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A multifunctional nanoaggregate-based system for detection of rheumatoid arthritis via Optoacoustic/NIR-Ⅱ fluorescent imaging and therapy via inhibiting JAK-STAT/NF-κB/NLRP3 pathways

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Aggregate 2024年第1期5卷 353-366页

作者： Junjie Chen Longqi Chen Zunpan She Fang Zeng Shuizhu Wu Biomedical Division State Key Laboratory of Luminescent Materials and DevicesGuangdong Provincial Key Laboratory of Luminescence from Molecular AggregatesCollege of Materials Science and EngineeringSouth China University of TechnologyGuangzhouChina

Rheumatoid arthritis(RA)is a debilitating autoimmune disease that causes chronic pain and serious complications,presenting a significant challenge to treat.Promising approaches for treating RA involve signaling pathways modulation and targeted therapy.To this end,a multifunctional nanosystem,TPC-U@HAT,has been designed for RA therapy,featuring multitargeting,dual-stimuli response,and on-demand drug release capabilities.TPC-U@HAT is composed of a probe/prodrug TPC,a JAK1 kinase inhibitor upadacitinib,and the drug carrier HAT.TPC is composed of an aggregation-induced emission(AIE)-active NIR-II chromophore TPY and an NF-κB/NLRP3 inhibitor caffeic acid phenethyl ester(CAPE),connected via boronic ester bond which serves as the reactive-oxygen-species-responsive linker.The carrier,HAT,is created by grafting bone-targeting alendronate and hydrophobic tocopheryl succinate onto hyaluronic acid chains,which can encapsulate TPC and upadacitinib to form TPC-U@HAT.Upon intravenous injection into mice,TPC-U@HAT accumulates at inflamed lesions of RA through both active and passive targeting,and the overexpressed hyaluronidase and H_(2)O_(2) therein cleave the hyaluronic acid polymer chains and boronate bonds,respectively.This generates an AIE-active chromophore for detection and therapeutic evaluation of RA via both optoacoustic imaging and NIR-II fluorescent imaging and concomitantly releases CAPE and upadacitinib to exert efficacious therapy by inhibiting NF-κB/NLRP3 and JAK-STAT pathways.

关键词： aggregation-induced emission dual-stimuli response multispectral optoacoustic tomography imaging multitargeting NIR-II fluorescence imaging rheumatoid arthritis

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Two-color emissive AIEgens with anti-Kasha property for dual-organelle imaging and phototherapy

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Science China Chemistry 2024年第5期67卷 1740-1752页

作者： Pu Chen Guogang Shan Qingli Nie Yuting Yan Pengfei Zhang Zujin Zhao Hai-Tao Feng Ben Zhong Tang AIE Research Center Shaanxi Key Laboratory of PhytochemistryCollege of Chemistry and Chemical EngineeringBaoji University of Arts and SciencesBaoji 721013China Institute of Functional Material Chemistry and National&Local United Engineering Lab for Power Battery Faculty of ChemistryNortheast Normal UniversityChangchun 130024China College of Chemistry&Materials Science Northwest UniversityXi’an 710127China guangdong key laboratory of Nanomedicine CAS-HK Joint Lab of BiomaterialsCAS Key Laboratory of Biomedical Imaging Science and SystemShenzhen Engineering Laboratory of Nanomedicine and NanoformulationsCAS Key Lab for Health InformaticsShenzhen Institutes of Advanced TechnologyChinese Academy of SciencesShenzhen 518055China State key laboratory of Luminescent Materials and Devices Key Laboratory of Luminescence from Molecular Aggregates of Guangdong ProvinceSouth China University of TechnologyGuangzhou 510640China School of Science and Engineering Shenzhen Institute of Aggregate Science and TechnologyThe Chinese University of Hong KongShenzhen(CUHK-Shenzhen)Shenzhen 518172China

