Design, Synthesis and Discovery of N,N’‐Carbazoyl‐aryl‐urea Inhibitors of Zika NS5 Methyltransferase and Virus Replication
The recent outbreaks of Zika virus (ZIKV) infection worldwide make the discovery of novel antivirals against flaviviruses a research priority. This work describes the identification of novel inhibitors of ZIKV through a structure‐based virtual screening approach using the ZIKV NS5‐MTase. A novel ser...
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| Veröffentlicht in: | ChemMedChem 2020-02, Vol.15 (4), p.385-390 |
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| creator | Spizzichino, Sharon Mattedi, Giulio Lauder, Kate Valle, Coralie Aouadi, Wahiba Canard, Bruno Decroly, Etienne Kaptein, Suzanne J. F. Neyts, Johan Graham, Carl Sule, Zakary Barlow, David J. Silvestri, Romano Castagnolo, Daniele |
| description | The recent outbreaks of Zika virus (ZIKV) infection worldwide make the discovery of novel antivirals against flaviviruses a research priority. This work describes the identification of novel inhibitors of ZIKV through a structure‐based virtual screening approach using the ZIKV NS5‐MTase. A novel series of molecules with a carbazoyl‐aryl‐urea structure has been discovered and a library of analogues has been synthesized. The new compounds inhibit ZIKV MTase with IC50 between 23–48 μM. In addition, carbazoyl‐aryl‐ureas also proved to inhibit ZIKV replication activity at micromolar concentration.
Novel antivirals targeting ZIKA virus: The recent outbreaks of Zika virus (ZIKV) worldwide make the discovery of novel antivirals a priority. Using a structure‐based virtual screening approach we were able to identify and develop a novel series of carbazoyl‐urea derivatives that are able to inhibit the ZIKV NS5‐MTase as well as ZIKV replication at micromolar concentration. |
| doi_str_mv | 10.1002/cmdc.201900533 |
| format | Article |
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Novel antivirals targeting ZIKA virus: The recent outbreaks of Zika virus (ZIKV) worldwide make the discovery of novel antivirals a priority. Using a structure‐based virtual screening approach we were able to identify and develop a novel series of carbazoyl‐urea derivatives that are able to inhibit the ZIKV NS5‐MTase as well as ZIKV replication at micromolar concentration.</description><identifier>ISSN: 1860-7179</identifier><identifier>EISSN: 1860-7187</identifier><identifier>DOI: 10.1002/cmdc.201900533</identifier><identifier>PMID: 31805205</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Antiviral agents ; Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Aromatic compounds ; Communication ; Communications ; Dose-Response Relationship, Drug ; Drug Discovery ; flavivirus ; Inhibitors ; Life Sciences ; Methyltransferase ; Methyltransferases - antagonists & inhibitors ; Methyltransferases - metabolism ; Microbial Sensitivity Tests ; Microbiology and Parasitology ; Models, Molecular ; Molecular Structure ; Replication ; Structure-Activity Relationship ; Urea ; Urea - analogs & derivatives ; Urea - chemistry ; Urea - pharmacology ; Ureas ; Vector-borne diseases ; Virology ; Virus Replication - drug effects ; Viruses ; Zika ; Zika virus ; Zika Virus - drug effects ; Zika Virus - enzymology</subject><ispartof>ChemMedChem, 2020-02, Vol.15 (4), p.385-390</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Attribution</rights><rights>2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5023-a741a64c78f3a3f11340d2ab61d5730e6061a8d2c6466c8de480328dbaff88e33</citedby><cites>FETCH-LOGICAL-c5023-a741a64c78f3a3f11340d2ab61d5730e6061a8d2c6466c8de480328dbaff88e33</cites><orcidid>0000-0002-7517-5732 ; 0000-0003-3497-5378 ; 0000-0002-0033-7514 ; 0000-0002-6046-024X ; 0000-0002-7935-0219 ; 0000-0003-4924-1991</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%2Fcmdc.201900533$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcmdc.201900533$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,776,780,881,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31805205$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-02890596$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Spizzichino, Sharon</creatorcontrib><creatorcontrib>Mattedi, Giulio</creatorcontrib><creatorcontrib>Lauder, Kate</creatorcontrib><creatorcontrib>Valle, Coralie</creatorcontrib><creatorcontrib>Aouadi, Wahiba</creatorcontrib><creatorcontrib>Canard, Bruno</creatorcontrib><creatorcontrib>Decroly, Etienne</creatorcontrib><creatorcontrib>Kaptein, Suzanne J. F.</creatorcontrib><creatorcontrib>Neyts, Johan</creatorcontrib><creatorcontrib>Graham, Carl</creatorcontrib><creatorcontrib>Sule, Zakary</creatorcontrib><creatorcontrib>Barlow, David J.</creatorcontrib><creatorcontrib>Silvestri, Romano</creatorcontrib><creatorcontrib>Castagnolo, Daniele</creatorcontrib><title>Design, Synthesis and Discovery of N,N’‐Carbazoyl‐aryl‐urea Inhibitors of Zika NS5 Methyltransferase and Virus Replication</title><title>ChemMedChem</title><addtitle>ChemMedChem</addtitle><description>The recent outbreaks of Zika virus (ZIKV) infection worldwide make the discovery of novel antivirals against flaviviruses a research priority. This work describes the identification of novel inhibitors of ZIKV through a structure‐based virtual screening approach using the ZIKV NS5‐MTase. A novel series of molecules with a carbazoyl‐aryl‐urea structure has been discovered and a library of analogues has been synthesized. The new compounds inhibit ZIKV MTase with IC50 between 23–48 μM. In addition, carbazoyl‐aryl‐ureas also proved to inhibit ZIKV replication activity at micromolar concentration.
Novel antivirals targeting ZIKA virus: The recent outbreaks of Zika virus (ZIKV) worldwide make the discovery of novel antivirals a priority. Using a structure‐based virtual screening approach we were able to identify and develop a novel series of carbazoyl‐urea derivatives that are able to inhibit the ZIKV NS5‐MTase as well as ZIKV replication at micromolar concentration.</description><subject>Antiviral agents</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>Aromatic compounds</subject><subject>Communication</subject><subject>Communications</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Discovery</subject><subject>flavivirus</subject><subject>Inhibitors</subject><subject>Life Sciences</subject><subject>Methyltransferase</subject><subject>Methyltransferases - antagonists & inhibitors</subject><subject>Methyltransferases - metabolism</subject><subject>Microbial Sensitivity Tests</subject><subject>Microbiology and Parasitology</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Replication</subject><subject>Structure-Activity Relationship</subject><subject>Urea</subject><subject>Urea - analogs & derivatives</subject><subject>Urea - chemistry</subject><subject>Urea - pharmacology</subject><subject>Ureas</subject><subject>Vector-borne diseases</subject><subject>Virology</subject><subject>Virus Replication - drug effects</subject><subject>Viruses</subject><subject>Zika</subject><subject>Zika virus</subject><subject>Zika Virus - drug effects</subject><subject>Zika Virus - enzymology</subject><issn>1860-7179</issn><issn>1860-7187</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>EIF</sourceid><recordid>eNqFkctu1DAUhi0EoqWwZYkisULqDMfxJc4GqcpQWmk6SBRYsLEcx2lcMvFgJ1OFVcUTsOX1-iR4OmW4bFidI_s7n330I_QUwxQDpC_1stLTFHAOwAi5h_ax4DDJsMju7_os30OPQrgEoFRg8RDtESyApcD20beZCfaiO0zOx65vYh8S1VXJzAbt1saPiauTxeHi5vrHzfX3QvlSfXVjG3vlb8vgjUpOu8aWtnc-bPBP9rNKFucsOTN9M7a9V12ojVfB3Ko_Wj-E5J1ZtVar3rruMXpQqzaYJ3f1AH04fv2-OJnM3745LY7mE80gJROVUaw41ZmoiSI1xoRClaqS44plBAwHjpWoUs0p51pUhgogqahKVddCGEIO0KutdzWUS1Np08WvtXLl7TIuI52y8u-bzjbywq1lhoFTkUXBi62g-Wfs5GguN2eQihxYztc4ss_vHvPuy2BCLy_d4Lu4n0wJE5TRnPNITbeU9i4Eb-qdFoPc5Cs3-cpdvnHg2Z877PBfgUYg3wJXtjXjf3SyOJsVv-U_AXxHtqw</recordid><startdate>20200217</startdate><enddate>20200217</enddate><creator>Spizzichino, Sharon</creator><creator>Mattedi, Giulio</creator><creator>Lauder, Kate</creator><creator>Valle, Coralie</creator><creator>Aouadi, Wahiba</creator><creator>Canard, Bruno</creator><creator>Decroly, Etienne</creator><creator>Kaptein, Suzanne J. 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F.</au><au>Neyts, Johan</au><au>Graham, Carl</au><au>Sule, Zakary</au><au>Barlow, David J.</au><au>Silvestri, Romano</au><au>Castagnolo, Daniele</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, Synthesis and Discovery of N,N’‐Carbazoyl‐aryl‐urea Inhibitors of Zika NS5 Methyltransferase and Virus Replication</atitle><jtitle>ChemMedChem</jtitle><addtitle>ChemMedChem</addtitle><date>2020-02-17</date><risdate>2020</risdate><volume>15</volume><issue>4</issue><spage>385</spage><epage>390</epage><pages>385-390</pages><issn>1860-7179</issn><eissn>1860-7187</eissn><abstract>The recent outbreaks of Zika virus (ZIKV) infection worldwide make the discovery of novel antivirals against flaviviruses a research priority. This work describes the identification of novel inhibitors of ZIKV through a structure‐based virtual screening approach using the ZIKV NS5‐MTase. A novel series of molecules with a carbazoyl‐aryl‐urea structure has been discovered and a library of analogues has been synthesized. The new compounds inhibit ZIKV MTase with IC50 between 23–48 μM. In addition, carbazoyl‐aryl‐ureas also proved to inhibit ZIKV replication activity at micromolar concentration.
Novel antivirals targeting ZIKA virus: The recent outbreaks of Zika virus (ZIKV) worldwide make the discovery of novel antivirals a priority. Using a structure‐based virtual screening approach we were able to identify and develop a novel series of carbazoyl‐urea derivatives that are able to inhibit the ZIKV NS5‐MTase as well as ZIKV replication at micromolar concentration.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31805205</pmid><doi>10.1002/cmdc.201900533</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-7517-5732</orcidid><orcidid>https://orcid.org/0000-0003-3497-5378</orcidid><orcidid>https://orcid.org/0000-0002-0033-7514</orcidid><orcidid>https://orcid.org/0000-0002-6046-024X</orcidid><orcidid>https://orcid.org/0000-0002-7935-0219</orcidid><orcidid>https://orcid.org/0000-0003-4924-1991</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | ChemMedChem, 2020-02, Vol.15 (4), p.385-390 |
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| subjects | Antiviral agents Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Aromatic compounds Communication Communications Dose-Response Relationship, Drug Drug Discovery flavivirus Inhibitors Life Sciences Methyltransferase Methyltransferases - antagonists & inhibitors Methyltransferases - metabolism Microbial Sensitivity Tests Microbiology and Parasitology Models, Molecular Molecular Structure Replication Structure-Activity Relationship Urea Urea - analogs & derivatives Urea - chemistry Urea - pharmacology Ureas Vector-borne diseases Virology Virus Replication - drug effects Viruses Zika Zika virus Zika Virus - drug effects Zika Virus - enzymology |
| title | Design, Synthesis and Discovery of N,N’‐Carbazoyl‐aryl‐urea Inhibitors of Zika NS5 Methyltransferase and Virus Replication |
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