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Frontiers of Chemical Science and Engineering 2022年第1期16卷 64-71页

作者： Yan Shi fangjun huo Yongkang Yue Caixia Yin Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education Institute of Molecular ScienceShanxi UniversityTaiyuan 030006China College of Food Sciences Shanxi Normal UniversityLinfen 041004China Research Institute of Applied Chemistry Shanxi UniversityTaiyuan 030006China

Heterocyclic compound quinoline and its derivatives exist in natural compounds and have a broad spectrum of biological activity.They play an important role in the design of new structural entities for medical applications.Similarly,indoles and their derivatives are found widely in nature.Amino acids,alkaloids and auxin are all derivatives of indoles,as are dyes,and their condensation with aldehydes makes it easy to construct reaction sites for nucleophilic addition agents.In this work,we combine these two groups organically to construct a rapid response site(within 30 s)for H_(2)S,and at the same time,a ratiometric fluorescence response is presented throughout the process of H_(2)S detection.As such,the lower detection limit can reach 55.7 nmol/L for H_(2)S.In addition,cell imaging shows that this probe can be used for the mitochondrial targeted detection of endogenous and exogenous H_(2)S.Finally,this probe application was verified by imaging H_(2)S in nude mice.

关键词： heterocyclic compound hydrogen sulfide ratiometric mitochondrial targeted

Novel strategy for accurate tumor labeling:endogenous metabolic imaging through metabolic probes

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Science China Chemistry 2022年第12期65卷 2517-2527页

作者： Ying Wen Zhiqing Long fangjun huo Caixia Yin Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education Key Laboratory of Materials for Energy Conversion and Storage of Shanxi ProvinceInstitute of Molecular ScienceShanxi UniversityTaiyuan030006China Research Institute of Applied Chemistry Shanxi UniversityTaiyuan030006China

Altered metabolism has long been recognized as a central hallmark of cancer;however,in the fluorescence imaging field,few studies have been conducted to label tumors by exploiting metabolic differences between cancer cells and normal cells.In this work,we successfully developed a metabolic probe MB-C for specific imaging of glutathione(GSH)dynamic metabolic pathways.GSH was endogenously metabolized to produce SO_(2)via Na_(2)S_(2)O_(3) and thiosulfate sulfurtransferase,equilibrating with sulfites/bisulfites.MB-C was allowed to be activated by GSH along with multi-fluorescence emission increased in red and green channels and further sequence-response metabolites(SO_(2))of GSH in significant fluorescence ratio change of red and green channels.Furthermore,such evident fluorescence ratio changes could be used to distinguish cancer cells from normal cells and identify tumor and normal tissues.Therefore,GSH metabolic imaging was successfully applied to accurately label tumors,which provides a new idea and practical case for the precise visualization of malignant tumors.

关键词： molecular probe metabolic imaging tumor labeling GSH

Rational design of a turn-on fluorescent probe for visualization of GRP78 protein in tumor models

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Chinese Chemical Letters 2023年第3期34卷 352-355页

作者： Ying Wen Ning Jing fangjun huo Caixia Yin Institute of Molecular Science Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of EducationShanxi UniversityTaiyuan 030006China Research Institute of Applied Chemistry Shanxi UniversityTaiyuan 030006China

Fluorescence image for accurate tumor label still faces challenges in cancer detection and diagnostics.Emerging evidence is indicating that glucose-regulated protein 78(GRP78), a stress-inducible protein chaperone, is a great potential biomarker and therapeutic target for cancer. However, currently available probe for image tumor based on GRP78 has not been reported, owning to no obvious strategy in probe design towards this protein. In this paper, a hairpin-shaped peptidyl probe(pep FAM) conjugated with a 5-FAM fluorophore and a dabcyl quencher at both ends was developed, respectively. The probe was designed by performing a traditional fluorescence resonance energy transfer mechanism and employing a GRP78 specifically-binding peptide. Furthermore, the probe was used to specifically image cancer cells,and accurately image xenograft tumors in mice models. The novel fluorescent probe is expected to be a useful tool for the diagnostics of cancer.

