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fluorescent probes and functional materials for biomedical applications

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Frontiers of Chemical Science and Engineering 2022年第10期16卷 1425-1437页

作者： Xi-Le Hu Hui-Qi Gan Fan-De Meng Hai-Hao Han De-Tai Shi Shu Zhang Lei Zou Xiao-Peng He Tony D.James Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering Feringa Nobel Prize Scientist Joint Research CenterSchool of Chemistry and Molecular EngineeringEast China University of Science and TechnologyShanghai 200237China Department of Chemistry University of BathBath BA27AYUK Liver Cancer Institute Zhongshan Hospitaland Key Laboratory of Carcinogenesis and Cancer Invasion(Ministry of Education)Fudan UniversityShanghai 200032China School of Chemistry and Chemical Engineering Henan Normal UniversityXinxiang 453007China School of Materials Science and Engineering Jingdezhen Ceramic InstituteJingdezhen 333403China

Due to their simplicity in preparation,sensitivity and selectivity,fluorescent probes have become the analytical tool of choice in a wide range of research and industrial fields,facilitating the rapid detection of chemical substances of interest as well as the study of important physiological and pathological processes at the cellular level.In addition,many long-wavelength fluorescent probes developed have also proven applicable for in vivo biomedical applications including fluorescenceguided disease diagnosis and theranostics(e.g.,fluorogenic prodrugs).Impressive progresses have been made in the development of sensing agents and materials for the detection of ions,organic small molecules,and biomacromolecules including enzymes,DNAs/RNAs,lipids,and carbohydrates that play crucial roles in biological and disease-relevant events.Here,we highlight examples of fluorescent probes and functional materials for biological applications selected from the special issues“fluorescent probes”and“Molecular Sensors and Logic Gates”recently published in this journal,offering insights into the future development of powerful fluorescence-based chemical tools for basic biological studies and clinical translation.

关键词： fluorescent probes imaging cell biomedicine biomolecules

Recent advances in small molecule fluorescent probes for simultaneous imaging of two bioactive molecules in live cells and in vivo

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Frontiers of Chemical Science and Engineering 2022年第1期16卷 4-33页

作者： Yongqing Zhou Xin Wang Wei Zhang Bo Tang Ping Li College of Chemistry Chemical Engineering and Materials ScienceKey Laboratory of Molecular and Nano Probes(Ministry of Education)Institutes of Biomedical SciencesShandong Normal UniversityJinan 250014China

The interrelationships and synergistic regulations of bioactive molecules play pivotal roles in physiological and pathological processes involved in the initiation and development of some diseases,such as cancer and neurodegenerative and cardiovascular diseases.Therefore,the simultaneous,accurate and timely detection of two bioactive molecules is crucial to explore their roles and pathological mechanisms in related diseases.Fluorescence imaging associated with small molecular probes has been widely used in the imaging of bioactive molecules in living cells and in vivo due to its excellent performances,including high sensitivity and selectivity,noninvasive properties,real-time and high spatial temporal resolution.Single organic molecule fluorescent probes have been successively developed to simultaneously monitor two biomolecules to uncover their synergistic relationships in living systems.Hence,in this review,we focus on summarizing the design strategies,classifications,and bioimaging applications of dual-response fluorescent probes over the past decade.Furthermore,future research directions in this field are proposed.

关键词： bioactive molecules fluorescent probes in living cells and in vivo review

From fluorescent probes to the Theranostics Platform

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Chinese Journal of Chemistry 2022年第16期40卷 1964-1974页

作者： Peng Wei Qing Wang Tao Yi State Key Laboratory for Modification of Chemical Fibers and Polymer Materials Shanghai Engineering Research Center of Nano-Biomaterials and Regenerative MedicineCollege of ChemistryChemical Engineering and BiotechnologyDonghua UniversityShanghai201620 China Department of Chemistry Fudan UniversityShanghai200438 China

Since the advent of fluorescent probes,they have been widely used in the field of life sciences.fluorescent probes can not only light up the cells,tissues and organs,but also be used to explore the bio-distribution of specific types of disease markers.Therefore,the development of new fluorescent probes capable of recognition of bio-markers is extremely important for the diagnosis of the related diseases.Herein,we focus on our recent works experienced the evolution from the beginning of simply fluorescent probes to the construction of theranostics platform.We have developed a series of new fluorescent probes for the detecting and imaging of reactive oxygen species(ROS)and specific enzymes in vitro and in living cells.With the shift of the fluorescence signal from visible to near-infrared region,we expanded the application of the fluorescent probes from in vitro to in vivo.Very recently,we further constructed theranostics platforms to combine the diagnosis immediately with the corresponding treatment.

