real-time fluorescence monitoring of metal ion detection and antibacterial process.

CAS / MDL: 77-86-1
研究领域: 生物医学 · 环境科学
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SENSORS AND ACTUATORS B-CHEMICAL · 2024 · IF 8

AIE-labeled fluorescent polystyrene nanoplastics for quantitative analysis in macrophages uptake

Long Zhang,Guozhou Li,Qi Xin,Haonan Liu,Xuezhi Yang,Yin Liu

Nanoplastics have attracted significant attention due to their harmful effects on the environment and organisms. However, accurately detecting and quantifying nanoplastics that are ingested by organisms poses a challenge. Conventional organic fluorescent-labeled nanoplastics have reduced labeling efficiency due to aggregation-caused quenching (ACQ), leading to artifacts caused by leakage of fluorescent molecules. To address these limitations, this study utilized AIE fluorescence for internally labeling polystyrene nanoparticles. AIE-active molecules do not emit fluorescence in dilute solutions, thus preventing accuracy issues associated with fluorescence leakage. Three model plastics (TPE@PS) of varying particle sizes were synthesized via the swelling method. The preparation parameters were optimized, followed by stability tests conducted on TPE@PS. Fluorescence microscopy imaging revealed significant uptake of TPE@PS by RAW246.7 cells. A successful standard curve of fluorescence intensity-concentration was established successfully and utilized to accurately quantify the amount of TPE@PS that was ingested by RAW246.7 cells. The results indicate a consistent increase with increasing concentration in TPE@PS uptake across all particle sizes during the fixed exposure duration of 48 h. Furthermore, RAW264.7 cells exhibited a higher propensity to uptake smaller TPE@PS particles. Flow cytometry was also employed to validated the suitability of TPE@PS as a model nanoplastic for tracing purposes.

CAS / MDL: 78-67-1 632-51-9
研究领域: 环境科学 · 生物医学
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DESIGNED MONOMERS AND POLYMERS · 2022 · IF 3.718

The preparation of novel AIE fluorescent microspheres by dispersion polymerization

Hui Wang,Zhizhou Liu,Xueyan Nan,Tong Wang,Xuming Sun,Liang He,Pengli Bai

An approach to prepare monodisperse polystyrene microspheres with aggregation-induced emission (AIE) characteristics has been developed which shows promising applications in fluorescence-encoding. The micron-sized, monodisperse polystyrene microspheres with AIE molecules were perfectly synthesized by two-stage dispersion polymerization. Fluorescent AIE monomer was synthesized by Suzuki reaction, confirmed by nuclear magnetic resonance (NMR). These AIE fluorogens (AIEgens) exhibited unique properties such as bright green emission in solid state and increased emission in tetrahydrofuran (THF) solution with the increase of water content. The influence of the AIE molecules concentration to microspheres synthesis was well investigated. The reaction conditions were optimized to obtain the functional polystyrene microspheres with a size distribution around 3%. The novel microspheres were characterized by scanning electron microscopy (SEM), confocal fluorescence microscope and flow cytometry. According to these results, two-stage dispersion polymerization was proved to be an efficient pathway for the preparation of AIE fluorescent and functionalized microspheres, which could be used in many biomedical industries.

研究领域: 材料科学 · 生物医学工程
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2021 · IF 4.098

Two-phase activated colorimetric and ratiometric fluorescent sensor for visual detection of phosgene via AIE coupled TICT processes

Qinghua Hu,Tao Gong,Yu Mao,Qiang Yin,Yuyuan Wang,Hongqing Wang

In this paper, we specifically designed and synthesized an excellent colorimetric and ratiometric fluorescent sensor DPA-CI for rapid and convenient detection of the highly toxic phosgene. DPA-CI was developed by incorporated a diphenylamine (DPA) and a 2-imine-3-benzo[d]imidazole as the enhanced push–pull electronic structure into the coumarin fluorophore matrix. The sensor DPA-CI towards phosgene sensing exhibited both visible colorimetric and ratiometric fluorescent color change in solution and in gaseous conditions with TICT and AIE mechanism respectively, which can be easily distinguished by using the naked eye. Also, the sensor DPA-CI showed splendid sensing performance such as excellent selectivity, rapid response (less than 8 s in THF and 2 min in gaseous condition), and fair sensitivity (limit of detection less than 0.11 ppm in gaseous condition and 0.27 μM in solution). The design strategy based on enhanced push–pull electronic structure with AIE and TICT properties will be helpful to construct a solid optical sensor with excellent potential application prospects for portable and visual sensing of gaseous phosgene through distinct color and ratiometric fluorescence change by the naked eyes.