Despite the rapid development of probes for targeting single organelle, the construction of robust dual-organelle targeting probes with multicolor emission was rarely reported. Herein, two dual-emissive aggregation-induced emission luminogens(AIEgens)with donor-π-acceptor structures were designed and synthesized, namely QT-1 and QF-2. Both two AIEgens exhibited excitation wavelength-dependence defying the Kasha's rule, and could stain lipid droplets(LDs) and mitochondria in blue and red fluorescence, respectively. Moreover, thanks to the near-infrared emission and abundant reactive oxygen species(ROS) generation efficiency of QT-1, it was chosen as a photodynamic therapy agent to selectively kill cancer cells from normal cells. Upon light irradiation, an obvious decrease of mitochondrial membrane potential(MMP) and serious change of mitochondrial shape in cells were observed, which corresponded to the efficient inhibition of tumor growth in vivo. This work afforded a promising strategy for the construction of multicolor emission by tuning anti-Kasha behaviors and expanding their application in dualorganelle targeting-based phototheranostics.

关键词： aggregation-induced emission anti-Kasha luminescence fluorescent probe bioimaging photodynamic therapy

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Targeted and activatable nanosystem for fluorescent and optoacoustic imaging of immune-mediated inflammatory diseases and therapy via inhibiting NF-κB/NLRP3 pathways

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Bioactive Materials 2022年第4期7卷 79-92页

作者： Lihe Sun Juan Ouyang Zhuo Zeng Cheng Zeng Yunqing Ma Fang Zeng Shuizhu Wu Biomedical Division State Key Laboratory of Luminescent Materials and DevicesGuangdong Provincial Key Laboratory of Luminescence from Molecular AggregatesCollege of Materials Science and EngineeringSouth China University of TechnologyGuangzhou510640China

Immune-mediated inflammatory diseases(IMIDs)represent a diverse group of diseases and challenges remain for the current medications.Herein,we present an activatable and targeted nanosystem for detecting and imaging IMIDs foci and treating them through blocking NF-κB/NLRP3 pathways.A ROS-activatable prodrug BH-EGCG is synthesized by coupling a near-infrared chromophore with the NF-κB/NLRP3 inhibitor epigallocatechin-3-gallate(EGCG)through boronate bond which serves as both the fluorescence quencher and ROS-responsive moiety.BH-EGCG molecules readily form stable nanoparticles in aqueous medium,which are then coated with macrophage membrane to ensure the actively-targeting capability toward inflammation sites.Additionally,an antioxidant precursor N-acetylcysteine is co-encapsulated into the coated nanoparticles to afford the nanosystem BH-EGCG&NAC@MM to further improve the anti-inflammatory efficacy.Benefiting from the inflammation-homing effect of the macrophage membrane,the nanosystem delivers payloads(diagnostic probe and therapeutic drugs)to inflammatory lesions more efficiently and releases a chromophore and two drugs upon being triggered by the overexpressed in-situ ROS,thus exhibiting better theranostic performance in the autoimmune hepatitis and hind paw edema mouse models,including more salient imaging signals and better therapeutic efficacy via inhibiting NF-κB pathway and suppressing NLRP3 inflammasome activation.This work may provide perceptions for designing other actively-targeting theranostic nanosystems for various inflammatory diseases.

关键词： Actively-targeting nanosystem Immune-mediated inflammatory disease Two-mode imaging NF-κB/NLRP3 pathways

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Metal-Free Synthesis of Benzo[a]phenanthridines from Aromatic Aldehydes,Cyclohexanones,and Aromatic Amines

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Chinese Journal of Chemistry 2022年第3期40卷 365-370页

作者： Pingyu Jiang Zhifei Shan Shanping Chen Quanyuan Wang Shuxin Jiang Haolin Zheng Guo-Jun Deng key laboratory for Green Organic Synthesis and Application of Hunan Province Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of EducationCollege of ChemistryXiongtan UniversityXiangtanHunon 411105China guangdong provincial key laboratory of luminescence from molecular aggregates(South China University of Technology) GuangzhouGuangdong 510640China

A three-component synthesis of benzo[a]phenanthridines from aromatic aldehydes,cyclohexanones,and aromatic amines has been developed,which is mediated by KI/DMSO/camphorsulfonic acid to afford a variety of functionalized benzo[a]phenanthridines in satisfactory yields.The present strategy provides a biaryl motif ortho to the nitrogen atom which has the potential to be used as ligand by further modification.With the advantages of readily available starting materials,transition-metal-free conditions,gram-scale synthesis,and broad substrate scope,this three-component protocol provides an efficient approach for the preparation of diverse benzo[a]phenanthridines.

