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AIEgen
ACS Applied Nano Materials · 2022 · IF 6.14

Supramolecular Luminol–AIEgen Nanoparticles for Deep-Tissue-Inflammation Imaging

Jia Chen,Qiaoxian Huang,Qingfu Wang,Yuanfu Ding,Siyu Lu,Lian-Hui Wang,Shengke Li,Ruibing Wang

Inflammation is one of the most common pathological processes involved in numerous diseases. Thus, bioimaging of inflammation is of great significance for the diagnosis and treatment of a variety of inflammatory diseases. Herein, for the first time, we report a supramolecular luminol–AIEgen nanoparticle (SLA NP)-based bioluminescent probe for deep-tissue-inflammation imaging. SLA NPs were facilely fabricated by anchoring adamantane–luminol (AdLum) onto NPs derived from AIEgen–cucurbit[7]uril (AIECB[7]) via CB[7]–Ad host–guest interactions. The designed SLA NPs are capable of efficient bioluminescence resonance energy transfer (BRET) from luminol (donor) to AIEgen (acceptor), enabling deep-tissue penetration and fluorescent imaging. SLA NPs possess uniform particle size and excellent stability and biocompatibility for in vitro and in vivo inflammation imaging, superior to commercial luminol. This work not only demonstrates the enhanced deep-tissue-inflammation imaging of luminol via its BRET pairing with AIEgen NPs but also offers important new insights into the construction of luminol–AIEgen BRET pairs through host–guest complexation.

CAS / MDL: 7681-52-9 16561-29-8
研究领域: 生物医学工程 · 分子影像学 · 纳米医学
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ADVANCED MATERIALS · 2021 ·Vol. 33 ·期 45 ·2104615 · IF 30.849

AIEgen-Based Lifetime-Probes for Precise Furin Quantification and Identification of Cell Subtypes

Hui Jia,Defang Ding,Jingjing Hu,Jun Dai,Juliang Yang,Guogang Li,Xiaoding Lou,Fan Xia

Biochemical sensing probes based on aggregation-induced-emission luminogens (AIEgens) are widely used in biological imaging and therapy, chemical sensing, and material sciences. However, it is still a great challenge to quantify the targets through fluorescence intensity of AIEgen probes due to their undesirable aggregations. Here, a PyTPA-ZGO probe with three lifetime signals for precise quantification of furin is constructed: the lifetime signal 1 and signal 2 comes from AIEgen PyTPA-P (τ Pn ) and inorganic nanoparticles Zn 2 GeO 4 :Mn 2+ -NH 2 (τ Zn ), respectively, while the lifetime signal 3 is marked as the composite dual-lifetime signal (CDLS n , C D L S n = τ Z n τ P n ). In contrast, the fluorescence intensity signal of PyTPA-P shows defectively quantitative performance. Furthermore, it is found that the CDLS n exhibits higher significant differences than the two other lifetime signals (τ Pn and τ Zn ) thanks to its wide range between the maximum and minimum signal values and small standard deviation. Therefore, CDLS n is further used to accurately identify cell subtypes based on the specific concentration of furin in each subtype. The lifetime criterion can realize precise quantification, and it should be a promising direction of AIEgen-based quantitative analysis in the future.

研究领域: 生物成像 · 化学传感 · 材料科学
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CARBOHYDRATE POLYMERS · 2023 · IF 11.2

Water soluble AIEgen-based thermosensitive and antibacterial hydroxypropyl chitin hydrogels for non-invasive visualization and wound healing

