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click chemistry-based pre-targeting cell delivery for cartilage regeneration

Regenerative Biomaterials 2021年第3期8卷 11-21页

作者： Cynthia M.Co Samira Izuagbe Jun Zhou Ning Zhou Xiankai Sun Joseph Borrelli Liping Tang Department of Bioengineering University of Texas at ArlingtonPO Box 19138ArlingtonTX 76019USA Department of Radiology University of Texas Southwestern MedicalDallasTX 75390USA

A fraction of the OA patient population is affected by post-traumatic osteoarthritis(PTOA)following acute joint *** or reversing the progression of PTOA following joint injury could improve long-term functional outcomes,reduced disability,and medical *** more effectively treat articular cartilage injury,we have developed a novel cell-based therapy that involves the pretargeting of apoptotic chondrocytes and the delivery of healthy,metabolically active chondrocytes using click ***,a pre-targeting agent was prepared via conjugating apoptotic binding peptide(ApoPep-1)and trans-cyclooctene(TCO)onto polyethylene glycol(PEG)polymer *** pre-targeting agent would be introduced to injured areas of articular cartilage,leading to the accumulation of TCO groups on the injured areas from actively binding to apoptotic ***,methyltetrazine(Tz)-bearing chondrocytes would be immobilized on the surface of TCO-coated injured cartilage via Tz-TCO click chemistry *** an ex vivo human cartilage explant PTOA model,the effectiveness of this new approach was *** studies show that this novel approach(Tz-TCO click chemistry)significantly enhanced the immobilization of healthy and metabolically active chondrocytes to the areas of apoptotic *** analyses demonstrated that this treatment regimen would significantly reduce the area of cartilage degeneration and enhance ECM *** results support that Tz-TCO click chemistry-mediated cell delivery approach has great potential in clinical applications for targeting and treatment of cartilage injury.

关键词： chondrocyte cartilage regeneration cell therapy click chemistry

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click chemistry approach to functionalize two-dimensional macromolecules of graphene oxide nanosheets

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Nano-Micro Letters 2010年第3期2卷 177-183页

作者： Liang Kou Hongkun He Chao Gao MOE Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and Engineering Zhejiang University

A facile "click chemistry" approach to functionalize 2D macromolecules of graphene oxide nanosheets with poly(ethylene glycol) of different molecular weights,polystyrene,palmitic acid and various amino acids was ***,TGA,Raman spectroscopy,XPS,XRD,TEM,AFM and SEM were utilized to characterize the *** degree of functionalization was achieved on the flat surfaces of graphene oxide,affording polymer-grafted 2D brushes and amino acids-immobilized nanosheets,which show improved solubility in organic *** click chemistry strategy reported herein provides a facile and general method for functionalization of graphene oxide with macromolecules and desired biomolecules.

关键词： Graphene click chemistry Chemical modification PEG Amino acids

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click chemistry extracellular vesicle/peptide/chemokine nanocarriers for treating central nervous system injuries

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Acta Pharmaceutica Sinica B 2023年第5期13卷 2202-2218页

作者： Huitong Ruan Yongfang Li Cheng Wang Yixu Jiang Yulong Han Yiwei Li Dandan Zheng Jing Ye Gang Chen Guo-yuan Yang Lianfu Deng Ming Guo Xingcai Zhang Yaohui Tang Wenguo Cui Department of Orthopaedics Shanghai Key Laboratory for Prevention and Treatment of Bone and Joint DiseasesShanghai Institute of Traumatology and OrthopaedicsRuijin HospitalShanghai Jiao Tong University School of MedicineShanghai 200025China Jiaxing Key Laboratory of Basic Research and Clinical Translation on Orthopedic Biomaterials Department of Orthopaedicsthe Second Affiliated Hospital of Jiaxing UniversityJiaxing 314000China Department of Rehabilitation Medicine Ruijin HospitalSchool of MedicineShanghai Jiao Tong UniversityShanghai 200025China Med-X Research Institute and School of Biomedical Engineering Shanghai Jiao Tong UniversityShanghai 200030China School of Engineering Massachusetts Institute of TechnologyCambridgeMA 02139USA School of Engineering and Applied Sciences Harvard UniversityCambridgeMA 02138USA