关键词： Nitrogen heterocycles Multicomponent reactions Dehydroaromatization Cyclization Metal-free

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Spherical lanthanide nanoclusters toward white-light emission and cell membrane imaging

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Nano Research 2023年第8期16卷 11495-11502页

作者： Hai-Ling Wang Zhiqiang Ni Ze-Yu Ruan Zhong-Hong Zhu Pei-Yu Liao Guangxue Feng Jian-Hua Jia Ming-Liang Tong key laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education School of ChemistrySun Yat-Sen UniversityGuangzhou 510006China State key laboratory of Luminescent Materials and Devices Guangdong Provincial Key Laboratory of Luminescence from Molecular AggregatesSchool of Materials Science and EngineeringSouth China University of TechnologyGuangzhou 510640China

Lanthanide doping is an effective strategy for modulating the emission of emitters.Herein,by changing the cluster composition to control the energy transfer pathway,the application potential of high-nuclearity lanthanide cluster(HLC)as white-light emitter has been confirmed for the first time.Specifically,by precisely controlling the proportion of GdIII,TbIII,and EuIII ions in reactants,we obtained a spherical heterotrimetallic nanocluster Gd_(10)Tb_(12)Eu_(10),a white-light emitter with quantum yield(QY)of 12.58%and lifetime of 327.14μs.High-resolution electrospray ionization mass spectrometry(HRESI-MS)demonstrates that homometallic nanoclusters Ln_(32)(Ln=Gd,Tb,and Eu)are tetracationic clusters and are highly stable in solution.The peripheral dense organic ligands provide a protective layer for the cluster core,which improves the stability of Ln_(32) in aqueous solution,avoids the contact between metal centers and bioactive molecules,and greatly reduces the biological toxicity.In cell imaging experiments,cationic clusters Ln_(32) are mainly localized on the cell membrane with negative charge distribution.As far as we know,this is the first time that spherical lanthanide nanoclusters have been used for membrane imaging of living cell,opening the door for the application of HLCs in biological imaging.

关键词： spherical lanthanide clusters white-light emission high stability low toxicity cell membrane imaging

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Unveiling size-fluorescence correlation of organic nanoparticles and its use in nanoparticle size determination

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Aggregate 2024年第1期5卷 331-336页

作者： Wu-Jie Guo Shixiang Ma Hui Wang Lu Qiao Lei Chen Chenyu Hong Bin Liu Xiaoyan Zheng Hui-Qing Peng State key laboratory of Chemical Resource Engineering Beijing Advanced Innovation Center for Soft Matter Science and EngineeringBeijing University of Chemical TechnologyBeijingChina key laboratory of Cluster Science of Ministry of Education Beijing Key Laboratory of Photoelectronic/Electro-photonic Conversion MaterialsKey Laboratory of Medicinal Molecule Science and Pharmaceutics Engineering of Ministry of Industry and Information TechnologySchool of Chemistry and Chemical EngineeringBeijing Institute of TechnologyBeijingChina

Quantitatively establishing the correlation between nanoparticle size and fluorescence is essential for understanding the behavior and functionality of fluorescent nanoparticles(FNPs).However,such exploration focusing on organic FNPs has not been achieved to date.Herein,we employ the use of supramolecular polymeric FNPs prepared from tetraphenylethylene-based bis-ureidopyrimidinone monomers(bis-UPys)to relate the size to the fluorescence of organic nanoparticles.At an equal concentration of bis-UPys,a logarithmic relationship between them is built with a correlation coefficient higher than 0.96.Theoretical calculations indicate that variations in fluorescence intensity among FNPs of different sizes are attributed to the distinct molecular packing environments at the surface and within the interior of the nanoparticles.This leads to different nonradiative decay rates of the embedded and exposed bis-UPys and thereby changes the overall fluorescence quantum yield of nanoparticles due to their different specific surface areas.The established fluorescence intensity-size correlation possesses fine universality and reliability,and it is successfully utilized to estimate the sizes of other nanoparticles,including those in highly diluted dispersions of FNPs.This work paves a new way for the simple and real-time determination of nanoparticle sizes and offers an attractive paradigm to optimize nanoparticle functionalities by the size effect.

