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Virtual screening, synthesis and biological evaluation of DNA intercalating antiviral agents
[Display omitted] •Virtual screening to discover potential nucleic acids intercalators.•Two hits active against Vaccinia virus were found.•Intercalating mechanism was proposed for the hits. This paper describes computer-aided design of new anti-viral agents against Vaccinia virus (VACV) potentially...
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| Published in: | Bioorganic & medicinal chemistry letters 2017-08, Vol.27 (16), p.3915-3919 |
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| Main Authors: | , , , , , , , , , , , , , , |
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| cited_by | cdi_FETCH-LOGICAL-c390t-a8c043304fc94a7927d3eedbf46268e6b83f1d453a4b484b4ddfe0c9314412373 |
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| cites | cdi_FETCH-LOGICAL-c390t-a8c043304fc94a7927d3eedbf46268e6b83f1d453a4b484b4ddfe0c9314412373 |
| container_end_page | 3919 |
| container_issue | 16 |
| container_start_page | 3915 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 27 |
| creator | Klimenko, Kyrylo Lyakhov, Sergey Shibinskaya, Marina Karpenko, Alexander Marcou, Gilles Horvath, Dragos Zenkova, Marina Goncharova, Elena Amirkhanov, Rinat Krysko, Andrei Andronati, Sergei Levandovskiy, Igor Polishchuk, Pavel Kuz'min, Victor Varnek, Alexandre |
| description | [Display omitted]
•Virtual screening to discover potential nucleic acids intercalators.•Two hits active against Vaccinia virus were found.•Intercalating mechanism was proposed for the hits.
This paper describes computer-aided design of new anti-viral agents against Vaccinia virus (VACV) potentially acting as nucleic acid intercalators. Earlier obtained experimental data for DNA intercalation affinities and activities against Vesicular stomatitis virus (VSV) have been used to build, respectively, pharmacophore and QSAR models. These models were used for virtual screening of a database of 245 molecules generated around typical scaffolds of known DNA intercalators. This resulted in 12 hits which then were synthesized and tested for antiviral activity against VaV together with 43 compounds earlier studied against VSV. Two compounds displaying high antiviral activity against VaV and low cytotoxicity were selected for further antiviral activity investigations. |
| doi_str_mv | 10.1016/j.bmcl.2017.06.035 |
| format | article |
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•Virtual screening to discover potential nucleic acids intercalators.•Two hits active against Vaccinia virus were found.•Intercalating mechanism was proposed for the hits.
This paper describes computer-aided design of new anti-viral agents against Vaccinia virus (VACV) potentially acting as nucleic acid intercalators. Earlier obtained experimental data for DNA intercalation affinities and activities against Vesicular stomatitis virus (VSV) have been used to build, respectively, pharmacophore and QSAR models. These models were used for virtual screening of a database of 245 molecules generated around typical scaffolds of known DNA intercalators. This resulted in 12 hits which then were synthesized and tested for antiviral activity against VaV together with 43 compounds earlier studied against VSV. Two compounds displaying high antiviral activity against VaV and low cytotoxicity were selected for further antiviral activity investigations.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2017.06.035</identifier><identifier>PMID: 28666733</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Antiviral activity ; Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Cell Line ; Cell Survival - drug effects ; Chemical Sciences ; Cheminformatics ; DNA - drug effects ; DNA affinity ; Dose-Response Relationship, Drug ; Drug Evaluation, Preclinical ; Humans ; Microbial Sensitivity Tests ; Molecular Structure ; Quantitative Structure-Activity Relationship ; Structure-activity modeling ; Vaccinia virus ; Vesicular stomatitis Indiana virus - drug effects ; Virtual screening</subject><ispartof>Bioorganic & medicinal chemistry letters, 2017-08, Vol.27 (16), p.3915-3919</ispartof><rights>2017 Elsevier Ltd</rights><rights>Copyright © 2017 Elsevier Ltd. All rights reserved.</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c390t-a8c043304fc94a7927d3eedbf46268e6b83f1d453a4b484b4ddfe0c9314412373</citedby><cites>FETCH-LOGICAL-c390t-a8c043304fc94a7927d3eedbf46268e6b83f1d453a4b484b4ddfe0c9314412373</cites><orcidid>0000-0003-1886-925X ; 0000-0003-1676-6708 ; 0000-0003-0173-5714</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28666733$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-03151681$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Klimenko, Kyrylo</creatorcontrib><creatorcontrib>Lyakhov, Sergey</creatorcontrib><creatorcontrib>Shibinskaya, Marina</creatorcontrib><creatorcontrib>Karpenko, Alexander</creatorcontrib><creatorcontrib>Marcou, Gilles</creatorcontrib><creatorcontrib>Horvath, Dragos</creatorcontrib><creatorcontrib>Zenkova, Marina</creatorcontrib><creatorcontrib>Goncharova, Elena</creatorcontrib><creatorcontrib>Amirkhanov, Rinat</creatorcontrib><creatorcontrib>Krysko, Andrei</creatorcontrib><creatorcontrib>Andronati, Sergei</creatorcontrib><creatorcontrib>Levandovskiy, Igor</creatorcontrib><creatorcontrib>Polishchuk, Pavel</creatorcontrib><creatorcontrib>Kuz'min, Victor</creatorcontrib><creatorcontrib>Varnek, Alexandre</creatorcontrib><title>Virtual screening, synthesis and biological evaluation of DNA intercalating antiviral agents</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
•Virtual screening to discover potential nucleic acids intercalators.•Two hits active against Vaccinia virus were found.•Intercalating mechanism was proposed for the hits.