Long Huang,Mingzhen Cai,Qianqian Qiao,Taotao Li,Junyu Chen,Xulin Jiang

Antimicrobial hydrogels containing antibacterial agents have been extensively studied for postoperative infections, wound repair and tissue engineering. However, the abuse of antibiotics has led to the enhancement of bacterial resistance and traditional antibacterial agents are losing their effect. Therefore, fabricating novel and efficient antibacterial hydrogels with enhanced photodynamic antimicrobial activity , good biocompatibility, biodegradability and injectability are highly desirable for clinical application. Herein, a fluorescent and sunlight-triggered synergetic antibacterial thermosensitive hydrogel (red fluorescent hydroxypropyl chitin , redFHPCH) is constructed based on a new water-soluble AIEgen (aggregation-induced emission fluorogen) covalently introduced in hydroxypropyl chitin for non-invasive visualization and wound healing. The thermosensitive redFHPCH solution showing good injectability with fluidity at low temperature was completely transformed into hydrogel under body temperature. The in vitro and in vivo visualization and reactive oxygen species (ROS) generation of the redFHPCH hydrogel are demonstrated clearly because of its excellent AIE fluorescence imaging quality in the red/near-infrared region and superefficient ROS production by sunlight. Moreover, the redFHPCH hydrogel with positively charged quaternary ammonium groups displays a strong synergistic antibacterial effect for healing of infected wound under sunlight irradiation. We believe that this novel strategy can open a new door to explore diversified and multifunctional hydrogels for clinical application.

研究领域: 生物材料学 · 医学工程 · 药剂学
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ACS Applied Nano Materials · 2024 · IF 5.3

AIEgen Photosensitizer-Loaded Silica Nanoparticles for Lysosomes-Targeting Photodynamic Therapy in Tumor

Mingyan Zhao,Wenguang Zhang,Miaozhuang Fan,Zhourui Xu,Yihang Jiang,Zhengzheng Li,Peng Zhai,Xinmeng Zhang,Ting Chen,Yibin Zhang,Chengbin Yang,Longfei Li,Gang Feng,Gaixia Xu

Aggregation-induced emission (AIE)-based photosensitizers (PSs) are well-known for their exceptional biocompatibility and high irradiation-induced reactive oxygen species (ROS) generation capacity, making them promising candidates for photodynamic therapy (PDT). In antitumor treatment, enhancing the spatiotemporal specificity of AIEgen PSs can maximize the efficacy of suppressing tumor cells. Lysosomes, as digestive cellular organelles, can be perturbed by various external stimuli, leading to cellular dysfunction and even apoptosis. This makes them ideal targets for effective and precise PDT. In this study, an AIE photosensitizer MEO-TTMN (MT) was encapsulated with a silica shell to develop AIE-based silica nanoparticles (NPs), MT@SiO2-MP NPs, for antitumor PDT. The absorption and emission peaks of these NPs were at 513 and 675 nm, respectively. Upon irradiation, MT@SiO2-MP NPs exhibited a stronger ROS generation capacity when compared with the commercial photosensitizer chlorin e6 (Ce6). The decoration of the morpholine group on the surface of the silica shell facilitated MT@SiO2-MP NPs to accumulate specifically in the cellular lysosomes. A high level of ROS was proven to be in situ generated at the lysosomal sites by irradiation, which led to the damage of lysosomes and subsequent apoptosis of tumor cells. The in vivo PDT of tumor-bearing mouse demonstrated that MT@SiO2-MP NPs significantly suppressed the growth of the tumor. This work has provided efficient lysosome-targeting NPs to improve PDT efficacy and accuracy, which is beneficial for cancer therapy in the field of nanomedicine research.

CAS / MDL: 9003-11-6
研究领域: 生物医学工程 · 纳米医学 · 肿瘤学
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CHEMICAL ENGINEERING JOURNAL · 2022 · IF 16.744

A colorimetric and ratiometric fluorescent paper chip for biogenic amine monitoring based on a simple pH-sensitive AIEgen

Xirui Chen,Yujie Tu,Song Cheng,Xujing Guo,Tianying Lu,Yuqian Guo,Xiaolin Huang,Yonghua Xiong,Ben Zhong Tang

