Discovery of a Potent Class I Protein Arginine Methyltransferase Fragment Inhibitor
Protein methyltransferases (PMTs) are a promising target class in oncology and other disease areas. They are composed of SET domain methyltransferases and structurally unrelated Rossman-fold enzymes that include protein arginine methyltransferases (PRMTs). In the absence of a well-defined medicinal...
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Veröffentlicht in: | Journal of medicinal chemistry 2016-02, Vol.59 (3), p.1176-1183 |
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container_title | Journal of medicinal chemistry |
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creator | Ferreira de Freitas, Renato Eram, Mohammad S Szewczyk, Magdalena M Steuber, Holger Smil, David Wu, Hong Li, Fengling Senisterra, Guillermo Dong, Aiping Brown, Peter J Hitchcock, Marion Moosmayer, Dieter Stegmann, Christian M Egner, Ursula Arrowsmith, Cheryl Barsyte-Lovejoy, Dalia Vedadi, Masoud Schapira, Matthieu |
description | Protein methyltransferases (PMTs) are a promising target class in oncology and other disease areas. They are composed of SET domain methyltransferases and structurally unrelated Rossman-fold enzymes that include protein arginine methyltransferases (PRMTs). In the absence of a well-defined medicinal chemistry tool-kit focused on PMTs, most current inhibitors were identified by screening large and diverse libraries of leadlike molecules. So far, no successful fragment-based approach was reported against this target class. Here, by deconstructing potent PRMT inhibitors, we find that chemical moieties occupying the substrate arginine-binding site can act as efficient fragment inhibitors. Screening a fragment library against PRMT6 produced numerous hits, including a 300 nM inhibitor (ligand efficiency of 0.56) that decreased global histone 3 arginine 2 methylation in cells, and can serve as a warhead for the development of PRMT chemical probes. |
doi_str_mv | 10.1021/acs.jmedchem.5b01772 |
format | Article |
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They are composed of SET domain methyltransferases and structurally unrelated Rossman-fold enzymes that include protein arginine methyltransferases (PRMTs). In the absence of a well-defined medicinal chemistry tool-kit focused on PMTs, most current inhibitors were identified by screening large and diverse libraries of leadlike molecules. So far, no successful fragment-based approach was reported against this target class. Here, by deconstructing potent PRMT inhibitors, we find that chemical moieties occupying the substrate arginine-binding site can act as efficient fragment inhibitors. Screening a fragment library against PRMT6 produced numerous hits, including a 300 nM inhibitor (ligand efficiency of 0.56) that decreased global histone 3 arginine 2 methylation in cells, and can serve as a warhead for the development of PRMT chemical probes.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/acs.jmedchem.5b01772</identifier><identifier>PMID: 26824386</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Dose-Response Relationship, Drug ; Drug Discovery ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Humans ; Models, Molecular ; Molecular Structure ; Protein-Arginine N-Methyltransferases - antagonists & inhibitors ; Protein-Arginine N-Methyltransferases - metabolism ; Repressor Proteins - antagonists & inhibitors ; Repressor Proteins - metabolism ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 2016-02, Vol.59 (3), p.1176-1183</ispartof><rights>Copyright © 2016 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a348t-d982178a97c9da35db6eac5484116d5b3d234563249415ecb6ac81d0669f4a1b3</citedby><cites>FETCH-LOGICAL-a348t-d982178a97c9da35db6eac5484116d5b3d234563249415ecb6ac81d0669f4a1b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.jmedchem.5b01772$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jmedchem.5b01772$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26824386$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ferreira de