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Supramolecular systems for bioapplications:recent research progress in China

Science China Chemistry 2024年第5期67卷 1397-1441页

作者： Yue-Yang liu Xiao-Yong Yu Yu-Chen Pan Hang Yin Shuang Chao Yujie li He Ma Minzan Zuo Kun-Xu Teng Jun-li Hou Yong Chen Dong-Sheng Guo Ruibing Wang Yuxin Pei Zhichao Pei Jiang-Fei Xu Xiao-Yu Hu chunju li Qing-Zheng Yang Leyong Wang Yu liu Zhan-Ting li State Key Laboratory of Organometallic Chemistry Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional MoleculesShanghai Institute of Organic ChemistryChinese Academy of SciencesUniversity of Chinese Academy of SciencesShanghai 200032China Department of Chemistry Fudan UniversityShanghai 200438China College of Chemistry State Key Laboratory of Elemento-Organic ChemistryCollaborative Innovation Center of Chemical Science and EngineeringNankai UniversityTianjin 300071China State Key Laboratory of Quality Research in Chinese Medicine Institute of Chinese Medical SciencesUniversity of MacaoMacao 999078China College of Chemistry&Pharmacy Northwest A&F UniversityYangling 712100China Key Lab of Organic Optoelectronics&Molecular Engineering Department of ChemistryTsinghua UniversityBeijing 100084China College of Materials Science and Technology Nanjing University of Aeronautics and AstronauticsNanjing 211106China Key Laboratory of Radiopharmaceuticals Ministry of EducationCollege of ChemistryBeijing Normal UniversityBeijing 100875China Tianjin Key Laboratory of Structure and Performance for Functional Molecules College of ChemistryTianjin Normal UniversityTianjin 300387China State Key Laboratory of Analytical Chemistry for life Science Jiangsu Key Laboratory of Advanced Organic MaterialsSchool of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023China

Supramolecular systems feature dynamic,reversible and stimuli-responsive characteristics,which are not easily achieved by molecular entities.The last decade has witnessed tremendous advances in the investigations of supramolecular systems for various bioapplications,which include drug delivery,anticancer therapy,antibacterial therapy,photodynamic therapy,photothermal therapy,combination therapy,antidotes for residual drugs or toxins,and bioimaging and biosensing.Host-guest chemistry has played a key role in the development of such bioactive supramolecular systems,and natural macrocycles(such as cyclodextrins),synthetic macrocycles(such as calixarenes,cucurbit[n]urils,and pillararenes),and porous framework polymers(such as supramolecular organic frameworks and flexible organic frameworks)have been most successfully used as hosts to build different kinds of host-guest systems for attaining designed biofunctions.The self-assembly of rationally designed amphiphilic molecules,macromolecules and polymers represent another important approach for the construction of supramolecular architectures with advanced biofunctions.In this review,we summarize the important contributions made by Chinese researchers in this field,with emphasis on those reported in the past five years.

关键词： host-guest chemistry drug delivery anticancer and antibacterial photodynamic therapy photothermal therapy antidote transmembrane channel bioimaging and biosensing

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Prospering the biphen[n]arenes family by tailoring reaction modules

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Chinese Chemical Letters 2022年第5期33卷 2451-2454页

作者： Kaidi Xu Zhi-Yuan Zhang Zihao Zhou chunju li College of Science Center for Supramolecular Chemistry and CatalysisShanghai UniversityShanghai 200444China Tianjin Key Laboratory of Structure and Performance for Functional Molecules College of ChemistryTianjin Normal UniversityTianjin 300387China

Reported here is the comprehensive investigation on the formation of biphen[n]arenes by tailoring reac-tion modules.Five new macrocyclic arenes and four oligomers were synthesized by the condensation of monomers possessing different multimethoxyphenyl reaction modules and paraformaldehyde.We proved that the number and sites of methoxy on reaction modules greatly affected the reaction activity,shape,and connection mode of macrocycles.Moreover,the triangular and saddle-shaped configuration of macro-cycles were revealed by single crystal structures.The results provided a typical and fundamental guidance in designing new macrocyclic arenes.