关键词： fluorescent probes Imaging agents Prodrugs Theranostics platform Nanoparticles

Recent development in fluorescent probes based on attacking of double bond and masking of functional group

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Chinese Chemical Letters 2022年第6期33卷 2765-2772页

作者： Nadeem Ahmed Wajeeha Zareen Yong Ye Phosphorus Chemical Engineering Research Center of Henan Province The College of ChemistryZhengzhou UniversityZhengzhou 450002China

The works on the procedure of fluorescent sensors for the detection of biological analytes are extremely momentous.Among diverse analytical approaches,fluorescence is the most eye-catching due to its high sensitivity,selectivity,rapidity,robustness,ease of measurement and non-destructive approaches.Herein,we show different fluorescent probes synthesized for estimation and detection of biological analytes(H_(2)S,SO_(3)^(2-)/HSO_(3)^(-),H_(2)O_(2),HOCl,HNO,ONOO^(-)).These probes were constructed by masking the functional groups (hydroxyl and amino) of fluorophore and formation of active C=C,C=N,C=O and N=N for specific analytes.In this review we concentrate on synthesis of the probe,their photophysical properties and applications to biological studies.

关键词： fluorescent probes Hypochlorous acid Peroxynitirite Biothiols Michael addition

fluorescent probes for the detection of reactive oxygen species in human spermatozoa

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Asian Journal of Andrology 2020年第5期22卷 465-471页

作者： Sara Escada-Rebelo Francisca G Mora Ana P Sousa Teresa Almeida-Santos Artur Paiva Joao Ramalho-Santos phD Programme in Experimental Biology and Biomedicine CNC-Center for Neuroscience and Cell BiologyUniversity of CoimbraCoimbra 3004-504Portugal Biology of Reproduction and Stem Cell Group CNC-Center for Neuroscience and Cell BiologyUniversity of CoimbraCoimbra 3004-504Portugal IIIUC-Institute for Interdisciplinary Research Casa Costa AlemaoUniversity of CoimbraCoimbra 3030-789Portugal Reproductive Medicine Unit University Hospitals of CoimbraCoimbra 3004-561Portugal Faculty of Medicine University of CoimbraCoimbra 3000-370Portugal Clinical Pathology Unit University Hospitals of CoimbraCoimbra 3004-561Portugal Department of Life Sciences University of CoimbraCoimbra 3000-456Portugal

Reactive oxygen species(ROS)production is a by-product of mitochondrial activity and is necessary for the acquisition of the capacitated state,a requirement for functional spermatozoa.However,an increase in oxidative stress,due to an abnormal production of ROS,has been shown to be related to loss of sperm function,highlighting the importance of an accurate detection of sperm ROS,given the specific nature of this cell.In this work,we tested a variety of commercially available fluorescent probes to detect ROS and reactive nitrogen species(RNS)in human sperm,to define their specificity.Using both flow cytometry(FC)and fluorescence microscopy(FM),we confirmed that MitoSOX™Red and dihydroethidium(DHE)detect superoxide anion(as determined using antimycin A as a positive control),while DAF-2A detects reactive nitrogen species(namely,nitric oxide).For the first time,we also report that RedoxSensor™Red CC-1,CellROX®Orange Reagent,and MitoPYl seem to be mostly sensitive to hydrogen peroxide,but not superoxide.Furthermore,mean fluorescence intensity(and not percentage of labeled cells)is the main parameter that can be reproducibly monitored using this type of methodology.

关键词： flow cytometry fluorescent probes human spermatozoa oxidative stress reactive oxygen species

fluorescent probes for recognition of ATP

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Chinese Chemical Letters 2017年第10期28卷 1916-1924页

作者： Ying Wu Jia Wen Hongjuan Li Shiguo Sun Yongqian Xu Shaanxi Key Laboratory of Natural Products & Chemical Biology College of Chemistry & Pharmacy Northwest A&F University Yangling 712100 China

Adenosine 5＇-triphosphate（ATP） not only participates in various physiological activities as the universal energy currency but also implicates in various pathological processes in living cells. Consequently,sensitive and selective detection ATP in live cells, tissues, as well as environmental samples, are urgently demanded. Due to the simple and convenient operation, economy cost, high selectivity for analyte, well biocompatibility and low cytotoxicity, fluorescent sensors for monitoring ATP have aroused great attention of researchers. In recent years, a large number of fluorescent sensors for detecting ATP have developed. This manuscript summarized most of these sensors and the interaction-mechanism between ATP and sensors, mainly including electrostatic interaction, p-p interaction, covalent bonding or hydrogen bond, or combinations of them, and the advantages of each strategy were also generalized.Here, a viewpoint of classification was shown where the sensors were divided into five typed ones according to the structure of probes used.