Existing single-signal-response fluorescent materials for biogenic amine detection have unsatisfactory detection performance. Herein, we developed a simple pH-sensitive aggregation-induced emission-active fluorogen (AIEgen) and demonstrated its potential for ratiometric monitoring of biogenic amines. This AIEgen, namely 4-(dimethylamino)styryl)quinoxalin-2(1 H )-one (ASQ), shows a typical donor (D)-acceptor (A) structure with nonmonotonic color and fluorescence responses to pH stimulation by its protonation/deprotonation on the D/A moieties. Subsequently, the H + ASQ-labeled paper chips were successfully prepared by physically depositing ASQ on qualitative filter paper, followed by the acidification by hydrochloric acid. Upon the exposure to ammonia vapour, the obtained H + ASQ-labeled paper chips exhibited obvious color and ratiometric fluorescence responses owing to the deprotonation of H + ASQ indicators, indicating that the proposed paper chips can be used for the detection of biological amines by bimodal colorimetry and ratiometric fluorescence. Under the optimal conditions, H + ASQ-labeled paper chip achieved the real-time, non-destructive, and visual monitoring of meat and seafood freshness by simultaneously quantify the biogenic amine index with high performance liquid chromatography (HPLC). The results of this work suggest that ratiometric AIEgen can serve as a promising alternative strategy to ensure accurate monitoring of biogenic amines and food freshness.

研究领域: 分析化学 · 食品安全 · 生物传感
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Journal of Materials Chemistry C · 2023 ·Vol. 11 ·期 10 ·3504-3512 · IF 6.4

Orthogonal integration of holographic and fluorescent dual images based on energy transfer from liquid crystals to a photocleavable AIEgen

Ming Yao,Ye Zhao,Xingping Zhou,Zhong’an Li,Haiyan Peng,Xiaolin Xie

Orthogonal integration of dual-mode optical images has become a hot topic in recent years due to the greatly increased information density, capacity and security. However, it remains challenging to improve the color diversity of the patterned images due to the stringent requirements of orthogonality during both image patterning and readout. Herein, we demonstrate a facile method to dial a fluorescent color when reconstructing dual images via Förster resonance energy transfer from liquid crystals (LCs) to a photocleavable AIEgen (e.g., TPE-Cou that comprises tetraphenylethylene and coumarin units). The energy transfer efficiency can be readily tuned from 0 to 99% by varying the TPE-Cou/LC weight ratio or controlling the photocleavage kinetics of TPE-Cou, making the fluorescent color readily tuned from blue-violet to yellow. Eventually, crosstalk-free integration of fluorescent and holographic dual-mode images has been successfully realized due to the orthogonality between the photocleavage reaction and holographic photopolymerization. Not only viewing-angle dependent structural color can be achieved owing to Bragg diffraction of the holographic patterns, but also multi-color fluorescent images can be encoded, which is highly promising for high security-level anticounterfeiting.

研究领域: 材料科学 · 光学工程 · 化学
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DYES AND PIGMENTS · 2023 · IF 4.5

Design the synthesis of AIEgen photosensitizers for regulating the level of PTX in drug-resistant tumor cells

Huifang Yao,Xiaobo Xiong,Feng Wu,Xiangyang Hu

The general mechanism of chemotherapeutic resistance is related to changes in the uptake and efflux rate of chemotherapeutic drugs or intracellular transport. In the progress of photodynamic and PTX combination therapy, the excessive use of photosensitizers (PSs) may cause side effects. Since PSs are exposed to light, they can still cause ongoing damage to normal cells. To effectively reduce this side effect, we propose a strategy to regulate the concentration of PTX in resistant cells using low concentrations of AIEgen PSs. In this work, the molecular structure of four AIEgen PSs ( TPEPy , TPECPy , TPAPy , and TPESPy ) were designed and synthesized featuring different “D−π−A” type structures. They displayed excellent optical properties , good biocompatibility , good PDT effect, mitochondrial targeting and cell imaging . Among these AIEgen PSs, TPESPy exhibited the strongest PDT effect in tumor cells and PTX resistant tumor cells. The reversal coefficient of PTX resistant tumor cells can be achieved as 2214. In addition, to demonstrate the transport mechanism of PTX within tumor cells, we further study the effect of uptake and expel PTX in the PTX resistant SKOV-3 cells. The results show the rate of uptake and expel PTX for PTX resistant SKOV-3 cells can be effectively changed by controlling the concentration of AIEgen PSs and light irradiation time, providing precise treatment options for drug-resistant tumor cells.