关键词： Biphen[n]arenes Macrocyclic arenes Synthetic receptors Supramolecular chemistry

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Leaching kinetics of fluorine during the aluminum removal from spent li-ion battery cathode materials

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Journal of Environmental Sciences 2024年第4期138卷 312-325页

作者： Shengjie li Jianxin Zhu Research Center for Eco-Environmental Sciences Chinese Academy of SciencesBeijing 100085China University of Chinese Academy of Sciences Beijing 100049China

The high content of aluminum(Al)impurity in the recycled cathode powder seriously affects the extraction efficiency of Nickel,Cobalt,Manganese,and lithium resources and the actual commercial value of recycled materials,so Al removal is crucially important to conform to the industrial standard of spent li-ion battery cathode materials.In this work,we systematically investigated the leaching process and optimum conditions associated with Al removal from the cathode powder materials collected in a wet cathode-powder peeling and recycling production line of spent li-ion batteries(liBs).Moreover,we specifically studied the leaching of fluorine(F)synergistically happened along with the removal process of Al,which was not concerned about in other studies,but one of the key factors affecting pollution prevention in the recovery process.The mechanism of the whole process including the leaching of Al and F from the cathode powder was indicated by using NMR,FTIR,and XPS,and a defluoridation process was preliminarily investigated in this study.The leaching kinetics of Al could be successfully described by the shrinking core model,controlled by the diffusion process and the activation energy was 11.14 kJ/mol.While,the leaching of F was attributed to the dissolution of liPF6and decomposition of PVDF,and the kinetics associated was described by Avrami model.The interaction of Al and F is advantageous to realize the defluoridation to some degree.It is expected that our investigation will provide theoretical support for the large-scale recycling of spent liBs.

关键词： Al removal F leaching Cathode powder Heating alkali leaching Leaching kinetics

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Development of a stable attenuated double-mutant of tobacco mosaic virus for cross-protection

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Journal of Integrative Agriculture 2024年第7期23卷 2318-2331页

作者： Xiaojie Xu Shaoyan Jiang chunju liu Xujie Sun Qing Zhu Xiuzhai Chen Pengchao Jiang Fenglong Wang Yanping Tian Xiangdong li The Engineering Research Institute of Agriculture and Forestry Ludong UniversityYantai 264025China Laboratory of Plant Virology Department of Plant PathologyCollege of Plant ProtectionShandong Agricultural UniversityTai’an 271018China Weifang Tobacco Corporation Weifang 261031China linyi Tobacco Corporation Linyi 276000China Tobacco Research Institute Chinese Academy of Agricultural SciencesQingdao 266101China

Tobacco(Nicotiana tabacum)and tomato(Solanum lycopersicum)are two major economic crops in China.Tobacco mosaic virus(TMV;genus Tobamovirus)is the most prevalent virus infecting both crops.Currently,some widely cultivated tobacco and tomato cultivars are susceptible to TMV and there is no effective strategy to control this virus.Cross-protection can be a safe and environmentally friendly strategy to prevent viral diseases.However,stable attenuated TMV mutants are scarce.In this study,we found that the substitutions in the replicase p126,arginine at position 196(R196)with aspartic acid(D),glutamic acid at position 614(E614)with glycine(G),serine at position 643(S643)with phenylalanine(F),or D at position 730(D730)with S,significantly reduced the virulence and replication of TMV.However,only the mutation of S643 to F reduced the RNA silencing suppression activity of TMV p126.A double-mutant TMV-E614G-S643F induced no visible symptom and was genetically stable through six successive passages in tobacco plants.Furthermore,our results showed that TMV-E614G-S643F double-mutant could provide effective protection against the wild-type TMV infection in tobacco and tomato plants.This study reports a promising mild mutant for cross-protection to control TMV in tobacco and tomato plants.

关键词： cross-protection double-mutant p126 tobacco mosaic virus virulence

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Reversing neuromuscular blocking agent decamethonium by carboxylatopillar[6]arene based on host-guest encapsulation

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Chinese Chemical Letters 2022年第6期33卷 3003-3006页

作者： Yao Chai Longming Chen Yahan Zhang liang Zhao Zhao Meng Junyi Chen chunju li Qingbin Meng State Key Laboratory of Toxicology and Medical Countermeasures Beijing Institute of Pharmacology and ToxicologyBeijing 100850China Key Laboratory of Inorganic-Organic Hybrid Functional Material Chemistry Ministry of EducationTianjin Key Laboratory of Structure and Performance for Functional MoleculesCollege of ChemistryTianjin Normal UniversityTianjin 300387China Key Laboratory of Natural Resources and Functional Molecules of the Changbai Mountain Affiliated Ministry of EducationCollege of PharmacyYanbian UniversityYanji 133002China

