{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,16]],"date-time":"2026-07-16T16:06:11Z","timestamp":1784217971479,"version":"3.55.0"},"reference-count":90,"publisher":"Informa UK Limited","issue":"1","license":[{"start":{"date-parts":[[2021,1,1]],"date-time":"2021-01-01T00:00:00Z","timestamp":1609459200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"J\u00e1nos Bolyai Research Scholarship of the Hungarian Academy of Sciences"},{"DOI":"10.13039\/501100018818","name":"National Research, Development and Innovation Office","doi-asserted-by":"publisher","award":["FK 124483"],"award-info":[{"award-number":["FK 124483"]}],"id":[{"id":"10.13039\/501100018818","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Medical School, University of Pecs","award":["KA-2019-27"],"award-info":[{"award-number":["KA-2019-27"]}]},{"name":"Higher Education Institutional Excellence Program of the Ministry of Human Capacities in Hungary","award":["20765-3\/2018\/FEKUTSTRAT"],"award-info":[{"award-number":["20765-3\/2018\/FEKUTSTRAT"]}]},{"name":"European Union, co-financed by the European Social Fund","award":["EFOP-3.6.1-16-2016-00004"],"award-info":[{"award-number":["EFOP-3.6.1-16-2016-00004"]}]},{"name":"Ministry of Finance, Hungary","award":["GINOP-2.3.3-15-2016-00025"],"award-info":[{"award-number":["GINOP-2.3.3-15-2016-00025"]}]},{"name":"Ministry of Finance, Hungary","award":["GINOP-2.3.2-15-2016-00049"],"award-info":[{"award-number":["GINOP-2.3.2-15-2016-00049"]}]}],"content-domain":{"domain":["www.tandfonline.com"],"crossmark-restriction":true},"short-container-title":["Journal of Enzyme Inhibition and Medicinal Chemistry"],"published-print":{"date-parts":[[2021,1,1]]},"DOI":"10.1080\/14756366.2021.1916010","type":"journal-article","created":{"date-parts":[[2021,7,6]],"date-time":"2021-07-06T08:58:20Z","timestamp":1625561900000},"page":"1356-1368","update-policy":"https:\/\/doi.org\/10.1080\/tandf_crossmark_01","source":"Crossref","is-referenced-by-count":13,"title":["Tetralone derivatives are MIF tautomerase inhibitors and attenuate macrophage activation and amplify the hypothermic response in endotoxemic mice"],"prefix":"10.1080","volume":"36","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3335-4169","authenticated-orcid":false,"given":"J\u00e1nos","family":"Garai","sequence":"first","affiliation":[{"name":"Department of Pathophysiology, Institute for Translational Medicine, University of P\u00e9cs, Medical School, P\u00e9cs, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4972-972X","authenticated-orcid":false,"given":"Marcell","family":"Krek\u00f3","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Semmelweis University, Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6149-2385","authenticated-orcid":false,"given":"L\u00e1szl\u00f3","family":"\u0150rfi","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Chemistry, Semmelweis University, Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1494-9837","authenticated-orcid":false,"given":"P\u00e9ter Bal\u00e1zs","family":"Jakus","sequence":"additional","affiliation":[{"name":"Department of Biochemistry and Medical Chemistry, University of P\u00e9cs, Medical School, P\u00e9cs, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2898-6628","authenticated-orcid":false,"given":"Zolt\u00e1n","family":"Rumbus","sequence":"additional","affiliation":[{"name":"Department of