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molecular recognition of cyclophanes in water

Chinese Chemical Letters 2024年第5期35卷 32-44页

作者： Fang-Yuan Chen Wen-Chao Geng Kang Cai Dong-Sheng Guo College of Chemistry State Key Laboratory of Elemento-Organic ChemistryKey Laboratory of Functional Polymer Materials(Ministry of Education)Frontiers Science Center for New Organic MatterCollaborative Innovation Center of Chemical Science and Engineering(Tianjin)Nankai UniversityTianjin 300071China College of Chemistry Nankai UniversityTianjin 300071China

molecular recognition in water,the biological solvent,always receives significant research focus in supramolecular chemistry.The mechanisms of molecular recognition in water is key to comprehending biological processes at the molecular level.Over the past five decades,supramolecular chemists have developed a vast array of synthetic receptors with highly diverse structures and recognition properties.Among them,cyclophanes represent an important family of macrocyclic receptors that have been extensively explored.The aromatic moieties in cyclophanes not only facilitate chemical modifications to impart water solubility but also enable forming hydrophobic cavities for guest inclusion in aqueous environments.Pioneered by Koga et al.,who reported the first inclusion complex of cyclophanes in water and solid state,numerous water-soluble cyclophanes,including derivatives of blue box,calixarenes,resorcinarenes,pillararenes,octopusarenes,biphenarenes,coronarenes,and naphthotubes,etc.,have been synthesized and subjected to investigation of the recognition capabilities in aqueous solutions.This review provides an overview of cyclophane receptors designed to bind organic guests in water.We categorize them into two classes based on the modifications made to their hydrophobic cavities:those with“exo-functionalized hydrophobic cavities”and those with“endo-functionalized hydrophobic cavities”.We introduce their distinctive features and discuss strategies to enhance recognition affinity and selectivity.This review aims to inspire the development of novel synthetic receptors with intriguing properties and foster practical applications of cyclophanes.

关键词： Biomimetic receptor Cyclophane molecular recognition Hydrophobic effect High-affinity Macrocycles

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Amide naphthotubes:Biomimetic macrocycles for selective molecular recognition

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Chinese Chemical Letters 2024年第4期35卷 124-131页

作者： Cheng-Da Zhao Huan Yao Shi-Yao Li Fangfang Du Li-Li Wang Liu-Pan Yang School of Pharmaceutical Science Postdoctoral Research Station of Basic MedicineHengyang Medical SchoolUniversity of South ChinaHengyang 421001China

Selective molecular recognition in water is routine for bioreceptors,but remains challenging for synthetic hosts.This is principally because noncovalent interactions are usually less efficient in aqueous environments.By mimicking the cavity feature of bioreceptors,Prof.Wei Jiang proposed and clarified the concept of“endo-functionalized cavity”.Through situating polar binding sites into a deep hydrophobic cavity,we designed and synthesized several macrocyclic hosts,among which amide naphthotubes are the most representative.The hosts can selectively recognize various polar molecules including organic micropollutants,drug molecules,and chiral molecules in water by employing the hydrophobic effect and shielded hydrogen bonding.In addition,these biomimetic hosts have been applied in spectroscopic analysis,adsorptive separation and self-assembly.In this review,we provide an overview of recent advances on amide naphthotubes with special emphasis on the efforts of Jiang's group.We are convinced that these biomimetic macrocycles will make further contributions to supramolecular chemistry and beyond.

