Selective Stabilization of Abasic Site-Containing DNA by Insertion of Sterically Demanding Biaryl Ligands
Biaryl derivatives that consist of one DNA‐intercalating unit and a sterically demanding component exhibit a specific behavior towards abasic site‐containing DNA (AP‐DNA) as determined by thermal DNA denaturation experiments, spectrometric titrations and CD spectroscopic analysis. Specifically, thes...
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| Veröffentlicht in: | Chemistry : a European journal 2014-08, Vol.20 (32), p.9883-9887 |
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| container_issue | 32 |
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| container_title | Chemistry : a European journal |
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| creator | Benner, Katja Bergen, Anna Ihmels, Heiko Pithan, Phil Marvin |
| description | Biaryl derivatives that consist of one DNA‐intercalating unit and a sterically demanding component exhibit a specific behavior towards abasic site‐containing DNA (AP‐DNA) as determined by thermal DNA denaturation experiments, spectrometric titrations and CD spectroscopic analysis. Specifically, these ligands strongly stabilize AP‐DNA towards dissociation, whereas they do not or only marginally affect the melting temperature of regular duplex DNA.
Perfect fit into imperfect DNA: Sterically congested biaryl derivatives are introduced as novel structural motifs for the design of ligands that bind to abasic site‐containing DNA (AP‐DNA). These ligands strongly stabilize AP‐DNA towards dissociation, whereas they do not, or only marginally, affect the melting temperature of regular duplex DNA (see scheme). |
| doi_str_mv | 10.1002/chem.201403622 |
| format | Article |
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Perfect fit into imperfect DNA: Sterically congested biaryl derivatives are introduced as novel structural motifs for the design of ligands that bind to abasic site‐containing DNA (AP‐DNA). These ligands strongly stabilize AP‐DNA towards dissociation, whereas they do not, or only marginally, affect the melting temperature of regular duplex DNA (see scheme).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201403622</identifier><identifier>PMID: 25044435</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>abasic DNA ; Chemistry ; Denaturation ; Deoxyribonucleic acid ; Derivatives ; Design engineering ; DNA ; DNA - chemistry ; DNA damage ; DNA ligands ; DNA recognition ; Heterocyclic Compounds - chemistry ; Heterocyclic Compounds - pharmacology ; Intercalating Agents - chemistry ; Intercalating Agents - pharmacology ; Ligands ; Melting ; nitrogen heterocycles ; Nucleic Acid Denaturation - drug effects ; Stabilization ; Temperature ; Titration</subject><ispartof>Chemistry : a European journal, 2014-08, Vol.20 (32), p.9883-9887</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6832-fabdb29c0119867dd3d61f458126f90f73b297a764312a3b5b58343c25ad4a4f3</citedby><cites>FETCH-LOGICAL-c6832-fabdb29c0119867dd3d61f458126f90f73b297a764312a3b5b58343c25ad4a4f3</cites></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.201403622$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201403622$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25044435$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Benner, Katja</creatorcontrib><creatorcontrib>Bergen, Anna</creatorcontrib><creatorcontrib>Ihmels, Heiko</creatorcontrib><creatorcontrib>Pithan, Phil Marvin</creatorcontrib><title>Selective Stabilization of Abasic Site-Containing DNA by Insertion of Sterically Demanding Biaryl Ligands</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>Biaryl derivatives that consist of one DNA‐intercalating unit and a sterically demanding component exhibit a specific behavior towards abasic site‐containing DNA (AP‐DNA) as determined by thermal DNA denaturation experiments, spectrometric titrations and CD spectroscopic analysis. Specifically, these ligands strongly stabilize AP‐DNA towards dissociation, whereas they do not or only marginally affect the melting temperature of regular duplex DNA.
