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pH-responsive polymersome Based on PMCP-b-PDPA as a Drug Delivery System to Enhance Cellular Internalization and Intracellular Drug Release

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Chinese Journal of Polymer Science 2017年第11期35卷 1352-1362页

作者： Wen-liang Wang 马晓晶于喜飞 The Polymer Composites Engineering Laboratory Changchun Institute of Applied ChemistryChinese Academy of Sciences University of Science and Technology of China

Choline phosphate （CP） as a novel zwitterion possesses specific and excellent properties compared with phosphorylcholine （PC）, as well as its polymer, such as poly（2-（methacryloyloxy）ethyl choline phosphate）（PMCP）, has been studied extensively due to its unique characteristics of rapid cellular internalization via the special quadrupole interactions with the cell membrane. Recently, we reported a novel PMCP-based drug delivery system to enhance the cellular internalization where the drug was conjugated to the polymer via reversible acylhydrazone bond. Herein, to make full use of this feature of PMCP, we synthesized the diblock copolymer poly（2-（methacryloyloxy）ethyl choline phosphate）-b-poly（2- （diisopropylamino）ethyl methacrylate）（PMCP-b-PDPA）, which could self-assemble into polymersomes with hydrophilic PMCP corona and hydrophobic membrane wall in mild conditions when the pH value is 〉 6.4. It has been found that these polymersomes can be successfully used to load anticancer drug Dox with the loading content of about 11.30 wt%. After the polymersome is rapidly internalized by the cell with the aid of PMCP, the loaded drug can be burst-released in endosomes since PDPA segment is protonated at low pH environment, which renders PDPA to transfer from hydrophobic to hydrophilic, and the subsequent polymersomes collapse thoroughly. Ultimately, the ＂proton sponge＂ effect of PDPA chain can further accelerate the Dox to escape from endosome to cytoplasm to exert cytostatic effects. Meanwhile, the cell viability assays showed that the Dox-loaded polymersomes exhibited significant inhibitory effect on tumor cells, indicating its great potential as a targeted intracellular delivery system with high efficiency.

关键词： Drug delivery Choline phosphate polymersome PDPA Enhanced cellular internalization

A pH-responsive polymersome depleting regulatory T cells and blocking A2A receptor for cancer immunotherapy

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Nano Research 2022年第3期15卷 2324-2334页

作者： Binfen Shao Xuehui Huang Funeng Xu Jingmei Pan Yi Wang Shaobing Zhou School of Life Science and Engineering Southwest Jiaotong UniversityChengdu 610031China Key Laboratory of Advanced Technologies of Materials Ministry of Education School of Materials Science and EngineeringSouthwest Jiaotong UniversityChengdu 610031China

The immunosuppressive tumor microenvironment(ITM)and low immunogenicity of tumors greatly limit cancer immunotherapy *** approach of solely depleting regulatory T cells(Tregs)cannot ameliorate ITM,but possibly worsen it since the produced apoptotic Tregs will activate the A2A signaling pathway and cause more severe immune *** address it,in this work a pH-responsive polymersome(CY/ZM@CS-BPA)based on chondroitin sulfate(CS)-poly(β-amino ester)is rationally *** the acidic tumor microenvironment,the tertiary amine groups in the polymersome will reverse from hydrophobic to hydrophilic due to protonation,which leads to the disintegration of nanostructures and the release of cyclophosphamide(CY)and A2A receptor(A2AR)antagonist ZM241385(ZM).CY can selectively deplete ***,CY can induce immunogenic cell death(ICD)of tumor cells,which results in the proapoptotic translocation of calreticulin to the cell surface,further initiating the antitumor immune *** can inhibit the activation of the adenosine A2A pathway,subsequently preventing the differentiation of CD4^(+)T cells into Tregs and enhancing the cytotoxicity of CD8+T *** a result,the combination of depleting regulatory T cells and blocking the A2A receptor can enhance cancer immunotherapy efficacy.

