Stearylated Antimicrobial Peptide Melittin and Its Retro Isomer for Efficient Gene Transfection
A crucial bottleneck in nonviral vector-mediated gene delivery is poor endosomal escape. Here, we constructed novel gene vectors by coupling the stearyl moiety to the N-terminus of the antimicrobial peptide melittin (stearyl-Mel) and its retro isomer (stearyl-rMel) due to their high membrane-lytic a...
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| Veröffentlicht in: | Bioconjugate chemistry 2013-11, Vol.24 (11), p.1805-1812 |
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| container_title | Bioconjugate chemistry |
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| creator | Zhang, Wei Song, Jingjing Liang, Ranran Zheng, Xin Chen, Jianbo Li, Guolin Zhang, Bangzhi Yan, Xiang Wang, Rui |
| description | A crucial bottleneck in nonviral vector-mediated gene delivery is poor endosomal escape. Here, we constructed novel gene vectors by coupling the stearyl moiety to the N-terminus of the antimicrobial peptide melittin (stearyl-Mel) and its retro isomer (stearyl-rMel) due to their high membrane-lytic activity. As expected, stearyl-Mel showed obvious increases in endosome-lytic activity and transfection efficiency compared with the reported stearyl-TP10. More gratifyingly, the transfection efficiency of stearyl-rMel was around 10-fold greater than that of stearyl-Mel and almost reached the transfection levels of Lipofectamine 2000 due to the enhanced endosome-lytic activity. Furthermore, the stearyl-rMel/p53 plasmid complex exhibited higher p53 expression and antitumor activity than stearyl-Mel, confirming the fact that stearyl-rMel displayed higher transfection efficiency. Taken together, the combination of the stearyl moiety with retro melittin provides a novel framework for the development of excellent nonviral gene vectors. |
| doi_str_mv | 10.1021/bc400053b |
| format | Article |
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Here, we constructed novel gene vectors by coupling the stearyl moiety to the N-terminus of the antimicrobial peptide melittin (stearyl-Mel) and its retro isomer (stearyl-rMel) due to their high membrane-lytic activity. As expected, stearyl-Mel showed obvious increases in endosome-lytic activity and transfection efficiency compared with the reported stearyl-TP10. More gratifyingly, the transfection efficiency of stearyl-rMel was around 10-fold greater than that of stearyl-Mel and almost reached the transfection levels of Lipofectamine 2000 due to the enhanced endosome-lytic activity. Furthermore, the stearyl-rMel/p53 plasmid complex exhibited higher p53 expression and antitumor activity than stearyl-Mel, confirming the fact that stearyl-rMel displayed higher transfection efficiency. Taken together, the combination of the stearyl moiety with retro melittin provides a novel framework for the development of excellent nonviral gene vectors.</description><identifier>ISSN: 1043-1802</identifier><identifier>EISSN: 1520-4812</identifier><identifier>DOI: 10.1021/bc400053b</identifier><identifier>PMID: 24107137</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Antimicrobial Cationic Peptides - chemistry ; Antimicrobial Cationic Peptides - metabolism ; Antimicrobial Cationic Peptides - pharmacology ; Antimicrobial peptides ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - metabolism ; Antineoplastic Agents - pharmacology ; Cell Proliferation - drug effects ; Cells, Cultured ; Cercopithecus aethiops ; CHO Cells ; COS Cells ; Cricetulus ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; Gene Transfer Techniques ; Genetic Vectors - chemistry ; Genetic Vectors - metabolism ; Genetic Vectors - pharmacology ; Humans ; Melitten - chemistry ; Melitten - metabolism ; Melitten - pharmacology ; Membranes ; Molecular Structure ; Peptides ; Plasmids ; Stearic Acids - chemistry ; Stearic Acids - metabolism ; Stearic Acids - pharmacology ; Stereoisomerism ; Structure-Activity Relationship ; Transfection ; Tumors</subject><ispartof>Bioconjugate chemistry, 2013-11, Vol.24 (11), p.1805-1812</ispartof><rights>Copyright © 2013 American Chemical Society</rights><rights>Copyright American Chemical Society Nov 20, 