关键词： molecular recognition Supramolecular chemistry Amide naphthotube Endo-functionalized cavity Biomimetic macrocycle

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Photoswitchable molecular recognition Enabled by Dithienylethene-Mediated Structural Changes of Dynamic Covalent Hydrazone Bonds

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CCS Chemistry 2024年第2期6卷 497-506页

作者： Lifeng Wang Hanxun Zou Hebo Ye Yu Hai Hanwei Lu Junmiao Deng Lei You State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of MatterChinese Academy of SciencesFuzhou 350002 College of Chemistry and Material Science Fujian Normal UniversityFuzhou 350007 University of Chinese Academy of Sciences Beijing 100049 Fujian Science&Technology Innovation Laboratory for Optoelectronic Information of China Fuzhou 350108

Light-induced recognition,assemblies,and materials are intensive areas of research due to their high spatiotemporal resolution.Herein,we demonstrated photoswitchable molecular recognition via dithienylethene-triggeredreversible structural regulation of dynamic covalent hydrazone bonds.By combining dithienylethenes and cyclic hemiacetals,the photochemical open-ring and closed-ring forms enabled turningoff and on the creation of awide range of hydrazones when desired.Light-induced bidirectional switching between hydrazones and their cyclization structures promoted by a neighboring carboxyl group was further achieved.By taking advantage of reversible structural changes totoggleon andoff the binding pocket,photoswitchable recognitionofmetal ionswas realized.Finally,the construction of an acylhydrazone polymer offered a facile way for light-mediated selective extraction/release.The strategies and results reported here should find applications in many contexts,such asdynamicassemblies,molecular switches,and smart materials.

关键词： molecular recognition photoswitch dynamic covalent chemistry hydrazone selective extraction/release

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taBOX: A water-soluble tetraanionic rectangular molecular container for conjugated molecules and taste masking for berberine and palmatine

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Chinese Chemical Letters 2024年第5期35卷 175-178页

作者： Qihan Lin Jiabin Xing Yue-Yang Liu Gang Wu Shi-Jia Liu Hui Wang Wei Zhou Zhan-Ting Li Dan-Wei Zhang Department of Chemistry Shanghai Key Laboratory of Molecular Catalysis and Innovative MaterialsFudan UniversityShanghai 200438China

A water-soluble macrocycle that bears four carboxylate anions has been designed and prepared,which forms a rectangular cavity that can efficiently encapsulate discrete electron-deficient aromatic compounds,including berberine and palmatine.This macrocycle is revealed to be highly biocompatible and able to inhibit the bitter taste of the two drugs.

关键词： Macrocycle Multianion molecular container molecular recognition Bitter taste masking

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Hematoma-like dynamic hydrogelation through natural glycopeptide molecular recognition for infected bone fracture repair

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Bioactive Materials 2023年第12期30卷 73-84页

作者： Shenghao Wang Wenbo He Huan Wang Dachuan Liu Miao Wang Huilin Yang Guoqing Pan Bin Li Orthopedic Institute Department of Orthopaedic SurgeryMedical 3D Printing CenterThe First Affiliated HospitalSchool of Biology&Basic Medical SciencesSuzhouMedical CollegeSoochow UniversitySuzhouJiangsu215006China Collaborative Innovation Center of Hematology Soochow UniversitySuzhouJiangsu215006China Institute for Advanced Materials School of Materials Science and EngineeringJiangsu UniversityZhenjiangJiangsu212013China

Infected bone fractures remain a major clinical challenge for orthopedic surgeons.From a tissue regeneration perspective,biomaterial scaffolds with antibacterial and osteoinductive activities are highly desired,while advanced materials capable of mimicking the pathological microenvironment during the healing process of infected tissues remain an area deserving more research.Hematoma,the gel-like blood coagulum,plays an essential role in bone fracture repair because of its ability to serve as a dynamic and temporary scaffold with cytokines for both pathogen elimination and tissue healing.In light of this,we designed a dynamic hydrogel with hematoma-like antimicrobial or reparative performance for infected bone fracture repair in this study.The proposed dynamic hydrogel network was based on the reversible recognition of a natural glycopeptide antibiotic vancomycin(Van)and its target dipeptide D-Ala-D-Ala(AA),which could serve as a hematoma-like scaffold for obliterating bacteria in the fracture region and promoting bone repair by introducing an endogenous osteogenic peptide(OGP).In vivo experiments demonstrated that the hydrogel could rapidly eradicate bacteria,improve bone regeneration and restore the local inflammatory microenvironment.Together,findings from this study imply that the use of hematoma-like dynamic hydrogel could lead to a biomimetic revolution in surgical strategies against susceptible bone fractures.

