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Discovery of covalent inhibitors for MIF tautomerase via cocrystal structures with phantom hits from virtual screening
Virtual screen hits were shown to be covalent inhibitors by biochemical and X-ray crystallographic studies. Biochemical and X-ray crystallographic studies confirmed that hydroxyquinoline derivatives identified by virtual screening were actually covalent inhibitors of the MIF tautomerase. Adducts wer...
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| Published in: | Bioorganic & medicinal chemistry letters 2009-12, Vol.19 (23), p.6717-6720 |
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| Main Authors: | , , , , , , , , , , , , |
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| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c412t-cb8fde44d5081a9f12593d17fca17ae9a25b2dffd37131ec8dec46c4ea7f0cea3 |
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| cites | cdi_FETCH-LOGICAL-c412t-cb8fde44d5081a9f12593d17fca17ae9a25b2dffd37131ec8dec46c4ea7f0cea3 |
| container_end_page | 6720 |
| container_issue | 23 |
| container_start_page | 6717 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 19 |
| creator | McLean, Larry R. Zhang, Ying Li, Hua Li, Ziyu Lukasczyk, Ulrike Choi, Yong-Mi Han, Zuoning Prisco, Joy Fordham, Jeremy Tsay, Joseph T. Reiling, Stephan Vaz, Roy J. Li, Yi |
| description | Virtual screen hits were shown to be covalent inhibitors by biochemical and X-ray crystallographic studies.
Biochemical and X-ray crystallographic studies confirmed that hydroxyquinoline derivatives identified by virtual screening were actually covalent inhibitors of the MIF tautomerase. Adducts were formed by N-alkylation of the Pro-1 at the catalytic site with a loss of an amino group of the inhibitor. |
| doi_str_mv | 10.1016/j.bmcl.2009.09.106 |
| format | article |
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Biochemical and X-ray crystallographic studies confirmed that hydroxyquinoline derivatives identified by virtual screening were actually covalent inhibitors of the MIF tautomerase. Adducts were formed by N-alkylation of the Pro-1 at the catalytic site with a loss of an amino group of the inhibitor.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2009.09.106</identifier><identifier>PMID: 19836948</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>ADDUCTS ; ALKYLATION ; Antineoplastic agents ; BASIC BIOLOGICAL SCIENCES ; Biological and medical sciences ; Bones, joints and connective tissue. Antiinflammatory agents ; Cardiovascular system ; Covalent inhibitor ; CRYSTALLOGRAPHY ; Crystallography, X-Ray ; Docking ; Drug Discovery ; Drug Evaluation, Preclinical - methods ; Enzyme inhibition ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; GENERAL AND MISCELLANEOUS//MATHEMATICS, COMPUTING, AND INFORMATION SCIENCE ; General aspects ; Hydroxyquinolines - chemical synthesis ; Hydroxyquinolines - chemistry ; Hydroxyquinolines - pharmacology ; Intramolecular Oxidoreductases - antagonists & inhibitors ; Macrophage migration inhibitory factor ; Macrophage Migration-Inhibitory Factors - antagonists & inhibitors ; Medical sciences ; MIF ; Miscellaneous ; Models, Molecular ; Molecular Structure ; PHANTOMS ; Pharmacology. Drug treatments ; Structure-Activity Relationship ; Tautomerase ; Virtual screening ; X-ray crystallography</subject><ispartof>Bioorganic & medicinal chemistry letters, 2009-12, Vol.19 (23), p.6717-6720</ispartof><rights>2009 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c412t-cb8fde44d5081a9f12593d17fca17ae9a25b2dffd37131ec8dec46c4ea7f0cea3</citedby><cites>FETCH-LOGICAL-c412t-cb8fde44d5081a9f12593d17fca17ae9a25b2dffd37131ec8dec46c4ea7f0cea3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,776,780,881,27903,27904</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22153720$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19836948$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/1006197$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>McLean, Larry R.</creatorcontrib><creatorcontrib>Zhang, Ying</creatorcontrib><creatorcontrib>Li, Hua</creatorcontrib><creatorcontrib>Li, Ziyu</creatorcontrib><creatorcontrib>Lukasczyk, Ulrike</creatorcontrib><creatorcontrib>Choi, Yong-Mi</creatorcontrib><creatorcontrib>Han, Zuoning</creatorcontrib><creatorcontrib>Prisco, Joy</creatorcontrib><creatorcontrib>Fordham, Jeremy</creatorcontrib><creatorcontrib>Tsay, Joseph T.</creatorcontrib><creatorcontrib>Reiling, Stephan</creatorcontrib><creatorcontrib>Vaz, Roy J.</creatorcontrib><creatorcontrib>Li, Yi</creatorcontrib><creatorcontrib>Argonne National Lab. (ANL), Argonne, IL (United States)</creatorcontrib><title>Discovery of covalent inhibitors for MIF tautomerase via cocrystal structures with phantom hits from virtual screening</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Virtual screen hits were shown to be covalent inhibitors by biochemical and X-ray crystallographic studies.