2013</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a442t-4f8eb5f39e1ce5fe3d84a7b84558c6dbd14aa73c515dd8980ea3c36fa597472f3</citedby><cites>FETCH-LOGICAL-a442t-4f8eb5f39e1ce5fe3d84a7b84558c6dbd14aa73c515dd8980ea3c36fa597472f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/bc400053b$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bc400053b$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24107137$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Wei</creatorcontrib><creatorcontrib>Song, Jingjing</creatorcontrib><creatorcontrib>Liang, Ranran</creatorcontrib><creatorcontrib>Zheng, Xin</creatorcontrib><creatorcontrib>Chen, Jianbo</creatorcontrib><creatorcontrib>Li, Guolin</creatorcontrib><creatorcontrib>Zhang, Bangzhi</creatorcontrib><creatorcontrib>Yan, Xiang</creatorcontrib><creatorcontrib>Wang, Rui</creatorcontrib><title>Stearylated Antimicrobial Peptide Melittin and Its Retro Isomer for Efficient Gene Transfection</title><title>Bioconjugate chemistry</title><addtitle>Bioconjugate Chem</addtitle><description>A crucial bottleneck in nonviral vector-mediated gene delivery is poor endosomal escape. Here, we constructed novel gene vectors by coupling the stearyl moiety to the N-terminus of the antimicrobial peptide melittin (stearyl-Mel) and its retro isomer (stearyl-rMel) due to their high membrane-lytic activity. As expected, stearyl-Mel showed obvious increases in endosome-lytic activity and transfection efficiency compared with the reported stearyl-TP10. More gratifyingly, the transfection efficiency of stearyl-rMel was around 10-fold greater than that of stearyl-Mel and almost reached the transfection levels of Lipofectamine 2000 due to the enhanced endosome-lytic activity. Furthermore, the stearyl-rMel/p53 plasmid complex exhibited higher p53 expression and antitumor activity than stearyl-Mel, confirming the fact that stearyl-rMel displayed higher transfection efficiency. Taken together, the combination of the stearyl moiety with retro melittin provides a novel framework for the development of excellent nonviral gene vectors.</description><subject>Animals</subject><subject>Antimicrobial Cationic Peptides - chemistry</subject><subject>Antimicrobial Cationic Peptides - metabolism</subject><subject>Antimicrobial Cationic Peptides - pharmacology</subject><subject>Antimicrobial peptides</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - metabolism</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Cell Proliferation - drug effects</subject><subject>Cells, Cultured</subject><subject>Cercopithecus aethiops</subject><subject>CHO Cells</subject><subject>COS Cells</subject><subject>Cricetulus</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Gene Transfer Techniques</subject><subject>Genetic Vectors - chemistry</subject><subject>Genetic Vectors - metabolism</subject><subject>Genetic Vectors - pharmacology</subject><subject>Humans</subject><subject>Melitten - chemistry</subject><subject>Melitten - metabolism</subject><subject>Melitten - pharmacology</subject><subject>Membranes</subject><subject>Molecular Structure</subject><subject>Peptides</subject><subject>Plasmids</subject><subject>Stearic Acids - chemistry</subject><subject>Stearic Acids - metabolism</subject><subject>Stearic Acids - pharmacology</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><subject>Transfection</subject><subject>Tumors</subject><issn>1043-1802</issn><issn>1520-4812</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqN0U1LHDEYB_BQLF1feugXkIAU9DCa10nmuMhWFyyW1p6HTPIEssxk1iR78NsbWZXSXnp6cvjxD8_zR-gLJZeUMHo1WEEIkXz4gA6pZKQRmrKD-iaCN1QTtkBHOW-q6ahmn9CCCUoU5eoQ9b8KmPQ0mgIOL2MJU7BpHoIZ8Q_YluAAf4cxlBIiNtHhdcn4J5Q043WeJ0jYzwmvvA82QCz4BiLgh2Ri9mBLmOMJ-ujNmOHz6zxGv7-tHq5vm7v7m_X18q4xQrDSCK9hkJ53QC1ID9xpYdSghZTatm5wVBijuJVUOqc7TcBwy1tvZKeEYp4fo_N97jbNjzvIpZ9CtjCOJsK8yz0VHWuZVl33H7SlXJBWqUrP_qKbeZdiXeRFMa0Z46Sqi72ql8s5ge-3KUz1qj0l_UtB_XtB1Z6-Ju6GCdy7fGukgq97YGz-47d_gp4BVPiV7A</recordid><startdate>20131120</startdate><enddate>20131120</enddate><creator>Zhang, Wei</creator><creator>Song, Jingjing</creator><creator>Liang, Ranran</creator><creator>Zheng, Xin</creator><creator>Chen, Jianbo</creator><creator>Li, Guolin</creator><creator>Zhang, Bangzhi</creator><creator>Yan, Xiang</creator><creator>Wang, Rui</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><scope>7T7</scope><scope>C1K</scope><scope>RC3</scope></search><sort><creationdate>20131120</creationdate><title>Stearylated Antimicrobial Peptide Melittin and Its Retro Isomer for Efficient Gene Transfection</title><author>Zhang, Wei ; Song, Jingjing ; Liang, Ranran ; Zheng, Xin ; Chen, Jianbo ; Li, Guolin ; Zhang, Bangzhi ; Yan, Xiang ; Wang, Rui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a442t-4f8eb5f39e1ce5fe3d84a7b84558c6dbd14aa73c515dd8980ea3c36fa597472f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Animals</topic><topic>Antimicrobial Cationic Peptides - chemistry</topic><topic>Antimicrobial Cationic Peptides - metabolism</topic><topic>Antimicrobial