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Synthesis and ultraviolet/aggregation-induced emission investigation of novel tetraphenylvinyl hydrazone derivatives: efficient multimodal chemosensors for fluoride ion

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Frontiers of Chemical Science and Engineering 2023年第12期17卷 2061-2073页

作者： Wenting Yin linqi shi Mengjiao Liang Yaodong Huang Junjiao Yang Key Laboratory of Systems Bioengineering(Ministry of Education) School of Chemical Engineering and TechnologyTianjin UniversityTianjin 300350China Analysis and Test Center of Beijing University of Chemical Technology Beijing University of Chemical TechnologyBeijing 100029China

Herein,three novel tetraphenylethylene hydrazone chemosensors TC12,SC16,and TC16 are prepared for the selective detection of F−.Two NH and one C=N units are incorporated into the sensors for better colorimetric responses,whereas the tetraphenyl unit is in charge of the aggregation-induced emission *** them,compounds SC16 and TC16 form stable gels with some organic *** the tetrahydrofuran/H2O solutions of the three compounds exhibit aggregation-induced emission effect,whereby the fluorescence emission increases by varying degrees with the volume of poor solvent ***,good aggregation-induced emission effects are observed in the self-assembly of SC16 and *** a sample chemosensor,TC12 in tetrahydrofuran responds to F−selectively with high sensitivity,with the colorimetric and fluorometric detection limits of 8.25×10^(−7) mol·L^(-1) and 2.69×10^(−7) mol·L^(-1),*** reversible gel-sol-gel phase transition and color changes indicate that both SC16-dimethyl sulfoxide and TC16-ethyl acetate gels specifically respond to F-with good *** detection results are well supported by ultraviolet-visible spectroscopy,fluorescent spectroscopy,and 1H nuclear magnetic *** importantly,the driving forces of gelation are visually clarified through the single crystal X-ray analysis of compound TOMe.

关键词： organogelator tetraphenylvinyldrazone single crystal aggregation-induced emission effect ion sensing

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11B 3Q MAS NMR Study on Glucose-Responsive Micelles Self-assembled from PEG-b-P(AA-co-AAPBA)

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Chinese Journal of Chemistry 2014年第1期32卷 97-102页

作者： Ma Rujiang Wang Beilei Sun Pingchuan shi linqi Institute of Polymer Chemistry Nankai University and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) Key Laboratory of Functional Polymer Materials Ministry of Education Tianjin 300071

Phenylboronic acid (PBA) based glucose-responsive materials have attracted great interests in recent years for developing insulin delivery *** is desired to obtain PBA based materials that can response to glucose under physiological pH and understand the *** using 11B triple-quantum magic-angle spinning nuclear magnetic resonance (11B 3Q MAS NMR) measurements,the glucose-responsive mechanism of micelles self-assembled from poly(ethylene glycol)-b-ploy(acrylic acid-co-acrylamidophenylboronic acid) PEG-b-P(AA-co-AAPBA) is deeply *** configurations of phenylboronic acid during various steps of glucose-responsive behaviors are clearly analyzed in the 11B 3Q MAS NMR spectra and coordination between carboxyl and PBA is *** increasing the AA units in PEG-b-P(AA-co-AAPBA),the carboxyl can coordinate with PBA moieties and cause the glucose-responsiveness of micelles even in the weak acid environment.

关键词： 11B 3Q MAS NMR coordination glucose-responsiveness micelles self-assembly

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Self-assembled nanochaperones enable the disaggregation of amyloid insulin fibrils

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Science China Chemistry 2022年第2期65卷 353-362页

作者： Hui Wang Ang Li Menglin Yang Yu Zhao linqi shi Rujiang Ma Key Laboratory of Functional Polymer Materials of Ministry of Education Institute of Polymer ChemistryCollege of ChemistryNankai UniversityTianjin 300071China State Key Laboratory of Medicinal Chemical Biology Nankai UniversityTianjin 300071China

The deposition of highly ordered amyloid fibrils is recognized as a hallmark of amyloidosis diseases such as Alzheimer’s disease and Parkinson’s *** the amyloid fibrils is considered as one of the effective strategies for the control and treatment of amyloidosis *** this article,by simulating the function of natural molecular chaperones,co-assembled block copolymer micelles with coordination groups of nitrilotriacetic acid(NTA)and hydrophobic microdomains of poly(Nisopropylacrylamide)(PNIPAM)on the surface were used as nanochaperones(n Chaps)to disaggregate amyloid insulin *** ions chelated by NTA can bind the histidine imidazole residues while the PNIPAM microdomains can interact with the exposed hydrophobic sites on the amyloid insulin fibrils,which synergistically perturb the stability of amyloid insulin fibrils,loosen their structure,and finally promote their disaggregation.A combination of characterizations with fluorescence spectroscopy,transmission electron microscopy(TEM),dynamic hight scattering(DLS),and quartz crystal microbalance(QCM)demonstrated that mature amyloid insulin fibrils were completely disaggregated after incubating with n Chaps for 90 *** study may provide a promising strategy for the development of n Chaps for the treatment of amyloidosis diseases.

