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A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H2S and its applications in living system

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Chinese Chemical Letters 2024年第5期35卷 296-301页

作者： Yudi Cheng Xiao Wang Jiao Chen Zihan Zhang Jiadong Ou Mengyao She Fulin Chen Jianli Li Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education Xi’an Key Laboratory of Functional Supramolecular Structure and MaterialsCollege of Chemistry&Materials ScienceNorthwest UniversityXi’an 710127China Key Laboratory of Resource Biology and Biotechnology in Western China Ministry of EducationBiomedicine Key Laboratory of Shaanxi ProvinceLab of Tissue Engineeringthe College of Life SciencesFaculty of Life Science&MedicineNorthwest UniversityXi’an 710069China

Sulfydryl-contained(-SH)substances including hydrogen sulfide(H_(2)S),cysteine(Cys),homocysteine(Hcy)and glutathione(GSH)play crucial roles in living systems,and their variations are closely associated with various ***,we developed a near-infrared intramolecular charge transfer(ICT)based fluorescent probe Y-NBD,achieving detection of Cys/Hcy and H_(2)S with different fluorescent signals(green-red for Cys/Hcy,red for H_(2)S),large Stokes shifts(∼100/105nm or 191 nm)and high signal-background-ratio,but not responding to GSH.Y-NBD was successfully applied to image exogenous/endogenous Cys/Hcy and H_(2)S in various living cancer cells(HeLa,A549,and HepG2)and in *** not only visualized the transformation pathway of several thiols in HepG2 cells but also verified that the intestine is the main site for the activation and metabolism of Y-NBD in zebrafish,as well as realized to evaluate the degree of drug-induced liver *** work provides a promising tool for imaging Cys/Hcy and H_(2)S in living systems and shows great potency in evaluating drug-induced liver injury and its treatment.

关键词： fluorescent probe Near-infrared Hydrogen sulfide Cysteine/homocysteine Large Stokes shift Dicyanoisophorone Drug-induced liver injury

Probing mitochondrial damage using a fluorescent probe with mitochondria-to-nucleolus translocation

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Chinese Chemical Letters 2024年第1期35卷 352-356页

作者： Chi Li Chong Zong Yang Liu Zhiqiang Liu Kang-Nan Wang Xiaoqiang Yu State Key Laboratory of Crystal Materials Shandong UniversityJi'nan 250100China Shenzhen Research Institute of Shandong University Shenzhen 518057China

Mitochondrial damage is closely related to the occurrence of many ***,accurate monitoring and reporting of mitochondrial damage are not ***,we developed a small molecule fluorescent probe named CB-Cl,which has splendid spectral properties(large Stokes shift,strong affinity for RNA,etc.)and excellent targeting ability to intracellular *** mitochondria were damaged by external stimuli,CB-Cl would light up the nucleolus as a signal *** cascade imaging of mitochondria and nucleolus using CB-Cl can monitor and visualize the mitochondrial status in living cells in *** on the above advantages,the probe CB-Cl has reference significance for the related research of mitochondrial damage and the prevention and treatment of related diseases.

关键词： fluorescent probe Mitochondria targeting Nucleolus translocation Mitochondrial damage diagnosis Fluorescence imaging

A novel flavonol-based colorimetric and turn-on fluorescent probe for rapid determination of hydrazine in real water samples and its bioimaging in vivo and in vitro

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Frontiers of Chemical Science and Engineering 2023年第1期17卷 24-33页

作者： Ahui Qin Yan Zhang Shuai Gong Mingxin Li Yu Gao Xu Xu Jie Song Zhonglong Wang Shifa Wang Co-Innovation Center of Efficient Processing and Utilization of Forest Resources International Innovation Center for Forest Chemicals and MaterialsCollege of Chemical EngineeringNanjing Forestry UniversityNanjing 210037China Department of Natural Sciences University of Michigan-FlintFlintMI 48502USA

Hydrazine is extremely toxic and causes severe harm to human ***,a novel fluorescent probe 4-oxo-2-styryl-4H-chromen-3-yl thiophene-2-carboxylate(FHT)was synthesized for detecting hydrazine by using natural cinnamaldehyde as starting *** probe exhibited significantly enhanced fluorescence response towards hydrazine over various common metal ions,anions,and amine *** detection limit of probe FHT for hydrazine was as low as 0.14μmol·L^(-1),significantly lower than that of the threshold value of 0.312μmoi·L^(-1),imposed by the Environmental Protection ***,the proposed probe was able to detect hydrazine within wide pH(5-10)and linear detection ranges(0-110μmol·L^(-1)).This probe was employed for determining trace hydrazine in different environmental water *** probe FHT-loaded filter paper strips werea able to conveniently detect hydrazine of low concentration through distinct naked-eye and fluorescent color ***,the probe FHT with low cytotoxicitywas successfullyapplied to visualize hydrazine in living Hela cells and zebrafish.