研究领域: 化学 · 材料科学
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TETRAHEDRON · 2015 · IF 2.641

Preparation of ultrabright AIE nanoprobes via dynamic bonds

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

Preparation and biomedical applications of aggregation induced emission (AIE) dye based fluorescent nanoprobes (FNPs) have been extensively investigated in recent years. And great efforts have been devoted toward fabrication of AIE dye based FNPs through both noncovalent and covalent strategies. However, to the best of our knowledge, the preparation of AIE dye based FNPs via dynamic bonds is rarely reported. In this work, ultrabright FNPs based on AIE dyes have been fabricated using aldehyde-terminated polyethylene glycol (CHO-PEG-CHO) with molecular weight of 2000 Da and 2,2′-diaminotetraphenyl ethylene (TPE-NH 2 ) through formation of Schiff base . The resulting TPE contained copolymers are prone to self-assemble into stabilized core shell nanoparticles (TPE@PEG FNPs). The successful formation of TPE@PEG FNPs was confirmed by 1 H nuclear magnetic resonance spectroscopy, transmission electron microscopy , fluorescence spectroscopy and Fourier transform infrared spectroscopy . Due to their amphipihlic properties, TPE@PEG FNPs displayed high water dispersibility and strong fluorescence intensity . Furthermore, biological evaluation results demonstrated that TPE@PEG FNPs possess excellent biocompatibility and can be facilely internalized by cells. The extraordinary fluorescent properties, excellent water dispersibility as well as the desirable biocompatibility make TPE@PEG FNPs promising candidates for biomedical applications. On the other hand, because of the pH stimuli responsiveness of Schiff base, TPE@PEG FNPs are expected to exhibit some advantages for biomedical applications as compared with the FNPs fabricated by noncovalent and covalent strategies.

研究领域: 生物医学 · 材料科学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2019 · IF 2.931

A benzothiazole-rhodol based luminophor: ESIPT-induced AIE and an application for detecting Fe2+ ion

Jianping Guan,Qin Tu,Long Chen,Mao-Sen Yuan,Jinyi Wang

Herein, we designed and synthesized a luminophor, Rh-F , which is an intergrant of rhodol and 2-hydroxy benzothiazole by introducing a benzothiazole unit onto the ortho-position of the phenolic hydroxy of rhodol. Rh-F exhibited excellent fluorescence properties such as a large Stokes shift (>180 nm) and the synergistic effect of aggregation-induced emission (AIE) and an excited state intramolecular proton transfer (ESIPT) feature. The AIE/ESIPT mechanism was thoroughly explored using X-ray single-crystal structures and photophysical determinations. Furthermore, Rh-F showed a sensitive fluorescence response to Fe 2+ with low detection limits of 115.2 nM and high selectivity. Studies of its sensing mechanism indicated that the Fe 2+ -induced blue-green fluorescence-quenched at 525 nm originates from an irreversible Fe 2 + chelate with the oxygen atom of the hydroxyl group and the N atom of the benzothiazole moiety. This blocked the ESIPT process of Rh-F which resulted in the quenching of the fluorescence sensor for Rh-F .

研究领域: 化学 · 材料科学 · 分析化学
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JOURNAL OF MOLECULAR STRUCTURE · 2024 · IF 4

A novel fluorescent probe used for the detection of Cu2+ in water system with AIE properties

Hao Hu,Lei Xue,Yelin Yao,Linlong Deng,Haibin Wang

A novel fluorescent probe, WH , was successfully designed and synthesized. WH demonstrated continuous detection capabilities for Cu 2+ and EDTA in the HEPES system. Specifically, the introduction of copper ions resulted in fluorescence quenching, while the addition of EDTA led to the recovery of fluorescence. The detection limits of WH for Cu 2+ and EDTA were calculated to be 29.66 and 172.13 nmol· L −1 , respectively. Moreover, WH exhibited AIE property in THF/H 2 O system. According to the Job's plot, 1 H NMR titration and mass spectrometry, WH could form a complex with Cu 2+ in a 1:1 ratio, and the combinding constant was 8.2 × 10 3 L mol −1 . WH exhibited outstanding selectivity, high sensitivity, large Stokes shift and strong anti-interference ability. Furthermore, WH had been successfully applied in the detection of Cu 2+ in beer and red wine, showcasing its promising potential for practical application.

研究领域: 分析化学 · 材料科学 · 环境科学
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Science China-Chemistry · 2016 ·Vol. 59 ·期 8 ·1003-1009 · IF 2.429

One-step preparation of branched PEG functionalized AIE-active luminescent polymeric nanoprobes

Chu Jun,Lv Qiulan,Guo Chunliang,Xu Dazhuang,Wang Ke,Liu Meiying,Huang Hongye,Zhang Xiaoyong,Wei Yen