Perfect fit into imperfect DNA: Sterically congested biaryl derivatives are introduced as novel structural motifs for the design of ligands that bind to abasic site‐containing DNA (AP‐DNA). These ligands strongly stabilize AP‐DNA towards dissociation, whereas they do not, or only marginally, affect the melting temperature of regular duplex DNA (see scheme).</description><subject>abasic DNA</subject><subject>Chemistry</subject><subject>Denaturation</subject><subject>Deoxyribonucleic acid</subject><subject>Derivatives</subject><subject>Design engineering</subject><subject>DNA</subject><subject>DNA - chemistry</subject><subject>DNA damage</subject><subject>DNA ligands</subject><subject>DNA recognition</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>Heterocyclic Compounds - pharmacology</subject><subject>Intercalating Agents - chemistry</subject><subject>Intercalating Agents - pharmacology</subject><subject>Ligands</subject><subject>Melting</subject><subject>nitrogen heterocycles</subject><subject>Nucleic Acid Denaturation - drug effects</subject><subject>Stabilization</subject><subject>Temperature</subject><subject>Titration</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqN0c1v0zAYBnALgVgZXDkiS1y4pLz-jo9dN7pJZQh1CMTFchxneDjJZqds5a8nVbcKcRknS_bvfSS_D0KvCUwJAH3vfvh2SoFwYJLSJ2hCBCUFU1I8RRPQXBVSMH2AXuR8BQBaMvYcHVABnHMmJiisfPRuCL88Xg22CjH8tkPoO9w3eFbZHBxehcEX874bbOhCd4mPz2e42uCzLvv0QFeDT8HZGDf42Le2q7fwKNi0iXgZLseL_BI9a2zM_tX9eYi-fDi5mJ8Wy0-Ls_lsWThZMlo0tqorqh0Qokup6prVkjRclITKRkOj2PiqrJKcEWpZJSpRMs4cFbbmljfsEL3b5V6n_mbt82DakJ2P0Xa-X2dDlCoBuObicSokEFCkLP-DCgJUKLpNffsPverXqRv_PCquqaIg5aimO-VSn3PyjblOoR0XZgiYbbVmW63ZVzsOvLmPXVetr_f8ocsR6B24DdFvHokz89OTj3-HF7vZkAd_t5-16aeRiilhvp4vzOI7fKb024U5Yn8A4KW8pg</recordid><startdate>20140804</startdate><enddate>20140804</enddate><creator>Benner, Katja</creator><creator>Bergen, Anna</creator><creator>Ihmels, Heiko</creator><creator>Pithan, Phil Marvin</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><scope>7TM</scope></search><sort><creationdate>20140804</creationdate><title>Selective Stabilization of Abasic Site-Containing DNA by Insertion of Sterically Demanding Biaryl Ligands</title><author>Benner, Katja ; Bergen, Anna ; Ihmels, Heiko ; Pithan, Phil Marvin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6832-fabdb29c0119867dd3d61f458126f90f73b297a764312a3b5b58343c25ad4a4f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>abasic DNA</topic><topic>Chemistry</topic><topic>Denaturation</topic><topic>Deoxyribonucleic acid</topic><topic>Derivatives</topic><topic>Design engineering</topic><topic>DNA</topic><topic>DNA - chemistry</topic><topic>DNA damage</topic><topic>DNA ligands</topic><topic>DNA recognition</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>Heterocyclic Compounds - pharmacology</topic><topic>Intercalating Agents - chemistry</topic><topic>Intercalating Agents - pharmacology</topic><topic>Ligands</topic><topic>Melting</topic><topic>nitrogen heterocycles</topic><topic>Nucleic Acid Denaturation - drug effects</topic><topic>Stabilization</topic><topic>Temperature</topic><topic>Titration</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Benner, Katja</creatorcontrib><creatorcontrib>Bergen, Anna</creatorcontrib><creatorcontrib>Ihmels, Heiko</creatorcontrib><creatorcontrib>Pithan, Phil Marvin</creatorcontrib><collection>Istex</collection><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><collection>Nucleic Acids Abstracts</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Benner, Katja</au><au>Bergen, Anna</au><au>Ihmels, Heiko</au><au>Pithan, Phil Marvin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selective Stabilization of Abasic Site-Containing DNA by Insertion of Sterically Demanding Biaryl Ligands</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2014-08-04</date><risdate>2014</risdate><volume>20</volume><issue>32</issue><spage>9883</spage><epage>9887</epage><pages>9883-9887</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>Biaryl derivatives that consist of one DNA‐intercalating unit and a sterically demanding component exhibit a specific behavior towards abasic site‐containing DNA (AP‐DNA) as determined by thermal DNA denaturation experiments, spectrometric titrations and CD spectroscopic analysis. Specifically, these ligands strongly stabilize AP‐DNA towards dissociation, whereas they do not or only marginally affect the melting temperature of regular duplex DNA.
Perfect fit into imperfect DNA: Sterically congested biaryl derivatives are introduced as novel structural motifs for the design of ligands that bind to abasic site‐containing DNA (AP‐DNA). These ligands strongly stabilize AP‐DNA towards dissociation, whereas they do not, or only marginally, affect the melting temperature of regular duplex DNA (see scheme).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25044435</pmid><doi>10.1002/chem.201403622</doi><tpages>5</tpages></addata></record> |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | abasic DNA Chemistry Denaturation Deoxyribonucleic acid Derivatives Design engineering DNA DNA - chemistry DNA damage DNA ligands DNA recognition Heterocyclic Compounds - chemistry Heterocyclic Compounds - pharmacology Intercalating Agents - chemistry Intercalating Agents - pharmacology Ligands Melting nitrogen heterocycles Nucleic Acid Denaturation - drug effects Stabilization Temperature Titration |
| title | Selective Stabilization of Abasic Site-Containing DNA by Insertion of Sterically Demanding Biaryl Ligands |
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