Thermophysiology, Institute for Translational Medicine, University of P\u00e9cs, Medical School, P\u00e9cs, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9171-6834","authenticated-orcid":false,"given":"Patrik","family":"K\u00e9ringer","sequence":"additional","affiliation":[{"name":"Department of Thermophysiology, Institute for Translational Medicine, University of P\u00e9cs, Medical School, P\u00e9cs, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2493-0571","authenticated-orcid":false,"given":"Andr\u00e1s","family":"Garami","sequence":"additional","affiliation":[{"name":"Department of Thermophysiology, Institute for Translational Medicine, University of P\u00e9cs, Medical School, P\u00e9cs, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0622-442X","authenticated-orcid":false,"given":"Eszter","family":"V\u00e1mos","sequence":"additional","affiliation":[{"name":"Department of Biochemistry and Medical Chemistry, University of P\u00e9cs, Medical School, P\u00e9cs, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8904-3976","authenticated-orcid":false,"given":"Dominika","family":"Kov\u00e1cs","sequence":"additional","affiliation":[{"name":"Department of Biochemistry and Medical Chemistry, University of P\u00e9cs, Medical School, P\u00e9cs, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7557-3004","authenticated-orcid":false,"given":"Viola","family":"Bag\u00f3n\u00e9 V\u00e1ntus","sequence":"additional","affiliation":[{"name":"Department of Biochemistry and Medical Chemistry, University of P\u00e9cs, Medical School, P\u00e9cs, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7147-0080","authenticated-orcid":false,"given":"Bal\u00e1zs","family":"Radnai","sequence":"additional","affiliation":[{"name":"Department of Biochemistry and Medical Chemistry, University of P\u00e9cs, Medical School, P\u00e9cs, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0599-0758","authenticated-orcid":false,"given":"Tam\u00e1s","family":"L\u00f3r\u00e1nd","sequence":"additional","affiliation":[{"name":"Department of Biochemistry and Medical Chemistry, University of P\u00e9cs, Medical School, P\u00e9cs, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"301","published-online":{"date-parts":[[2021,7,6]]},"reference":[{"key":"CIT0001","doi-asserted-by":"publisher","DOI":"10.1126\/science.153.3731.80"},{"key":"CIT0002","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.56.1.72"},{"key":"CIT0003","doi-asserted-by":"publisher","DOI":"10.1142\/8032"},{"key":"CIT0004","doi-asserted-by":"publisher","DOI":"10.1016\/j.immuni.2007.03.005"},{"key":"CIT0005","doi-asserted-by":"publisher","DOI":"10.1006\/jsbi.1997.3904"},{"key":"CIT0006","doi-asserted-by":"publisher","DOI":"10.1021\/bi7007189"},{"key":"CIT0007","doi-asserted-by":"publisher","DOI":"10.1016\/S0003-9861(02)00052-8"},{"key":"CIT0008","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.93.11.5191"},{"key":"CIT0009","doi-asserted-by":"publisher","DOI":"10.1002\/pro.5560051016"},{"key":"CIT0010","doi-asserted-by":"publisher","DOI":"10.1023\/B:NERE.0000026403.06238.73"},{"key":"CIT0011","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-5347(05)00650-6"},{"key":"CIT0012","doi-asserted-by":"publisher","DOI":"10.1007\/BF03402210"},{"key":"CIT0013","doi-asserted-by":"publisher","DOI":"10.1016\/S0014-5793(97)01261-1"},{"key":"CIT0014","doi-asserted-by":"publisher","DOI":"10.1093\/emboj\/17.13.3534"},{"key":"CIT0015","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.C500243200"},{"key":"CIT0016","doi-asserted-by":"publisher","DOI":"10.4155\/fmc.10.281"},{"key":"CIT0017","doi-asserted-by":"publisher","DOI":"10.1002\/jcp.21346"},{"key":"CIT0018","doi-asserted-by":"publisher","DOI":"10.1016\/j.intimp.2011.04.017"},{"key":"CIT0019","doi-asserted-by":"publisher","DOI":"10.2174\/092986709787581842"},{"key":"CIT0020","doi-asserted-by":"publisher","DOI":"10.1038\/s41584-019-0238-2"},{"key":"CIT0021","doi-asserted-by":"publisher","DOI":"10.1021\/jm801100v"},{"key":"CIT0022","doi-asserted-by":"publisher","DOI":"10.1177\/1087057114523317"},{"key":"CIT0023","doi-asserted-by":"publisher","DOI":"10.1021\/jm401908w"},{"key":"CIT0024","doi-asserted-by":"publisher","DOI":"10.1021\/jm010534q"},{"key":"CIT0025","doi-asserted-by":"publisher","DOI":"10.2174\/1381612023394674"},{"key":"CIT0026","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.5b00921"},{"key":"CIT0027","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.011569399"},{"key":"CIT0028","doi-asserted-by":"publisher","DOI":"10.1016\/j.intimp.2004.12.017"},{"key":"CIT0029","doi-asserted-by":"publisher","DOI":"10.1016\/j.canlet.2004.09.041"},{"key":"CIT0030","doi-asserted-by":"publisher","DOI":"10.1016\/j.intimp.2007.09.014"},{"key":"CIT0031","doi-asserted-by":"publisher","DOI":"10.1042\/BJ20140612"},{"key":"CIT0032","doi-asserted-by":"publisher","DOI":"10.7150\/ijbs.9672"},{"key":"CIT0033","first-page":"1035","volume":"45","author":"Matsunaga J","year":"1999","journal-title":"Cell Mol Biol (Noisy-le-Grand)"},{"key":"CIT0034","doi-asserted-by":"publisher","DOI":"10.1159\/000050368"},{"key":"CIT0035","unstructured":"A GB1255080 19711124; Nishio M, Ito T, Koeda T, Shibata U; Meiji Seika Kaisha Ltd. 1971 11 24. 1-Oxy- 3-benzal-thiochromanone derivatives and process for the production thereof. Great Britain, GB1255080A."},{"key":"CIT0036","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)89320-0"},{"key":"CIT0037","doi-asserted-by":"publisher","DOI":"10.1039\/P19960000395"},{"key":"CIT0038","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-1395(199709)10:9<687::AID-POC932>3.0.CO;2-A"},{"key":"CIT0039","doi-asserted-by":"publisher","DOI":"10.1016\/0223-5234(90)90010-Z"},{"key":"CIT0040","first-page":"971","volume":"105","author":"Azzolina O","year":"1975","journal-title":"Gazz Chim Ital"},{"key":"CIT0041","doi-asserted-by":"publisher","DOI":"10.1039\/a804796k"},{"key":"CIT0042","doi-asserted-by":"publisher","DOI":"10.1021\/jm010559p"},{"key":"CIT0043","doi-asserted-by":"publisher","DOI":"10.1002\/mrc.1260300112"},{"key":"CIT0044","doi-asserted-by":"publisher","DOI":"10.1002\/ardp.19843171010"},{"key":"CIT0045","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570230127"},{"key":"CIT0046","doi-asserted-by":"publisher","DOI":"10.1002\/jhet.5570240310"},{"key":"CIT0047","unstructured":"Bowen PJ, Robinson TP, Ehlers T, Goldsmith D, Arbiser J; University of Georgia Research Foundation and Emory University, USA, 2001 06 28, Chalcone and its analogs as agents for the inhibition of angiogenesis and related disease states. United States Patent, WO2001046110A2."},{"key":"CIT0048","unstructured":"Kawamata A, Jokura H, Imokawa G. Cosmetics containing alfa-benzylidene ketone derivatives and ultraviolet absorbents. (Kao Corp., Japan). Japan. Kokai Tokkyo Koho; 1992. 