关键词： Dynamic biomaterial molecular recognition Hematoma mimicking Infected fracture repair Inflammatory microenvironment restoration

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New Promises of Advanced molecular recognition:Bioassays,Single Cell Analysis,Cancer Therapy,and Beyond

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Chinese Journal of Chemistry 2022年第5期40卷 635-650页

作者： Shuxin Xu Hui He Zhen Liu State Key Laboratory of Analytical Chemistry for Life Science School of Chemistry and Chemical EngineeringNanjing University163 Xianlin AvenueNanjingJiangsu210023 China

The development of biomimetic affinity materials holds great value for scientific research and practical applications.Starting from boronic acid chemistry,we developed a series of boronate affinity materials(BAMs)with desired binding properties in aspects of binding pH,affinity and selectivity.Based on BAMs,molecularly imprinted polymers(MIPs)and aptamers capable of targeting vital biomolecules were rationally designed and prepared.Using these affinity reagents as potent tools and combining with advanced analytical techniques particularly liquid chromatography,mass spectrometry and spectrometry allowed for the construction of promising analytical methods to provide new qualitative and quantitative solutions to challenging applications including targeted proteomics analysis,single cell analysis and disease diagnostics.In addition,the targeting capability of these affinity reagents particularly nanoscale MIPs opened a unique access to develop innovative nanotherapeutics for cancer treatment.

关键词： molecular recognition Boronate afinity molecularly imprinted polymers Immunoassays Cancer

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A Stable Luminescent Covalent Organic Framework Nanosheet for Sensitive molecular recognition

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CCS Chemistry 2023年第9期5卷 2033-2045页

作者： Yaozu Liu Junxia Ren Yujie Wang Xin Zhu Xinyu Guan Zisheng Wang Yida Zhou Liangkui Zhu Shilun Qiu Shengxiong Xiao Qianrong Fang State Key Laboratory of Inorganic Synthesis and Preparative Chemistry College of Chemistry Jilin UniversityChangchun 130012 The Education Ministry Key Laboratory of Resource Chemistry Shanghai Key Laboratory of Rare Earth Functional MaterialsShanghai Frontiers Science Center of Biomimetic CatalysisCollege of Chemistry and Materials ScienceShanghai Normal UniversityShanghai 200234

Despite rapid advances in fluorescence detectors over the past decade,the development of a highly stable,sensitive,and selective fluorescence platform for molecular recognition remains a considerable challenge.Here we report a stable carbazole-based sp2 carbon fluorescence covalent organic framework(COF)nanosheet,termed a JUC-557 nanosheet.Owing to the synergistic effect of aggregation-induced emission-and aggregation-caused quenching-based chromophores,the architecture of the JUC-577 shows high absolute quantum yields(up to 23.0%)in the solid state and when dispersed in various solvents as well as excellent sensing performance toward specific analytes,such as iodine(Ka:2.10×10^(5)M−1 and LOD:302 ppb),2,4,6-trinitrotoluene(Ka:4.38×10^(5)M−1 and LOD:129 ppb),and especially nitrobenzene(Ka:6.18×10^(6)M−1 and LOD:5 ppb)that is superior to that of fluorescence detection materials reported so far.Furthermore,the JUC-557 nanosheet preserves strong luminescence and sensitive recognition,even under harsh conditions,and allows trace detection of various analytes via a handheld UV lamp.These findings pave the way for developing stable ultrathin COF nanomaterials for highly sensitive and selective molecular detection.