关键词： polymersome regulatory T cells adenosine A2A pathway immunogenic cell death immunotherapy

Brain-targeted polymersome codelivery of siRNA and temozolomide for effective glioblastoma chemo-RNAi synergistic therapy

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ChemPhysMater 2022年第3期1卷 203-210页

作者： Meng Zheng Chengnan Yan Qingshan Yang Feiyan Zhu Qiuli Du Xue Xia Marco Morsch Albert Lee Jinglong Yin Yan Zou Bingyang Shi Henan-Macquarie University Joint Centre for Biomedical Innovation School of Life SciencesHenan UniversityKaifeng 475004China Henan Key Laboratory of Brain Targeted Bio-nanomedicine School of Life Sciences and School of PharmacyHenan UniversityKaifeng 475004China Department of Biomedical Sciences Faculty of MedicineHealth and Human SciencesMacquarie UniversitySydneyAustralia

Temozolomide (TMZ) is a clinically approved drug for glioblastoma (GBM) therapy. However, as a result of methylguanine-DNA-methyltransferase (MGMT), which is able to repair damaged DNA-damage repairing, TMZ usually yields unsatisfactory therapeutic effects. Small interfering RNA (siRNA) is a potential alteration tool for sensitivity of TMZ by targeting DNA repair enzymes. However, a suitable TMZ and siRNA codelivery system that can effectively and actively co-deliver siRNA/TMZ into the brain tumor is lacking. In this study, we constructed an angiopep-2 decorated polymersomal delivery system to co-deliver TMZ/siRNA for synergistic GBM therapy. This targeted polymersomal nanomedicine not only enhanced the circulation time of siRNA/TMZ in blood but also improved their blood-brain barrier (BBB) crossing and GBM targeting ability. Moreover, when we co-administered siRNAs specific to retinoblastoma binding protein 4 (RBBP4) together with TMZ in GBM cells, these RBBP4- specific siRNA (siRBBP4) modulated the sensitivity of TMZ by regulating MGMT, and thus showed a powerful synergistic anti-tumor effect. We demonstrated that angiopep-2 decorated polymersomal siRBBP4/TMZ co-loaded nanomedicines are capable of inhibiting tumor growth and significantly improved life expectancy of orthotropic GBM bearing mice. Overall, our study suggests that such a polymersomal TMZ/siRNA codelivery system provides a robust and potent nanoplatform for targeted GBM chemo-RNAi therapy.

关键词： polymersome siRNA TMZ Glioblastoma Brain targeting

polymersomes scalably fabricated via flash nano- precipitation are non-toxic in non-human primates and associate with leukocytes in the spleen and kidney following intravenous administration

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Nano Research 2018年第10期11卷 5689-5703页

作者： Sean D. Allen Yu-Gang Liu Sharan Bobbala Lei Cai Peter I. Hecker Ryan Temel Evan A. Scott Interdisciplinary Biological Sciences Northwestern University IL 60208 USA Department of Biomedical Engineering Northwestern University IL 60208 USA Saha Cardiovascular Research Center University of Kentucky KY40506 USA Department of Pharmacology and Nutritional Sciences University of Kentucky KY40506 USA

Vesicular nanocarrier formulations confer the ability to deliver hydrophobic and hydrophilic cargos simultaneously to cells of interest in vivo. While liposomal formulations reached the clinic long ago, younger technologies such as polymeric vesicles （polymersomes） have yet to make the transition to clinical approval and use, in part due to difficulties in ensuring their safe and scalable production. In this work, we demonstrate the scalable production of poly（ethylene glycol）-block-poly（propylene sulfide）（PEG-bl-PPS） polymersomes via flash nanoprecipitation, and further show the safe administration of these nanocarriers to mice and non-human primates. In mice, PEG-bl-PPS polymersomes were found to be well tolerated at up to 200 mg/（***）. Following the administration of a more relevant 20 mg/（***） dosage in non-human primates, polymersomes were found to associate with numerous phagocytic immune cell populations, including a remarkable 68% of plasmacytoid dendritic cells and 〉 95% of macrophages in the spleen, while showing no toxicity or abnormalities in the liver, kidney, spleen, or blood. Despite the presence of a dense PEG corona, neither anti-PEG antibodies nor complement activation were detected. This work provides evidence of the translatability of PEG-bI-PPS polymersomes into the clinic for therapeutic applications in humans.