Cationic Peptides - pharmacology</topic><topic>Antimicrobial peptides</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - metabolism</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Cell Proliferation - drug effects</topic><topic>Cells, Cultured</topic><topic>Cercopithecus aethiops</topic><topic>CHO Cells</topic><topic>COS Cells</topic><topic>Cricetulus</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Gene Transfer Techniques</topic><topic>Genetic Vectors - chemistry</topic><topic>Genetic Vectors - metabolism</topic><topic>Genetic Vectors - pharmacology</topic><topic>Humans</topic><topic>Melitten - chemistry</topic><topic>Melitten - metabolism</topic><topic>Melitten - pharmacology</topic><topic>Membranes</topic><topic>Molecular Structure</topic><topic>Peptides</topic><topic>Plasmids</topic><topic>Stearic Acids - chemistry</topic><topic>Stearic Acids - metabolism</topic><topic>Stearic Acids - pharmacology</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><topic>Transfection</topic><topic>Tumors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Wei</creatorcontrib><creatorcontrib>Song, Jingjing</creatorcontrib><creatorcontrib>Liang, Ranran</creatorcontrib><creatorcontrib>Zheng, Xin</creatorcontrib><creatorcontrib>Chen, Jianbo</creatorcontrib><creatorcontrib>Li, Guolin</creatorcontrib><creatorcontrib>Zhang, Bangzhi</creatorcontrib><creatorcontrib>Yan, Xiang</creatorcontrib><creatorcontrib>Wang, Rui</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Genetics Abstracts</collection><jtitle>Bioconjugate chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Wei</au><au>Song, Jingjing</au><au>Liang, Ranran</au><au>Zheng, Xin</au><au>Chen, Jianbo</au><au>Li, Guolin</au><au>Zhang, Bangzhi</au><au>Yan, Xiang</au><au>Wang, Rui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stearylated Antimicrobial Peptide Melittin and Its Retro Isomer for Efficient Gene Transfection</atitle><jtitle>Bioconjugate chemistry</jtitle><addtitle>Bioconjugate Chem</addtitle><date>2013-11-20</date><risdate>2013</risdate><volume>24</volume><issue>11</issue><spage>1805</spage><epage>1812</epage><pages>1805-1812</pages><issn>1043-1802</issn><eissn>1520-4812</eissn><abstract>A crucial bottleneck in nonviral vector-mediated gene delivery is poor endosomal escape. Here, we constructed novel gene vectors by coupling the stearyl moiety to the N-terminus of the antimicrobial peptide melittin (stearyl-Mel) and its retro isomer (stearyl-rMel) due to their high membrane-lytic activity. As expected, stearyl-Mel showed obvious increases in endosome-lytic activity and transfection efficiency compared with the reported stearyl-TP10. More gratifyingly, the transfection efficiency of stearyl-rMel was around 10-fold greater than that of stearyl-Mel and almost reached the transfection levels of Lipofectamine 2000 due to the enhanced endosome-lytic activity. Furthermore, the stearyl-rMel/p53 plasmid complex exhibited higher p53 expression and antitumor activity than stearyl-Mel, confirming the fact that stearyl-rMel displayed higher transfection efficiency. Taken together, the combination of the stearyl moiety with retro melittin provides a novel framework for the development of excellent nonviral gene vectors.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24107137</pmid><doi>10.1021/bc400053b</doi><tpages>8</tpages></addata></record> |
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| ispartof | Bioconjugate chemistry, 2013-11, Vol.24 (11), p.1805-1812 |
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| source | MEDLINE; ACS Publications |
| subjects | Animals Antimicrobial Cationic Peptides - chemistry Antimicrobial Cationic Peptides - metabolism Antimicrobial Cationic Peptides - pharmacology Antimicrobial peptides Antineoplastic Agents - chemistry Antineoplastic Agents - metabolism Antineoplastic Agents - pharmacology Cell Proliferation - drug effects Cells, Cultured Cercopithecus aethiops CHO Cells COS Cells Cricetulus Dose-Response Relationship, Drug Drug Screening Assays, Antitumor Gene Transfer Techniques Genetic Vectors - chemistry Genetic Vectors - metabolism Genetic Vectors - pharmacology Humans Melitten - chemistry Melitten - metabolism Melitten - pharmacology Membranes Molecular Structure Peptides Plasmids Stearic Acids - chemistry Stearic Acids - metabolism Stearic Acids - pharmacology Stereoisomerism Structure-Activity Relationship Transfection Tumors |
| title | Stearylated Antimicrobial Peptide Melittin and Its Retro Isomer for Efficient Gene Transfection |
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