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fluorescence imaging mitochondrial copper(Ⅱ) via photocontrollable fluorogenic probe in live cells

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Chinese Chemical Letters 2017年第10期28卷 1965-1968页

作者： Liulin Wang Buxiang Chen Pingping Peng Wenbo Hu Zhipeng Liu Xiaohua Pei Weihong Zhao Chengwu Zhang Lin Li Wei Huang Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM) Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM) Nanjing Tech University (Nanjing Tech) Division of Nephrology Department of Geriatrics The First Affiliated Hospital of Nanjing Medical University Key Laboratory for Organic Electronics and Information Displays & Institute of Advanced Materials (IAM) Nanjing University of Posts &Telecommunications

Monitoring mitochondrial derived copper（Ⅱ） in live cells is highly demanded, but accurately detecting is unmet due to the interference with cytoplasmic copper（Ⅱ）. Herein, we have reported the design,synthesis and characterization of photocontrollable fluorogenic probe, MCu-3, which is equipped with a photo-labile group（nitrobenzyl group） and mitochondria targeting unit（triphenylphosphonium salt）.This novel probe showed an intense fluorescence enhancement in response to copper（Ⅱ） without interference from other metal cations in the biological condition（p H 6–9）. The detection limit is 1.7 ×10^（-7） mol/L in HEPES buffer. The confocal fluorescence imaging results demonstrated MCu-3 can visualize mitochondrial copper（Ⅱ） in live mammalian cells. The clear advantage of our photocontrollable method is successful to avoid the influence of cytoplasmic copper（Ⅱ） during mitochondria specific detection.

关键词： Mitochondria Photocontrollable Fluorogenic probe fluorescence imaging Copper(Ⅱ)

Highly crystallization-induced emissive luminophores with mechanoluminescent features for two-photon harvesting fluorescence imaging and latent fingerprint identification

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Nano Research 2024年第7期17卷 6475-6482页

作者： Jian Lu Juan Gao Rui-Xuan Qian Shuai-Hua Wang Fa-Kun Zheng Guo-Cong Guo Fujian Science and Technology Innovation Laboratory for Optoelectronic Information of China Fuzhou 350108China State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of MatterChinese Academy of SciencesFuzhou 350002China

fluorescence imaging can be employed in fields of medical treatment,astronomical exploration,and national defense *** fluorescence imaging often takes the single-photon techniques,which is vulnerable to background interference and ***,two-photon fluorescence imaging can achieve much higher-resolution fluorescence imaging for reducing scattering and deeper ***,by assembling the tetraphenylethylene backbones with nontoxic and non-noble K^(+)ions,compound 1([(Hdma)K(H_(2)ettc)]_(n),H_(4)ettc=4',4''',4''''',4'''''''-(ethene-1,1,2,2-tetrayl)tetrakis(([1,1'-biphenyl]-4-carboxylic acid)))with the crystallization-induced emissions exhibited charming fluorescence imaging under two-photon excitation microscopy(TPEM).Besides,luminescent powders based on compound 1 can achieve high-resolution fingerprint recognition,providing secure access control and identification for a novel authentication *** with the commercial fluorescent dyes coumarin-6,the as-synthesized compound 1 showed great solvent stability,indicating its durability against harsh ***,compound 1 shows mechanoluminescent properties for the perturbation of weak supramolecular interactions within ordered arrangements of the H_(2)ettc^(2−)*** novel compound has provided an important insight to the development of twophoton fluorescence imaging and advanced external-stimuli responsive materials.

关键词： crystallization-induced emission fluorescence imaging two-photon absorption fingerprint recognition mechanoluminescence

NIR photosensitizers activated byγ-glutamyl transpeptidase for precise tumor fluorescence imaging and photodynamic therapy

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Science China Chemistry 2021年第5期64卷 808-816页

作者： Yingchao Chen Xueze Zhao Tao Xiong Jianjun Du Wen Sun Jiangli Fan Xiaojun Peng State Key Laboratory of Fine Chemicals Dalian University of TechnologyDalian 116024China Ningbo Institute of Dalian University of Technology Ningbo 315016China