Central nervous system(CNS)injuries,including stroke,traumatic brain injury,and spinal cord injury,are essential causes of death and long-term disability and are difficult to cure,mainly due to the limited neuron regeneration and the glial scar ***,we apply extracellular vesicles(EVs)secreted by M2 microglia to improve the differentiation of neural stem cells(NSCs)at the injured site,and simultaneously modify them with the injured vascular targeting peptide(DA7R)and the stem cell recruiting factor(SDF-1)on their surface via copper-free click chemistry to recruit NSCs,inducing their neuronal differentiation,and serving as the nanocarriers at the injured site(Dual-EV).Results prove that the Dual-EV could target human umbilical vascular endothelial cells(HUVECs),recruit NSCs,and promote the neuronal differentiation of NSCs in ***,10 miRNAs are found to be upregulated in Dual-M2-EVs compared to Dual-M0-EVs via bioinformatic analysis,and further NSC differentiation experiment by flow cytometry reveals that among these miRNAs,miR30b-3p,miR-222-3p,miR-129-5p,and miR-155-5p may exert effect of inducing NSC to differentiate into *** vivo experiments show that Dual-EV nanocarriers achieve improved accumulation in the ischemic area of stroke model mice,potentiate NSCs recruitment,and increase *** work provides new insights for the treatment of neuronal regeneration after CNS injuries as well as endogenous stem cells,and the click chemistry EV/peptide/chemokine and related nanocarriers for improving human health.

关键词： Central nervous system injuries Stroke Neural stem cell Neurogenesis click chemistry Extracellular vesicles Microglia Targeted delivery

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click chemistry in the design of AIEgens for biosensing and bioimaging

Aggregate

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Aggregate 2023年第4期4卷 71-92页

作者： Marie-Claire Giel Yuning Hong Department of Biochemistry and chemistry La Trobe Institute for Molecular ScienceLa Trobe UniversityMelbourneVictoriaAustralia

The development of rapid,selective,and sensitivefluorescent sensors is essential for visualizing and quantifying biological molecules and processes in vitro,ex vitro,and in vivo,which is important for not only fundamental biological studies but the accurate diagnosis of *** emergingfield of activity-based sensing(ABS),a sensing method that utilizes molecular reactivity for analyte detection possesses many advantages including high specificity,sensitivity and *** aggrega-tion caused quenching phenomenon which occurs in most conventionalfluorophores results in reduced labeling efficiency of the target analytes and low photobleaching resistance,therefore limiting the applications of the ABS *** contrast,aggre-gation induced emission(AIE)active luminogens(AIEgens)provide exceptional molecular frameworks for *** the many reaction classes utilized in the AIEgen ABS approach,click chemistry has become increasing *** this review,the sensing concepts of the ABS approach with AIEgens and the principles of click chemistry are discussed,followed by a systematic summary of the application of specific click chemistry reactions in AIEgen ABS protocols for the detection of an array of target ***,the utility of click chemistry in the construction of AIEgens for bioimaging will also be showcased throughout the review.

关键词： activity-based sensing aggregation induced emission bioconjugation chemistry click chemistry

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click chemistry and natural products

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Chinese Journal of Natural Medicines 2024年第2期22卷 97-99页

作者： ZHANG Chen WU Jianbing ZHANG Yihua HUANG Zhangjian State Key Laboratory of Natural Medicines Jiangsu Key Laboratory of Drug Discovery for Metabolic DiseasesCenter of Drug DiscoveryChina Pharmaceutical UniversityNanjing 210009China State Key Laboratory of Pathogenesis Prevention and Treatment of High Incidence Diseases in Central AsiaXinjiang Key Laboratory of Natural Medicines Active Components and Drug Release TechnologySchool of PharmacyXinjiang Medical UniversityUrumqi 830054China

The 2022 Nobel Prize in chemistry was awarded to American scientists Carolyn Bertozzi,*** Sharpless,and Danish scientist Morten *** for their contributions to the development of click chemistry and bioorthogonal chemi... 详细信息

关键词： click chemistry Natural product Target identification Drug discovery

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Water-soluble Cu30 nanoclusters as a click chemistry catalyst for living cell labeling via azide-alkyne cycloaddition