关键词： Glucose-regulated protein 78 Fluorescence probe Living cell imaing Tumor diagnosis

Spiropyran isomerization triggering ESIPT for visualization of pH fluctuations during oxidative stress in living cells

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Chinese Chemical Letters 2023年第5期34卷 470-474页

作者： Jingdong Wang fangjun huo Yongbin Zhang Caixia Yin Institute of Molecular Science Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of EducationShanxi UniversityTaiyuan 030006China Research Institute of Applied Chemistry Shanxi UniversityTaiyuan 030006China

Intracellular pH homeostasis is foundation of maintaining normal physiological functions.More and more evidences show that intracellular pH fluctuations were usually associated with many diseases(such as cancer,epilepsy and neurodegenerative diseases).It is very important to develop in situ real-time determination of pH.In recent years,it has been verified that pH can regulate the isomerization process of spiropyran.Thus,we report a pH fluorescent probe BSL,which is a closed loop spiropyran structure by coupling benzothiazole derivatives with indole salts.We utilizes the process of spiropyran isomerization as the trigger of excited state intramolecular proton transfer(ESIPT)effect,and adjust the process of spiropyran isomerization through pH,and then the molecular transformation from enol to ketone(enol:525 nm,ketone:677 nm)through the ESIPT effect.This process achieved accurate measurement of pH.The probe BSL showed sensitive and reversible fluorescence response to pH in vitro.Ultimately,BSL was successfully applied to detect pH fluctuations in cell oxidative stress model.

关键词： pH Spiropyran isomerization ESIPT Reversible Oxidative stress

Organelle targetable fluorescent probes for hydrogen peroxide

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Chinese Chemical Letters 2019年第10期30卷 1834-1842页

作者： Ying Wen fangjun huo Caixia Yin Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education Key Laboratory of Materials for Energy Conversion and Storage of Shanxi ProvinceInstitute of Molecular ScienceShanxi UniversityTaiyuan 030006China Research Institute of Applied Chemistry Shanxi UniversityTaiyuan 030006China

Hydrogen peroxide(H2 O2), as important products of oxygen metabolism, plays an important role in many biological processes, such as immune responses and cellular signal transduction. However, abnormal production of H2 O2 can damage cellular biomolecules, which was closely associated with many diseases.Thus, it is urgent to monitor the level change of H2 O2 in living cells, particularly at subcellular levels.Toward this end, a wide variety of H2 O2 fluorescent probes have been designed, developed and applied for imaging of H2 O2 in subcellular levels. In this review, we highlight the representative cases of H2 O2 fluorescent probes with mitochondria, nuclei and lysosomes-targetable ability. The review contains organelle target strategies, structures, fluorescence behavior and biological applications of these probes.

关键词： Hydrogen peroxide Fluorescence probes Mitochondria target Nuclei target Lysosomes target Living cells

Design strategy and bioimaging of small organic molecule multicolor fluorescent probes

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Science China Chemistry 2020年第12期63卷 1742-1755页

作者： Yongfei Huang Yongbin Zhang fangjun huo Ying Wen Caixia Yin Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education Institute of Molecular ScienceShanxi UniversityTaiyuan 030006China Key Laboratory of Functional Molecules of Shanxi Province Research Institute of Applied ChemistryShanxi UniversityTaiyuan 030006China

Multicolor fluorescent probes based on small organic molecules have the advantages of low cost, good biocompatibility, easily modifiable molecular structures and adjustable fluorescence performance. In addition, small molecule multicolor fluorescent probes generally undergo multi-site or multi-step reactions, which means that they can be used for the specific detection of structurally similar substances in complex bio-systems. In this review, we focus on the design and application of multicolor fluorescent probes based on small organic molecules: single fluorophores with multiple reaction sites, multiple fluorophores with single reaction sites, or multiple fluorophores with multiple reaction sites. Moreover, a design strategy for multicolor fluorescent probes and its application in biological imaging are also summarized, providing a systematic plan for future research on fluorescent probes functionalized by small organic molecules. It will also play an important role in the development of additional functions for small organic molecule fluorescent probes.