关键词： polymersome non-human primate nanoprecipitation toxicity biodistribution

Controlling Membrane Phase Separation of polymersomes for Programmed Drug Release

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Chinese Journal of Polymer Science 2022年第9期40卷 1006-1015页

作者： Shuai Chen Erik Jan Cornel Jian-Zhong Du Department of Orthopedics Shanghai Tenth People’s HospitalSchool of MedicineTongji UniversityShanghai 200072China Department of Polymeric Materials School of Materials Science and EngineeringTongji UniversityShanghai 201804China

Programmed release of small molecular drugs from polymersomes is of great importance in drug delivery.A significant challenge is to adjust the membrane permeability in a well-controlled ***,we propose a strategy for controlling membrane phase separation by photo-cross-linking of the membrane-forming blocks with different molecular *** synthesized three amphiphilic block copolymers with different membrane-forming blocks,which are poly(ethylene oxide)_(43)-b-poly((ε-caprolactone)_(45)-stat-((α-(cinnamoyloxymethyl)-1,2,3-triazol)caprolactone)_(25))(PEO_(43)-b-P(CL_(45)-stat-CTCL_(25))),PEO_(43)-b-P(CL_(108)-stat-CTCL_(16)),and PEO_(43)-b-PCTCL_(4)-b-PCL_(79).These polymers were self-assembled into polymersomes using either a solvent-switch or powder rehydration method,and the obtained polymersomes were characterized by dynamic light scattering and transmission electron *** the phase separation patterns within the polymersome membranes were investigated by mesoscopic dynamics(MesoDyn)*** further confirm the change of the membrane permeability that resulted from the phase separation within the membrane,doxorubicin,as a small molecular drug,was loaded and released from the *** to the incompatibility between membrane-forming moieties(PCTCL and PCL),phase separation occurs and the release rate can be tuned by controlling the membrane phase pattern or by ***,besides the compacting effect by formation of chemical bonds in the membrane,the cross-linking process can act as a driving force to facilitate the rearrangement and re-orientation of the phase pattern,which also influences the drug release behavior by modulating the cross-membrane distribution of the amorphous PCTCL *** this way,the strategy of focusing on the membrane phase separation for the preparation of the polymersomes with finely tunable drug release rate can be envisioned and designed accordingly,which is of great signifi

关键词： polymersome Drug delivery Phase separation Programmed drug release

Synthesis and self-assembly of poly(ethylene glycol)-block-poly(N-3-(methylthio)propyl glycine)and their oxidation-sensitive polymersomes

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Chinese Chemical Letters 2020年第7期31卷 1931-1935页

作者： Yangwei Deng Hui Chen Xinfeng Tao Sylvain Trepout Jun Ling Min-Hui Li Chimie ParisTech PSL University ParisCNRSInstitut de Recherche de Chimie ParisParis 75005France MOE Key Laboratory of Macromolecular Synthesis and Functionalization Department of Polymer Science and EngineeringZhejiang UniversityHangzhou 310027China Beijing Advanced Innovation Center for Soft Matter Science and Engineering Beijing University of Chemical TechnologyBeijing 100029China Institut Curie Inserm US43University Paris SaclayOrsay Cedex 91405France Shanghai Key Laboratory of Advanced Polymeric Materials School of Materials Science and EngineeringEast China University of Science and TechnologyShanghai 200237China

Amphiphilic block copolymers poly(ethylene glycol)-block-poly(N-3-(methylthio)propyl glycine)(PEGb-PMeSPG)were synthesized via ring-opening polymerization of N-3-(methylthio)propyl glycine Nthiocarboxyanhydride(MeSPG-NTA)initiated by amino-terminated *** self-assemblies of three PEG-b-PMeSPG copolymers with different PMeSPG block lengths were first prepared by nanoprecipitation method using THF and DMF,respectively,as the organic solvent,and their morphologies were studied by Cryo-EM and *** prepare polymersomes loaded with glucose oxidase(GOx),double emulsion method followed by extrusion treatment was *** oxidation-responsive disruption of polymersomes was achieved upon the introduction of glucose because of the oxidants generated insitu by GOx/glucose.