关键词： cinnamaldehyde 3-hydroxychromone derivative hydrazine fluorescent probe

A highly selective fluorescent probe for real-time imaging of UDP-glucuronosyltransferase 1A8 in living cells and tissues

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Frontiers of Chemical Science and Engineering 2022年第1期16卷 103-111页

作者： Mingyue Zhu Zhenhao Tian Lingling Jin Xiaokui Huo Chao Wang Jingnan Cui Yan Tian Xiangge Tian Lei Feng College of Pharmacy School of MedicineKey Laboratory of Elemene Class Anti-Cancer Chinese MedicinesEngineering Laboratory of Development and Application of Traditional Chinese MedicinesHangzhou Normal UniversityHangzhou 311121China Dalian Key Laboratory of Metabolic Target Characterization and Traditional Chinese Medicine Intervention College of PharmacyCollege of Integrative MedicineDalian Medical UniversityDalian 116044China School of Life Sciences Northwestern Polytechnical UniversityXi’an 710072China State Key Laboratory of Fine Chemicals Dalian University of TechnologyDalian 116024China

Uridine diphosphate(UDP)-glucuronosyltransferases(UGTs)are enzymes involved in the biotransformation of important endogenous compounds such as steroids,bile acids,and hormones as well as exogenous substances including drugs,environmental toxicants,and ***,a novel fluorescent probe BDMP was developed based on boron-dipyrromethene(BODIPY)with high sensitivity for the detection of *** glucuronidation of BDMP not only exhibited a redemission wavelength(lex/lem=500/580 nm),but also displayed an excellent UGT1A8-dependent fluorescence signal with a good linear relationship with UGT1A8 *** on this perfect biocompatibility and cell permeability,BDMP was successfully used to image endogenous UGT1A8 in human cancer cell lines(LoVo and HCT15)in real *** addition,BDMP could also be used to visualize UGT1A8 in tumor *** results suggested that BDMP is a promising molecular tool for the investigation of UGT1A8-mediated physiological function in humans.

关键词： UDP-glucuronosyltransferase 1A8 fluorescent probe subtype selectivity fluorescence imaging

Endogenous formaldehyde responsive fluorescent probe for bioimaging

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Nano Research 2023年第12期16卷 13029-13041页

作者： Ning-Bo Yi Xing-Jie Hu Fei Wang Si-Yi Chen Xiao-Xue Xu Xin Li Hao Wang Taolei Sun Zeng-Ying Qiao Dong-Bing Cheng Hubei Key Laboratory of Nanomedicine for Neurodegenerative Diseases School of ChemistryChemical Engineering&Life ScienceWuhan University of TechnologyWuhan 430070China CAS Center for Excellence in Nanoscience Laboratory for Biological Effects of Nanomaterials and Nanosafety National Center for Nanoscience and Technology(NCNST)Beijing 100190China Department of Biology and the School of Natural Sciences Went Worth CollegeUniversity of YorkHeslingtonYorkYO105DDUK

Formaldehyde(FA),as the simplest endogenous carbonyl molecule,participates in many biosynthesis and metabolism in living organisms,such as nucleotides and adenosine triphosphate(ATP).FA concentrations are sub-millimolar in the normal healthy body,but can rise significantly in a number of disease *** a result,detecting endogenous FA is critical for illness diagnosis and rehabilitation therapy *** studies have focused on the FA-responsive turn-on fluorescence probe,which has huge promise in the detection and visualization of FA in living cells and organisms,as well as exceptional use in disease diagnosis and therapeutic *** review summarizes the fluorescence luminescence mechanism and design concepts of FA fluorescent probes,as well as their recent applications in bioimaging and illness ***,this article indicates the present dilemma of FA-responsive fluorescent probe,including selectivity,specificity,and detection mode,which may provide references for the development of FA-responsive fluorescent probes.

关键词： endogenous formaldehyde fluorescent probe tumor cell bioimaging

A fluorescent probe based on a Carbazole Derivative for Detecting Brilliant Blue in Food

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Journal of Wuhan University of Technology(Materials Science) 2023年第2期38卷 308-311页

作者： YANG Yunqiong YANG Jiaxin FEI Shaojun ZHANG Zhirui LIU Yang ZHANG Hao School of Environmental and Chemical Engineering Jiangsu Ocean UniversityLianyungang222005China

Here a fluorescent probe based on a carbazole derivative(CNS)was developed to increase the detection range and reduce the detection limit of brilliant *** of CNS are *** to the quenching ability of colorants,CNS shows an excellent current response to brilliant blue(from 1 to 10μM)with a detection limit of 2.7×10^(-8)mol/L(3σ/k)in the conditions of a 1:1 volume ratio of water to *** the stability and reproducibility of CNS in the detection of actual samples indicate great potential for application.

