Copper−1,10-Phenanthroline Complexes Binding to DNA: Structural Predictions from Molecular Simulations
Copper−1,10-phenanthroline (phen) complexes Cu(phen)2 , Cu(2-Clip-phen), and Cu(3-Clip-phen) (Clip = a serinol bridge between the phen parts) are typically employed as DNA-cleaving agents and are now becoming increasingly important for building multifunctional drugs with improved cytotoxic propertie...
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| Veröffentlicht in: | The journal of physical chemistry. B 2009-08, Vol.113 (31), p.10881-10890 |
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| container_end_page | 10890 |
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| container_issue | 31 |
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| container_title | The journal of physical chemistry. B |
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| creator | Robertazzi, Arturo Vargiu, Attilio Vittorio Magistrato, Alessandra Ruggerone, Paolo Carloni, Paolo de Hoog, Paul Reedijk, Jan |
| description | Copper−1,10-phenanthroline (phen) complexes Cu(phen)2 , Cu(2-Clip-phen), and Cu(3-Clip-phen) (Clip = a serinol bridge between the phen parts) are typically employed as DNA-cleaving agents and are now becoming increasingly important for building multifunctional drugs with improved cytotoxic properties. For instance, Cu(3-Clip-phen) has been combined with distamycin-like minor-groove binders and cisplatin-derivatives, leading to promising results. Density Functional Theory (DFT) and docking calculations as well as molecular dynamics (MD) simulations were performed to describe the mode of binding to DNA of these complexes. Our data suggest the minor-groove binding to be more probable than (partial) intercalation and major-groove binding. In addition, it was found that a combination of factors including planarity, van der Waals interactions with DNA, and structural complementarities may be the key for the cleavage efficiency of these copper complexes. |
| doi_str_mv | 10.1021/jp901210g |
| format | Article |
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For instance, Cu(3-Clip-phen) has been combined with distamycin-like minor-groove binders and cisplatin-derivatives, leading to promising results. Density Functional Theory (DFT) and docking calculations as well as molecular dynamics (MD) simulations were performed to describe the mode of binding to DNA of these complexes. Our data suggest the minor-groove binding to be more probable than (partial) intercalation and major-groove binding. In addition, it was found that a combination of factors including planarity, van der Waals interactions with DNA, and structural complementarities may be the key for the cleavage efficiency of these copper complexes.</description><identifier>ISSN: 1520-6106</identifier><identifier>EISSN: 1520-5207</identifier><identifier>DOI: 10.1021/jp901210g</identifier><identifier>PMID: 19719275</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>B: Biophysical Chemistry ; Binding Sites ; DNA - chemistry ; DNA - metabolism ; Models, Molecular ; Nucleic Acid Conformation ; Organometallic Compounds - chemistry ; Organometallic Compounds - metabolism ; Phenanthrolines - chemistry ; Phenanthrolines - metabolism ; Quantum Theory</subject><ispartof>The journal of physical chemistry. 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In addition, it was found that a combination of factors including planarity, van der Waals interactions with DNA, and structural complementarities may be the key for the cleavage efficiency of these copper complexes.</description><subject>B: Biophysical Chemistry</subject><subject>Binding Sites</subject><subject>DNA - chemistry</subject><subject>DNA - metabolism</subject><subject>Models, Molecular</subject><subject>Nucleic Acid Conformation</subject><subject>Organometallic Compounds - chemistry</subject><subject>Organometallic Compounds - metabolism</subject><subject>Phenanthrolines - chemistry</subject><subject>Phenanthrolines - metabolism</subject><subject>Quantum