Triggering G‐Quadruplex Conformation Switching with [7]Helicenes
The dynamic interplay between two types of chiral structures; fully conjugated racemic hetero[7]helicenes and DNA strands prone to fold into G‐quadruplex structures is described. Both the [7]helicenes and the G‐quadruplex DNA structures exist in more than one conformation in solution. We show that t...
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Veröffentlicht in: | Chemistry : a European journal 2021-04, Vol.27 (19), p.6064-6069 |
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creator | Lousen, Bodil Pedersen, Stephan K. Răsădean, Dora M. Pantoş, G. Dan Pittelkow, Michael |
description | The dynamic interplay between two types of chiral structures; fully conjugated racemic hetero[7]helicenes and DNA strands prone to fold into G‐quadruplex structures is described. Both the [7]helicenes and the G‐quadruplex DNA structures exist in more than one conformation in solution. We show that the structures interact with and stabilise each other, mutually amplifying and stabilising certain conformations at increased temperatures. The [7]helicene ligands L1 and L2 stabilise the parallel conformation of k‐ras significantly, whereas hybrid (K+) and antiparallel (Na+) h‐telo G‐quadruplexes are stabilised upon conformational switching into altered G‐quadruplex conformations. Both L1 and L2 induce parallel G‐quadruplexes from hybrid structures (K+) and L1 induces hybrid G‐quadruplexes from antiparallel conformations (Na+). Enantioselective binding of one helicene enantiomer is observed for helicene ligand L2, and VTCD melting experiments are used to estimate the racemisation barrier of the helicene.
Stabilized by flexibility: Heterocyclic [7]helicenes and DNA strands prone to fold into G‐quadruplex structures interact with and stabilise each other, mutually amplifying and stabilising certain conformations at increased temperatures. The [7]helicene ligands stabilise the parallel conformation of k‐ras significantly, whereas hybrid (K+) and antiparallel (Na+) h‐telo G‐quadruplexes are stabilised upon conformational switching into altered G‐quadruplex conformations. |
doi_str_mv | 10.1002/chem.202004990 |
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Stabilized by flexibility: Heterocyclic [7]helicenes and DNA strands prone to fold into G‐quadruplex structures interact with and stabilise each other, mutually amplifying and stabilising certain conformations at increased temperatures. The [7]helicene ligands stabilise the parallel conformation of k‐ras significantly, whereas hybrid (K+) and antiparallel (Na+) h‐telo G‐quadruplexes are stabilised upon conformational switching into altered G‐quadruplex conformations.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202004990</identifier><identifier>PMID: 33326174</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Chemistry ; chirality ; Circular Dichroism ; Conformation ; conformational analysis ; Deoxyribonucleic acid ; DNA ; Enantiomers ; G-Quadruplexes ; helical structures ; Hybrid structures ; Ligands ; Nucleic Acid Conformation ; Polycyclic Compounds ; Racemization ; Switching ; Telomere</subject><ispartof>Chemistry : a European journal, 2021-04, Vol.27 (19), p.6064-6069</ispartof><rights>2020 Wiley‐VCH GmbH</rights><rights>2020 Wiley-VCH GmbH.</rights><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4100-a7169438c3396ba1bc3f1d87d8e82a228bad167587e62bf82103533b27d096523</citedby><cites>FETCH-LOGICAL-c4100-a7169438c3396ba1bc3f1d87d8e82a228bad167587e62bf82103533b27d096523</cites><orcidid>0000-0002-3371-9500</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.202004990$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.202004990$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33326174$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lousen, Bodil</creatorcontrib><creatorcontrib>Pedersen, Stephan K.</creatorcontrib><creatorcontrib>Răsădean, Dora M.</creatorcontrib><creatorcontrib>Pantoş, G. Dan</creatorcontrib><creatorcontrib>Pittelkow, Michael</creatorcontrib><title>Triggering G‐Quadruplex Conformation Switching with [7]Helicenes</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>The dynamic interplay between two types of chiral structures; fully conjugated racemic hetero[7]helicenes and DNA strands prone to fold into G‐quadruplex structures is described. Both the [7]helicenes and the G‐quadruplex DNA structures exist in more than one conformation in solution. We show that the structures interact with and stabilise each other, mutually amplifying and stabilising certain conformations at increased temperatures. The [7]helicene ligands L1 and L2 stabilise the parallel conformation of k‐ras significantly, whereas hybrid (K+) and antiparallel (Na+) h‐telo G‐quadruplexes are stabilised upon conformational switching into altered G‐quadruplex conformations. Both L1 and L2 induce parallel G‐quadruplexes from hybrid structures (K+) and L1 induces hybrid G‐quadruplexes from antiparallel conformations (Na+). Enantioselective binding of one helicene enantiomer is observed for helicene ligand L2, and VTCD melting experiments are used to estimate the racemisation barrier of the helicene.