关键词： fluorescent probe carbazole derivative brilliant blue detection

Constructing D-π-A-π dye to obtain red-emission fluorescent probe for structured illumination microscopy imaging of lipid droplet dynamics

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Green Chemical Engineering 2023年第4期4卷 387-392页

作者： Wenchao Jiang Jie Chen Kai An Pengjun Bao Qinglong Qiao Xiaogang Liu Zhaochao Xu CAS Key Laboratory of Separation Science for Analytical Chemistry Dalian Institute of Chemical PhysicsChinese Academy of SciencesDalian116023China University of Chinese Academy of Sciences Beijing100049China Fluorescence Research Group Singapore University of Technology and Design8 Somapah RoadSingapore487372Singapore

Lipid droplets(LDs)are dynamic organelles interacting with a variety of intracellular *** intracellular LD dynamics employing synthetic small molecules is crucial for biological *** imaging in the red and near infrared(NIR)region is more suitable for biological imaging due to its low phototoxicity and high signal-to-noise ***,available LD-dyes in the red region with remarkable environmental sensitivity,selectivity for LDs staining are ***,we constructed a red-emission D-π-A-π type LDdye LD 688P with higher environmental sensitivity and suitable“calculated log P”(Clog P)for LDs dynamic *** 688P was proved to be highly selective and photostable for tracing LD fusion including multiple consecutive fusions and fusions in a centrosymmetric manner by super-resolution *** believe that the D-π-A-π skeleton would be an efficient strategy to construct red and even NIR-emission dyes.

关键词： Lipid droplets fluorescent probe Red-emission D-π-A-π Super-resolution imaging

A Novel Salicylaldehyde Schiff-base fluorescent probe for Selective Detection of Cu^(2+)Ion

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Chinese Journal of Structural Chemistry 2022年第3期41卷 132-136,I0010页

作者： LI Yuan-Da KUANG Jin-Hao QIN Hai-Bo LIU Ke-Xiang FAN Xu LI Zhong-Yan YUAN Lin Hunan University of Science and Engineering Yongzhou 425199China

A novel Schiff-base fluorescent probe 6,6'-((1E,1'E)-(ethane-1,2-diylbis(azaneylylidene))bis-(methaneylylidene))bis(3-(diethylamino)phenol)(L)was derived from the 2:1 M condensation of 4-(diethylamino)-2-hydroxybenzaldehyde with ethylenediamine and characterized by ^(1)H NMR,^(13)C NMR and FT-IR *** results of spectral analysis showed that the probe L is selective and sensitive to Cu^(2+).The detection limit of L is found to be 19 nmol·L^(-1).There is a good linear relationship between the fluorescence intensity of probe L and the concentration of Cu^(2+)in the range of 0 to 20μmol×L^(-1).X-ray crystal structure of the L-Cu^(2+)complex and the Job plot revealed a 1:1 L-Cu^(2+)identification.

关键词： Cu^(2+) salicylaldehyde Schiff-base fluorescent probe

A benzothiazole-based ratiometric fluorescent probe with large Stokes shifts for quantitative profiling of sulfite in real samples and living cells

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Green Chemical Engineering 2023年第4期4卷 427-432页

作者： Fengpei Qi Xiuxiu Yue Yitong Yang Qin Liang Ruiren Tang Xiangzhi Song College of Chemistry&Chemical Engineering Central South UniversityChangsha410083China College of Materials&Chemical Engineering Hunan City UniversityYiyang413000China

Rapid,selective,and quantitative profiling of SO_(3)^(2-)is a prerequisite for investigating its effect on different physiopathological *** address this challenge,our team prepared a ratiometric fluorescent probe HBTCS,based on 4-(benzothiazol-2-yl)-3-hydroxybenzaldehyde for specific detection of SO_(3)^(2-)under a singlewavelength *** solution of probe HBTC-S itself exhibited orange fluorescence(λ_(em)=614 nm),and became green fluorescent(λ_(em)=471 nm)after the addition of SO_(3)^(2-).The vitro experiments suggested that the probe displayed high sensitivity,excellent selectivity,and a low detection limit(0.15μM).Moreover,probe HBTC-S was successfully applied for qualitative and quantitative monitoring of SO_(3)^(2-)in realistic samples and living HeLa cells in a ratiometric manner.

关键词： Ratiometric fluorescent probe Sulfite(SO_(3)^(2-)) Single-wavelength excitation Living imaging