Biochemical and X-ray crystallographic studies confirmed that hydroxyquinoline derivatives identified by virtual screening were actually covalent inhibitors of the MIF tautomerase. Adducts were formed by N-alkylation of the Pro-1 at the catalytic site with a loss of an amino group of the inhibitor.</description><subject>ADDUCTS</subject><subject>ALKYLATION</subject><subject>Antineoplastic agents</subject><subject>BASIC BIOLOGICAL SCIENCES</subject><subject>Biological and medical sciences</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>Cardiovascular system</subject><subject>Covalent inhibitor</subject><subject>CRYSTALLOGRAPHY</subject><subject>Crystallography, X-Ray</subject><subject>Docking</subject><subject>Drug Discovery</subject><subject>Drug Evaluation, Preclinical - methods</subject><subject>Enzyme inhibition</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>GENERAL AND MISCELLANEOUS//MATHEMATICS, COMPUTING, AND INFORMATION SCIENCE</subject><subject>General aspects</subject><subject>Hydroxyquinolines - chemical synthesis</subject><subject>Hydroxyquinolines - chemistry</subject><subject>Hydroxyquinolines - pharmacology</subject><subject>Intramolecular Oxidoreductases - antagonists & inhibitors</subject><subject>Macrophage migration inhibitory factor</subject><subject>Macrophage Migration-Inhibitory Factors - antagonists & inhibitors</subject><subject>Medical sciences</subject><subject>MIF</subject><subject>Miscellaneous</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>PHANTOMS</subject><subject>Pharmacology. Drug treatments</subject><subject>Structure-Activity Relationship</subject><subject>Tautomerase</subject><subject>Virtual screening</subject><subject>X-ray crystallography</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNp9kU-LFDEQxYMo7rj6BTxIEMRTj0l3-k_Ay7K6urDiRcFbSFdX7AzdyZikW-bbm2YGvQkFqcPvvVTVI-QlZ3vOePPusO9nmPYlY3Kfi7PmEdlx0YiiEqx-THZMNqzopPhxRZ7FeGCMCybEU3LFZVc1UnQ7sn6wEfyK4US9obnTE7pErRttb5MPkRof6Jf7O5r0kvyMQUekq9WZhXCKSU80prBAWgJG-tumkR5H7TJKR5uyPORutSEtGwkB0Vn38zl5YvQU8cXlvSbf7z5-u_1cPHz9dH9781CA4GUqoO_MgEIMNeu4loaXtawG3hrQvNUodVn35WDMULW84gjdgCAaEKhbwwB1dU1en319TFZFsAlhBO8cQlKcsYbLNkNvz9Ax-F8LxqTmfBScJu3QL1G1VR5GyJZlsjyTEHyMAY06BjvrcMpeastEHdSWidoyUblyJln06mK_9DMO_ySXEDLw5gLoCHoyQTuw8S9Xlryu2nL7_f2Zw3yx1WLYFkIHONiw7TN4-785_gDNpq3L</recordid><startdate>20091201</startdate><enddate>20091201</enddate><creator>McLean, Larry R.</creator><creator>Zhang, Ying</creator><creator>Li, Hua</creator><creator>Li, Ziyu</creator><creator>Lukasczyk, Ulrike</creator><creator>Choi, Yong-Mi</creator><creator>Han, Zuoning</creator><creator>Prisco, Joy</creator><creator>Fordham, Jeremy</creator><creator>Tsay, Joseph T.</creator><creator>Reiling, Stephan</creator><creator>Vaz, Roy J.</creator><creator>Li, Yi</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</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>7X8</scope><scope>OTOTI</scope></search><sort><creationdate>20091201</creationdate><title>Discovery of covalent inhibitors for MIF tautomerase via cocrystal structures with phantom hits from virtual screening</title><author>McLean, Larry R. ; Zhang, Ying ; Li, Hua ; Li, Ziyu ; Lukasczyk, Ulrike ; Choi, Yong-Mi ; Han, Zuoning ; Prisco, Joy ; Fordham, Jeremy ; Tsay, Joseph T. ; Reiling, Stephan ; Vaz, Roy J. ; Li, Yi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c412t-cb8fde44d5081a9f12593d17fca17ae9a25b2dffd37131ec8dec46c4ea7f0cea3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>ADDUCTS</topic><topic>ALKYLATION</topic><topic>Antineoplastic agents</topic><topic>BASIC BIOLOGICAL SCIENCES</topic><topic>Biological and medical sciences</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>Cardiovascular system</topic><topic>Covalent inhibitor</topic><topic>CRYSTALLOGRAPHY</topic><topic>Crystallography, X-Ray</topic><topic>Docking</topic><topic>Drug Discovery</topic><topic>Drug Evaluation, Preclinical - methods</topic><topic>Enzyme inhibition</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>GENERAL AND MISCELLANEOUS//MATHEMATICS, COMPUTING, AND INFORMATION SCIENCE</topic><topic>General