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Recent advances in zwitterionic nanoscale drug delivery systems to overcome biological barriers

Asian Journal of Pharmaceutical Sciences 2024年第1期19卷 49-68页

作者： Xumei Ouyang Yu Liu Ke Zheng Zhiqing Pang Shaojun Peng Zhuhai Institute of Translational Medicine Zhuhai Precision Medical CenterZhuhai People’s Hospital(Zhuhai Hospital Affiliated with Jinan University)Zhuhai 519000China Key Laboratory of Smart Drug Delivery Ministry of EducationDepartment of PharmaceuticsSchool of PharmacyFudan UniversityShanghai 201203China School of Materials Science and Engineering Dongguan University of TechnologyDongguan 523808China

Nanoscale drug delivery systems(nDDS)have been employed widely in enhancing the therapeutic efficacy of drugs against diseases with reduced side effects.Although several nDDS have been successfully approved for clinical use up to now,biological barriers between the administration site and the target site hinder the wider clinical adoption of nDDS in disease treatment.Polyethylene glycol(PEG)-modification(or PEGylation)has been regarded as the gold standard for stabilising nDDS in complex biological environment.However,the accelerated blood clearance(ABC)of PEGylated nDDS after repeated injections becomes great challenges for their clinical applications.zwitterionic polymer,a novel family of antifouling materials,have evolved as an alternative to PEG due to their super-hydrophilicity and biocompatibility.zwitterionic nDDS could avoid the generation of ABC phenomenon and exhibit longer blood circulation time than the PEGylated analogues.More impressively,zwitterionic nDDS have recently been shown to overcome multiple biological barriers such as nonspecific organ distribution,pressure gradients,impermeable cell membranes and lysosomal degradation without the need of any complex chemical modifications.The realization of overcoming multiple biological barriers by zwitterionic nDDS may simplify the current overly complex design of nDDS,which could facilitate their better clinical translation.Herein,we summarise the recent progress of zwitterionic nDDS at overcoming various biological barriers and analyse their underlyingmechanisms.Finally,prospects and challenges are introduced to guide the rational design of zwitterionic nDDS for disease treatment.

关键词： zwitterionic polymer Nano drug delivery system Biological barrier Targeting delivery Disease treatment

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Conjugation of a zwitterionic polymer with dimethyl chains to lipase significantly increases the enzyme activity and stability

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Chinese Journal of Chemical Engineering 2022年第7期35卷 48-53页

作者： Chunyu Zhang Yan Sun Xiaoyan Dong Department of Biochemical Engineering School of Chemical Engineering and Technology and Key Laboratory of Systems Bioengineering and Frontiers Science Center for Synthetic Biology(Ministry of Education)Tianjin UniversityTianjin 300350China College of Life Sciences Yantai UniversityYantai 264005China

Enzyme-polymer conjugates are complex molecules with great practical significance.This work was designed to develop a novel enzyme-polymer conjugate by covalently coupling a zwitterionic polymer with side dimethyl chains(pID)to Candida rugosa lipase(CRL)via the reaction between the anhydrides of polymer chains with the amino groups of the enzyme.The resulting two CRL-pID conjugates with different pID grafting densities were investigated in term of the catalytic activity,stability and structural changes.In comparison with native CRL,both the CRL conjugates displayed 2.2 times higher activity than the native enzyme,and showed an increase in the maximum reaction rate(V_(max))and a decrease in the Michaelis constant(K_(m)),thus resulting in about three-fold increases in the catalytic efficiency(k_(cat)/K_(m)).These are mainly attributed to the activation of lipase by the hydrophobic alky side chains.Moreover,the thermostability and pH tolerance of the lipase conjugates were significantly enhanced due to the stabilizing effect of the zwitterion moieties.For instance,a five-fold increase of the enzyme half-life at 50℃ for the high-pID conjugated CRL was observed.Spectroscopic studies reveal that the pID conjugation protected the enzyme in the changes in its microenvironment and conformation,well correlating with enhanced activity and stability of lipase conjugates.The findings indicate that enzyme conjugation to the zwitterionic polymer is promising for improving enzyme performance and deserves further development.