This paper describes computer-aided design of new anti-viral agents against Vaccinia virus (VACV) potentially acting as nucleic acid intercalators. Earlier obtained experimental data for DNA intercalation affinities and activities against Vesicular stomatitis virus (VSV) have been used to build, respectively, pharmacophore and QSAR models. These models were used for virtual screening of a database of 245 molecules generated around typical scaffolds of known DNA intercalators. This resulted in 12 hits which then were synthesized and tested for antiviral activity against VaV together with 43 compounds earlier studied against VSV. Two compounds displaying high antiviral activity against VaV and low cytotoxicity were selected for further antiviral activity investigations.</description><subject>Antiviral activity</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>Cell Line</subject><subject>Cell Survival - drug effects</subject><subject>Chemical Sciences</subject><subject>Cheminformatics</subject><subject>DNA - drug effects</subject><subject>DNA affinity</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Evaluation, Preclinical</subject><subject>Humans</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Quantitative Structure-Activity Relationship</subject><subject>Structure-activity modeling</subject><subject>Vaccinia virus</subject><subject>Vesicular stomatitis Indiana virus - drug effects</subject><subject>Virtual screening</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp9kUFr3DAQhUVoSbZJ_kAOxccWamdkybINvSxJ2hSW5JKWHgpClsYbLV4pleSF_Pto2TTHHoaBmW_ewHuEXFCoKFBxuamGrZ6qGmhbgaiANUdkQbngJePQvCML6AWUXc9_n5APMW4AKAfOj8lJ3QkhWsYW5M8vG9KspiLqgOisW38p4rNLjxhtLJQzxWD95NdWZwZ3appVst4Vfiyu75aFdQlDXuWhW2c82Z0NmVRrdCmekfejmiKev_ZT8vPbzcPVbbm6__7jarkqNeshlarTwBkDPuqeq7avW8MQzTByUYsOxdCxkRreMMUH3uUyZkTQPaOc05q17JR8Pug-qkk-BbtV4Vl6ZeXtciX3M2C0oaKjO5rZTwf2Kfi_M8YktzZqnCbl0M9R0p42jHcAkNH6gOrgYww4vmlTkPsE5EbuE5D7BCSI_KbJRx9f9edhi-bt5J_lGfh6ADA7srMYZNQWnUZjA-okjbf_038BL42XBw</recordid><startdate>20170815</startdate><enddate>20170815</enddate><creator>Klimenko, Kyrylo</creator><creator>Lyakhov, Sergey</creator><creator>Shibinskaya, Marina</creator><creator>Karpenko, Alexander</creator><creator>Marcou, Gilles</creator><creator>Horvath, Dragos</creator><creator>Zenkova, Marina</creator><creator>Goncharova, Elena</creator><creator>Amirkhanov, Rinat</creator><creator>Krysko, Andrei</creator><creator>Andronati, Sergei</creator><creator>Levandovskiy, Igor</creator><creator>Polishchuk, Pavel</creator><creator>Kuz'min, Victor</creator><creator>Varnek, Alexandre</creator><general>Elsevier Ltd</general><general>Elsevier</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><scope>1XC</scope><orcidid>https://orcid.org/0000-0003-1886-925X</orcidid><orcidid>https://orcid.org/0000-0003-1676-6708</orcidid><orcidid>https://orcid.org/0000-0003-0173-5714</orcidid></search><sort><creationdate>20170815</creationdate><title>Virtual screening, synthesis and biological evaluation of DNA intercalating antiviral agents</title><author>Klimenko, Kyrylo ; Lyakhov, Sergey ; Shibinskaya, Marina ; Karpenko, Alexander ; Marcou, Gilles ; Horvath, Dragos ; Zenkova, Marina ; Goncharova, Elena ; Amirkhanov, Rinat ; Krysko, Andrei ; Andronati, Sergei ; Levandovskiy, Igor ; Polishchuk, Pavel ; Kuz'min, Victor ; Varnek, Alexandre</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-a8c043304fc94a7927d3eedbf46268e6b83f1d453a4b484b4ddfe0c9314412373</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Antiviral activity</topic><topic>Antiviral Agents - chemical synthesis</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - pharmacology</topic><topic>Cell Line</topic><topic>Cell Survival - drug effects</topic><topic>Chemical Sciences</topic><topic>Cheminformatics</topic><topic>DNA - drug effects</topic><topic>DNA affinity</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Evaluation, Preclinical</topic><topic>Humans</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Quantitative