关键词： aggregation-induced emission fluorescence detection fluorescent nanoparticle nanoparticle size supramolecular polymer

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Diamines,CS2 and Monoisocyanide-participated Polymerizations for Large-scale Synthesis of Polythioureas and Thioformamide

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高分子科学:英文版 2023年第10期41卷 1563-1576页

作者： Jie Zhang Fan Ye Jin-Lei Huo Jian-Wen Peng Rong-Rong Hu Ben Zhong Tang State key laboratory of Luminescent Materials and Devices Guangdong Provincial Key Laboratory of Luminescence from Molecular AggregatesSouth China University of TechnologyGuangzhou510640China Shenzhen Institute of Aggregate Science and Technology School of Science and EngineeringThe Chinese University of Hong KongShenzhenGuangdong518172China AIE Institute Guangzhou510530China

Multicomponent polymerizations(MCPs)are powerful tools to synthesize functional polymers with great structural diversity,low cost and high efficiency,which usually generate single polymer product.Herein,a robust one-pot diamines,CS_(2)and monoisocyanide-participated catalyst-free polymerization was developed at room temperature to produce polythiourea and thioformamide simultaneously in equal equivalent,which was featured with cheap monomers,simple operation and mild condition,affording various polythioureas with high Mws of up to 4.75×10^(4)g/mol in high yields of up to 98%.Polythioureas with varied chain composition and sequence-controlled structure could be synthesized in 62 g-scale from copolymerization or multicomponent tandem polymerization,enabling facile tuning of thermal property,crystallinity,mechanical property,and fluorescence.The abundant irregular hydrogen bonds endowed the polythioureas excellent glassy state self-healing property at room temperature or below 0℃.This polymerization provided an efficient and economic approach to access functional polythioureas.

关键词： CS_(2) Multicomponent polymerization Sequence-controlled polythiourea Scale-up synthesis Self-healing

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Switching on/off phosphorescent or non-radiative channels by aggregation-induced quantum interference

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Aggregate 2024年第1期5卷 175-184页

作者： Yi Kong Yu-Chen Wang Xunkun Huang WanZhen Liang Yi Zhao Department of Chemistry State Key Laboratory of Physical Chemistry of Solid SurfacesiChEMFujian Provincial Key Laboratory of Theoretical and Computational Chemistryand College of Chemistry and Chemical EngineeringXiamen UniversityXiamenPeople’s Republic of China

Pure organic materials with persistent and efficient room-temperature phosphorescence have recently aroused great research interest due to their vast potential in applications.One crucial design principle for such materials is to suppress as much as possible the non-radiative decay of the triplet exciton while maintaining a moderate phosphorescent radiative rate.However,molecular engineering often exhibits similar regulation trends for the two processes.Here,we propose that the quantum interference caused by aggregation can be utilized to control the phosphorescent and non-radiative decay channels.We systematically analyze various constructive and destructive transition pathways in aggregates with different molecular packing types and establish clear relationships between the luminescence characters and the signs of the singlet and triplet excitonic couplings.It is shown that the decay channels can be flexibly switched on or off by regulating the packing type and excitonic couplings.Most importantly,an enhanced phosphorescent decay and a completely suppressed non-radiative decay can be simultaneously realized in the aggregate packed with inversion symmetry.This work lays the theoretical foundation for future experimental realization of quantum interference effects in phosphorescence.