Stabilized by flexibility: Heterocyclic [7]helicenes and DNA strands prone to fold into G‐quadruplex structures interact with and stabilise each other, mutually amplifying and stabilising certain conformations at increased temperatures. The [7]helicene ligands stabilise the parallel conformation of k‐ras significantly, whereas hybrid (K+) and antiparallel (Na+) h‐telo G‐quadruplexes are stabilised upon conformational switching into altered G‐quadruplex conformations.</description><subject>Chemistry</subject><subject>chirality</subject><subject>Circular Dichroism</subject><subject>Conformation</subject><subject>conformational analysis</subject><subject>Deoxyribonucleic acid</subject><subject>DNA</subject><subject>Enantiomers</subject><subject>G-Quadruplexes</subject><subject>helical structures</subject><subject>Hybrid structures</subject><subject>Ligands</subject><subject>Nucleic Acid Conformation</subject><subject>Polycyclic Compounds</subject><subject>Racemization</subject><subject>Switching</subject><subject>Telomere</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1LwzAch4Mobk6vHqXgxUvnP0mbl6OWuQkTEedJJKRtulX6MpOVuZsfwc_oJ7Fjc4IXT8nh-T_8eBA6xdDHAOQymZmyT4AABFLCHurikGCfchbuoy7IgPsspLKDjpx7BQDJKD1EHUopYZgHXXQ9sfl0amxeTb3h18fnQ6NT28wL8-5FdZXVttSLvK68x2W-SGZrqv3MvGf-MjJFnpjKuGN0kOnCmZPt20NPN4NJNPLH98Pb6GrsJ0E71dccMxlQkVAqWaxxnNAMp4KnwgiiCRGxTjHjoeCGkTgTBAMNKY0JT9vZIaE9dLHxzm391hi3UGXuElMUujJ14xQJODAiAHCLnv9BX-vGVu06RUKQBMtAsJbqb6jE1s5Zk6m5zUttVwqDWtdV67pqV7c9ONtqm7g06Q7_ydkCcgMs88Ks_tGpaDS4-5V_A1fHhP8</recordid><startdate>20210401</startdate><enddate>20210401</enddate><creator>Lousen, Bodil</creator><creator>Pedersen, Stephan K.</creator><creator>Răsădean, Dora M.</creator><creator>Pantoş, G. Dan</creator><creator>Pittelkow, Michael</creator><general>Wiley Subscription Services, Inc</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>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3371-9500</orcidid></search><sort><creationdate>20210401</creationdate><title>Triggering G‐Quadruplex Conformation Switching with [7]Helicenes</title><author>Lousen, Bodil ; Pedersen, Stephan K. ; Răsădean, Dora M. ; Pantoş, G. Dan ; Pittelkow, Michael</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4100-a7169438c3396ba1bc3f1d87d8e82a228bad167587e62bf82103533b27d096523</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Chemistry</topic><topic>chirality</topic><topic>Circular Dichroism</topic><topic>Conformation</topic><topic>conformational analysis</topic><topic>Deoxyribonucleic acid</topic><topic>DNA</topic><topic>Enantiomers</topic><topic>G-Quadruplexes</topic><topic>helical structures</topic><topic>Hybrid structures</topic><topic>Ligands</topic><topic>Nucleic Acid Conformation</topic><topic>Polycyclic Compounds</topic><topic>Racemization</topic><topic>Switching</topic><topic>Telomere</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lousen, Bodil</creatorcontrib><creatorcontrib>Pedersen, Stephan K.</creatorcontrib><creatorcontrib>Răsădean, Dora M.</creatorcontrib><creatorcontrib>Pantoş, G. Dan</creatorcontrib><creatorcontrib>Pittelkow, Michael</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lousen, Bodil</au><au>Pedersen, Stephan K.</au><au>Răsădean, Dora M.</au><au>Pantoş, G. Dan</au><au>Pittelkow, Michael</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Triggering G‐Quadruplex Conformation Switching with [7]Helicenes</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2021-04-01</date><risdate>2021</risdate><volume>27</volume><issue>19</issue><spage>6064</spage><epage>6069</epage><pages>6064-6069</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>The dynamic interplay between two types of chiral structures; fully conjugated racemic hetero[7]helicenes and DNA strands prone to fold into G‐quadruplex structures is described. Both the [7]helicenes and the G‐quadruplex DNA structures exist in more than one conformation in solution. We show that the structures interact with and stabilise each other, mutually amplifying and stabilising certain conformations at increased temperatures. The [7]helicene ligands L1 and L2 stabilise the parallel conformation of k‐ras significantly, whereas hybrid (K+) and antiparallel (Na+) h‐telo G‐quadruplexes are stabilised upon conformational switching into altered G‐quadruplex conformations. Both L1 and L2 induce parallel G‐quadruplexes from hybrid structures (K+) and L1 induces hybrid G‐quadruplexes from antiparallel conformations (Na+). Enantioselective binding of one helicene enantiomer is observed for helicene ligand L2, and VTCD melting experiments are used to estimate the racemisation barrier of the helicene.
Stabilized by flexibility: Heterocyclic [7]helicenes and DNA strands prone to fold into G‐quadruplex structures interact with and stabilise each other, mutually amplifying and stabilising certain conformations at increased temperatures. The [7]helicene ligands stabilise the parallel conformation of k‐ras significantly, whereas hybrid (K+) and antiparallel (Na+) h‐telo G‐quadruplexes are stabilised upon conformational switching into altered G‐quadruplex conformations.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>33326174</pmid><doi>10.1002/chem.202004990</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-3371-9500</orcidid></addata></record> |
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subjects | Chemistry chirality Circular Dichroism Conformation conformational analysis Deoxyribonucleic acid DNA Enantiomers G-Quadruplexes helical structures Hybrid structures Ligands Nucleic Acid Conformation Polycyclic Compounds Racemization Switching Telomere |
title | Triggering G‐Quadruplex Conformation Switching with [7]Helicenes |
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