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Polymeric prodrug for bio-controllable gene and drug co-delivery

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Science China Chemistry 2016年第11期59卷 1397-1404页

作者： Huizhen Jia Si Chen renxi zhuo Jun Feng Xianzheng Zhang Key Laboratory of Biomedical Polymers of Ministry of Education Department of Chemistry Wuhan University Wuhan 430072 China School of Materials Science and Engineering Tianjin Key Laboratory of Composite and Functional Materials Tianjin University Tianjin 300072 China

A polymeric polyethylenimine(PEI)-based prodrug of anticancer doxorubicin(DOX)(PEI-hyd-DOX) was designed by attaching DOX to PEI via an acid-labile hydrazone bond, for the achievement of biocontrollable gene and drug co-delivery in response to the intracellular acid microenvironments in the late endosome/lysosome compartments. The cytotoxicity of PEI-hyd-DOX was evaluated by the MTT assay and the cellular uptake was monitored using confocal laser scanning microscopy. The polymeric prodrug can respond with a high sensitivity to the specific acid condition inside cells, thus permitting the precise biocontrol over intracellular drug liberation with high drug efficacy. The chemical attachment of drug molecules also led to the relatively reduced toxicity and the enhanced transfection efficiency compared with parent PEI. The resulting data adumbrated the potential of PEI-hyd-DOX to co-deliver DOX and therapeutic gene for the combination of chemotherapy and gene therapy.

关键词： gene/drug co-delivery hydrazone bond p H-sensitivity polymeric prodrug transfection efficiency

Current progress of polymeric gene vectors

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Science China(Life Sciences) 2011年第11期54卷 1064-1067页

作者： ZENG Xuan SUN YunXia zhuo renxi ZHANG XianZheng Key Laboratory of Biomedical Polymers of Ministry of Education ＆ Department of Chemistry Wuhan University Wuhan 430072 China

After over 40 years of progress,gene therapy provides great opportunities for treating diseases from various genetic disorders,infections and *** success of gene therapy largely depends on the availability of suitab... 详细信息

关键词：基因载体聚合物遗传性疾病基因治疗基因疗法可用性吸引力

Recent progress in polymer-based gene delivery vectors

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Chinese Science Bulletin 2003年第13期48卷 1304-1309页

作者： HUANG Shiwen & zhuo renxi Department of Chemistry, Wuhan University, Wuhan 430072, China Correspondence should be addressed to zhuo renxi (e-mail: pibmp@ ***) Department of Chemistry Wuhan University Wuhan China

The gene delivery system is one of the three components of a gene medicine, which is the bottle neck of current gene therapy. Nonviral vectors offer advantages over the viral system of safety, ease of manufacturing, etc. As important nonviral vectors, polymer gene delivery systems have gained increasing attention and have begun to show increasing promising. In this review, the fundamental and recent progress of polymer-based gene delivery vectors is reviewed.

关键词：基因治疗基因转移内吞作用质粒DNA

Study on Synthesis and Herbicidal Activity of Heterocyclic Compounds Containing P-P Bond

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Wuhan University Journal of Natural Sciences 1998年第1期3卷 126-128页

作者： He Liangnian zhuo renxi Cai Lei Lu Alhong Department of Chemistry Wuhan University Wuhan China Institute of Organic Synthesis Central China Normal University Wuhan China

N,N′-diphenylurea reacted with phosphorus trichloride and phenyl dichlorophosphane giving the heterocyclic compounds 1 and 2 with a direct phosphorus-phosphorus bond (P-P bond), respectively. The new compounds were characterized by elementary analysis, NMR and IR spectra. The results of preliminary bioassay showed that these heterocycles possess selective herbicidal activity at 1.5 kg/hm2.

关键词： heterocycle containing P-P bond synthesis herbicidal activity

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

Novel Cyclopeptide Bolaamphiphile for Constructing Supramolecular Nanotubes

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Chinese Journal of Chemistry 2014年第1期32卷 22-26页

作者： Siyong Qin Qingrong Wang Yi Pei Mengyun Peng renxi zhuo Xianzheng Zhang[*] Key Laboratory of Biomedical Polymers of Ministry of Education & Department of Chemistry Wuhan University Wuhan Hubei 430072 China Email: Xianzheng Zhang (xz-zhang@***)[*]Key Laboratory of Biomedical Polymers of Ministry of Education & Department of Chemistry Wuhan University Wuhan Hubei 430072 China

A novel dicyclopeptide-based bolaamphiphile was *** hydrophilic cyclopeptide fragments were linked to an alkyl chain 1,6-bis(maleimido)hexane,which acted as a hydrophobic *** transmission electron microscopy (TEM) observation indicated that the cyclopeptide bolaamphiphile (CPB) self-assembled into the nanotubes with a thickness of about 3 *** on the optimized molecular conformation obtained via MM2 method,the length of CPB was demonstrated to be around 4 nm,implying that the nanotubes were *** transform infrared spectroscopy (FT-IR) and circular dichroism (CD) analysis showed that the cyclopeptides in CPB mainly acted as the hydrophilic headgroups,rather than providing the well-ordered hydrogen bonding interaction responsible for β-sheet *** investigate the special self-assembly behavior of CPB,the single cyclopeptide (CP) without the connection of the linker was *** investigation indicated that the CP molecules can not form tubular structures but nanofibers.

