Host−[2]Rotaxanes as Cellular Transport Agents
Host−[2]rotaxanes, containing a diarginine-derivatized dibenzo-24-crown-8 (DB24C8) ether as the ring and a cyclophane pocket or an aromatic cleft as one blocking group, are cell transport agents. These hosts strongly associate with a variety of amino acids, dipeptides, and fluorophores in water (1 m...
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| Veröffentlicht in: | Journal of the American Chemical Society 2003-07, Vol.125 (27), p.8290-8301 |
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| container_title | Journal of the American Chemical Society |
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| creator | Dvornikovs, Vadims House, Brian E Kaetzel, Marcia Dedman, John R Smithrud, David B |
| description | Host−[2]rotaxanes, containing a diarginine-derivatized dibenzo-24-crown-8 (DB24C8) ether as the ring and a cyclophane pocket or an aromatic cleft as one blocking group, are cell transport agents. These hosts strongly associate with a variety of amino acids, dipeptides, and fluorophores in water (1 mM phosphate buffer, pH 7.0), DMSO, and a 75/25 (v/v) buffer to DMSO solution. All peptidic guests in all solvent systems have association constants (K A's) in the range of 1 × 104 to 5 × 104 M-1, whereas the K A range for the fluorophores is 1 × 104 to 9 × 105 M-1. Association constants for the cyclophane itself, cyclophane 3, are smaller. These values are in the 1 × 103 to 5 × 103 M-1 range, which shows that the rotaxane architecture is advantageous for guest binding. Cyclophane−[2]rotaxane 1 efficiently transports fluorescein and a fluorescein-protein kinase C (PKC) inhibitor into eukaryotic COS-7 cells, including the nucleus. Interestingly, cleft−[2]rotaxane 2 does not transport fluorescein as efficiently, even though the results from the fluorescence assays show that both [2]rotaxanes bind fluorescein with the same ability. |
| doi_str_mv | 10.1021/ja034918c |
| format | Article |
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These hosts strongly associate with a variety of amino acids, dipeptides, and fluorophores in water (1 mM phosphate buffer, pH 7.0), DMSO, and a 75/25 (v/v) buffer to DMSO solution. All peptidic guests in all solvent systems have association constants (K A's) in the range of 1 × 104 to 5 × 104 M-1, whereas the K A range for the fluorophores is 1 × 104 to 9 × 105 M-1. Association constants for the cyclophane itself, cyclophane 3, are smaller. These values are in the 1 × 103 to 5 × 103 M-1 range, which shows that the rotaxane architecture is advantageous for guest binding. Cyclophane−[2]rotaxane 1 efficiently transports fluorescein and a fluorescein-protein kinase C (PKC) inhibitor into eukaryotic COS-7 cells, including the nucleus. Interestingly, cleft−[2]rotaxane 2 does not transport fluorescein as efficiently, even though the results from the fluorescence assays show that both [2]rotaxanes bind fluorescein with the same ability.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja034918c</identifier><identifier>PMID: 12837101</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Arginine - analogs & derivatives ; Arginine - chemistry ; Arginine - pharmacokinetics ; Biological and medical sciences ; Biomimetic Materials - chemistry ; Biomimetic Materials - metabolism ; Carrier Proteins - chemistry ; Carrier Proteins - metabolism ; Cercopithecus aethiops ; COS Cells ; Drug Carriers - chemical synthesis ; Drug Carriers - chemistry ; Drug Carriers - pharmacokinetics ; Ethers, Cyclic - chemistry ; Ethers, Cyclic - pharmacokinetics ; Fluorescein - chemistry ; Fluorescein - pharmacokinetics ; Fundamental and applied biological sciences. Psychology ; Kinetics ; Models, Molecular ; Molecular and cellular biology ; Rotaxanes</subject><ispartof>Journal of the American Chemical Society, 2003-07, Vol.125 (27), p.8290-8301</ispartof><rights>Copyright © 2003 American Chemical