A host-rotaxane derivatized with carboxylic acids efficiently delivers a highly cationic fluoresceinated peptide
A cleft-[2]rotaxane (CR2+2−) was derivatized with carboxylic acids to enhance the intracellular delivery of a highly cationic or anionic pentapeptide. CR2+2− delivers the fluorescein (Fl) tagged peptide Fl-KKALR to a greater amount than Fl-QEAVD, and at a higher concentration, a greater amount than...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2007-09, Vol.17 (18), p.5058-5062 |
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| container_issue | 18 |
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| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 17 |
| creator | Zhu, Jing House, Brian E. Fleck, Erin Isaacsohn, Idit Drew, Angela F. Smithrud, David B. |
| description | A cleft-[2]rotaxane (CR2+2−) was derivatized with carboxylic acids to enhance the intracellular delivery of a highly cationic or anionic pentapeptide. CR2+2− delivers the fluorescein (Fl) tagged peptide Fl-KKALR to a greater amount than Fl-QEAVD, and at a higher concentration, a greater amount than Fl-AVWAL. The level of delivery is largely temperature and ATP independent, suggesting that the Fl-peptide·CR2+2− complexes pass through the cellular membrane without requiring active cell-mediated processes. This study shows that selective delivery of peptides is possible by using a suitably derivatized host-rotaxane as the transporter. |
| doi_str_mv | 10.1016/j.bmcl.2007.07.013 |
| format | Article |
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CR2+2− delivers the fluorescein (Fl) tagged peptide Fl-KKALR to a greater amount than Fl-QEAVD, and at a higher concentration, a greater amount than Fl-AVWAL. The level of delivery is largely temperature and ATP independent, suggesting that the Fl-peptide·CR2+2− complexes pass through the cellular membrane without requiring active cell-mediated processes. 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CR2+2− delivers the fluorescein (Fl) tagged peptide Fl-KKALR to a greater amount than Fl-QEAVD, and at a higher concentration, a greater amount than Fl-AVWAL. The level of delivery is largely temperature and ATP independent, suggesting that the Fl-peptide·CR2+2− complexes pass through the cellular membrane without requiring active cell-mediated processes. This study shows that selective delivery of peptides is possible by using a suitably derivatized host-rotaxane as the transporter.</description><subject>Biological and medical sciences</subject><subject>Carboxylic Acids - chemistry</subject><subject>Cations</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Fluorescence</subject><subject>General pharmacology</subject><subject>Host-guest chemistry</subject><subject>Medical sciences</subject><subject>Organic chemistry</subject><subject>Peptide mimics</subject><subject>Peptides</subject><subject>Peptides - chemistry</subject><subject>Pharmaceutical technology. Pharmaceutical industry</subject><subject>Pharmacology. 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Pharmaceutical industry</topic><topic>Pharmacology. Drug treatments</topic><topic>Preparations and properties</topic><topic>Rotaxanes</topic><topic>Rotaxanes - chemistry</topic><topic>Transporters</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhu, Jing</creatorcontrib><creatorcontrib>House, Brian E.</creatorcontrib><creatorcontrib>Fleck, Erin</creatorcontrib><creatorcontrib>Isaacsohn, Idit</creatorcontrib><creatorcontrib>Drew, Angela F.</creatorcontrib><creatorcontrib>Smithrud, David B.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhu, Jing</au><au>House, Brian E.</au><au>Fleck, Erin</au><au>Isaacsohn, Idit</au><au>Drew, Angela F.</au><au>Smithrud, David B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A host-rotaxane derivatized with carboxylic acids efficiently delivers a highly cationic fluoresceinated peptide</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2007-09-15</date><risdate>2007</risdate><volume>17</volume><issue>18</issue><spage>5058</spage><epage>5062</epage><pages>5058-5062</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A cleft-[2]rotaxane (CR2+2−) was derivatized with carboxylic acids to enhance the intracellular delivery of a highly cationic or anionic pentapeptide. 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| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2007-09, Vol.17 (18), p.5058-5062 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Biological and medical sciences Carboxylic Acids - chemistry Cations Chemistry Exact sciences and technology Fluorescence General pharmacology Host-guest chemistry Medical sciences Organic chemistry Peptide mimics Peptides Peptides - chemistry Pharmaceutical technology. Pharmaceutical industry Pharmacology. Drug treatments Preparations and properties Rotaxanes Rotaxanes - chemistry Transporters |
| title | A host-rotaxane derivatized with carboxylic acids efficiently delivers a highly cationic fluoresceinated peptide |
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