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Overcoming oral insulin delivery barriers： application of cell penetrating peptide and silica-based nanoporous composites

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Frontiers of Chemical Science and Engineering 2013年第1期7卷 9-19页

作者： Huining HE Junxiao YE Jianyong SHENG Jianxin WANG Yongzhuo HUANG Guanyi CHEN Jingkang WANG Victor C YANG School of Chemical Engineering and Technology Tianjin University Tianjin 300072 China Department of Pharmaceutics School of Pharmacy Fudan University Key Laboratory of Smart Drug Delivery Ministry of Education & PLA Shanghai 201203 China Shanghai Institute of Materia Medica Chinese Academy of Sciences Shanghai 201203 China School of Environmental Science and Engineering State Key Laboratory of Engines Tianjin University Tianjin 300072 China Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics School of Pharmacy Tianjin Medical University Tianjin 300070 China Department of Pharmaceutical Sciences College of Pharmacy University of Michigan Michigan 48109-1065 USA

Oral insulin delivery has received the most attention in insulin formulations due to its high patient compliance and, more importantly, to its potential to mimic the physiologic insulin secretion seen in non-diabetic individuals. However, oral insulin delivery has two major limitations： the enzymatic barrier that leads to rapid insulin degradation, and the mucosal barrier that limits insulin＇s bioavailability. Several approaches have been actively pursued to circumvent the enzyme barrier, with some of them receiving promising results. Yet, thus far there has been no major success in overcoming the mucosal barrier, which is the main cause in undercutting insulin＇s oral bioavailability. In this review of our group＇s research, an innovative silica-based, mucoadhesive oral insulin formulation with encapsulated-insulin/cell penetrating peptide （CPP） to overcome both enzyme and mucosal barriers is discussed, and the preliminary and convincing results to confirm the plausibility of this oral insulin delivery system are reviewed. In vitro studies demonstrated that the CPPinsulin conjugates could facilitate cellular uptake of insulin while keeping insulin＇s biologic functions intact. It was also confirmed that low molecular weight protamine （LMWP） behaves like a CPP peptide, with a cell translocation potency equivalent to that of the widely studied TAT. The mucoadhesive properties of the produced silica-chitosan composites could be controlled by varying both the pH and composition; the composite consisting of chitosan （25wt-%） and silica （75 wt-%） exhibited the greatest mucoadhesion at gastric pH. Furthermore, drugrelease from the composite network could also be regulated by altering the chitosan content. Overall, the universal applicability of those technologies could lead to development of a generic platform for oral delivery of many other bioactive compounds, especially for peptide or protein drugs which inevitably encounter the poor bioavailability issues.

关键词： insulin cell penetrating peptide mucoadhesive composites oral delivery

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Overcoming the cellular barriers and beyond: Recent progress on cell penetrating peptide modified nanomedicine in combating physiological and pathological barriers

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Asian Journal of Pharmaceutical Sciences 2022年第4期17卷 523-543页

作者： Yingke Liu Zhihe Zhao Man Li State Key Laboratory of Oral Diseases National Clinical Research Center for Oral DiseasesWest China Hospital of StomatologySichuan UniversityChengdu 610041China Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial TechnologyWest China School of PharmacySichuan UniversityChengdu 610041China

The complex physiological and pathological conditions form barriers against efficient drug *** penetrating peptides(CPPs),a class of short peptides which translocate drugs across cell membranes with various mechanisms,provide feasible solutions for efficient delivery of biologically active agents to circumvent biological *** years of development,the function of CPPs is beyond cell *** CPPs with bioactivity or active targeting capacity have been designed and successfully utilized in delivery of various cargoes against tumor,myocardial ischemia,ocular posterior segment disorders,*** this review,we summarize recent progress in CPP-functionalized nano-drug delivery systems to overcome the physiological and pathological barriers for the applications in cardiology,ophtalmology,mucus,neurology and cancer,*** also highlight the prospect of clinical translation of CPP-functionalized drug delivery systems in these areas.