关键词： cyclopeptide bolaamphiphile self-assembly nanotube

Redox-Responsive Molecular Gels Based on Camptothecin Prodrug with Disulfide Linkage for Controlled and Sustained Drug Release

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Wuhan University Journal of Natural Sciences 2017年第5期22卷 411-419页

作者： CHANG Xiupeng LI Youmei CHEN Shu HE Feng zhuo renxi College of Chemistry and Molecular Science Wuhan UniversityWuhan 430072HubeiChina

A novel camptothecin （CPT） prodrug was successfully synthesized by conjugating CPT to adamantanecarboxylic acid （AD） via a cleavable disulfide linkage. The resulting CPT-ss-AD prodrug could act as a low molecular weight gelator to form molecular gels in water/water-miscible organic solvent mixture. Meanwhile, biode- gradable amphiphilic block copolymer mPEG-b-P （MAC-co-DTC）（PPMD） was also employed as an organic framework together with CPT-ss-AD to form gel structure. CPT-ss-AD/PPMD gel exhibited less compact molecular arrangement but much more stability than CPT-ss-AD gel. The two kinds of gels could effectively release the original CPT under reductive condition at a near-constant rate without any initial burst. As compared to CPT-ss-AD single-component gel, the two-component gel, CPT-ss-AD/PPMD, had a significantly higher release rate of CPT, while 3-[4,5-dimethylthiazol-2-yl]-2, 5-diphenyltetrazolium bromide （MTT） assays also indicated highly potent cytotoxic activity against HeLa cells.

关键词： delivery prodrug molecular gels self-assembly polycarbonates

An indicator-guided photo-controlled drug delivery system based on mesoporous silica/gold nanocomposites

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Nano Research 2015年第6期8卷 1893-1905页

作者： Guofeng Luo Weihai Chen Huizhen Jia Yunxia Sun Han Cheng renxi zhuo Xianzheng Zhang Key Laboratory of Biomedical Polymers of Ministry of Education & Department of Chemistry Wuhan University Wuhan 430072 China

A mesoporous silica/gold （MSN/Au） nanocomposite was designed for photo- controlled drug delivery targeted specifically at tumor cells. The MSN/Au nanocomposite was composed of MSN-based drug carriers and gold nanoparticle （AuNP）-based indicators. While the MSN-based drug carrier was a mesoporous silica nanoparticle immobilized with photo-switchable azobenzene （Azo） moieties, the AuNP-based indicator was a fluorescence-quenched AuNP modified with a matrix metalloproteinase （MMP） substrate and poly（ethylene glycol）. The two kinds of nanoparticles were connected by an α,β cyclodextrin （α,β CD） dimer ＂bridge.＂ In vitro studies demonstrated that the nanocomposite specifically interacted with tumor sites overexpressing MMP-2, which enabled guidance of the subsequent UV light irradiation for releasing entrapped drugs. Through integration of the AuNP-based indicator and the MSN-based drug carrier, the MSN/Au nanocomposite could precisely localize the released drug to tumor sites, thereby significantly improving therapeutic efficacy.

关键词： MSN/Au nanocomposite photo-controlled MMP-2 sensitive drug delivery tumor therapy

Template-module assembly to prepare low-molecular-weight gene transport system with enhanced transmembrane capability

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Science China Chemistry 2014年第4期57卷 558-567页

作者： YANG Bin LV Yin WANG QingRong LIU Yun AN Hong FENG Jun ZHANG XianZheng zhuo renxi Key Laboratory of Biomedical Polymers of Ministry of Education Department of Chemistry Wuhan University Construction Engineering Research Institute of the General Logistics Department

Based on specific host-guest interactions between amine-modified [3-cyclodextrin （CD-TAEA） and functional adamantane （AD） derivatives, a module-template strategy has been proposed for the construction of low-molecular-weight cationic assem- blies for gene transport. This strategy offers great flexibility in terms of the introduction of mono- or multi-functionality by the inclusion of one or more adamantane-based modules with the desired functionalities. As proof of concept, phenylboronic acid （PB） containing adamantane （PB-AD） was used as a model module in the hope of offering enhanced cytosolic delivery in con- sideration of the special affinity of PB groups with cell membranes. The physicochemical properties of the complexes formed with plasmid DNA, such as particle size, zeta potential and morphology were investigated. Confocal laser scanning microsco- py and flow cytometry experiments demonstrated the important contribution of the functional PB-AD module to the consider- ably enhanced intracellular internalization and uptake by cellular nuclei. Compared to the parent CD-TAEA, PB-AD/CD- TAEA assemblies mediated higher transfection rates, which were even comparable to that of PEI25K. In addition, PB-AD/CD- TAEA displayed much lower cytotoxicity than PEI25K in both 293T and HeLa cell lines. The encouraging results suggest that CD-TAEA can be developed as a powerful template capable of readily accommodating various AD-based modules giving versatile functionalities for improved transfection.

关键词： template-module assembly host-guest interaction gene delivery