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Nano Research 2023年第1期16卷 1748-1754页

作者： Ge Yang Yali Xie Yaru Wang Ying Tang Leng Leng Chng Fuyi Jiang Fanglin Du Xianfeng Zhou Jackie Y.Ying Xun Yuan School of Materials Science and Engineering Qingdao University of Science and TechnologyQingdao 266042China Key Lab of Biobased Polymer Materials of Shandong Provincial Education Department School of Polymer Science and EngineeringQingdao University of Science and TechnologyQingdao 266042China NanoBio Lab Institute of Materials Research and Engineering(IMRE)Agency for ScienceTechnology and Research(A*STAR)31 Biopolis WayThe NanosSingapore 138669Singapore School of Environment and Material Engineering Yantai UniversityYantai 264005China NanoBio Lab A*STAR Infectious Diseases LabsA*STAR31 Biopolis WayThe NanosSingapore 138669Singapore

Cu(I)-catalyzed azide-alkyne cycloadditions(CuAAC)have gained increasing interest in the selective labeling of living cells and organisms with ***,their application is constrained either by the high cytotoxicity of Cu(I)ions or the low activity of CuAAC in the internal space of living *** paper reports the design of a novel Cu-based nanocatalyst,watersoluble thiolated Cu30 nanoclusters(NCs),for living cell labeling via *** Cu30 NCs offer good biocompatibility,excellent stability,and scalable synthesis(e.g.,gram scale),which would facilitate potential commercial *** combining the highly localized Cu(I)active species on the NC surface and good structural stability,the Cu30 NCs exhibit superior catalytic activities for a series of Huisgen cycloaddition reactions with good *** importantly,the biocompatibility of the Cu30 NCs enables them to be a good catalyst for CuAAC,whereby the challenging labeling of living cells can be achieved via CuAAC on the cell *** study sheds light on the facile synthesis of atomically precise Cu NCs,as well as the design of novel Cu NCs-based nanocatalysts for CuAAC in intracellular bioorthogonal applications.

关键词： Cu nanocluster click chemistry catalysis azide-alkyne cycloaddition living cell labeling

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Synthesis of Triazole-Linked Amino Acid-Aryl C-Glycoside Hybrids via click chemistry as Novel PTPIB Inhibitors

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Chinese Journal of chemistry 2011年第6期29卷 1227-1232页

作者： Wang, Jia He, Xiaopeng Gao, Lixin Sheng, Li Shi, Xiaoxin Li, Jia Chen, Guorong Key Laboratory for Advanced Materials and Institute of Fine Chemicals and School of Pharmacy East China University of Science and Technology Shanghai 200237 China National Center for Drug Screening State Key Laboratory of Drug Research Shanghai Institute of Materia Medica Shanghai Institutes of Biological Sciences Chinese Academy of Sciences Shanghai 201203 China

Triazolyl phenylalanine and tyrosine-aryl C-glycoside hybrids were readily synthesized via microwave-assisted Cu（I）-catalyzed azide-alkyne 1,3-dipolar cycloaddition in high yields. Successive enzymatic assay identified the synthesized glycoconjugates as novel PTPlB inhibitors with low micromole-ranged inhibitory activity and at least several-fold selectivity over other homologous PTPs tested found crucial toward PTP1 B inhibition. In addition, the benzyl groups on glucosyl moiety were

关键词： click chemistry C-glycoside triazolyl amino acid PTP inhibitors

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Copper-Free click chemistry-Mediated Assembly of Single Quantum Dot Nanosensor for Accurately Monitoring Locus-Specific m^(6)A in Cancer Cells

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Chinese Journal of chemistry 2024年第5期42卷 499-504页

作者： Yue-Ying Li Ning-Ning Zhao Yi-Xuan Geng Qian Han Jian-Ge Qiu Bing-Hua Jiang Zi-Yue Wang Chun-Yang Zhang Translational Medicine Center The First Affiliated Hospital of Zhengzhou UniversityThe Academy of Medical SciencesHenan Institute of Medical and Pharmaceutical Sciences BGI CollegeZhengzhou UniversityZhengzhouHenan450052 China College of chemistry Chemical Engineering and Materials ScienceShandong Normal UniversityJinanShandong250014 China School of chemistry and Chemical Engineering Southeast UniversityNanjingJiangsu211189 China