Society</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-e4398c75af3e5918ba501caa9d29a3bc22bbab7456b66befe04b16eec6d498773</citedby><cites>FETCH-LOGICAL-a445t-e4398c75af3e5918ba501caa9d29a3bc22bbab7456b66befe04b16eec6d498773</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/ja034918c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja034918c$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14949892$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12837101$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dvornikovs, Vadims</creatorcontrib><creatorcontrib>House, Brian E</creatorcontrib><creatorcontrib>Kaetzel, Marcia</creatorcontrib><creatorcontrib>Dedman, John R</creatorcontrib><creatorcontrib>Smithrud, David B</creatorcontrib><title>Host−[2]Rotaxanes as Cellular Transport Agents</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Host−[2]rotaxanes, containing a diarginine-derivatized dibenzo-24-crown-8 (DB24C8) ether as the ring and a cyclophane pocket or an aromatic cleft as one blocking group, are cell transport agents. These hosts strongly associate with a variety of amino acids, dipeptides, and fluorophores in water (1 mM phosphate buffer, pH 7.0), DMSO, and a 75/25 (v/v) buffer to DMSO solution. All peptidic guests in all solvent systems have association constants (K A's) in the range of 1 × 104 to 5 × 104 M-1, whereas the K A range for the fluorophores is 1 × 104 to 9 × 105 M-1. Association constants for the cyclophane itself, cyclophane 3, are smaller. These values are in the 1 × 103 to 5 × 103 M-1 range, which shows that the rotaxane architecture is advantageous for guest binding. Cyclophane−[2]rotaxane 1 efficiently transports fluorescein and a fluorescein-protein kinase C (PKC) inhibitor into eukaryotic COS-7 cells, including the nucleus. Interestingly, cleft−[2]rotaxane 2 does not transport fluorescein as efficiently, even though the results from the fluorescence assays show that both [2]rotaxanes bind fluorescein with the same ability.</description><subject>Animals</subject><subject>Arginine - analogs & derivatives</subject><subject>Arginine - chemistry</subject><subject>Arginine - pharmacokinetics</subject><subject>Biological and medical sciences</subject><subject>Biomimetic Materials - chemistry</subject><subject>Biomimetic Materials - metabolism</subject><subject>Carrier Proteins - chemistry</subject><subject>Carrier Proteins - metabolism</subject><subject>Cercopithecus aethiops</subject><subject>COS Cells</subject><subject>Drug Carriers - chemical synthesis</subject><subject>Drug Carriers - chemistry</subject><subject>Drug Carriers - pharmacokinetics</subject><subject>Ethers, Cyclic - chemistry</subject><subject>Ethers, Cyclic - pharmacokinetics</subject><subject>Fluorescein - chemistry</subject><subject>Fluorescein - pharmacokinetics</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Kinetics</subject><subject>Models, Molecular</subject><subject>Molecular and cellular biology</subject><subject>Rotaxanes</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtKA0EQRRtRND4W_oBko-BitJ_TM0sJGpWAohFEkaa60yOJk5nYNQPxD1z7iX6JLQlm46oo6nA5dQnZZ_SEUc5OJ0CFzFnm1kiHKU4TxXi6TjqUUp7oLBVbZBtxElfJM7ZJthjPhGaUdQi9rLH5_vx65i93dQNzqDx2Abs9X5ZtCaE7DFDhrA5N9-zVVw3uko0CSvR7y7lDHi7Oh73LZHDTv-qdDRKQUjWJlyLPnFZQCK-imgVFmQPIRzwHYR3n1oLVUqU2Ta0vPJWWpd67dCTzTGuxQ44WubNQv7ceGzMdo4tW0bBu0WghOWNSRfB4AbpQIwZfmFkYTyF8GEbNbz3mr57IHixDWzv1oxW57CMCh0sA0EFZxOfdGFeczKNdziOXLLgxNn7-d4fwZlIttDLD23sjnwYZ77NHc73KBYdmUrehit39I_gDlnyHnA</recordid><startdate>20030709</startdate><enddate>20030709</enddate><creator>Dvornikovs, Vadims</creator><creator>House, Brian E</creator><creator>Kaetzel, Marcia</creator><creator>Dedman, John R</creator><creator>Smithrud, David B</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>20030709</creationdate><title>Host−[2]Rotaxanes as Cellular Transport Agents</title><author>Dvornikovs, Vadims ; House, Brian E ; Kaetzel, Marcia ; Dedman, John R ; Smithrud, David