关键词： cell penetrating peptide Nanomedicine Physiological barriers Drug delivery system

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Folate and cell penetrating peptide modification effects on penetration behavior of nanostructured lipid carriers using multicellular tumor spheroids

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Journal of Chinese Pharmaceutical Sciences 2015年第10期24卷 666-672页

作者：庄鸿蒙孟婷婷高玮袁兰齐宪荣北京大学医学部药学院分子药剂学和新释药系统北京重点实验室北京100191 北京大学医学部药学院药剂学系北京100191 北京大学医学部药学院药剂学系北京100191 北京大学医学部医学分析中心北京100191

Surface modification may have important influences on the penetration behavior of nanoscale drug delivery system. In the present study, we mainly focused on whether cell targeting or cell penetration could affect penetration abilities of nanostructured lipid carriers（NLC）. Real--time penetration of folate--or cell penetrating peptide（CPP）-modified NLC was evaluated using a multicellular tumor spheroid（MTS） established by stacking culture method as an in vitro testing platform. The results suggested that CPP modification had a better penetration behavior both on penetration depth and intensity compared with folate-modified NLC at the early stage of penetration process.

关键词： Nanostructured lipid carriers Multicellular tumor spheroids Stacking method Folate cell penetrating peptide

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A detachable coating of cholesterol-anchored PEG improves tumor targeting of cell-penetrating peptide-modified liposomes

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Acta Pharmaceutica Sinica B 2014年第1期4卷 67-73页

作者： Jie Tang Li Zhang Han Fu Qifang Kuang Huile Gao Zhirong Zhang Qin Hen Key Laboratory of Drug Targeting and Drug Delivery Systems Ministry of EducationWest China School of PharmacySichuan UniversityChengdu 610041China

cell-penetrating peptides(CPPs)have been widely used to enhance the membrane transloca-tion of various carriers for many years,but the non-specificity of CPPs seriously limits their utility in *** this study,cholesterol-anchored,reduction-sensitive PEG(first synthesized by our laboratory)was applied to develop a co-modified liposome with improved tumor *** optimization of the formulation,the in vitro and in vivo properties of the co-modified liposome were *** co-modified liposome had a much lower cellular uptake and tumor spheroid uptake,but a much higher tumor accumulation compared to CPP-modified liposome,indicating the non-specific penetration of CPPs could be attenuated by the outer PEG *** the addition of exogenous reducing agent,both the in vitro and in vivo cellular uptake was markedly increased,demonstrating that the reduction-sensitive PEG coating achieved a controllable detachment from the surface of liposomes and did not affect the penetrating abilities of *** present results demonstrate that the combination of cholestervsitive PEG and CPPs is an ideal alternative for the application of CPP-modified carriers in vivo.

关键词： cell penetrating peptide Reduction-sensitive PEG Tumor targeting Cholesterol Liposome

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Self-assembly of peptide-based nanostructures： Synthesis and biological activity

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Nano Research 2018年第5期11卷 2315-2335页

作者： Lena Guyon Elise Lepeltier Catherine Passirani Micro & Nanomedecines Translationnelles-MINT UNIV Angers INSERM U 1066 CNRS UMR 6021 UBL Universite Bretagne Loire Angers F-49933 France

peptide-based nanostructures have received much attention in the field of drug targeting. In fact, peptides have many advantages such as simplicity of the structure, biocompatibility, and chemical diversity. Moreover, some peptides, which are called cell-penetrating peptides, can cross cellular membranes and carry small molecules, small interfering RNA, or viruses inside live cells. These molecules are often covalently or noncovalently linked to cargoes, thus forming amphiphilic conjugates that can self-assemble. Supramolecular nanostructures formed from peptides are used in nanomedicine as a carrier to protect a drug and to target cancer cells. This review explores aliphatic-chain-conjugated peptides and drug-conjugated peptides that can self-assemble. Special emphasis is placed on the synthesis procedure, nanostructure formation, and biological activity.