N6-methyladenosine(m^(6)A)plays an important role in embryogenesis,nuclear export,transcription splicing,and protein translation ***,we demonstrate a copper-free click chemistry-mediated assembly of single quantum dot(QD)nanosensor for accurately monitoring locus-specific m^(6)A in cancer *** m^(6)A-sensitive endoribonuclease MazF can digest the unmethylated A-RNA,and the intact m^(6)A-RNA then hybridizes with DNA probes a and b to produce a sandwich hybrid,initiating the click chemistry to generate probe a–b ligation product via first tandem ligation detection reaction(LDR)***,DNA probes c and d can hybridize with the probe a–b ligation product to generate the probe c–d ligation product via second LDR *** LDR cycles can be repeated through denaturation and annealing reaction to generate abundant biotin-/fluorophore-modified probe c–d ligation products that can easily assemble on the QD surface to induce distinct fluorescence resonance energy transfer(FRET)between QD and *** assay can be homogenously performed without the involvement of copper catalyst,m^(6)A-specific antibody,radioactive labeling,ligase enzyme,enzymatic reverse transcription,and next-generation ***,it can discriminate even 0.01% m^(6)A level in complex samples and accurately measure cellular m^(6)A-RNA expression,providing a promising avenue for clinical diagnostics and biomedical research.

关键词： RNA methylation click chemistry Förster resonance energy transfer Biosensor Cancer

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Post-functionalization of disubstituted polyacetylenes via click chemistry

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Science China chemistry 2011年第12期54卷 1948-1954页

作者： TONG Li QIN AnJun ZHANG XiaoA MAO Yu SUN JingZhi TANG Ben Zhong Institute of Biomedical Macromolecules MOE Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and Engineering Zhejiang University Hangzhou 310027 China Department of chemistry The Hong Kong University of Science ＆ Technology Clear Water Bay Kowloon Hong Kong China

We report a synthetic design and the experimental exploration of preparation of disubstituted polyacetylenes （PAs, P3） through 1,3-dipolar cycloaddition of azides with precursor PA bearing alkyne pendants. The precursor PA （P2） was derived by desilylation of the pristine PA with trimethylethynylsilane side chains （P1）. P1 was obtained by polymerization of a dual-alkyne containing monomer with one of the alkynes end-capping by trimethylsilane （M） under the promotion of WC16-Ph4Sn catalyst. Two synthetic routes, i.e. two-steps （from P1 to P3 via precursor P2） and one-pot （from P1 to P3 without separation and purification of P2） were tried and the results indicated that one-pot strategy is more facile and resultant P3-1 showed higher purity and higher molecular weight than the resultant of P3-2. By using the techniques such as GPC, FTIR and 1H NMR spectroscopy the polymerization behavior and the structures of the polymers were well characterized.

关键词： disubstituted polyacetylene click chemistry one-pot method selective polymerization

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Synthesis of 7-Triazole-substituted Camptothecin via click chemistry and Evaluation of in vitro Antitumor Activity

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Chinese Journal of chemistry 2014年第2期32卷 157-162页

作者： Lei Wang Wei Yuan Jie Zhang Linjiang Tong Yu Luo Yi Chen Wei Lu Qingqing Huang Institute of Drug Discovery and Development Shanghai Engineering Research Center of Molecular Therapeutics and New Drug DevelopmentEast China Normal UniversityShanghai 200062China State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaSIBSChinese Academy of SciencesShanghai 201203China

Camptothecin(CPT)is a natural topoisomerase I inhibitor with powerful antineoplastic activity against colorectal,breast,lung and ovarian *** discover more potent antitumor agents,a series of new CPT derivatives were synthesized utilizing click *** compounds were assessed for cytotoxicity against A549,HCT-116,HT-29,LoVo,MDA-MB-231 cell lines,and some compounds exhibited good in vitro ***,all compounds kept or enhanced Topo I inhibition.

关键词： camptothecin 7-triazole-substituted camptothecin click chemistry antitumor

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