Neuromuscular blocking agents(NMBAs)are extensively used during anesthesia to improve surgical conditions by relaxing skeletal muscle movements.Rapid neuromuscular recovery after surgery is desirable to facilitate the recovery of muscle function and prevent residual blockade.Decamethonium(C10)is a classic NMBA,which has been restricted over the past decades ascribed to lack of a suitable antidote in clinic.Herein we used carboxylatopillar[6]arene(CP6A)to reverse neuromuscular blocker effect of C10 through direct host-guest encapsulation.NMR and isothermal titration calorimetry served to confirm the complexation between CP6A and C10 with robust affinity[(1.07±0.14)×10^(7)L/mol].The CP6A was further used as a reversal agent of C10,which facilitated to decrease C10 concentration in mice blood and excrete via urinary clearance,resulting in rapid recovery from muscle relaxation.These favorable outcomes might lead us to suggest that this supramolecular strategy could allow patients to regain lucidity much faster than spontaneous recovery from anesthesia.

关键词： Host-guest encapsulation Decamethonium Neuromuscular blocking agents Supramolecular strategy Carboxylatopillararene

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Additives strategies to improving cycling stability of li metal batteries by modifying electrode electrolyte interphases

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Progress in Natural Science:Materials International 2024年第2期34卷 338-344页

作者： Yuan li Pengfei Huang Chunyu Cui Xiaoyuan Ma li Chen Zekun li linhai li Yuhong Tian School of Biological and Chemical Engineering Guangxi University of Science and Technology School of College of Chemistry and Chemical Engineering Hunan University Isky Future Energy Institute

li metal batteries（LMBs） have attracted much attention due to the ultra-high theoretical capacity of the li metal anode（LMA）.However,the uncontrollable dendrites growth and low coulombic efficiency hinder their practical application.Here,we explore 3,5-difluoropyridine（2F-BD） as a novel electrolyte additive to enable highperformance LMBs.The 2F-BD additive participates in and modifies the solvation structure of li ions by reducing the coordinated number of PF6-at the electrode surface,leading to the formation of a liF and li3N-rich solid electrolyte interphase（SEI）.The liF component increases the robustness of SEI and suppresses the formation of li dendrites,while the li3N component facilitates the transportation and reaction kinetics of li ions.As a result,the li‖li symmetric cell presents a stable cycling performance of up to 500 h at a current density of 1 mA cm-2.After coupling with liFePO4cathode,the obtained full cell achieves high specific capacities of 106.06 mA h g-1and 84.98 mA h g-1at 2.55 mA cm-2and 5.10 mA cm-2,respectively,and maintains a high capacity retention of84.0% after 1000 cycles at 0.13 mA cm-2,with an average cycling CE of 99.58%.

关键词： Electrolyte additive li dendrites li metal batteries liF and li3N-Rich electrode-electrolyte interphase liFePO4 cathode

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A Pillar[6]arene-[2]pseudorotaxane Based pH-Sensitive Molecular Switch

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中国化学:英文版 2015年第3期33卷 343-345页

作者： Huanqing Chen Xueshun Jia chunju li Department of Chemistry Shanghai UniversityShanghai 200444China

A novel pH-responsive[2]pseudorotaxane based on ethylated pillar[6]arene and bis(1,2,3-triazolium)butane cation was constructed.The dethreading and rethreading could be reversibly controlled by adding base and acid,i.e.,the deprotonation and reprotonation of the guest.In contrast,such responsible switching behavior does not occur for the complexation between the guest and ethylated pillar[5]arene,since both the cationic axle and the deprotonated one can be strongly bound by ethylated pillar[5]arene.Furthermore,the bis(1,2,3-triazolium)butane⊂pillar[6]-arene-[2]pseudorotaxane can also disassemble upon the addition of competitive ethylated pillar[5]arene.