Photodynamic therapy(PDT),a light triggered therapeutic mode,has been recognized as an attractive treatment for *** phototoxicity to normal tissues during treatment limited the development of PDT owing to the always“on”properties of *** photosensitizers are of great importance for improving the selectivity of ***,we regarded the overexpressed GGT(γ-Glutamyl transpeptidase)enzyme in tumor cells as a biomarker and developed an activatable photosensitizer Cy-GGT by decorating a specific recognition moiety of GGT,L-glutamic acid,to a hemicyanine dye based on photosensitizer Cy-NH_(2).Cy-GGT was in the“off”state with negligible fluorescence and suppressed singlet oxygen generation,but it could be specifically hydrolyzed to Cy-NH_(2) in the presence of GGT,accompanied with significant fluorescence recovery and singlet oxygen generation increase under light *** in vitro and in vivo studies indicated that Cy-GGT was suitable for precise tumor imaging and could work as an efficient photosensitizer for inhibiting tumor growth.

关键词： photodynamic therapy γ-glutamyl transpeptidase activatable fluorescence imaging

Polycyclic naphthalenediimide-based nanoparticles for NIR-Ⅱ fluorescence imaging guided phototherapy

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Science China Chemistry 2020年第7期63卷 946-956页

作者： Chuanchao Tang Chuanhui Song Zheng Wei Chen Liang Jianchuan Ran Yu Cai Xiaochen Dong Wei Han Central Laboratory'of Stomatology Nanjing Stomatological HospitalMedical School of Nanjing UniversityNanjing 210008China Department of Oral and Maxillofacial Surgery Nanjing Stomatological HospitalMedical School of Nanjing UniversityNanjing 2 J0008China School of Chemistry and Materials Science Nanjing University of Information Science&TechnologyNanjing 210044China

Optical imaging and phototherapy in the second near-infrared window(NIR-Ⅱ, 900–1700 nm) can reduce tissue auto-fluorescence and photon scattering, which facilitates higher spatial resolution and deeper tissue penetration depth for solid tumor theranostics. Herein, a polycyclic naphthalenediimide(NDI) based chromophore 13-amino-4,5-dibromo-2,7-di(dodecan-6-yl)-1 H-isoquinolino[4,5,6-fgh]naphtho[1,8-bc][1,9]phenanthroline-1,3,6,8(2H,7H,9H)-tetraone(NDI-NA) was designed and synthesized. With large polycyclic π-systems, NDI-NA molecule possesses broad near-infrared(NIR) absorption(maximum at777 nm) and emission(maximum at 921 nm). By nanoprecipitation, NDI-NA nanoparticles(NPs) were formed in aqueous solution with J-aggregative state, which showed huge red-shift in both absorption spectrum(maximum at 904 nm) and emission spectrum(maximum at 1,020 nm), endowing NDI-NA NPs efficient NIR-Ⅱ fluorescence imaging capability. Besides, the NPs present effective tumor-targeting capability in vivo based on the enhanced permeation and retention(EPR) effect. More importantly, NDI-NA NPs simultaneously have high photothermal conversion efficiency(30.8%) and efficient reactive oxygen species generation ability, making them remarkably phototoxic to cancer cells. The polycyclic chromophore based multifunctional NDI-NA NPs as NIR-Ⅱ phototheranostic agents possess bright future for clinical NIR-Ⅱ imaging-guided cancer phototherapy.

关键词： second near-infrared window fluorescence imaging phototherapy phototheranostics polycyclic naphthalenediimide

Boron difluoride formazanate dye for high-efficiency NIR-Ⅱ fluorescence imaging-guided cancer photothermal therapy

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Chinese Chemical Letters 2022年第5期33卷 2501-2506页

作者： Hanming Dai Zijin Cheng Tian Zhang Weili Wang Jinjun Shao Wenjun Wang Yongxiang Zhao Xiaochen Dong Liping Zhong Key Laboratory of Flexible Electronics(KLOFE)&Institute of Advanced Materials(IAM) Nanjing Tech University(NanjingTech)Nanjing 211800China School of Physical Science and Information Technology Liaocheng UniversityLiaocheng 252059China National Center for International Biotargeting Theranostics Guangxi Key Laboratory of Biotargeting TheranosticsCollaborative Innovation Center for Targeting Tumor TheranosticsGuangxi Medical UniversityNanning 530021China