关键词： multicolor fluorescence probes small organic molecules design strategy bioimaging

Rearrangement regulated cysteine fluorescent probe for cellular oxidative stress evaluation induced by copper(Ⅱ)

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Chinese Chemical Letters 2020年第11期31卷 2970-2974页

作者： Na Zhou fangjun huo Yongkang Yue Kaiqing Ma Caixia Yin Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education Institute of Molecular ScienceShanxi UniversityTaiyuan 030006China Research Institute of Applied Chemistry Shanxi UniversityTaiyuan 030006China

Cysteine(Cys)plays an important role in regulating cellular redox balance.But due to the constant changes in the concentration of Cys in organisms,fast response sensors are urgent required for practical application.In this work,a fluorescent probe with a fast response was developed by linking coumarin derivatives containingα,β-unsaturated ketones to NBD.The PET effect made the system non-fluorescent.When the probe reacted with Cys,the bond between the coumarin derivative and the NBD was cut off,meanwhile a rapid rearrangement and reactive site passivation occurred.Then two fluorophores with the same emission peak are released,among them,strong fluorescence signal of NBD dominated.Thus,although the similar reaction occurred for Hcy,the rate of NBD derivative rearrangement was slow,in a short time,fluorescence signal was still weak.As for GSH,cleavage could occur,but no rearrange within the NBD molecule due to GSH with large volume.Because of strong fluorescent emission,this probe was successfully used in biological imaging about cell and zebrafish.More importantly,the probe was successfully used to evaluate the oxidative stress caused by copper(Ⅱ)in living cells.This fluorescence strategy and application will provide a new way of studying intracellular oxidative stress processes and damage.

关键词： Cysteine Rearrangement In vivo imaging Oxidative stress Copper(Ⅱ)

Distinguishable multi-substance detection based on three-channel NIR fluorescent probe in physiology and pathology of living cells and zebrafish

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Chinese Chemical Letters 2021年第12期32卷 3870-3875页

作者： Sha Li fangjun huo Yongkang Yue Kaiqing Ma Ying Wen Caixia Yin Institute of Molecular Science Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of EducationShanxi UniversityTaiyuan 030006China Research Institute of Applied Chemistry Shanxi UniversityTaiyuan 030006China

Mitochondria is the main organelle for the production of reactive sulfur species(RSS), such as homocysteine(Hcy), cysteine(Cys), glutathione(GSH) and sulfur dioxide(SO_(2)). These compounds participate in a large number of physiological processes and play an extremely important role in maintaining the balance of life systems. Abnormal concentration and metabolism are closely related to many diseases. Due to their similarities in chemical properties, it is challenging to develop a single fluorescent probe to distinguish them simultaneously. Here, we synthesized the probe PI-CO–NBD with three fluorophores, NBD-Cl and benzopyranate as the reaction sites of GSH/Cys/Hcy and SO_(2), respectively. Three biothiols all could cleavage ether bond to release benzopyrylium and coumarin moiety, which emitted red and blue fluorescence,but Cys/Hcy also could do intramolecular rearrangement after nucleophilic substitution, resulting in yellow fluorescence. Thus the probe can distinguish Cys/Hcy and GSH. Subsequently, only SO_(2)could quench red fluorescence by adding C=C of benzopyrylium. The probe also could localize well in mitochondria by oxonium ion for all kinds of cells. The probe not only could detect above sulfur-containing active substances of intracellular and extracellular but also monitor the level of them under oxidative stress and apoptosis process in living cells and zebrafish.