关键词： self-assembly cell penetrating peptide nanoparticle peptide

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The progress and perspective of strategies to improve tumor penetration of nanomedicines

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Chinese Chemical Letters 2021年第4期32卷 1341-1347页

作者： Jiang Hu Xinwei Yuan Fei Wang Huile Gao Xilin Liu Wei Zhang Department of Orthopedics Sichuan Provincial People's Hospital&Sichuan Academy of Medical Sciences&Affiliated Hospital of University of Electronic Science and TechnologyChengdu 610072China Key Laboratory of Drug Targeting and Drug Delivery System of the Education Ministry Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial TechnologyWest China School of Pharmacy Sichuan UniversityChengdu 610041China

Tumor penetration is important for effectively tumor targeting drug ***,many researches are published to overcome the barriers that restrict tumor penetration and improve drug delivery *** the mini review,we first analyzed the barriers influence the tumor penetration,including tumor microenvironment barriers,nanoparticle properties,and interaction barriers between tumor and *** overcome the barrier,several strategies are developed,including modulating tumor microenvironment,changing particle size,transcytosis enabled tumor penetration,cell penetrating peptide modification and overcoming binding site barrier,which could effectively improve tumor penetration,and finally enhance tumor treatment outcome.

关键词： Tumor penetration Tumor microenvironment Size changeable cell penetrating peptide Nanoparticles

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Improved method for synthesis of low molecular weight protamine–siRNA conjugate

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Acta Pharmaceutica Sinica B 2018年第1期8卷 116-126页

作者： Zhili Yu Junxiao Ye Xing Pei Lu Sun Ergang Liu Jianxin Wang Yongzhuo Huang Seung Jin Lee Huining He Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics School of PharmacyTianjin Medical University College of Pharmacy Tsinghua University Collaborative Innovation Center of Chemical Science and Chemical Engineering and Technology Tianjin University Key Laboratory of Smart Drug Delivery Ministry of Education & PLA Department of Pharmaceutics School of Pharmacy Fudan University Ministry of Education & PLA Shanghai Institute of Materia Medica Chinese Academy of Sciences Department of Pharmacy Ewha Womans University Seodaemun-gu

RNAi technology has aroused wide public interest due to its high efficiency and specificity to treat multiple types of diseases. However, the effective delivery of siRNA remains a challenge due to its large molecular weight and strong anionic charge. Considering their remarkable functions in vivo and features that are often desired in drug delivery carriers, biomimetic systems for siRNA delivery become an effective and promising strategy. Based on this, covalent attachment of synthetic cell penetrating peptides(CPP) to siRNA has become of great interest. We developed a monomeric covalent conjugate of low molecular weight protamine(LMWP, a well-established CPP) and siRNA via a cytosol-cleavable disulfide linkage using PEG as a crosslinker. Results showed that the conjugates didn't generate coagulation, and exhibited much better RNAi potency and intracellular delivery compared with the conventional charge-complexed CPP/siRNA aggregates. Three different synthetic and purification methods were compared in order to optimize synthesis efficiency and product yield. The methodology using hetero-bifunctional NHS–PEG–OPSS as a crosslinker to synthesize LMWP–siRNA simplified the synthesis and purification process and produced the highest yield. These results pave the way towards siRNA biomimetic delivery and future clinical translation.

关键词： cell penetrating peptide siRNA Conjugate Conjugation yield Biomimetic delivery Crosslinker

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Fabrication of self-assembling nanofibers with optimal cell uptake and therapeutic delivery efficacy

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Bioactive Materials 2017年第4期2卷 260-268页

作者： Dawei Xu Damien SKSamways He Dong Department of Chemistry&Biomolecular Science Clarkson UniversityPotsdamUSA Department of Biology Clarkson UniversityPotsdamUSA

Effective strategies to fabricate finite organic nanoparticles and understanding their structure-dependent cell interaction is highly important for the development of long circulating nanocarriers in cancer *** this contribution,we will capitalize on our recent development of finite supramolecular nanofibers based on the self-assembly of modularly designed cationic multidomain peptides(MDPs)and use them as a model system to investigate structure-dependent cell penetrating *** selfassembled into nanofibers with high density of cationic charges at the fiber-solvent interface to interact with the cell ***,despite the multivalent charge presentation,not all fibers led to high levels of membrane activity and cellular *** flexibility of the cationic charge domains on self-assembled nanofibers plays a key role in effective membrane *** were found to sacrifice their dimension,thermodynamic and kinetic stability for a more flexible charge domain in order to achieve effective membrane *** increased membrane activity led to improved cell uptake of membrane-impermeable chemotherapeutics through membrane pore *** vitro cytotoxicity study showed co-administering of water-soluble doxorubicin with membrane-active peptide nanofibers dramatically reduced the IC50 by eight folds compared to drug *** these detailed structure and activity studies,the acquired knowledge will provide important guidelines for the design of a variety of supramolecular cell penetrating nanomaterials not limited to peptide assembly which can be used to probe various complex biological processes.