CAS / MDL: 307554-62-7
研究领域: 生物化学 · 肿瘤学 · 药理学
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Nature Communications · 2020 ·Vol. 11 ·期 1 ·1-10 · IF 12.121

Chiral recognition and enantiomer excess determination based on emission wavelength change of AIEgen rotor

Hu Ming,Yuan Ying-Xue,Wang Weizhou,Li Dong-Mi,Zhang Hong-Chao,Wu Bai-Xing,Liu Minghua,Zheng Yan-Song

Chiral recognition, such as enantioselective interactions of enzyme with chiral agents, is one of the most important issues in the natural world. But artificial chiral receptors are much less efficient than natural ones. For tackling the chiral recognition and enantiomer excess (ee) analysis, up until now all the fluorescent receptors have been developed based on fluorescence intensity changes. Here we report that the chiral recognition of a large number of chiral carboxylic acids, including chiral agrochemicals 2,4-D, is carried out based on fluorescent colour changes rather than intensity changes of AIEgen rotors. Moreover, the fluorescence wavelength of the AIEgen rotor linearly changes with ee of the carboxylic acid, enabling the ee to be accurately measured with average absolute errors (AAE) of less than 2.8%. Theoretical calculation demonstrates that the wavelength change is ascribed to the rotation of the AIEgen rotor upon interaction with different enantiomers.

研究领域: 化学 · 分析化学 · 材料科学 · 光学
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Materials Horizons · 2018 ·Vol. 6 ·期 3 ·546-553 · IF 13.183

A two-photon AIEgen for simultaneous dual-color imaging of atherosclerotic plaques

Bo Situ,Meng Gao,Xiaojing He,Shiwu Li,Bairong He,Fengxia Guo,Chunmin Kang,Shan Liu,Lei Yang,Meijuan Jiang,Yanwei Hu,Ben Zhong Tang,Lei Zheng

High-resolution imaging of lipids within the artery is of great value to obtain fundamental knowledge about their roles in atherosclerosis, but ideal probes are still lacking. In this study, we report a smart probe, namely, IND with aggregation-induced emission property for two-photon visualization of lipids within cell lines and arteries. Taking advantage of high lipid specificity, deep tissue penetrability, and excellent two-photon imaging performance, IND is capable of high-resolution imaging of lipids in cultured cells and in situ mapping of three-dimensional lipid distributions in mouse atherosclerotic plaques without tedious histological preparations. Importantly, we find that IND exhibits distinct emissive properties in the molecular monomer and dimer states; also, we uncover its remarkable applications for single-excitation dual-color imaging of lipid/water in the tissue microenvironment to reveal the ultra-structure of atherosclerotic plaques. The findings described herein provide a simple tool with minimal disruptive procedures for studying atherosclerosis at the tissue level and a powerful strategy for the development of imaging-based diagnostic techniques with color switching capability.

研究领域: 生物医学工程 · 成像科学 · 心血管疾病
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ANALYTICAL CHEMISTRY · 2023 · IF 7.4

Cascade-Activated AIEgen-Peptide Probe for Noninvasively Monitoring Chymotrypsin-like Activity of Proteasomes in Cancer Cells

Qishu Jiao,Yaxin Zheng,Shicheng Pei,Xuan Luo,Xiaoxing Wu,Keming Xu,Wenying Zhong

Noninvasive monitoring of chymotrypsin-like (ChT-L) activity of proteasomes is of great significance for the diagnosis and prognosis of various cancers. However, commercially available proteasome probes usually lack adequate cancer-cell selectivity. To noninvasively monitor ChT-L activity of proteasomes in living cells, we rationally designed a cascade-activated AIEgen-peptide probe (abbreviated as TPE-1p), which self-assembled in aqueous solution to exhibit bright fluorescence in response to sequential treatment of alkaline phosphatase (ALP) and ChT-L. Transmission electron microscopy, enzymatic kinetics, and in vitro fluorescence experiments validated that TPE-1p was efficiently dephosphorylated by ALP to generate TPE-1, which was recognized by ChT-L in the proteasome, and transformed to form nanofibers with strong fluorescence signals. Cell imaging experiments revealed that bright blue fluorescence was observed in TPE-1p-treated HeLa cells, whereas NIH3T3 and HepG2 cells showed less fluorescence at the same condition. The enhanced fluorescence signals in HeLa cells were attributed to the high activities of endogenous ALP and ChT-L. Moreover, TPE-1p was utilized to noninvasively assess the inhibition efficiency of a ChT-L inhibitor (bortezomib, abbreviated as Btz) in HeLa cells. Significant correlation was found between the fluorescence signals of TPE and the viabilities of Btz-treated cells in concentration ranges from 0 to 1 μM, indicating that TPE-1p could be employed to predict the activity of ChT-L inhibitors. The design of the cascade-activated AIEgen-peptide probe provides a viable approach for noninvasively monitoring the ChT-L activity of proteasomes in living cells, which facilitates high-throughput screening of ChT-L inhibitors in cancer therapy.