The synthesis of amphiphilic aggregation-induced emission (AIE) dyes based organic nanoparticles has recently attracted increasing attention in the biomedical fields. These AIE dyes based nanoparticles could effectively overcome the aggregation caused quenching effect of conventional organic dyes, making them promising candidates for fabrication of ultrabright organic luminescent nanomaterials. In this work, AIE-active luminescent polymeric nanoparticles (4-NH 2 -PEG-TPE-E LPNs) were facilely fabricated through Michael addition reaction between tetraphenylethene acrylate (TPE-E) and 4-arm-poly(ethylene glycol)-amine (4-NH 2 -PEG) in rather mild ambient. The 4-NH 2 -PEG can not only endow these AIE-active LPNs good water dispersibility, but also provide functional groups for further conjugation reaction. The size, morphology and luminescent properties of 4-NH 2 -PEG-TPE-E LPNs were characterized by a series of techniques in detail. Results suggested that these AIE-active LPNs showed spherical morphology with diameter about 100–200 nm. The obtained 4-NH 2 -PEG-TPE-E LPNs display high water dispersibility and strong fluorescence intensity because of their self assembly and AIE properties of TPE-E. Biological evaluation results demonstrated that 4-NH 2 -PEG-TPE-E LPNs showed negative toxicity toward cancer cells and good fluorescent imaging performance. All of these features make 4-NH 2 -PEG-TPE-E LPNs promising candidates for biological imaging and therapeutic applications.

研究领域: 材料科学 · 生物医学工程 · 分子影像学
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CHEMICAL ENGINEERING JOURNAL · 2022 · IF 16.744

H2O brace molecules to slip stack: Transform ACQ to AIE for latent fingerprints recognition

Bingyan Han,Dan Li,Xiangshan Lei,Qingdong Liu,Yajun Chen,Qifang Yan,Jiao Wang,Gaohong He

Aggregation-induced emission (AIE) materials have received a lot of attention in recent years, however, it remains a great challenge to develop a facile method for the conversion of aggregation-caused quenching (ACQ) molecules to AIE. In this paper, the ACQ molecule, 3,5-diacetyl-1,4-dihydro-2,6-lutidine (DDL), is successfully transformed from face-to-face stacking to slip stacking under the induction of H 2 O, achieving the transformation of ACQ molecule to AIE. Experimental analysis and theoretical calculations show that H 2 O is inserted into DDL molecules through hydrogen bonds, and its spatial configuration makes an angle between the H 2 O and DDL planes, thus increasing the horizontal and vertical distances between adjacent DDL molecules, so that DDL is arranged in a slip stacking pattern. Meanwhile, hydrogen bonds fix the DDL molecules in a relatively rigid structure, leading to the generation of other weak interactions, which further restrict the molecular motion and reduce the non-radiative transitions, so that the DDL possesses the AIE property, and the quantum yield increases from 0.95 % to 25.60 %. Based on the high fluorescence intensity of DDL-H 2 O, it has been successfully applied to the first-, second- and tertiary-level structures of latent fingerprints (LFPs) identification, which provides more possibilities for the practical application of ACQ molecules.

CAS / MDL: 631-61-8
研究领域: 化学 · 材料科学 · 法医学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2020 · IF 3.232

“Turn-on” fluorescent sensor for Th4+ in aqueous media based on a combination of PET-AIE effect

Shibing Chen,Shengjie Jiang,Hongyu Guo,Fafu Yang

Previously reported fluorescent sensors for Th 4+ experienced emission quenching or generated false positive signal upon aggregate formation in aqueous media. Herein, a simple and novel thorium sensor ( CDB-BA ) based on cyanodistyrene structure was designed and synthesized, which integrated the highly emitting characteristic of AIE effect and off-on response of PET modulation for the first time to construct the “turn-on” fluorescent probe for Th 4+ . Besides excellent selectivity, CDB-BA exhibited remarkable fluorescent enhancement which was linearly related to the concentration of Th 4+ in the range of 0.25–8 μM. The detection limit was attained 0.074 μM, which was lower than that of most previously reported sensors. The mechanism of tris-chelate complex of CDB-BA with Th 4+ was confirmed by mass spectra, IR spectra and DFT calculation. The excellent Th 4+ sensing ability of CDB-BA was successfully applied to detecting Th 4+ on TLC plates, in real water samples and living-cell imaging. This work suggested that the combination of AIE and PET photophysical mechanism could offer the merits of minimized background and enhanced signal fidelity to develop novel “turn-on” fluorescent probe in complicated aqueous environment and biological research.

研究领域: 化学 · 生物医学
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RSC Advances · 2018 ·Vol. 8 ·期 13 ·6798-6804 · IF 2.936

A novel biocompatible zwitterionic polyurethane with AIE effect for cell imaging in living cells

Junhuai Xu,Rui Yan,Haibo Wang,Zongliang Du,Jun Gu,Xu Cheng,Junjie Xiong

In this work, a novel and stable zwitterionic polymer (TPE-CB PUs) was prepared to realize a cellular imaging system. TPE was conjugated into the backbone of zwitterionic polyurethane, which could be well dispersed in aqueous solution and emitted strong blue fluorescence because the TPE segment was aggregated in the core of TPE-CB PUs micelles. More importantly, the TPE-CB PUs micelles showed significant stability in a large pH window and with different storage times. In addition, the micelles exhibited low cytotoxicity in HeLa cells and mainly distributed in the cytoplasm after being incubated with cells. The outstanding properties of TPE-CB PUs combining the merits of AIE and a zwitterionic segment highlight its potential for use as a cell imaging material with remarkable capability.

研究领域: 材料科学 · 生物医学工程 · 细胞生物学
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