Lipophilic Pyrylium Salts in the Synthesis of Efficient Pyridinium-Based Cationic Lipids, Gemini Surfactants, and Lipophilic Oligomers for Gene Delivery
Several new classes of pyridinium cationic lipids were synthesized and tested as gene delivery agents. They were obtained through a procedure that generates simultaneously the heterocyclic ring and the positively charged nitrogen atom, using lipophilic pyrylium salts as key intermediates that react...
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| Veröffentlicht in: | Journal of medicinal chemistry 2006-06, Vol.49 (13), p.3872-3887 |
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| container_title | Journal of medicinal chemistry |
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| creator | Ilies, Marc Antoniu Seitz, William A Johnson, Betty H Ezell, Edward L Miller, Aaron L Thompson, E. Brad Balaban, Alexandru T |
| description | Several new classes of pyridinium cationic lipids were synthesized and tested as gene delivery agents. They were obtained through a procedure that generates simultaneously the heterocyclic ring and the positively charged nitrogen atom, using lipophilic pyrylium salts as key intermediates that react with primary amines, yielding pyridinium salts. The choice of the appropriately substituted primary amine, diamine or polyamine, allows the design of the shape of the final lipids, gemini surfactants, or lipophilic polycations. We report also a comprehensive structure−activity relationship study that identified the most efficient structural variables at the levels of the hydrophobic anchor, linker, and counterion for these classes of pyridinium cationic lipids. This study was also aimed at finding the best liposomal formulation for the new transfection agents. |
| doi_str_mv | 10.1021/jm0601755 |
| format | Article |
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Drug treatments ; Polymers - chemical synthesis ; Polymers - chemistry ; Pyridines - chemical synthesis ; Pyridines - chemistry ; Pyrones - chemical synthesis ; Pyrones - chemistry ; Structure-Activity Relationship ; Surface-Active Agents - chemical synthesis ; Surface-Active Agents - chemistry</subject><ispartof>Journal of medicinal chemistry, 2006-06, Vol.49 (13), p.3872-3887</ispartof><rights>Copyright © 2006 American Chemical Society</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a447t-a9dbe264b57526feb5f7a06e0dd4093e02d595d0bc595ccac7c06504a7f8784e3</citedby><cites>FETCH-LOGICAL-a447t-a9dbe264b57526feb5f7a06e0dd4093e02d595d0bc595ccac7c06504a7f8784e3</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/jm0601755$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm0601755$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17913636$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16789743$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ilies, Marc Antoniu</creatorcontrib><creatorcontrib>Seitz, William A</creatorcontrib><creatorcontrib>Johnson, Betty H</creatorcontrib><creatorcontrib>Ezell, Edward L</creatorcontrib><creatorcontrib>Miller, Aaron L</creatorcontrib><creatorcontrib>Thompson, E. Brad</creatorcontrib><creatorcontrib>Balaban, Alexandru T</creatorcontrib><title>Lipophilic Pyrylium Salts in the Synthesis of Efficient Pyridinium-Based Cationic Lipids, Gemini Surfactants, and Lipophilic Oligomers for Gene Delivery</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Several new classes of pyridinium cationic lipids were synthesized and tested as gene delivery agents. They were obtained through a procedure that generates simultaneously the heterocyclic ring and the positively charged nitrogen atom, using lipophilic pyrylium salts as key intermediates that react with primary amines, yielding pyridinium salts. The choice of the appropriately substituted primary amine, diamine or polyamine, allows the design of the shape of the final lipids, gemini surfactants, or lipophilic polycations. We report also a comprehensive structure−activity relationship study that identified the most efficient structural variables at the levels of the hydrophobic anchor, linker, and counterion for these classes of pyridinium cationic lipids. This study was also aimed at finding the best liposomal formulation for the new transfection agents.