关键词： covalent organic framework nanosheet fluorescence detection molecular recognition

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molecular recognition of Porphyrin-Salen Compound towards N-Heterocyclic-guests

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Chinese Journal of Chemistry 2006年第8期24卷 1031-1036页

作者：赵小菁阮文娟章应辉戴放刘丹朱志昂范圣弟 Department of Biochemical Engineering Dalian Nationalities University Dalian Liaoning 116600 China Department of Chemistry Nankai Universitry Tianjin 300071 China

A novel porphyrin-salen compound and corresponding zinc（Ⅱ） porphyrin-salen compound （ZnPSC10） covalently linked by a flexible alkoxy chain （-O（CH）10O--） have been synthesized and characterized. molecular recognition of three N-heterocyclic guests, pyridine, 1,4-diazobycyclo[2,2,2]octane （DABCO） and pyrazine, with the host ZnPSC10 was investigated. Binding constants were determined by means of UV-vis titration method. The binding mode of ZnPSC10 with DABCO has been discussed in detail by using ^1H NMR. It was found that the conformations of the recognition system changed from closed to open with the adding of DABCO.

关键词： molecular recognition porphyrin-salen compound N-heterocyclic guest

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molecular recognition of Chiral Zinc Porphyrin with Amino Acid Esters

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Chinese Journal of Chemistry 2005年第1期23卷 44-49页

作者：王树军阮文娟赵小菁罗代兵朱志昂 DepartmentofChemistry NanKaiUniversityTianjin300071China

One kind of novel chiral porphyrin and its zinc complex were synthesized and characterized. The molecular recognition of chiral zinc porphyrin towards amino acid esters in CHCl 3 was investigated by UV‐vis spectral titration method. The associative constants of the molecular recognition reactions were all K D > K L and followed the order of K (PheOMe)> K (LeuOMe)> K (ValOMe)> K (AlaOMe) in host (Zn( L ‐BocTyr)TAPP). Circular dichroism spectra were used to explain chiral molecular recognition. The minimal energy conformation of host‐guest molecular system was sought by molecular dynamics method. The molecular recognition process of this host‐guest system was calculated by quantum chemistry and the results were explained by the experiments

关键词： chiral zinc porphyrin molecular recognition amino acid ester molecular dynamics quantum chemical calculation

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Synthetic host-guest pairs as novel bioorthogonal tools for pre-targeting

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Chinese Chemical Letters 2024年第2期35卷 44-56页

作者： Yan-Long Ma Shi Yan Xiong-Jie Xu Hua Cao Ruibing Wang School of Chemistry and Chemical Engineering and Guangdong Cosmetics Engineering & Technology Research Center Guangdong Pharmaceutical UniversityZhongshan 528458China State Key Laboratory of Quality Research in Chinese Medicine and the Institute of Chinese Medical ScienceUniversity of MacaoMacao 999078China

Due to its simplicity, high efficiency, and chemo-selectivity, bioorthogonal chemistry has shown a great application potential in pre-targeting.Currently, four bioorthogonal pairs as targeting tools, including (strept)avidin/biotin, antibody/antigen, oligonucleotide hybridization and IEDDA tools, have been developed and applied in targeted delivery.Nevertheless, all of these tools still suffer from some limitations, such as difficult modification, biochemical fragility and larger molecular weight for biological association tools, as well as chemical instability for IEDDA tools.Synthetic host-guest pairs with relatively small molecular sizes not only possess strong chemical stability, but also have the features of fast conjugation rate, tunable binding affinity , easy modification, and high chemo-selectivity.Consequently, they can be used as a novel non-covalent bioorthogonal tool for pre-targeting.In order to further promote the development of host-guest pairs as novel bioorthogonal tools for pre-targeted delivery, we firstly calculate their conversion rate to make researcher aware of their unique advantages;next, we summarize the recent research progress in this area.The future perspectives and limitations of these unique tools will be discussed.This review will provide a systemic overview of the development of synthetic host-guest pairs as novel bioorthogonal tools for pre-targeting, and may serve as a “go for” resort for researchers who are interested in searching for new synthetic tools to improve pre-targeting.

关键词： Bioorthogonal chemistry Synthetic host-guest pairs Pre-targeting molecular recognition Biomedical applications

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