关键词： excitonic coupling intersystem crossing organic aggregates organic room temperature phosphorescence quantum interference

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Visualization of supramolecular assembly by aggregation-induced emission

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聚集体(英文) 2023年第2期4卷 102-122页

作者： Wu-Jie Guo Tuokai Peng Wenping Zhu Shixiang Ma Guang Wang Ying Li Bin Liu Hui-Qing Peng Beijing Advanced Innovation Center for Soft Matter Science and Engineering State Key Laboratory of Chemical Resource EngineeringBeijing University of Chemical TechnologyBeijingChina Innovation Research Center for AIE Pharmaceutical Biology Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target and Clinical PharmacologyThe NMPA and State Key Laboratory of Respiratory DiseaseSchool of Pharmaceutical Sciences and The Fifth Affiliated HospitalGuangzhou Medical UniversityGuangzhouChina guangdong provincial key laboratory of luminescence from molecular aggregates South China University of TechnologyGuangzhouChina

Supramolecular architectures are constructed by the self-assembly of small building blocks via the use of metal-ligand coordination,π–πstacking interactions,hydrogen bonding,host-guest interactions,and other noncovalent driving forces,which confer unique dynamic reversibility and stimulus responsiveness to the supramolecular materials and also lead to the demand of expensive and complex equipment for the characterization of supramolecular assembly processes.Fortunately,the self-assembly processes bring the monomeric chromophores together,offering possibilities to establish ties between the supramolecular assembly and aggregation-induced emission(AIE)techniques.Compared to conventional luminescent molecules,AIE luminogens(AIEgens)exhibit significant fluorescence enhancement upon the restriction of molecular motions,thus displaying the advantages of signal amplification and low background noises.Given the above,the real-time,sensitive,and in situ visualization of the formation of self-assemblies and their stimuli responsiveness based on AIE becomes accessible.Here,we review recent works that encompass the visualization of supramolecular assembly-related behaviors by means of AIE characteristics of chromophores.The organization of this review will be by different types of supramolecular architectures,including metallacycles/cages,micelles/vesicles,supramolecular polymers,and supramolecular gels.An overview of future opportunities and challenges for the real-time monitoring of supramolecular assembly by AIE is also provided.

关键词： aggregation-induced emission metallacycles/cages micelles/vesicles supramolecular gels supramolecular polymers visualization

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Towards Efficient Blue DelayedFluorescence Molecules by Modulating Torsion Angle Between Electron Donor and Acceptor

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CCS Chemistry 2023年第3期5卷 598-606页

作者： Jinke Chen Xing Wu Hao Liu Nuoling Qiu Zhangshan Liu Dezhi Yang Dongge Ma Ben Zhong Tang Zujin Zhao State key laboratory of Luminescent Materials and Devices Guangdong Provincial Key Laboratory of Luminescence from Molecular AggregatesSouth China University of TechnologyGuangzhou 510640 School of Science and Engineering Shenzhen Institute of Aggregate Science and TechnologyThe Chinese University of Hong KongShenzhenGuangdong 518172 AIE Institute Guangzhou Development DistrictHuangpuGuangzhou 510530

Constructing blue thermally activated delayedfluorescence materials for high-performance organic light-emitting diodes(OLEDs)remains challenging due to the intrinsically strong intramolecular charge transfer nature of the nearly orthogonal connection of electron donor(D)and acceptor(A),which results in long-wavelength emission.Herein,an effective delayed-fluorescence design strategy of modulating D–A torsion angles is proposed and efficient sky-blue,pure-blue,and deep-blue delayed-fluorescence molecules consisting of a xanthenone acceptor and carbazole-based donors are created by decreasing the torsion angles.They exhibit strong delayed fluorescence with high photoluminescence quantum yields of 85–94%in doped films,and their delayed-fluorescence lifetimes are elongated from 1.0 to 27.6μs as the torsion angles decrease.These molecules can function as excellent emitters in OLEDs,providing efficient electroluminescence peaking at 442 nm(CIEx,y=0.15,0.08),462 nm(CIEx,y=0.15,0.18),and 482 nm(CIEx,y=0.17,0.30)with state-of-the-art external quantum efficiencies of up to 22.2%,33.7%,and 32.1%,respectively,demonstrating the proposed molecular design for efficient blue delayed-fluorescence molecules is successful and promising.

关键词： blue luminescent material thermally activated delayed fluorescence torsion angle electroluminescence organic light-emitting diode

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