关键词： amyloid fibrils insulin nanochaperones disaggregation

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Complex micelles with the bioactive function of reversible oxygen transfer

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Nano Research 2015年第2期8卷 491-501页

作者： Liangliang Shen Lizhi Zhao Rui Qu Fan Huang Hongjun Gao Yingli An linqi shi State Key Laboratory of Medicinal Chemical Biology Key Laboratory of Functional Polymer Materials Ministry of Education Collaborative Innovation Center of Chemical Science and Engineering(Tianjin) Institute of Polymer Chemistry Nankai University Tianjin 300071 China State Key Laboratory of Hollow Fiber Membrane Materials and Processes School of Materials Science and Engineering Tianjin Polytechnic University Tianjin 300387 China

A complex micelle as a hemoglobin functional model with the biaoactive function of reversible oxygen transfer has been constructed through the hierarchical assembly of the diblock copolymer poly（ethylene glycol）-block- poly（4-vinylpyridine-co-N-heptyl-4-vinylpyridine）（PEG-b-P（4VP-co-4VPHep））, tetrakis（4-sulfonatophenyl）porphinato iron（II）（Fe（II）TPPS） and β-cyclodextrin （β-CD）. The μ-oxo dimer of Fe（II）TPPS was successfully inhibited because the Fe（II）TPPS was included into the cavities of β-CDs through host-guest interaction. Fe（II）TPPS coordinated with pyridine groups functions as the active site to reversibly bind dioxygen. In adition, the host-guest inclusion （β-CD/Fe（II）TPPS） was encapsulated in the hydrophobic core of the complex micelle and tightly fixed by P4VP chains. The hydrophilic PEG blocks stretched in aqueous solution to constitute the shells which stabilize the structure of the complex micelle as well as endow the complex micelle with sufficient blood circulation time. Dioxygen can be bound to the Fe（II）TPPS located in the confined space and excellent reversibility of the binding-release process of dioxygen can be achieved. The quaternary amine N-heptyl-4-vinylpyridine can coerce abundant S2O4^2- ions into the core of the complex micelle to facilitate the self-reduction process. Dioxygen adducts （Fe（II）TPPS（O2）） were effectively protected by the double hydrophobic barriers constructed by the cavity of the cyclodextrin and the core of the complex micelle which enhances the ability to resist nucleophilic molecules. Therefore, the rationally designed amphiphilic structure can work as a promising artificial O2 carrier. Potentially, the complex micelle can be expected to improve the treatment of diseases linked with hypoxia.

关键词： ionic block copolymer bioactive self-assembly metalloporphyrin reversibledioxygen-binding proton sponge effect

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Recent advances and future challenges in the use of nanoparticles for the dispersal of infectious biofilms

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Journal of Materials Science & Technology 2021年第25期84卷 208-218页

作者： Shuang Tian Henny C.van der Mei Yijin Ren Henk J.Busscher linqi shi State Key Laboratory of Medicinal Chemical Biology Key Laboratory of Functional Polymer Materials of Ministry of EducationInstitute of Polymer ChemistryCollege of ChemistryNankai UniversityTianjin300071China University of Groningen and University Medical Center Groningen Department of Biomedical EngineeringAntonius Deusinglaan 19713 AVGroningenthe Netherlands University of Groningen and University Medical Center Groningen Department of OrthodonticsHanzeplein 19700 RBGroningenthe Netherlands

Increasing occurrence of intrinsically antimicrobial-resistant,human pathogens and the protective biofilm-mode in which they grow,dictates a need for the alternative control of infectious *** bacteria utilize dispersal mechanisms to detach parts of a biofilm as part of the biofilm life-cycle during times of nutrient scarcity or *** here identify recent advances and future challenges in the development of dispersants as a new infection-control ***(DNase)and other extracellular enzymes can disrupt the extracellular matrix of a biofilm to cause ***,a variety of small molecules,reactive oxygen species,nitric oxide releasing compounds,peptides and molecules regulating signaling pathways in biofilms have been described as *** their own,dispersants do not inhibit bacterial growth or kill bacterial *** natural,as well as artificial dispersants,are unstable and hydrophobic which necessitate their encapsulation in smart nanocarriers,like p H-responsive micelles,liposomes or *** on their composition,nanoparticles can also possess intrinsic dispersant *** dispersed from an infectious biofilm end up in the blood circulation where they are cleared by host immune ***,this sudden increase in bacterial concentration can also cause *** antibiotic loading of nanoparticles with dispersant properties or combined administration of dispersants and antibiotics can counter this ***,biofilm remaining after dispersant administration appears more susceptible to existing *** part of the natural biofilm life-cycle,no signs of"dispersant-resistance"have been *** are therewith promising for the control of infectious biofilms.