10 pp. CODEN: JKXXAF JP 04134043 A 19920507 Heisei. Patent written in Japanese. Application: JP 90-254738 19900925. Priority: CAN 117:157422 AN 1992:557422."},{"key":"CIT0049","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2007.06.017"},{"key":"CIT0050","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2860(98)00805-9"},{"key":"CIT0051","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2004.02.006"},{"key":"CIT0052","doi-asserted-by":"publisher","DOI":"10.1002\/mrc.1260290810"},{"key":"CIT0053","doi-asserted-by":"publisher","DOI":"10.1021\/jm950377t"},{"key":"CIT0054","doi-asserted-by":"publisher","DOI":"10.1016\/j.jchromb.2005.02.014"},{"key":"CIT0055","doi-asserted-by":"publisher","DOI":"10.1021\/bi9904048"},{"key":"CIT0056","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(73)90196-2"},{"key":"CIT0057","doi-asserted-by":"crossref","unstructured":"Bowers KJ, Chow E, Xu H, et al. Scalable algorithms for molecular dynamics simulations on commodity clusters. Proceedings of the ACM\/IEEE Conference on Supercomputing (SC06), 2006, Tampa, Florida, USA. Schr\u00f6dinger, LLC. Desmond User Manual, Chapter 3. 222 Third Street, Suite 2230, Cambridge, MA 02142, USA. D. E. Shaw Research.","DOI":"10.1145\/1188455.1188544"},{"key":"CIT0058","doi-asserted-by":"publisher","DOI":"10.1007\/s12031-014-0361-0"},{"key":"CIT0059","doi-asserted-by":"publisher","DOI":"10.1523\/JNEUROSCI.4671-10.2011"},{"key":"CIT0060","doi-asserted-by":"publisher","DOI":"10.1016\/j.niox.2017.01.012"},{"key":"CIT0061","doi-asserted-by":"publisher","DOI":"10.1016\/j.physbeh.2008.09.023"},{"key":"#cr-split#-CIT0062.1","doi-asserted-by":"crossref","unstructured":"(ai) Crichlow GV, Cho Y, Lolis EJ. Ternary complex of macrophage Migration Inhibitory Factor (MIF) bound both to 4-hydroxyphenylpyruvate and to the allosteric inhibitor AV1013 (R-stereoisomer). 2009. doi:10.2210\/pdb3IJJ\/pdb (aii) Cho Y, Crichlow GV, Vermeire JJ, et al . Allosteric inhibition of macrophage migration inhibitory factor revealed by ibudilast. Proc Natl Acad Sci U S A 2010;107:11313-11318. doi:10.1073\/pnas.1002716107","DOI":"10.2210\/pdb3ijj\/pdb"},{"key":"#cr-split#-CIT0062.2","doi-asserted-by":"crossref","unstructured":"(bi) Mclean LR, Zhang Y. Crystal structure of macrophage migration inhibitory factor (mif) with hydroxyquinoline inhibitor 707 at 1.58a resolution. 2009. doi:10.2210\/pdb3JSG\/pdb (bii) McLean LR, Zhang Y, Li H, et al. Discovery of covalent inhibitors for MIF tautomerase via cocrystal structures with phantom hits from virtual screening. Bioorg Med Chem Lett 2009;19:6717-6720. doi:10.1016\/j.bmcl.2009.09.106","DOI":"10.2210\/pdb3jsg\/pdb"},{"key":"#cr-split#-CIT0062.3","doi-asserted-by":"crossref","unstructured":"(ci) Oki H, Igaki S, Moriya Y, et al. Crystal structure of macrophage migration inhibitory factor in complex with BTZO-14. 2016. doi:10.2210\/pdb5B4O\/pdb (cii) Kimura H, Sato Y, Tajima Y, et al . BTZO-1, a cardioprotective agent, reveals that macrophage migration inhibitory factor regulates ARE-mediated gene expression. Chem Biol 2010;17:1282-1294. doi:10.1016\/j.chembiol.2010.10.011","DOI":"10.1016\/j.chembiol.2010.10.011"},{"key":"#cr-split#-CIT0062.4","doi-asserted-by":"crossref","unstructured":"(di) Robertson MJ, Jorgensen WL. Crystal structure of Macrophage Migration Inhibitory Factor (MIF) with a Potent Inhibitor (NVS-2). 2016. doi:10.2210\/pdb5HVT\/pdb (dii) