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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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molecular recognition and homochirality preservation of guanine tetrads in the presence of melamine

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Nano Research 2020年第9期13卷 2427-2430页

作者： Yanghan Chen Chong Chen Pengcheng Ding Guoqiang Shi Ye Sun Lev N.Kantorovich Flemming Besenbacher Miao Yu Condensed Matter Science and Technology Institute School of Instrumentation Science and Engineerinz Harbin Institute of TechnologryHarbin 150001China State Key Laboratory of Urban Water Resource and Environment School of Chemistry and Chemical EngineeringHarbin Institute oj TechnologyHarbin 150001China Department of Physics Kings College LondonLondon WC2R 2LSUK Interdisciplinary Nanoscience Center Aarhus UniversityAarhus 8000Denmark

molecular recognition between nucleobases plays a crucial role in all kinds of biological processes.However,real-space investigation of the recognition capability of nucleobases in the presence of interfering compounds remains unexplored.Herein,based on the combination of scanning tunneling microscopy imaging and density functional theory modeling,we report the impact of the presence of melamine(M)on the formation and chirality of guanine(G)-tetrads on Au(111).Although M can interact with G by double hydrogen bonding,the Hoogsteen base pairing of G is not compromised,forming identical individual G-tetrads as would have happened without the presence of M.G-tetrads coexist with M on the surface not only in separate domains,but also within the mixture network of G-tetrads and M-dimers.Although the adsorption orientation of G-tetrads in the mixture network diversifies into two distinct angles,all G-tetrads in the network keep the same chirality,emphasizing the high preference of homochirality in such biochemical systems.

关键词： molecular recognition guanine-tetrad base pairing homcxjhirality biochemical synthesis

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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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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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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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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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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 Based on Hydrogen-bonding in the Coliposomes of Phosphatidylcholine and Amphiphiles Using Nucleobases

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Chemical Research in Chinese Universities 2006年第6期22卷 803-807页

作者： SONG Li-ming ZHU Tao WANG Qiu-sheng ZHANG Xiao LI Guo-wen Key Lab for Supramolecular Structure and Materials of Ministry of Education Jilin University Changchun 130012 P. R. China

A functional amphiphile, N^6 -myristoyl-9-[ 8-（ 1-trimethylamino） octyl ] adenine bromide （MTOAB）, was used to form coliposomes of phosphatidyleholine（PC）, PC/thymine, and PC/TOTB using sonication . The morphologies of the coliposomes were characterized using TEM （transmission electron microscopy）. The UV-Vis spectroscopic behavior of PC/MTOAB/thymine （molar ratio = 5： 1： 1 ） and PC/MTOAB/TOTB （molar ratio = 5： 1： 1 ） of coliposomal solutions showed that as a result of base pairing, absorption intensity showed a decrease at 263 nm with increase of time. The decrease of absorption intensity is ascribed to the hypochromic effect, which is because of the formation of hydrogen bonds between adenine and thymine in the coliposomes. The same effect was also observed for the mixture of aqueous PC/MTOAB liposomes and PC/TOTB liposomes after fusion, whereas the nocomplementary coliposomcs formed from PC/MTOAB and PC/TOTB did not show these spectroscopic changes. The molecular recognition through hydrogen interactions between adenine and thymine is very slow because of the possible occurrence of molecular lateral diffusion and exchange of amphiphile before recognition progresses in coliposomes. These results provide useful information for the design of supramolecular devices such as vesicles and liposomes,which can be used to mimic primitive recognition processes observed in biological systems.

关键词： Coliposomes Nueleobase molecular recognition Amphiphile

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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 titra-tion 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 molecular recognition Amino Acids zinc hematoporphyrin esters molecular Dynamics

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Synthesis of O6-Corona[3]arene[3]pyridazines and Their molecular recognition Property in Organic and Aqueous Media

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Chinese Journal of Chemistry 2018年第7期36卷 630-634页

作者： Yao Lu Dong-Dong Liang Zhan-Da Fu Qing-Hui Guo Mei-Xiang Wang Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education) Department of Chemistry Tsinghua University Beijing 100084 China

O6-Corona[3]arene[3]pyridazines were synthesized from the one-pot macrocyclic condensation reaction of 3,6-dichlorotetrazine with 1,4-dihydroquinone derivatives followed by the inverse electron demand Diels-Alder reaction of the tetrazine rings with a cyclopentanone-derived enamine. Conversion of six ester groups within macrocycle into all sodium acetate moieties afforded a water soluble O6-corona[3]arene[3]pyridazine. The coronary macrocycle host formed complexes selectively with organic ammoniums and dinitrile guests in a 1 ： 1 stoichiometric ratio in organic solvents with association constants ranging from （2.96± 0.10）× 10^1 to （2.53±0.33）× 10^5 L·mol^-1. Water soluble O6-corona[3]arene[3]pyridazine was also able to complex strongly with organic ammoniums in water to give an association constant up to （2.67 ± 0.21） × 10^4 L·mol^-1. The pseudo-rotaxane and inclusion structures of the host-guest complexes were revealed by the X-ray crystallography.

关键词： coronarene O6-coronaarenepyridazine inverse electron demand Diels-Alder reaction molecular recognition organic ammonium dinitrile

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