关键词： Supramolecular assembly cell penetrating peptide Drug delivery cell uptake Membrane activity

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Development of a potent peptide inhibitor of estrogen receptor α

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Chinese Chemical Letters 2018年第7期29卷 1160-1162页

作者： Xuan Qin Hui Zhao Yanhong Jiang Feng Yin Yuan Tian Mingsheng Xie Xiyang Ye Naihan Xu Zigang Li School of Chemical Biology and Biotechnology Shenzhen Graduate School of Peking University School of Life Science and Engineering Southwest Jiaotong University Department of Gynecology The Second Clinical Medical College of Jinan UniversityShenzhen People's Hospital Key Lab in Healthy Science and Technology Division of Life ScienceShenzhen Graduate School of Tsinghua University

We have developed a facile N-terminus helix-nucleating strategy using an unnaturally tethered aspartic acid(TD strategy). Relatively weak nuclear translocation efficiency of TD PERM limits its further biological applications. A potent peptide inhibitor of estrogen receptor α(ER-α) with significantly increased cellular uptake and cellular distribution was developed by cell penetrating peptide *** resulted peptide conjugate showed selective toxicity towards estrogen receptor positive cell lines and induced decreased transcription of estrogen receptor a downstream genes.

关键词： peptide inhibitor TD strategy N-terminus helix-nucleating strategy Estrogen receptor α cell penetrating peptide

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Essential Gene(s) Targeted by peptide Nucleic Acids Kills <i>Mycobacterium smegmatis</i>in Culture and in Infected Macrophages

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Advances in Infectious Diseases 2021年第2期11卷 156-164页

作者： Md. Ariful Islam Mst. Minara Khatun Nammalwar Sriranganathan Stephen M. Boyle Center for One Health Research Virginia-Maryland College of Veterinary Medicine Virginia Tech Blacksburg VA USA Department of Microbiology & Hygiene Bangladesh Agricultural University Mymensingh Bangladesh

Background: Antisense peptide nucleic acids (PNAs) exhibit growth inhibitory effects on bacteria by inhibiting the expression of essential genes and could be promising therapeutic agents for treating bacterial infections. A study was carried out to determine the efficacy of several antisense PNAs in inhibiting extracellular and intracellular growth of Mycobacterium smegmatis. Methods: Six PNAs obtained from a commercial supplier were tested to evaluate the inhibitory effect on bacterial growth by inhibiting the expression of the following essential genes: inhA (a fatty acid elongase), rpsL (ribosomal S12 protein), gyrA (DNA gyrase), pncA (pyrazinamidase), polA (DNA polymerase I) and rpoC (RNA polymerase β subunit) of M. smegmatis. Each PNA was tested at 20 μM, 10 μM, 5 μM and 2.5 μM concentrations to determine whether they caused a dose dependent killing of M. smegmatis cultured in Middlebrook 7H9 broth or in a J774A.1 murine macrophage cell line. Results: In Middlebrook broth, the strong growth inhibitory effect against M. smegmatis was observed by PNAs targeting the inhA and rpsL genes at all four concentrations. The PNAs targeting the pncA, polA and rpoC genes were found to exhibit strong growth inhibition against M. smegmatis but only at 20 μM concentration. No growth inhibition of M. smegmatis was seen in pure culture when treated with PNAs targeting gyrA and a mismatch PNA targeting dnaG (DNA primase). All six PNAs showed killing of M. smegmatis in J774A.1 macrophage cell line that were statistically significant (p Conclusion: It may be concluded from this study that PNAs could be potential therapeutics for mycobacterial infections.

关键词： Middlebrook 7H9 Broth Culture J774A.1 Murine Macrophage cell Line Antisense Therapy peptide Nucleic Acid cell penetrating peptide Mycobacterium

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