Theory</subject><issn>1520-6106</issn><issn>1520-5207</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtKw0AUhgdRbK0ufAGZjYJgdM4kk4u7Gq9QtVBdh8nkpE1JMnEmAX0D1z6iT2K0RTcuDv-B8_HD-QjZB3YKjMPZsokYcGDzDTIEwZnTT7C53n1g_oDsWLtkjAse-ttkAFEAEQ_EkCxi3TRoPt8_4ASYM11gLet2YXRZ1EhjXTUlvqKlF0WdFfWctppePozP6aw1nWo7I0s6NZgVqi10bWludEXvdYmqK6Whs6Lq8-e0S7ZyWVrcW-eIPF9fPcW3zuTx5i4eTxzpBlHrhJBhkHsIGWAYIFeZqzzhMs6YSlOeCSWkG3oRCh754CkZpSBCVHnkpYEfMndEjla9jdEvHdo2qQqrsCxljbqziR_4vQUXevB4BSqjrTWYJ40pKmneEmDJt9bkV2vPHqxLu7TC7I9ce-yBwxUglU2WujN1_-M_RV_xkH_P</recordid><startdate>20090806</startdate><enddate>20090806</enddate><creator>Robertazzi, Arturo</creator><creator>Vargiu, Attilio Vittorio</creator><creator>Magistrato, Alessandra</creator><creator>Ruggerone, Paolo</creator><creator>Carloni, Paolo</creator><creator>de Hoog, Paul</creator><creator>Reedijk, Jan</creator><general>American Chemical Society</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>7X8</scope></search><sort><creationdate>20090806</creationdate><title>Copper−1,10-Phenanthroline Complexes Binding to DNA: Structural Predictions from Molecular Simulations</title><author>Robertazzi, Arturo ; Vargiu, Attilio Vittorio ; Magistrato, Alessandra ; Ruggerone, Paolo ; Carloni, Paolo ; de Hoog, Paul ; Reedijk, Jan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-81de7f4e1d1e87e2cd3c4530200cbb2d5c5a3849e529614ca9b158ecf94b76803</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>B: Biophysical Chemistry</topic><topic>Binding Sites</topic><topic>DNA - chemistry</topic><topic>DNA - metabolism</topic><topic>Models, Molecular</topic><topic>Nucleic Acid Conformation</topic><topic>Organometallic Compounds - chemistry</topic><topic>Organometallic Compounds - metabolism</topic><topic>Phenanthrolines - chemistry</topic><topic>Phenanthrolines - metabolism</topic><topic>Quantum Theory</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Robertazzi, Arturo</creatorcontrib><creatorcontrib>Vargiu, Attilio Vittorio</creatorcontrib><creatorcontrib>Magistrato, Alessandra</creatorcontrib><creatorcontrib>Ruggerone, Paolo</creatorcontrib><creatorcontrib>Carloni, Paolo</creatorcontrib><creatorcontrib>de Hoog, Paul</creatorcontrib><creatorcontrib>Reedijk, Jan</creatorcontrib><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>The journal of physical chemistry. B</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Robertazzi, Arturo</au><au>Vargiu, Attilio Vittorio</au><au>Magistrato, Alessandra</au><au>Ruggerone, Paolo</au><au>Carloni, Paolo</au><au>de Hoog, Paul</au><au>Reedijk, Jan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper−1,10-Phenanthroline Complexes Binding to DNA: Structural Predictions from Molecular Simulations</atitle><jtitle>The journal of physical chemistry. B</jtitle><addtitle>J. Phys. Chem. B</addtitle><date>2009-08-06</date><risdate>2009</risdate><volume>113</volume><issue>31</issue><spage>10881</spage><epage>10890</epage><pages>10881-10890</pages><issn>1520-6106</issn><eissn>1520-5207</eissn><abstract>Copper−1,10-phenanthroline (phen) complexes Cu(phen)2 , Cu(2-Clip-phen), and Cu(3-Clip-phen) (Clip = a serinol bridge between the phen parts) are typically employed as DNA-cleaving agents and are now becoming increasingly important for building multifunctional drugs with improved cytotoxic properties. For instance, Cu(3-Clip-phen) has been combined with distamycin-like minor-groove binders and cisplatin-derivatives, leading to promising results. Density Functional Theory (DFT) and docking calculations as well as molecular dynamics (MD) simulations were performed to describe the mode of binding to DNA of these complexes. Our data suggest the minor-groove binding to be more probable than (partial) intercalation and major-groove binding. In addition, it was found that a combination of factors including planarity, van der Waals interactions with DNA, and structural complementarities may be the key for the cleavage efficiency of these copper complexes.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>19719275</pmid><doi>10.1021/jp901210g</doi><tpages>10</tpages></addata></record> |
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| subjects | B: Biophysical Chemistry Binding Sites DNA - chemistry DNA - metabolism Models, Molecular Nucleic Acid Conformation Organometallic Compounds - chemistry Organometallic Compounds - metabolism Phenanthrolines - chemistry Phenanthrolines - metabolism Quantum Theory |
| title | Copper−1,10-Phenanthroline Complexes Binding to DNA: Structural Predictions from Molecular Simulations |
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