The small molecular second near-infrared(NIR-Ⅱ, 1000–1700 nm) dye-based nanotheranostics can concurrently combine deep-tissue photodiagnosis with in situ phototherapy, which occupies a vital position in the early detection and precise treatment of tumors. However, the development of small molecular NIR-Ⅱ dyes is still challenging due to the limited electron acceptors and cumbersome synthetic ***, we report a novel molecular electron acceptor, boron difluoride formazanate(BDF). Based on BDF, a new small molecular NIR-Ⅱ dye BDF1005 is designed and synthesized with strong NIR-I absorption at 768 nm and bright NIR-Ⅱ peak emission at 1034 nm. In vitro and in vivo experiments demonstrate that BDF1005-based nanotheranostics can be applied for NIR-Ⅱ fluorescence imaging-guided photothermal therapy of 4T1 tumor-bearing mice. Under 808 nm laser irradiation, tumor growth can be effectively inhibited. This work opens up a new road for the exploitation of NIR-Ⅱ small molecular dyes for cancer phototheranostics.

关键词： NIR-II nanotheranostics Boron difluoride formazanate fluorescence imaging Photothermal therapy Phototheranostics

Selective and sensitive fluorescence imaging reveals microenvironment-dependent behavior of NO modulators in the endothelial system

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Journal of Pharmaceutical Analysis 2020年第5期10卷 466-472页

作者： Ying Dong Xiao-Rong Li Jia Li Yi Zang Xin Li College of Pharmaceutical Sciences Zhejiang UniversityHangzhou310058China State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of SciencesShanghai201203China University of Chinese Academy of Sciences Beijing100049China Open Studio for Draggability Research of Marine Natural Products Pilot National Laboratory for Marine Science and Technology(Qingdao)1 Wenhai RoadAoshanweiJimoQingdao266237China

Nitric oxide(NO)is a second messenger playing crucial roles in the signaling of a variety of cellular *** to its pathophysiological significance,various NO modulators have been developed to explore NO pathways and some have been used as *** modulators are often used directly to observe pharmacological effects in cell lines,but their actual effect on intracellular NO level is seldom ***,facilitated by a selective and sensitive fluorescence probe,we observed that some NO modulators displayed unexpected behaviors with both NO scavenger carboxy-PTIO and endothelial nitric oxide synthase(eNOS)inhibitor N(u)-nitro-L-arginine methyl ester(L-NAME)failing to decrease intracellular free NO level in ***926 cells while NO donor diethylamine-NONOate(DEA$NONOate)and eNOS activator calcimycin(A23187)failing to increase free NO level in human umbilical vein endothelial cell line(HUV-EC-C),although the reagents were confirmed to work normally in the primary human umbilical vein endothelial cells(primary HUVECs)and RAW 264.7 macrophage *** research suggested that these unusual behaviors might be attributed to the cellular microenvironments including both the NO synthase(NOS)level and the endogenous glutathione(GSH)*** manipulating eNOS level in both cells restores the expected response,while decreasing GSH level restores the ability of DEA$NONOate to increase NO level in *** results reveal that the cellular microenvironment has a profound impact on pharmacological *** study suggests GSH as a reservoir for NO in live cells and highlights the value of chemical probes as valuable tools to reveal microenvironmentdependent pharmacological effects.

关键词： Nitric oxide modulator Drug screen fluorescence imaging Microenvironment Endothelial cell

Recent advances in fluorescence imaging of alkaline phosphatase

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Chinese Chemical Letters 2021年第4期32卷 1316-1330页

作者： Meng Li Bhaskar Gurram Shan Lei Nicholas TBlum Peng Huang Jing Lin Marshall Laboratory of Biomedical Engineering.International Cancer Center Laboratory of Evolutionary Theranostics(LET)School of Biomedical Engineering.Shenzhen University Health Science CenterShenzhen 518060China

Phosphatase plays a vital important role in many biological functions due to the dephosphorylation serves varied roles in cellular regulation and *** the family of phosphatase,alkaline phosphatase(ALP)could act as crucial prognostic indicators for many diseases such as bone diseases and ***,the detection of ALP is mainly limited to in vitro colorimetric method in ***,huge efforts have been paid on the fluorescence imaging that provides a reliable method to detect the real-time and in vivo changes of the level of *** this review,we summarize recent advances in fluorescence imaging of phosphatase,mainly focused on *** imaging probes of phosphatase are mainly classified according to their luminescence *** the end,we assessed the challenges and future prospects of phosphatase probes.