Freitas, Renato</creatorcontrib><creatorcontrib>Eram, Mohammad S</creatorcontrib><creatorcontrib>Szewczyk, Magdalena M</creatorcontrib><creatorcontrib>Steuber, Holger</creatorcontrib><creatorcontrib>Smil, David</creatorcontrib><creatorcontrib>Wu, Hong</creatorcontrib><creatorcontrib>Li, Fengling</creatorcontrib><creatorcontrib>Senisterra, Guillermo</creatorcontrib><creatorcontrib>Dong, Aiping</creatorcontrib><creatorcontrib>Brown, Peter J</creatorcontrib><creatorcontrib>Hitchcock, Marion</creatorcontrib><creatorcontrib>Moosmayer, Dieter</creatorcontrib><creatorcontrib>Stegmann, Christian M</creatorcontrib><creatorcontrib>Egner, Ursula</creatorcontrib><creatorcontrib>Arrowsmith, Cheryl</creatorcontrib><creatorcontrib>Barsyte-Lovejoy, Dalia</creatorcontrib><creatorcontrib>Vedadi, Masoud</creatorcontrib><creatorcontrib>Schapira, Matthieu</creatorcontrib><title>Discovery of a Potent Class I Protein Arginine Methyltransferase Fragment Inhibitor</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Protein methyltransferases (PMTs) are a promising target class in oncology and other disease areas. They are composed of SET domain methyltransferases and structurally unrelated Rossman-fold enzymes that include protein arginine methyltransferases (PRMTs). In the absence of a well-defined medicinal chemistry tool-kit focused on PMTs, most current inhibitors were identified by screening large and diverse libraries of leadlike molecules. So far, no successful fragment-based approach was reported against this target class. Here, by deconstructing potent PRMT inhibitors, we find that chemical moieties occupying the substrate arginine-binding site can act as efficient fragment inhibitors. Screening a fragment library against PRMT6 produced numerous hits, including a 300 nM inhibitor (ligand efficiency of 0.56) that decreased global histone 3 arginine 2 methylation in cells, and can serve as a warhead for the development of PRMT chemical probes.</description><subject>Dose-Response Relationship, Drug</subject><subject>Drug Discovery</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Humans</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Protein-Arginine N-Methyltransferases - antagonists & inhibitors</subject><subject>Protein-Arginine N-Methyltransferases - metabolism</subject><subject>Repressor Proteins - antagonists & inhibitors</subject><subject>Repressor Proteins - metabolism</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kF1LAkEUhoco0qx_EDF_YG2-d_ZSLEswEqrrZb5WR9xZmVmD_fetqV12dTic93nhPADcYzTGiOBHZdJ4Uztr1q4ec41wnpMLMMScoIxJxC7BECFCMiIIHYCblDYIIYoJvQYDIiRhVIoh-HjyyTTfLnawqaCCy6Z1oYXTrUoJzuEy9rsPcBJXPvjg4Jtr1922jSqkykWVHJxFtaoPzDysvfZtE2_BVaW2yd2d5gh8zZ4_p6_Z4v1lPp0sMkWZbDNbSIJzqYrcFFZRbrVwynAmGcbCck0toYwLSljBMHdGC2UktkiIomIKazoC7NhrYpNSdFW5i75WsSsxKg-Oyt5ReXZUnhz12MMR2-11f_uDzlL6ADoGfvFmH0P_xf-dP3njdnM</recordid><startdate>20160211</startdate><enddate>20160211</enddate><creator>Ferreira de Freitas, Renato</creator><creator>Eram, Mohammad S</creator><creator>Szewczyk, Magdalena M</creator><creator>Steuber, Holger</creator><creator>Smil, David</creator><creator>Wu, Hong</creator><creator>Li, Fengling</creator><creator>Senisterra, Guillermo</creator><creator>Dong, Aiping</creator><creator>Brown, Peter J</creator><creator>Hitchcock, Marion</creator><creator>Moosmayer, Dieter</creator><creator>Stegmann, Christian M</creator><creator>Egner, Ursula</creator><creator>Arrowsmith, Cheryl</creator><creator>Barsyte-Lovejoy, Dalia</creator><creator>Vedadi, Masoud</creator><creator>Schapira, Matthieu</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></search><sort><creationdate>20160211</creationdate><title>Discovery of a Potent Class I Protein Arginine Methyltransferase Fragment Inhibitor</title><author>Ferreira de Freitas, Renato ; Eram, Mohammad S ; Szewczyk, Magdalena M ; Steuber, Holger ; Smil, David ; Wu, Hong ; Li, Fengling ; Senisterra, Guillermo ; Dong, Aiping ; Brown, Peter J ; Hitchcock, Marion ; Moosmayer, Dieter ; Stegmann, Christian M ; Egner, Ursula ; Arrowsmith, Cheryl ; Barsyte-Lovejoy, Dalia ; Vedadi, Masoud ; Schapira, Matthieu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a348t-d982178a97c9da35db6eac5484116d5b3d234563249415ecb6ac81d0669f4a1b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Dose-Response Relationship, Drug</topic><topic>Drug Discovery</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Humans</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Protein-Arginine N-Methyltransferases - antagonists & inhibitors</topic><topic>Protein-Arginine N-Methyltransferases - metabolism</topic><topic>Repressor Proteins - antagonists & inhibitors</topic><topic>Repressor Proteins - metabolism</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ferreira de Freitas, Renato</creatorcontrib><creatorcontrib>Eram, Mohammad S</creatorcontrib><creatorcontrib>Szewczyk, Magdalena M</creatorcontrib><creatorcontrib>Steuber, Holger</creatorcontrib><creatorcontrib>Smil, David</creatorcontrib><creatorcontrib>Wu, Hong</creatorcontrib><creatorcontrib>Li, Fengling</creatorcontrib><creatorcontrib>Senisterra, Guillermo</creatorcontrib><creatorcontrib>Dong, Aiping</creatorcontrib><creatorcontrib>Brown, Peter J</creatorcontrib><creatorcontrib>Hitchcock, Marion</creatorcontrib><creatorcontrib>Moosmayer, Dieter</creatorcontrib><creatorcontrib>Stegmann, Christian M</creatorcontrib><creatorcontrib>Egner, Ursula</creatorcontrib><creatorcontrib>Arrowsmith, Cheryl</creatorcontrib><creatorcontrib>Barsyte-Lovejoy, Dalia</creatorcontrib><creatorcontrib>Vedadi, Masoud</creatorcontrib><creatorcontrib>Schapira, Matthieu</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ferreira de Freitas, Renato</au><au>Eram, Mohammad S</au><au>Szewczyk, Magdalena M</au><au>Steuber, Holger</au><au>Smil, David</au><au>Wu, Hong</au><au>Li, Fengling</au><au>Senisterra, Guillermo</au><au>Dong, Aiping</au><au>Brown, Peter J</au><au>Hitchcock, Marion</au><au>Moosmayer, Dieter</au><au>Stegmann, Christian M</au><au>Egner, Ursula</au><au>Arrowsmith, Cheryl</au><au>Barsyte-Lovejoy, Dalia</au><au>Vedadi, Masoud</au><au>Schapira, Matthieu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Discovery of a Potent Class I Protein Arginine Methyltransferase Fragment Inhibitor</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2016-02-11</date><risdate>2016</risdate><volume>59</volume><issue>3</issue><spage>1176</spage><epage>1183</epage><pages>1176-1183</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>Protein methyltransferases (PMTs) are a promising target class in oncology and other disease areas. They are composed of SET domain methyltransferases and structurally unrelated Rossman-fold enzymes that include protein arginine methyltransferases (PRMTs). In the absence of a well-defined medicinal chemistry tool-kit focused on PMTs, most current inhibitors were identified by screening large and diverse libraries of leadlike molecules. So far, no successful fragment-based approach was reported against this target class. Here, by deconstructing potent PRMT inhibitors, we find that chemical moieties occupying the substrate arginine-binding site can act as efficient fragment inhibitors. Screening a fragment library against PRMT6 produced numerous hits, including a 300 nM inhibitor (ligand efficiency of 0.56) that decreased global histone 3 arginine 2 methylation in cells, and can serve as a warhead for the development of PRMT chemical probes.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26824386</pmid><doi>10.1021/acs.jmedchem.5b01772</doi><tpages>8</tpages></addata></record> |
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subjects | Dose-Response Relationship, Drug Drug Discovery Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Humans Models, Molecular Molecular Structure Protein-Arginine N-Methyltransferases - antagonists & inhibitors Protein-Arginine N-Methyltransferases - metabolism Repressor Proteins - antagonists & inhibitors Repressor Proteins - metabolism Structure-Activity Relationship |
title | Discovery of a Potent Class I Protein Arginine Methyltransferase Fragment Inhibitor |
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