B</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-e4398c75af3e5918ba501caa9d29a3bc22bbab7456b66befe04b16eec6d498773</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Animals</topic><topic>Arginine - analogs & derivatives</topic><topic>Arginine - chemistry</topic><topic>Arginine - pharmacokinetics</topic><topic>Biological and medical sciences</topic><topic>Biomimetic Materials - chemistry</topic><topic>Biomimetic Materials - metabolism</topic><topic>Carrier Proteins - chemistry</topic><topic>Carrier Proteins - metabolism</topic><topic>Cercopithecus aethiops</topic><topic>COS Cells</topic><topic>Drug Carriers - chemical synthesis</topic><topic>Drug Carriers - chemistry</topic><topic>Drug Carriers - pharmacokinetics</topic><topic>Ethers, Cyclic - chemistry</topic><topic>Ethers, Cyclic - pharmacokinetics</topic><topic>Fluorescein - chemistry</topic><topic>Fluorescein - pharmacokinetics</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Kinetics</topic><topic>Models, Molecular</topic><topic>Molecular and cellular biology</topic><topic>Rotaxanes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dvornikovs, Vadims</creatorcontrib><creatorcontrib>House, Brian E</creatorcontrib><creatorcontrib>Kaetzel, Marcia</creatorcontrib><creatorcontrib>Dedman, John R</creatorcontrib><creatorcontrib>Smithrud, David B</creatorcontrib><collection>Istex</collection><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>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dvornikovs, Vadims</au><au>House, Brian E</au><au>Kaetzel, Marcia</au><au>Dedman, John R</au><au>Smithrud, David B</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Host−[2]Rotaxanes as Cellular Transport Agents</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2003-07-09</date><risdate>2003</risdate><volume>125</volume><issue>27</issue><spage>8290</spage><epage>8301</epage><pages>8290-8301</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>Host−[2]rotaxanes, containing a diarginine-derivatized dibenzo-24-crown-8 (DB24C8) ether as the ring and a cyclophane pocket or an aromatic cleft as one blocking group, are cell transport agents. These hosts strongly associate with a variety of amino acids, dipeptides, and fluorophores in water (1 mM phosphate buffer, pH 7.0), DMSO, and a 75/25 (v/v) buffer to DMSO solution. All peptidic guests in all solvent systems have association constants (K A's) in the range of 1 × 104 to 5 × 104 M-1, whereas the K A range for the fluorophores is 1 × 104 to 9 × 105 M-1. Association constants for the cyclophane itself, cyclophane 3, are smaller. These values are in the 1 × 103 to 5 × 103 M-1 range, which shows that the rotaxane architecture is advantageous for guest binding. Cyclophane−[2]rotaxane 1 efficiently transports fluorescein and a fluorescein-protein kinase C (PKC) inhibitor into eukaryotic COS-7 cells, including the nucleus. Interestingly, cleft−[2]rotaxane 2 does not transport fluorescein as efficiently, even though the results from the fluorescence assays show that both [2]rotaxanes bind fluorescein with the same ability.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12837101</pmid><doi>10.1021/ja034918c</doi><tpages>12</tpages></addata></record> |
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| subjects | Animals Arginine - analogs & derivatives Arginine - chemistry Arginine - pharmacokinetics Biological and medical sciences Biomimetic Materials - chemistry Biomimetic Materials - metabolism Carrier Proteins - chemistry Carrier Proteins - metabolism Cercopithecus aethiops COS Cells Drug Carriers - chemical synthesis Drug Carriers - chemistry Drug Carriers - pharmacokinetics Ethers, Cyclic - chemistry Ethers, Cyclic - pharmacokinetics Fluorescein - chemistry Fluorescein - pharmacokinetics Fundamental and applied biological sciences. Psychology Kinetics Models, Molecular Molecular and cellular biology Rotaxanes |
| title | Host−[2]Rotaxanes as Cellular Transport Agents |
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