关键词： Polypeptoid Self-assembly polymersome Oxidation-responsive Glucose oxidase

Highly uniform ultrasound-sensitive nanospheres produced by a pH-induced micelle-to-vesicle transition for tumor-targeted drug delivery

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Nano Research 2018年第7期11卷 3710-3721页

作者： Yiru Wang Tinghui Yin Zhenwei Su Chen Qiu Yong Wang Rongqin Zheng Meiwan Chen Xintao Shuai Guangdong Provincial Key Lab of Liver Disease and Department of Medical Ultrasonics The Third Affiliated Hospital of Sun Yat-sen University Guangzhou 510630 China PCFM Lab of Ministry of Education School of Materials Sdence and Engineering Sun Yat-sen University Guangzhou 510275 China State Key Laboratory of Quality Research in Chinese Medicine Institute of Chinese Medical Sciences University of Macao Macao 999078 China

Although gas-filled microbubbles with high echogenicity are widely applied in clinical ultrasonography, the micron scale particle size impedes their use in the treatment of solid tumors, which are accessible to objects less than several hundred nanometers. We herein propose an unusual approach involving a pH-induced core-shell micelle-to-vesicle transition to prepare ultrasound-sensitive polymeric nanospheres （polymersomes in structure） possessing multiple features, including nanosize, monodispersity, and incorporation of a phase- transitional imaging agent into the aqueous lumen. These features are not achievable via the conventional double-emulsion method for polymersome preparation. The nanospheres were constructed based on a novel triblock copolymer with dual pH sensitivity. The liquid-to-gas phase transition of the imaging agent induced by external low-frequency ultrasound may destroy the nanospheres for a rapid drug release, with simultaneous tissue-penetrating drug delivery inside a tumor. These effects may provide new opportunities for the development of an effective cancer therapy with few adverse effects.

关键词： micelle polymersome morphological transition ultrasound-sensitive tumor-penetratingdelivery

A Three-drug co-Delivery System Based on Reduction-sensitive Polymeric Prodrug to Effectively Reverse Multi-drug Resistance

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Chemical Research in Chinese Universities 2017年第3期33卷 484-491页

作者： XU Jiaqi YI Xiaoqing ZHAO Dan YUAN Gongdao ZHUO Renxi LI Feng Key Laboratory of Biomedical Polymers Ministry of Education College of Chemistry and Molecular Sciences Wuhan University Wuhan 430072 P. R. China

In the present study, we prepared a multi-drug delivery system based on reduction-sensitive paclitaxel （PTX） polymeric prodrug（PEG-b-PMPMC-g-PTX, PMP） polymersomes to co-deliver PTX, doxorubicin hydrochlo- ride（***1） and the P-glycoprotein（P-gp） inhibitor Tariquidar（TQR） to effectively reverse drug resistance by inhibiting the expression of P-gp and improving the accumulation of the encapsulated anticancer drugs. The PTX was linked to the backbone by reduction-sensitive disulphide, making the polymersomes prone to collapse in the reductive environment and to release the drugs. Transmission electron microscope（TEM） was used to confirm the morphology of polymeric assemblies. Moreover, the rupture process of polymersomes was verified by dynamic light scattering （DLS）. The results of confocal laser scanning microscopy（CLSM） and flow cytometry indicate that the PMP/***/TQR three-drug-loaded polymersomes show the strongest fluorescence intensity for DOX-HC1 compared with PMP/DOX-HC1 polymersomes and free DOX-HCl in drug-resistant MCF-7/ADR cells. More importantly, the PMP/***/TQR multi-drug co-delivery system shows a greater growth-inhibitory effect on tumour cells than the other two samples, including PMP/***1 nanoparticles without the TQR component and free DOX-HCl, when co-incubated with either nonresistant HeLa cells or drug-resistant MCF-7/ADR cells. This growth-inhibitory effect was especially evident in drug-resistant cells. These results imply that the co-delivery of PTX, DOX-HCl and TQR based on reduction-sensitive polymeric prodrug may be promising for overcoming multi-drug resistance in tumour treatments.

关键词： Multi-drug resistance co-Delivery polymersome Multi-drug resistance co-Delivery polymersome