关键词： Lipase zwitterionic polymer Enzyme-polymer conjugate Stability Interfacial activation

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Programming Shape-Morphing Behavior of zwitterionic polymer/Liquid Crystal Composite with Humidity-responsive Self-healing Performance

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Chinese Journal of polymer Science 2023年第2期41卷 212-221页

作者： Shao-Jun Chen Hui-Feng Cheng Bin Du Jiao-Shi Liu Wen-Bo Shen Hai-Tao Zhuo Shenzhen Key Laboratory of polymer Science and Technology Guangdong Research Center for Interfacial Engineering of Functional MaterialsCollege of Materials Science and EngineeringShenzhen UniversityShenzhen518060China Shenzhen Key Laboratory of Functional polymer College of Chemistry and Environmental EngineeringShenzhen UniversityShenzhen518060China

In this study,a zwitterionic polymer/liquid crystals composite film with programming shape-morphing behavior and humidityresponsive self-healing performance was prepared by blending a zwitterionic polymer and liquid crystalline azobenzene compound in solution,followed by film-forming in a mold without tedious or multistep synthetic route.The as-obtained zwitterionic polymer/liquid crystal composite film exhibited programming shape-morphing behavior under different stimuli.In this process,the temporary shape of the composite film was memorized after the removal of the stimuli.Such characteristics would fit the requirements of intelligence and energy-saving for stimuliresponsive shape-changing materials.Moreover,the composite film showed humidity-responsive self-healing performances under wet conditions at room temperature.In summary,the simple design and preparation route of the zwitterionic polymer/liquid crystal composite film with programming shape-morphing behavior and mild condition-responsive self-healing performance look promising for the fabrication and practical application of novel photo-driven devices and soft robotics.

关键词： zwitterionic polymer polymer/liquid crystals composite Programming shape-morphing behavior Humidity-responsive self-healing performance Stimuli-responsive shape-changing

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Impact of the polymer backbone chemistry on interactions of amino-acid-derived zwitterionic polymers with cells

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生物活性材料(英文) 2023年第6期24卷 524-534页

作者： Meike N.Leiske Bruno G.De Geest Richard Hoogenboom Supramolecular Chemistry Group Centre of Macromolecular Chemistry(CMaC)Department of Organic and Macromolecular ChemistryGhent UniversityKrijgslaan 281 S4B-9000GhentBelgium Department of Pharmaceutics and Cancer Research Institute Ghent(CRIG) Ghent UniversityOttergemsesteenweg 460B-9000GhentBelgium Faculty of Biology Chemistry&Earth SciencesUniversity of BayreuthUniversitätsstraße 3095447 BayreuthGermany

zwitterionic polymers are known to interact with cells and have been shown to reveal cancer cell specificity.In this work,the importance of the chemistry of the polymer backbone for the cellular specificity of amino-acid-derived polyzwitterions is demonstrated.A series of glutamic acid(Glu)-based vinyl monomers(i.e.,an acrylate,a methacrylate,an acrylamide,and a methacrylamide)were prepared and used for reversible addition-fragmentation chain-transfer(RAFT)polymerisation,yielding defined polymers with narrow size distribution(Ðzwitterionic polymers revealed high cytocompatibility;however,differences in cellular association and specificity were observed.In particular,the methacrylamide-derived polymers showed high association with both,breast cancer cells and non-cancerous dendritic cells and,consequently,lack specificity.In contrast,high specificity to only breast cancer cells was observed for polyacrylates,-methacrylates,and-acrylamides.Detailed analysis of the polymers revealed differences in hydrophobicity,zeta potential,and potential side chain hydrolysis,which are impacted by the polymer backbone and might be responsible for the altered the cell association of these polymers.It is shown that a slightly negative net charge is preferred over a neutral charge to retain cell specificity.This was also confirmed by association experiments in the presence of competitive amino acid transporter substrates.The affinity of slightly negatively charged Glu-derived polymers to the xCT Glu/cystine cell membrane antiporter was found to be higher than that of neutrally charged polymers.Our results emphasise the importance of the polymer backbone for the design of cell-specific polymers.This study further highlights the potential to tailor amino-acid-derived zwitterionic materials beyond their side chain functionality.