关键词： fluorescent probes Adenosine 5＇-triphosphate（ATP） Cell imaging Sensitive detection Multi-interactions Recognition mechanism

Heptamethine cyanines in bioorthogonal chemistry

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Chinese Chemical Letters 2024年第2期35卷 131-137页

作者： Yuanyuan Liao Yuting Liang Yurou Huang Xiaoyan Zeng Tian He Jun Yin National Key Laboratory of Green Pesticide International Joint Research Center for Intelligent Biosensor Technology and HealthCollege of ChemistryCentral China Normal UniversityWuhan 430079China

Due to their excellent fluorescence properties and biological function,cyanine dyes have been widely applied in biological imaging.Heptamethine cyanine(Cy7)dyes,as a type of classic near-infrared(NIR)fluorescent dyes,are considered as one of the effective fluorescent tools in the living organisms due to their good biocompatibility and very low background interference.Bioorthogonal reactions performed in living cells and tissues have developed by leaps and bounds in recent years.The NIR fluorescent labeling technique involving cyanine has attracted widespread attention.This review summarizes their recent application in the field of bioorthogonal imaging,mainly concluding Cy7-type dyes,labeling strategy,bioimaging application,etc.We expect this work can provide some helps for the studies of NIR bioorthogonal reaction in vivo.

关键词： fluorescent probes Heptamethine cyanines Bioorthogonal reaction Imaging Cell

A highly sensitive fluorescent HClO probe for discrimination between cancerous and normal cells/tissues

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Chinese Chemical Letters 2024年第6期35卷 417-420页

作者： Linfang Wang Jing Liu Minghao Ren Wei Guo Department of Chemistry Changzhi UniversityChangzhi 046011China School of Chemistry and Chemical Engineering Shanxi UniversityTaiyuan 030006China

Elevated level of hypochlorous acid(HClO)is closely associated with cancer development.Identifying HClO level in cancer cells would provide important evidence in either early-stage cancer diagnostics or monitoring of its treatment efficiency.In this work,a new pyronine-based fluorescent probe for rapid and sensitive detection of HClO was developed by condensing meso-formyl pyronine(PyCHO)with 2-hydrazinopyridine to form meso-pyridylhydrazone-functionalized pyronine PyHP,PyHP is nonfluorescent due to the excited-state C=N isomerization nonradiative decay,whereas the HClO-triggered formation of meso-triazolopyridyl pyronine PyTP abolishes the C=N isomerization and thus greatly enhances the fluorescence.With the probe,the cancer cells/tumor were distinguished with high-contrast from normal ones by laser confocal fluorescence imaging,and the tumor-to-normal(T/N)ratios obtained exceed the clinically acceptable threshold of 2.0.Moreover,its capability of in vivo imaging tumor was also demonstrated.These results indicate the potential of PyHP as an effective tool in the early clinical diagnosis of cancers.

关键词： Meso-pyridylhydrazone-functionalized pyronine Meso-substituents Tumor-to-normal(T/N)ratios fluorescent probes Hypochlorous acid

Hydroxylated graphene quantum dots as fluorescent probes for sensitive detection of metal ions

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International Journal of Minerals,Metallurgy and Materials 2020年第1期27卷 91-99页

作者： Qiang Ge Wen-hui Kong Xin-qian Liu Ying-min Wang Li-feng Wang Ning Ma Yan Li Department of Inorganic Nonmetallic Material School of Materials Science and EngineeringUniversity of Science and Technology BeijingBeijing 100083China College of Materials Science and Chemical Engineering Harbin Engineering UniversityHarbin 150001China

Highly sensitive methods are important for monitoring the concentration of metal ions in industrial wastewater.Here,we developed a new probe for the determination of metal ions by fluorescence quenching.The probe consists of hydroxylated graphene quantum dots(H-GQDs),prepared from GQDs by electrochemical method followed by surface hydroxylation.It is a non-reactive indicator with high sensitivity and detection limits of 0.01μM for Cu2+,0.005μM for Al3+,0.04μM for Fe3+,and 0.02μM for Cr3+.In addition,the low biotoxicity and excellent solubility of H-GQDs make them promising for application in wastewater metal ion detection.

关键词： graphene quantum dots surface hydroxylation metal ions detection fluorescent probes