</description><subject>Antineoplastic agents</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Cations</subject><subject>Cell Line, Tumor</subject><subject>Drug Carriers - chemical synthesis</subject><subject>Drug Carriers - chemistry</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Gene therapy</subject><subject>Gene Transfer Techniques</subject><subject>General aspects</subject><subject>Health. Pharmaceutical industry</subject><subject>Humans</subject><subject>Industrial applications and implications. Economical aspects</subject><subject>Lipids - chemical synthesis</subject><subject>Lipids - chemistry</subject><subject>Liposomes - chemistry</subject><subject>Medical sciences</subject><subject>Onium Compounds - chemical synthesis</subject><subject>Onium Compounds - chemistry</subject><subject>Pharmacology. Drug treatments</subject><subject>Polymers - chemical synthesis</subject><subject>Polymers - chemistry</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - chemistry</subject><subject>Pyrones - chemical synthesis</subject><subject>Pyrones - chemistry</subject><subject>Structure-Activity Relationship</subject><subject>Surface-Active Agents - chemical synthesis</subject><subject>Surface-Active Agents - chemistry</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkcGO0zAQhi0EYkvhwAsgX0BCImA7sZ0coexukYp2pZaz5dhj1iVxip0g8iY8Ll612nJAPvyS5_M31gxCLyl5TwmjH_Y9EYRKzh-hBeWMFFVNqsdoQQhjBROsvEDPUtoTQkrKyqfoggpZN7IqF-jPxh-Gw53vvMG3c5w7P_V4q7sxYR_weAd4O4ccySc8OHzpnDcewngPe-tDxotPOoHFKz36IWRNNnqb3uFr6HMdb6fotBl1GPOdDhb_0_Gm89-HHmLCboj5QQD8GTr_C-L8HD1xukvw4pRL9O3qcrdaF5ub6y-rj5tCV5UcC93YFpioWi45Ew5a7qQmAoi1FWlKIMzyhlvSmhzGaCMNEZxUWrpa1hWUS_Tm6D3E4ecEaVS9Twa6TgcYpqRETYmQTZnBt0fQxCGlCE4dou91nBUl6n4N6mENmX11kk5tD_ZMnuaegdcnQCejOxd1MD6dOdnQUuSzRMWR82mE3w91HX8oIUvJ1e52q9Y7frXm669qdfZqk9R-mGLIs_vPB_8CXfKscQ</recordid><startdate>20060629</startdate><enddate>20060629</enddate><creator>Ilies, Marc Antoniu</creator><creator>Seitz, William A</creator><creator>Johnson, Betty H</creator><creator>Ezell, Edward L</creator><creator>Miller, Aaron L</creator><creator>Thompson, E. Brad</creator><creator>Balaban, Alexandru T</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><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>7X8</scope></search><sort><creationdate>20060629</creationdate><title>Lipophilic Pyrylium Salts in the Synthesis of Efficient Pyridinium-Based Cationic Lipids, Gemini Surfactants, and Lipophilic Oligomers for Gene Delivery</title><author>Ilies, Marc Antoniu ; Seitz, William A ; Johnson, Betty H ; Ezell, Edward L ; Miller, Aaron L ; Thompson, E. 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Economical aspects</topic><topic>Lipids - chemical synthesis</topic><topic>Lipids - chemistry</topic><topic>Liposomes - chemistry</topic><topic>Medical sciences</topic><topic>Onium Compounds - chemical synthesis</topic><topic>Onium Compounds - chemistry</topic><topic>Pharmacology. 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| subjects | Antineoplastic agents Biological and medical sciences Biotechnology Cations Cell Line, Tumor Drug Carriers - chemical synthesis Drug Carriers - chemistry Fundamental and applied biological sciences. Psychology Gene therapy Gene Transfer Techniques General aspects Health. Pharmaceutical industry Humans Industrial applications and implications. Economical aspects Lipids - chemical synthesis Lipids - chemistry Liposomes - chemistry Medical sciences Onium Compounds - chemical synthesis Onium Compounds - chemistry Pharmacology. Drug treatments Polymers - chemical synthesis Polymers - chemistry Pyridines - chemical synthesis Pyridines - chemistry Pyrones - chemical synthesis Pyrones - chemistry Structure-Activity Relationship Surface-Active Agents - chemical synthesis Surface-Active Agents - chemistry |
| title | Lipophilic Pyrylium Salts in the Synthesis of Efficient Pyridinium-Based Cationic Lipids, Gemini Surfactants, and Lipophilic Oligomers for Gene Delivery |
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