关键词： Amino-acid-functionalised polymer zwitterionic polymer Cell-specific polymer Cancer-targeting RAFT-polymerisation

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Grafting Branch Length and Density Dependent Performance of zwitterionic polymer Decorated Polypropylene Membrane

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Chinese Journal of polymer Science 2018年第4期36卷 528-535页

作者： Jing-Jing Wu Jin Zhou Jing-Qiu Rong Yao Lu Hui Dong Hai-Yin Yu Jia-Shan Gu College of Chemistry and Materials Science Anhui Normal University Department of Material and Chemical Engineering Chizhou University

Branch length and density have critical effects on membrane performances; however, it is regarded to be traditionally difficult to investigate the relationship due to the uncontrolled membrane modification methods. In this study, zwitterionic polymer with controlled grafting branch chain length（degree of polymerization） and grafting density（grafting chains per membrane area） was tethered to the microporous polypropylene membrane surface based on the combination of reversible addition-fragmentation chain transfer（RAFT） polymerization technique with click reaction. The modified membranes were tested by filtrating protein dispersion to highlight the correlations of branch chain length and grafting density with the membrane permeation performances. The pure water flux, the flux recovery ratio are positively and significantly, and the irreversible fouling negatively and significantly correlated with grafting density. These results demonstrate that the larger the coverage of the membrane with poly{[2-（methacryloyloxy）ethyl]-dimethyl-（3-sulfopropyl） ammonium hydroxide}（PMEDSAH）, the higher the pure water flux and the higher the flux recover ratio, and the lower the irreversible fouling, which shows that high grafting density is favorable to fouling reducing.

关键词： Grafting branch length Grafting density Polypropylene membrane Protein fouling zwitterionic polymer

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Gelatin-based composite hydrogels with biomimetic lubrication and sustained drug release

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Friction 2022年第2期10卷 232-246页

作者： Kuan ZHANG Jielai YANG Yulong SUN Yi WANG Jing LIANG Jing LUO Wenguo CUI Lianfu DENG Xiangyang XU Bo WANG Hongyu ZHANG State Key Laboratory of Tribology Department of Mechanical EngineeringTsinghua UniversityBeijing 100084China School of Chemical and Biological Engineering Shandong University of Science and TechnologyQingdao 266590China Department of Orthopedics Ruijin HospitalShanghai Jiao Tong University School of MedicineShanghai 200025China Shanghai Key Laboratory for Prevention and Treatment of Bone and Joint Diseases Shanghai Institute of Traumatology and OrthopaedicsRuijin HospitalShanghai Jiao Tong University School of MedicineShanghai 200025China Beijing Research Institute of Automationfor Machinery Industry Co. Ltd.Beijing 100120China

The occurrence of osteoarthritis is closely related to progressive and irreversible destruction of the articular cartilage,which increases the friction significantly and causes further inflammation of the joint.Thus,a scaffold for articular cartilage defects should be developed via lubrication restoration and drug intervention.In this study,we successfully synthesized gelatin-based composite hydrogels,namely GelMA–PAM–PMPC,with the properties of biomimetic lubrication and sustained drug release by photopolymerization of methacrylic anhydride modified gelatin(GelMA),acrylamide(AM),and 2-methacryloyloxyethyl phosphorylcholine(MPC).Tribological test showed that the composite hydrogels remarkably enhanced lubrication due to the hydration lubrication mechanism,where a tenacious hydration shell was formed around the zwitterionic phosphocholine headgroups.In addition,drug release test indicated that the composite hydrogels efficiently encapsulated an anti-inflammatory drug(diclofenac sodium)and achieved sustained release.Furthermore,the in vitro test revealed that the composite hydrogels were biocompatible,and the mRNA expression of both anabolic and catabolic genes of the articular cartilage was suitably regulated.This indicated that the composite hydrogels could effectively protect chondrocytes from inflammatory cytokine-induced degeneration.In summary,the composite hydrogels that provide biomimetic hydration lubrication and sustained local drug release represent a promising scaffold for cartilage defects in the treatment of osteoarthritis.