aspects</topic><topic>Hydroxyquinolines - chemical synthesis</topic><topic>Hydroxyquinolines - chemistry</topic><topic>Hydroxyquinolines - pharmacology</topic><topic>Intramolecular Oxidoreductases - antagonists & inhibitors</topic><topic>Macrophage migration inhibitory factor</topic><topic>Macrophage Migration-Inhibitory Factors - antagonists & inhibitors</topic><topic>Medical sciences</topic><topic>MIF</topic><topic>Miscellaneous</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>PHANTOMS</topic><topic>Pharmacology. Drug treatments</topic><topic>Structure-Activity Relationship</topic><topic>Tautomerase</topic><topic>Virtual screening</topic><topic>X-ray crystallography</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>McLean, Larry R.</creatorcontrib><creatorcontrib>Zhang, Ying</creatorcontrib><creatorcontrib>Li, Hua</creatorcontrib><creatorcontrib>Li, Ziyu</creatorcontrib><creatorcontrib>Lukasczyk, Ulrike</creatorcontrib><creatorcontrib>Choi, Yong-Mi</creatorcontrib><creatorcontrib>Han, Zuoning</creatorcontrib><creatorcontrib>Prisco, Joy</creatorcontrib><creatorcontrib>Fordham, Jeremy</creatorcontrib><creatorcontrib>Tsay, Joseph T.</creatorcontrib><creatorcontrib>Reiling, Stephan</creatorcontrib><creatorcontrib>Vaz, Roy J.</creatorcontrib><creatorcontrib>Li, Yi</creatorcontrib><creatorcontrib>Argonne National Lab. (ANL), Argonne, IL (United States)</creatorcontrib><collection>Pascal-Francis</collection><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>OSTI.GOV</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>McLean, Larry R.</au><au>Zhang, Ying</au><au>Li, Hua</au><au>Li, Ziyu</au><au>Lukasczyk, Ulrike</au><au>Choi, Yong-Mi</au><au>Han, Zuoning</au><au>Prisco, Joy</au><au>Fordham, Jeremy</au><au>Tsay, Joseph T.</au><au>Reiling, Stephan</au><au>Vaz, Roy J.</au><au>Li, Yi</au><aucorp>Argonne National Lab. (ANL), Argonne, IL (United States)</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Discovery of covalent inhibitors for MIF tautomerase via cocrystal structures with phantom hits from virtual screening</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2009-12-01</date><risdate>2009</risdate><volume>19</volume><issue>23</issue><spage>6717</spage><epage>6720</epage><pages>6717-6720</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Virtual screen hits were shown to be covalent inhibitors by biochemical and X-ray crystallographic studies.
Biochemical and X-ray crystallographic studies confirmed that hydroxyquinoline derivatives identified by virtual screening were actually covalent inhibitors of the MIF tautomerase. Adducts were formed by N-alkylation of the Pro-1 at the catalytic site with a loss of an amino group of the inhibitor.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>19836948</pmid><doi>10.1016/j.bmcl.2009.09.106</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2009-12, Vol.19 (23), p.6717-6720 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_osti_scitechconnect_1006197 |
| source | ScienceDirect Freedom Collection |
| subjects | ADDUCTS ALKYLATION Antineoplastic agents BASIC BIOLOGICAL SCIENCES Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents Cardiovascular system Covalent inhibitor CRYSTALLOGRAPHY Crystallography, X-Ray Docking Drug Discovery Drug Evaluation, Preclinical - methods Enzyme inhibition Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology GENERAL AND MISCELLANEOUS//MATHEMATICS, COMPUTING, AND INFORMATION SCIENCE General aspects Hydroxyquinolines - chemical synthesis Hydroxyquinolines - chemistry Hydroxyquinolines - pharmacology Intramolecular Oxidoreductases - antagonists & inhibitors Macrophage migration inhibitory factor Macrophage Migration-Inhibitory Factors - antagonists & inhibitors Medical sciences MIF Miscellaneous Models, Molecular Molecular Structure PHANTOMS Pharmacology. Drug treatments Structure-Activity Relationship Tautomerase Virtual screening X-ray crystallography |
| title | Discovery of covalent inhibitors for MIF tautomerase via cocrystal structures with phantom hits from virtual screening |
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