Structure-Activity Relationship</topic><topic>Structure-activity modeling</topic><topic>Vaccinia virus</topic><topic>Vesicular stomatitis Indiana virus - drug effects</topic><topic>Virtual screening</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Klimenko, Kyrylo</creatorcontrib><creatorcontrib>Lyakhov, Sergey</creatorcontrib><creatorcontrib>Shibinskaya, Marina</creatorcontrib><creatorcontrib>Karpenko, Alexander</creatorcontrib><creatorcontrib>Marcou, Gilles</creatorcontrib><creatorcontrib>Horvath, Dragos</creatorcontrib><creatorcontrib>Zenkova, Marina</creatorcontrib><creatorcontrib>Goncharova, Elena</creatorcontrib><creatorcontrib>Amirkhanov, Rinat</creatorcontrib><creatorcontrib>Krysko, Andrei</creatorcontrib><creatorcontrib>Andronati, Sergei</creatorcontrib><creatorcontrib>Levandovskiy, Igor</creatorcontrib><creatorcontrib>Polishchuk, Pavel</creatorcontrib><creatorcontrib>Kuz'min, Victor</creatorcontrib><creatorcontrib>Varnek, Alexandre</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><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Klimenko, Kyrylo</au><au>Lyakhov, Sergey</au><au>Shibinskaya, Marina</au><au>Karpenko, Alexander</au><au>Marcou, Gilles</au><au>Horvath, Dragos</au><au>Zenkova, Marina</au><au>Goncharova, Elena</au><au>Amirkhanov, Rinat</au><au>Krysko, Andrei</au><au>Andronati, Sergei</au><au>Levandovskiy, Igor</au><au>Polishchuk, Pavel</au><au>Kuz'min, Victor</au><au>Varnek, Alexandre</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Virtual screening, synthesis and biological evaluation of DNA intercalating antiviral agents</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2017-08-15</date><risdate>2017</risdate><volume>27</volume><issue>16</issue><spage>3915</spage><epage>3919</epage><pages>3915-3919</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
•Virtual screening to discover potential nucleic acids intercalators.•Two hits active against Vaccinia virus were found.•Intercalating mechanism was proposed for the hits.
This paper describes computer-aided design of new anti-viral agents against Vaccinia virus (VACV) potentially acting as nucleic acid intercalators. Earlier obtained experimental data for DNA intercalation affinities and activities against Vesicular stomatitis virus (VSV) have been used to build, respectively, pharmacophore and QSAR models. These models were used for virtual screening of a database of 245 molecules generated around typical scaffolds of known DNA intercalators. This resulted in 12 hits which then were synthesized and tested for antiviral activity against VaV together with 43 compounds earlier studied against VSV. Two compounds displaying high antiviral activity against VaV and low cytotoxicity were selected for further antiviral activity investigations.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>28666733</pmid><doi>10.1016/j.bmcl.2017.06.035</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-1886-925X</orcidid><orcidid>https://orcid.org/0000-0003-1676-6708</orcidid><orcidid>https://orcid.org/0000-0003-0173-5714</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2017-08, Vol.27 (16), p.3915-3919 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_hal_03151681v1 |
| source | ScienceDirect Freedom Collection 2022-2024 |
| subjects | Antiviral activity Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Cell Line Cell Survival - drug effects Chemical Sciences Cheminformatics DNA - drug effects DNA affinity Dose-Response Relationship, Drug Drug Evaluation, Preclinical Humans Microbial Sensitivity Tests Molecular Structure Quantitative Structure-Activity Relationship Structure-activity modeling Vaccinia virus Vesicular stomatitis Indiana virus - drug effects Virtual screening |
| title | Virtual screening, synthesis and biological evaluation of DNA intercalating antiviral agents |
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