关键词： hydrogel articular cartilage zwitterionic polymer hydration lubrication drug delivery

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Preparation and characterization of enzyme-responsive zwitterionic nanoparticles for monoclonal antibody delivery

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Frontiers of Materials Science 2023年第4期17卷 115-126页

作者： Changxin Hou Huike Xing Xubo Yuan Tianjin Key Laboratory of Composite and Functional Materials Tianjin UniversityTianjin 300350China School of Materials Science and Engineering Tianjin UniversityTianjin 300350China

Monoclonal antibodies have been used in many diseases,but how to improve their delivery efficiency is still a key issue.As the modification of zwitterionic polymers can maintain the stability and biological activity of monoclonal antibodies,in this study,zwitterionic monomers,sulfobetaine methacrylate(SBMA),and 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propionate(CBMA)were used to prepare monoclonal antibody-loaded zwitterionic nanoparticles with the aid of the crosslinker of MMP-2 enzyme-responsive peptide which was a rapid synthesis process under mild conditions.The results from dynamic light scattering(DLS),Fourier transform infrared spectroscopy(FTIR)and transmission electron microscopy(TEM)indicated that a series of zwitterionic nanoparticles had been successfully prepared by the in situ free radical polymerization using the MMP-2 enzyme-responsive peptide as the cross-linking agent.These nanoparticles were spherical with the sizes of(18.7±1.9)nm(SBMA nanoparticle)and(18.2±2.1)nm(CBMA nanoparticle),and the surface contained zwitterionic polymers.It was revealed that they had no cytotoxicity,could be released in tumor microenvironment by enzyme to inhibit the growth of tumor cells,and was able to effectively penetrate endothelial cells(>2%)by transwell.Therefore,the development of this strategy has a great prospect for the delivery of monoclonal antibodies.

关键词： zwitterionic polymer monoclonal antibody delivery enzyme responsive release penetration of endothelial cell

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Structures,properties,and applications of zwitterionic polymers

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ChemPhysMater 2022年第4期1卷 294-309页

作者： Keyu Qu Zhiang Yuan Yanyan Wang Zhaohui Song Xuyang Gong Yi Zhao Qiyu Mu Qinghong Zhan Wenlong Xu Linlin Wang School of Chemistry and Materials Science Ludong UniversityYantai 264025China State Key Laboratory of Long-Acting and Targeting Drug Delivery System Shandong Luye Pharmaceutical Co.Ltd.Yantai 264000China

zwitterionic polymers have attracted research attention in recent years owing to their unique molecular struc-tures.In the same repeat unit,positive and negative charges are simultaneously located on a pair of cationic and anionic groups;therefore,zwitterionic polymers have a large dipole moment and numerous charged groups.Al-though the molecular chain of the zwitterionic polymer can be maintained in an electrically neutral state overall,the coexistence of the oppositely charged groups confers extremely high polarity and excellent hydrophilicity to the polymer.At the same time,the electricality of the polymer can be further regulated by the environmental pH and salt ions,which greatly broadens the scope of applications in different fields.This review introduces various structures of zwitterionic polymers and analyzes the reasons why zwitterionic polymers exhibit pH responsive-ness,anti-polyelectrolyte effects,and superior electrical conductivity.The application fields are also summarized by generalizing the research status of zwitterionic polymers,including applications in antifouling coatings,drug delivery,wastewater treatment,and sensors,etc.