关键词： Dispersant Enzymes EPS eDNA Antibiotic resistance Dispersal mechanism Nanoparticles

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Micellization of copolymers via noncovalent interaction with TPPS and aggregation of TPPS

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Science China Chemistry 2011年第2期54卷 343-350页

作者： ZHAO LiZhi XIANG Rui ZHANG LiYan WU ChengLin MA RuJiang AN YingLi shi linqi Key Laboratory of Functional Polymer Materials Ministry of EducationInstitute of Polymer ChemistryNankai UniversityTianjin 300071China

Aggregation of 5,10,15,20-tetrakis-(4-sulfonatophenyl)-porphyrin (TPPS) was investigated in complex micelles composed of poly(ethylene glycol)-block-poly(4-vinylpyridine) (PEG-b-P4VP) and poly(2-(dimethylamino)ethyl methylacrylate)-b-poly(Nisopropylacrylamide) (PDMAEMA-b-PNIPAM) in aqueous *** resultant complex micelles had a complex P4VP/ PDMAEMA/TPPS core and a mixed PEG/PNIPAM *** noncovalent interaction modes between the porphyrin and each copolymer accomplished a co-effect on the aggregation of *** formation of aggregates was *** pH 3.2–6.5,TPPS existed as a mixture of H-aggregates and monomers because of the aromatic-aromatic interaction with P4VP and electrostatic interaction with *** monomers translated into J-aggregates,stabilized by electrostatic interaction with the both polyelectrolyte blocks,upon decreasing the pH to *** free-base monomer was the one and only form for the dye at pH 11.0 due to aromatic stacking with the pyridyl rings.

关键词： block copolymer TPPS H-aggregates J-aggregates

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Calixarene-integrated nano-drug delivery system for tumortargeted delivery and tracking of anti-cancer drugsin vivo

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Nano Research 2022年第8期15卷 7295-7303页

作者： Lina Xu Jingshan Chai Ying Wang Xinzhi Zhao Dong-Sheng Guo linqi shi Zhanzhan Zhang Yang Liu Key Laboratory of Functional Polymer Materials of Ministry of Education College of ChemistryNankai UniversityTianjin 300071China State Key Laboratory of Medicinal Chemical Biology Nankai UniversityTianjin 300071China State Key Laboratory of Elemento-Organic Chemistry Nankai UniversityTianjin 300071China

Nano-drug delivery systems(nanoDDS)have been extensively investigated clinically to improve the therapeutic effect of anticancer ***,the complicated synthesis during the preparation as well as the potential drug leakage during transportation has greatly limited their general *** this work,a calixarene-integrated nanoDDS(CanD)that achieves tumor-targeted delivery and tracking of anti-cancer drugs in vivo is *** hypoxia-responsive calixarene(SAC4A)exhibits high binding affinity to a series of anti-cancer drugs and rhodamine B(RhB)under normoxic condition while decreasing the binding affinity under hypoxic condition,which leads to the drug release and fluorescence recovery ***,the hypoxia-responsiveness of SAC4A conveys CanD with tumor-targeting ability,resulting in the enrichment of the drug in tumors and enhancement in tumor suppression in ***,CanD could become a general platform allowing the delivery of a wide scope of anti-cancer drugs that have strong host-guest interaction with SAC4A.

关键词： drug delivery system calixarene host-guest interaction hypoxia-responsiveness drug tracking

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Protein@PP-Zn nanocomplex assembled by coordination of zinc ions used for intracellular protein delivery

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Science China Chemistry 2023年第8期66卷 2354-2362页

作者： Liyun Cui Sainan Liu Fan Wu Hua Chen Yuanfeng Li linqi shi Yong Liu Rujiang Ma Key Laboratory of Functional Polymer Materials of Ministry of Education Institute of Polymer ChemistryCollege of ChemistryNankai UniversityTianjin300071China Wenzhou Institute University of Chinese Academy of SciencesWenzhou Key Laboratory of Interdiscipline and Translational MedicineWenzhou325001China Translational Medicine Laboratory the First Affiliated Hospital of Wenzhou Medical UniversityWenzhou325035China