关键词： Alkaline phosphatase Acid phosphatase fluorescence imaging Luminescence mechanism

Biocompatible organic dots with aggregation-induced emission for in vitro and in vivo fluorescence imaging

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Science China Chemistry 2013年第9期56卷 1228-1233页

作者： LI Kai DING Dan ZHAO QiuLi SUN JingZhi TANG Ben Zhong LIU Bin Institute of Materials Research and Engineering 3 Research Link Department of Chemical and Biomolecular Engineering National University of Singapore4 Engineering Drive 4 MOE Key Laboratory of Macromolecule Synthesis & Functionalization Institute of Biomedical MacromoleculesDepartment of Polymer Science & EngineeringZhejiang University Department of Chemistry The Hong Kong University of Science & Technology SCUT-HKUST Joint Research Laboratory State Key Laboratory of Luminescent Materials and Devices South China University of Technology

Fluorescent probes play a key role in modern biomedical research. As compared to inorganic quantum dots (QDs) composed with heavy metal elements, organic dye-based fluorescent nanoparticles have higher biocompatibility and are richer in variety. However, traditional organic fluorophores tend to quench fluorescence upon aggregation, which is known as aggregation-caused quenching (ACQ) effect that hinders the fabrication of highly emissive fluorescent nanoparticles. In this work, we demonstrate the synthesis of organic fluorescent dots with aggregation-induced emission (AIE) in far-red/near-infrared (FA/NIR) region. A conventional ACQ-characteristic fluorescent dye, 3,4:9,10-tetracarboxylic perylene bisimide (PBI), is converted into an AIE fluorogen through attaching two tetraphenylethylene (TPE) moieties. The fluorescent dots with surface folic acid groups are fabricated from PBI derivative (DTPEPBI), showing specific targeting effect to folate receptor-overexpressed cancer cells. In vivo studies also suggest that the folic acid-functionalized AIE dots preferentially accumulate in the tumor site through enhanced permeability and retention (EPR) effect and folate receptor-mediated active targeting effect. The low cyto-toxicity, good FR/NIR contrast and excellent targeting ability in in vitro/in vivo imaging indicate that the AIE dots have great potentials in advanced bioimaging applications.

关键词： aggregation-induced emission AIE dots targeted imaging fluorescence imaging

On fluorescence imaging:The diffusion equation model and recovery of the absorption coefficient of fluorophores

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Science China Mathematics 2022年第6期65卷 1179-1198页

作者： Jijun Liu Manabu Machida Gen Nakamura Goro Nishimura Chunlong Sun School of Mathematics Southeast UniversityNanjing 210096China Institute for Medical Photonics Research Hamamatsu University School of MedicineHamamatsu 431-3192Japan Department of Mathematics Hokkaido UniversitySapporo 060-0810Japan Research Institute for Electronic Science Hokkaido UniversitySapporo 060-0810Japan

To quantify fluorescence imaging of biological tissues,we need to solve an inverse problem for the coupled radiative transfer equations which describe the excitation and emission fields in biological *** begin by giving a concise mathematical argument to derive coupled diffusion equations with the Robin boundary condition as an approximation of the radiative transfer *** by using this coupled system of equations as a model for the fluorescence imaging,we have a nonlinear inverse problem to identify the absorption coefficient in this *** associated linearized inverse problem is to ignore the absorbing effect on the excitation *** firstly establish the estimates of errors on the excitation field and the solution to the inverse problem,which ensures the reasonability of the model approximation *** numerical verification is presented to show the validity of such a linearizing process ***,based on the analytic expressions of excitation and emission fields,the identifiability of the absorption coefficient from the linearized inverse problem is rigorously analyzed for the absorption coefficient in the special form,revealing the physical difficulty of the3-dimensional imaging model by the back scattering diffusive system.

关键词： fluorescence imaging diffusion equation inverse problem linearization error estimates identifiability