关键词： zwitterionic polymer Structural characteristic Charged group Property Application

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Polydopamine/poly(sulfobetaine methacrylate)Co-deposition coatings triggered by CuSO_(4)/H_(2)O_(2)on implants for improved surface hemocompatibility and antibacterial activity

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Bioactive Materials 2021年第8期6卷 2546-2556页

作者： Zhongqiang Zhu Qiang Gao Ziyue Long Qiuyi Huo Yifan Ge Ntakirutimana Vianney Nishimwe Anodine Daliko Yongchun Meng Jia Qu Hao Chen Bailiang Wang School of Ophthalmology&Optometry Eye HospitalWenzhou Medical UniversityWenzhou325027China Central Laboratory Yantai Affiliated Hospital of Binzhou Medical University717 Jinbu StreetYantaiShandong264100China

Implanted biomaterials such as medical catheters are prone to be adhered by proteins,platelets and bacteria due to their surface hydrophobicity characteristics,and then induce related infections and thrombosis.Hence,the development of a versatile strategy to endow surfaces with antibacterial and antifouling functions is particularly significant for blood-contacting materials.In this work,CuSO_(4)/H_(2)O_(2)was used to trigger polydopamine(PDA)and poly-(sulfobetaine methacrylate)(PSBMA)co-deposition process to endow polyurethane(PU)antibacterial and antifouling surface(PU/PDA(Cu)/PSBMA).The zwitterions contained in the PU/PDA(Cu)/PSBMA coating can significantly improve surface wettability to reduce protein adsorption,thereby improving its blood compatibility.In addition,the copper ions released from the metal-phenolic networks(MPNs)imparted them more than 90%antibacterial activity against E.coli and S.aureus.Notably,PU/PDA(Cu)/PSBMA also exhibits excellent performance in vivo mouse catheter-related infections models.Thus,the PU/PDA(Cu)/PSBMA has great application potential for developing multifunctional surface coatings for blood-contacting materials so as to improve antibacterial and anticoagulant properties.

关键词： zwitterionic polymer Copper ions Surface modification Hemocompatibility Antibacterial

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Novel polyzwitterion shell with adaptable surface chemistry engineered to enhance anti-fouling and intracellular imaging of detonation nanodiamonds under tumor pHe

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Frontiers of Materials Science 2020年第4期14卷 402-412页

作者： Biyu ZHOU Junbo LI Binzhong LU Wenlan WU Leitao ZHANG Ju LIANG Junpeng YI Xin LI School of Chemical Engineering&Pharmaceutics Henan University of Science&TechnologyLuoyang 471023China School of Medicine Henan University of Science&TechnologyLuoyang 471023China College of Food and Bioengineering Henan University of Science&TechnologyLuoyang 471023China

In this work,zwitterionic polymer(polyzwitterion)coated nanodiamonds(ND)with tumorous pH responsiveness were prepared for efficient application of commercial NDS in tumor cells imaging.Poly(carboxybetaine methacrylate)was firstly grafted on the pristine NDS(PCBMA-@-NDs)by surface-initiated reversible addition-fragmentation chain transfer(RAFT)polymerization.To achieve pH responsiveness and activated interaction with tumor cells,PCBMA-@-NDs were subsequently modified with benzene sulfonamide(PCBSA-@-NDs)via one step carbodiimide chemistry.The surface polymer functionalization was characterized by FTIR,1H NMR and TGA,and PCBMA-@-NDs and PCBSA-@-NDs showed great dispersibility,enhanced fluorescence intensity and excellent antifouling property in contrast to pristine NDs.Moreover,PCBSA-@-NDs was able to switch zwitterionic surface(at pH 7.4)reversibly into positive charge(at pH 6.5)via protonated or deprotonated acylsulfonamide.As expected,PCBSA-@-NDS demonstrated higher cell affinity and better imaging performance than those of zwitterionic NDS at tumor slight acid environment,proven by fluorescence microscopy and flow cytometry.Overall,we provide a feasible and valuable strategy to construct smart NDS,thus encouraging the application of cost-effective fluorescence nanomater-ials in biomedical fields.

关键词： zwitterionic polymer surface coating pH-responsive charge-reversal cell imaging

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