关键词： Mitochondrial-targeted Discrimination detection Distinguishable Multi-substance Three channels

A special o-dialdehyde fluorescent probe simultaneously sensing Hcy,GSH and its application in living cells and zebrafish imaging

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Chinese Chemical Letters 2021年第9期32卷 2873-2876页

作者： Yongbin Zhang Yu Zhang Yongkang Yue Jianbin Chao fangjun huo Caixia Yin Shanxi Key Laboratory of Functional Molecules Research Institute of Applied ChemistryShanxi UniversityTaiyuan 030006China School of Chemistry and Chemical Engineering Shanxi UniversityTaiyuan 030006China Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education Institute of Molecular ScienceShanxi UniversityTaiyuan 030006China Scientific Instrument Center Shanxi UniversityTaiyuan 030006China

The development of fluorescent probes enabling to distinguish Cys,Hcy and GSH has always been a considerable challenge,in particular the distinction of Hcy and other two biothiols,because Hcy has a very similar structure with Cys and a relatively lower concentration in living organisms.In this work,a special o-dialdehyde fluorescent probe,quinoline-2,3-dicarboxaldehyde(QDA),has been synthesized and demonstrated superior performance in differentiating detection of Hcy and GSH,which is different from the previous reported o-dialdehyde probes specifically detecting GSH.Furthermore,the probe can selectively distinguish Hcy and GSH from different signal channels in living cells and zebrafish,meaning it has great potential in biological applications.This finding will provide a novel idea for the design of fluorescent probes to distinguish biothiols.

关键词： o-Dialdehyde Distinguish Hcy GSH Bioimaging

Recruited CD68^(+)CD206^(+)macrophages orchestrate graft immune tolerance to prompt xenogeneic-dentin matrix-based tooth root regeneration

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Bioactive Materials 2021年第4期6卷 1051-1072页

作者： Hui Li Jingjing Sun Hefeng Yang Xue Han Xiangyou Luo LiJun Liao Bo Yang Tian Zhu fangjun huo Weihua Guo Weidong Tian State Key Laboratory of Oral Diseases West China Hospital of StomatologySichuan UniversityChengduChina National Engineering Laboratory for Oral Regenerative Medicine West China Hospital of StomatologySichuan UniversityChengduChina Department of Oral and Maxillofacial Surgery West China Hospital of StomatologySichuan UniversityChengduChina Department of Stomatology Beijing Shijitan HospitalCapital Medical UniversityBeijingChina Department of Stomatology The First Affiliated Hospital of Zhengzhou UniversityZhengzhouChina Department of Dental Research The Affiliated Stomatological Hospital of Kunming Medical UniversityKunmingChina Department of Pediatric Dentistry West China Hospital of StomatologySichuan UniversityChengduChina

Successful regenerative medicine strategies of xenogeneic extracellular matrix need a synergistic balance among inflammation,fibrosis,and remodeling process.Adaptive macrophage subsets have been identified to modulate inflammation and orchestrate the repair of neighboring parenchymal tissues.This study fabricated PPARγ-primed CD68+CD206+M2 phenotype(M2γ),and firstly verified their anti-inflammatory and tissue-regenerating roles in xenogeneic bioengineered organ regeneration.Our results showed that Th1-type CD3^(+)CD8^(+)T cell response to xenogeneic-dentin matrix-based bioengineered root complex(xeno-complex)was significantly inhibited by M2γmacrophage in vitro.PPARγactivation also timely recruited CD68^(+)CD206^(+)tissue macrophage polarization to xeno-complex in vivo.These subsets alleviated proinflammatory cytokines(TNF-α,IFN-γ)at the inflammation site and decreased CD3^(+)CD8^(+)T lymphocytes in the periphery system.When translated to an orthotopic nonhuman primate model,PPARγ-primed M2 macrophages immunosuppressed IL-1β,IL-6,TNF-α,MMPs to enable xeno-complex to effectively escape immune-mediated rejection and initiate graft-host synergistic integrity.These collective activities promoted the differentiation of odontoblast-like and periodontal-like cells to guide pulp-dentin and cementum-PDLs-bone regeneration and rescued partially injured odontogenesis such as DSPP and periostin expression.Finally,the regenerated root showed structure-biomechanical and functional equivalency to the native tooth.The timely conversion of M1-to-M2 macrophage mainly orchestrated odontogenesis,fibrogenesis,and osteogenesis,which represents a potential modulator for intact parenchymal-stromal tissue regeneration of targeted organs.

关键词： Xenogeneic extracellular matrix Macrophage polarization Cellular response Organ regeneration Parenchymal and stromal tissues regeneration