研究领域: 癌症生物学 · 分子生物学 · 生物医学工程
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ADVANCED FUNCTIONAL MATERIALS · 2024 · IF 18.5

Reversible Emission Color, Brightness, and Shape Changes of AIEgen-containing Bulk Polymers

Kaojin Wang,Han Si,Xianchao Du,Pengbo Han,Gaohuai Mei,Yanhua Cheng,Anjun Qin,Ben Zhong Tang

Bulk polymers generally exhibit faster response, higher shape-deformation speed, and stronger mechanical properties than the hydrogels. However, it still remains a formidable challenge to enable bulk polymers to exhibit reversible changes in shape and fluorescence simultaneously. Herein, for the first time, the temperature-responsive reversible changes in fluorescence color, brightness, and shape of semi-crystalline poly( ε -caprolactone) (PCL) network doped with a D-A based aggregation-induced emission luminogen (AIEgen) is realized. The fabricated flower-like and dragonfly-shaped actuators show reversible blooming-closing and wing fanning behaviors, respectively, as well as reversible fluorescence-changing effects. Notably, the response and shape-deformation speed as well as mechanical properties of the system is much better than the reported hydrogels. Moreover, a smart switch is developed to demonstrate the potential applications. The stick fabricated by the sample can lift and release an object 1000 times larger than its weight, serving as a color-changing artificial muscle. This material design strategy may shine light on the design and preparation of other reversible shape-deformation polymers in combination with stimuli-responsive luminescence-changing AIEgens, such as mechanochromic, thermochromic, and photochromic luminogens.

CAS / MDL: 10294-33-4 301-10-0
研究领域: 材料科学 · 聚合物化学 · 智能材料 · 纳米技术
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Science China-Chemistry · 2021 ·Vol. 64 ·期 10 ·1770-1777 · IF 9.445

Lighted up by hydrogen-bonding: luminescence behavior and applications of AIEgen-doped interpenetrating network hydrogel

Xu Mengdi,Hua Luqin,Gong Lihao,Lu Jianlei,Wang Jinhui,Zhao Chuanzhuang

The interaction between the aggregation-induced emissive (AIE) luminogens (AIEgen) and the polymer is the key scientific question in the design of functional AIE hydrogels. In this study, we report the AIE behavior of a poly(acrylic acid) (PAAc) and poly(acrylamide) (PAAm) interpenetrating network (IPN) hydrogel doped with tetra-cationic tetraphenylethene (TCTPE). The cationic AIEgen can bind with PAAc through ionic interaction, while PAAc and PAAm chains can associate with each other through hydrogen-bonds (H-bonds). These two interactions can restrict the intramolecular rotation and thus activate the luminescence of the AIEgen. The PAAc-PAAm H-bonds can be broken by increasing temperature or pH, restoring the intramolecular rotation of the AIEgen and quenching the fluorescence of the hydrogel. Therefore, the TCTPE-doped IPN hydrogel is designed as temperature- and pH-sensitive displayers which can record information imprinted by photo-printing or iono-printing with good switchability and reversibility. Another application of this TCTPE-doped hydrogel is demonstrated as a luminescent soft actuator, which has fast shape deformation and editable fluorescence pattern. The above results reveal a pathway to tune the emission behavior through tuning polymer-polymer and polymer-AIEgen interactions, which may inspire new design strategies of aggregation-induced emissive polymers and broaden their applications.

研究领域: 材料科学 · 化学 · 高分子科学 · 光学
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