In recent years,intracellular delivery of protein drugs has attracted great attention,and polymer-based systems have been extensively exploited to develop efficient and safe ***,efficient intracellular delivery of protein drugs remains a challenge because of the cell membrane barrier and endosome ***,we report a protein@PP-Zn nanocomplex,which consists of an imidazole-containing block polymer poly(ethylene glycol)-block-poly(β-amino ester)(PEG-b-PAE(Im),PP),zinc ions,and protein drugs,for efficient intracellular protein ***-b-PAE(Im)could conjugate proteins via the bridging effect of zinc ions which simultaneously coordinate with imidazole groups on polymer and electron donor groups,such as imidazole and primary amine groups,on protein to improve the loading stability of *** a slightly acidic environment near cancer cells,the protonation of PAE(Im)backbone increases the positive charge density of the nanocomplex and promotes *** under a more acidic environment in endosomes,further protonation of imidazole groups leads to the disintegration of the nanocomplex and the breakdown of endosomes because of the proton sponge ***,protein is released into the *** the assistance of the nanocomplex,proteins with different sizes and isoelectric points are effectively delivered into *** work provides a stable,efficient and universal strategy for intracellular protein delivery.

关键词： protein zinc ions intracellular delivery coordination polymer

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Electrostatic and hydrophobic interaction cooperative nanochaperone regulates protein folding

Aggregate

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Aggregate 2024年第1期5卷 419-426页

作者： Xiaohui Wu Fei Deng Yujie Chen Mengchen Xu Feihe Ma linqi shi Key Laboratory of Functional Polymer Materials of Ministry of Education State Key Laboratory of Medicinal Chemical BiologyInstitute of Polymer Chemistry and College of ChemistryNankai UniversityTianjinP.R.China School of Materials Science and Engineering and State Key Laboratory of Separation Membranes and Membrane Processes Tiangong UniversityTianjinP.R.China

Natural molecular chaperones utilize spatially ordered multiple molecular forces to effectively regulate protein ***,synthesis of such molecules is a big *** concept of“aggregate science”provides insights to construct chemical entities(aggregates)beyond molecular levels to mimic both the structure and function of natural *** by this concept,herein we fabricate a novel multi-interaction(i.e.,electrostatic and hydrophobic interaction)cooperative nanochaperone(multi-co-nChap)to regulating protein *** multi-co-nChap is fabricated by rationally introducing electrostatic interactions to the surface(corona)and confined hydrophobic microdomains(shell)of traditional single-hydrophobic interaction *** demonstrate that the corona electrostatic attraction facilitates the diffusion of clients into the hydrophobic microdomains,while the shell electrostatic interaction balances the capture and release of *** finely synergizing corona electrostatic attraction with shell electrostatic repulsion and hydrophobic interaction,the optimized multi-co-nChap effectively facilitated de novo folding of nascent ***,the synergy between corona electrostatic attraction,shell electrostatic attraction and shell hydrophobic interaction significantly enhanced the capability of multi-co-nChap to protect native proteins from denaturation at harsh *** work provides important insights for understanding and design of nanochaperone,which is a kind of ordered aggregate with chaperone-like activity that beyond the level of single molecule.

关键词： chaperone-like activity cooperative effect nanochaperones ordered aggregates protein folding

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Optic and catalytic properties of gold nanoparticles tuned by homopolymers

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Science China Chemistry 2009年第9期52卷 1372-1381页

作者： CHEN Xi ZHAO DongYun ZHAO LiZhi AN YingLi MA RuJiang shi linqi HE QiJun CHEN Li Tianjin Key Laboratory of Fiber Modification and Functional Fiber School of Materials Science and Chemical EngineeringTianjin Polytech UniversityTianjin 300160China Key Laboratory of Functional Polymer Materials Ministry of EducationInstitute of Polymer ChemistryNankai UniversityTianjin 300071China

Gold nanoparticles (GNs) are prepared through in situ reduction using NaBH4 in the presence of homopolymer PDMAEMA. The sizes of the GNs can be adjusted by alternating the molar ratio of gold to DMAEMA. Pure PDMAEMA aqueous solution shows a phase-transition at 50°C at pH 10 and 25°C at pH 14, while PDMAEMA-supported GNs aqueous solution shows a phase-transition at 47°C at pH 10 because of the increasing hydrophobic property resulting from GNs. Due to the pH and temperature-responsible characteristics of PDMAEMA, the resulting PDMAEMA-supported GNs exhibit pH adjustable temperature-responsive characteristics in optic and catalytic aspects. Under an acidic condition (pH 2), the GNs show unchanged surface Plasmon absorbance with a peak of 518 nm in a temperature range from 20 to 65°C. Under a basic condition (pH 10), the GNs first show the same absorbance with a peak at 518 nm in a temperature range from 20 to 40°C, and then the absorbance red shifts from 518 to 545 nm as temperature increases from 40 to 65°C. When the GNs are used as catalysts to catalyze the reduction of p-nitrophenol, the catalytic activity can be adjusted by changing the permeation of reactants in the PDMAEMA layer at low and high temperatures, respectively.

关键词： gold nanoparticles catalyst homopolymer

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