{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,16]],"date-time":"2026-03-16T13:17:10Z","timestamp":1773667030067,"version":"3.50.1"},"reference-count":55,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2012,12,5]],"date-time":"2012-12-05T00:00:00Z","timestamp":1354665600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecular Informatics"],"published-print":{"date-parts":[[2013,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Binding of the Dengue virus <jats:italic>S<\/jats:italic>\u2010adenosyl\u2010<jats:sc>L<\/jats:sc>\u2010methionine (AdoMet)\u2010dependent mRNA cap methyltransferase (NS5MTase<jats:sub>DV<\/jats:sub>) with adamantane derivatives was explored using molecular modeling methods and (nucleoside\u20102\u2032<jats:italic>O<\/jats:italic>)\u2010methyltransferase bioassay. The studied compounds include urea derivatives of adamantane and the antiviral drugs amantadine and rimantadine. The urea derivatives of adamantanes had previously been identified as inhibitors of NS5MTase<jats:sub>DV<\/jats:sub>. The docking simulations using GOLD, Glide, and Dock give consistent binding modes and binding affinities of adamantanes in the AdoMet\u2010binding site of NS5MTase<jats:sub>DV<\/jats:sub> and, in particular, yield similar positions for the previously found inhibitors. Combined, they perfectly correspond to the bioassay measurements of nucleoside\u20102\u2032<jats:italic>O<\/jats:italic>\u2010methyltransferase activity of NS5Tase<jats:sub>DV<\/jats:sub>, which confirmed inhibitory properties of the active urea adamantane but did not show inhibitory activity for amantadine and rimantadine. We also employed microscopic molecular dynamics (MD) simulations and a linear interaction energy (LIE) method to verify the docking results. The MD\/LIE binding free energies of selected protein\u2013inhibitor complexes agree overall with the binding affinities from docking and demonstrate that amantadine and rimantadine only weakly bind at the explored site. The MD simulations also demonstrated the flexible character of a protein loop that is located between the \u03b22 and \u03b23 strands and is part of the AdoMet\u2010binding pocket of NS5MTase<jats:sub>DV<\/jats:sub>.<\/jats:p>","DOI":"10.1002\/minf.201200107","type":"journal-article","created":{"date-parts":[[2012,12,5]],"date-time":"2012-12-05T23:23:25Z","timestamp":1354749805000},"page":"155-164","source":"Crossref","is-referenced-by-count":12,"title":["Evaluation of Adamantane Derivatives as Inhibitors of Dengue Virus mRNA Cap Methyltransferase by Docking and Molecular Dynamics Simulations"],"prefix":"10.1002","volume":"32","author":[{"given":"Victor","family":"Luzhkov","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Etienne","family":"Decroly","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Bruno","family":"Canard","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Barbara","family":"Selisko","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Johan","family":"\u00c5qvist","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2012,12,5]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0065-3527(00)55003-9"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0079-6603(00)66025-7"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrmicro2675"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.antiviral.2012.07.007"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1128\/JVI.02681-06"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1128\/JVI.00407-08"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.antiviral.2008.01.004"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.antiviral.2008.05.003"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.antiviral.2008.08.005"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.antiviral.2008.08.004"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrmicro975"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.antiviral.2007.12.007"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1128\/JVI.02704-06"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1093\/emboj\/21.11.2757"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M400460200"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmb.2007.07.005"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1110\/ps.072758107"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmb.2008.10.028"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0959-440X(02)00391-3"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00178a001"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/0168-1702(94)00085-Q"},{"key":"e_1_2_6_22_2","first-page":"247","volume":"61","author":"Kreander K.","year":"2006","journal-title":"Pharmazie"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm061213n"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2007.08.049"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.antiviral.2009.03.001"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm900776m"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.144.3620.862"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/med.20013"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.18.1.125"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.pharmtox.37.1.71"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1096361"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrd1549"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1359-6446(05)03484-7"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/med.20067"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbpa.2008.02.016"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.2174\/157340908785747474"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar010014p"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1006\/jmbi.1996.0897"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm050543p"},{"key":"e_1_2_6_40_2","unstructured":"Glide Version 4.5 Schr\u00f6dinger LLC New York2007 1\u201397."},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm0306430"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm051256o"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.540130412"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1096-987X(19970715)18:9<1175::AID-JCC6>3.0.CO;2-O"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1099\/vir.0.015511-0"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1093\/protein\/7.3.385"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1093-3263(98)80006-5"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/ct700106b"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/elps.1150181505"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.20084"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp003919d"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/ct600252r"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.462997"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1097-461X(1998)69:1<77::AID-QUA10>3.0.CO;2-2"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkl1119"}],"container-title":["Molecular Informatics"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fminf.201200107","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/minf.201200107","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,9]],"date-time":"2023-10-09T23:42:39Z","timestamp":1696894959000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/minf.201200107"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,12,5]]},"references-count":55,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2013,2]]}},"alternative-id":["10.1002\/minf.201200107"],"URL":"https:\/\/doi.org\/10.1002\/minf.201200107","archive":["Portico"],"relation":{},"ISSN":["1868-1743","1868-1751"],"issn-type":[{"value":"1868-1743","type":"print"},{"value":"1868-1751","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,12,5]]}}}