关键词： pillararene pseudorotaxane pH-sensitive molecular switch

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Complexation of linear Aliphatic Ester,Aldehyde and Ketone Guests by Per-ethylated Pillar[5]arene

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中国化学:英文版 2015年第3期33卷 335-338页

作者： Xiaobing Lou Huanqing Chen Xueshun Jia chunju li Department of Chemistry Shanghai UniversityShanghai 200444China Department of Physics East China Normal UniversityShanghai 200062China

The complexation of four neutral guest molecules containing carbon-oxygen double bonds,i.e.,1,6-diacetoxy-hexane(1),dimethyl hexanedioate(2),hexanal(3),and 2-hexanone(4),by per-ethylated pillar[5]arene is reported.These guests show remarkably different binding affinities.For example,ester 1 could be fully engulfed by the host cavity to form a[2]pseudorotaxane-type inclusion complex,while for 2,no obvious host-guest interaction was ob-served.

关键词： pillararene molecular recognition ester aldehyde ketone

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Supramolecular liquid barrier for sulfur mustard utilizing host-guest complexation of pillar[5]arene with triethylene oxide substituents

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Chinese Chemical Letters 2023年第4期34卷 254-257页

作者： Yahan Zhang Junyi Chen Longming Chen liang Zhao Mengke Ma Xinbei Du Zhao Meng Han Zhang Zhibing Zheng Yongan Wang chunju li Qingbin Meng State Key Laboratory of Toxicology and Medical Countermeasures Beijing Institute of Pharmacology and ToxicologyBeijing 100850China Key Laboratory of Inorganic-Organic Hybrid Functional Material Chemistry Ministry of EducationTianjin Key Laboratory of Structure and Performance for Functional MoleculesCollege of ChemistryTianjin Normal UniversityTianjin 300387China

Sulfur mustard(SM) can be absorbed by skin quickly and cause serious system damage via reacting with nearly all cell constituents. Until now, there is still lack of effective antidotal therapy for SM and skin protection is highly important to defend SM. In this article, supramolecular liquid barrier based on pillar[5]arene with triethylene oxide substituents(EGP5) has been designed to impede the skin permeation of SM and further interaction with the skin tissue. EGP5 could encapsulate SM within its cavity, with a Kavalue of(5.10 ± 0.47) × 10^(2)L/mol. In vitro skin absorption test proved that EGP5 was capable to effectively prevent SM from penetrating through skin. This supramolecular liquid barrier was employed on rat models to systematically evaluate protective effect against SM intoxication. Pretreatment of EGP5could alleviate skin and system damage induced by SM and improve survival rate of poisoned rat models from 10% to 90%. Additionally, EGP5 served as protective materials could be highly reused after recycling several times. Overall, these findings have provided the first insight into the construction of convenient liquid material for SM protection.

关键词： Supramolecular barrier Host-guest complexation liquid pillararene Sulfur mustard Skin protection

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Highly-chlorinated inert and robust interphase without mineralization of oxide enhancing high-rate li metal batteries

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Chinese Chemical Letters 2024年第6期35卷 239-243页

作者： Long li Kang Yang Chenpeng Xi Mengchao li Borong li Gui Xu Yuanbin Xiao Xiancai Cui Zhiliang liu lingyun li Yan Yu Chengkai Yang Key Laboratory of Advanced Materials Technologies International(HongKong Macao and Taiwan)Joint Laboratory on Advanced Materials TechnologiesSchool of Materials Science and EngineeringFuzhou UniversityFuzhou 350108China College of Material Sciences and Chemical Engineering Harbin Engineering UniversityHarbin 150001China

Side reactions and dendrite growth triggered by the unstable interface and inhomogeneous deposition have become the biggest obstacle to the commercialization for lithium metal batteries.In this study,a highly-chlorinated organic-inorganic hybrid interfacial protective layer is developed by rationally tuning the interfacial passivation and robustness to achieve the convenient and efficient li metal anode.The polyvinyl chloride(PVC)can effectively resist water and oxygen,which is confirmed by density functional theory.The organic-dominant solid electrolyte interphases(SEI)with lithium chloride are investigated by the X-ray photoelectron spectroscopy(XPS)with little mineralization of oxide,such as li_(2)O and li_(2)CO_(3).With such artificial SEI,a uniform and dense lithium deposition morphology are formed and an ultra-long stable cycle of over 500 h are achieved even at an ultra-high current density of 10 m A/cm^(2).Moreover,the simple and convenient protected anode also exhibits excellent battery stability when paired with the liNi_(0.8)Co_(0.1)Mn_(0.1)O_(2)(NCM811)and liFePO_(4)(LFP)cathode,showing great potential for the commercial application of lithium metal batteries.

关键词： Highly-chlorinated Water/oxygen resistance Stable interphase Dendrite-free lithium metal batteries High-rate

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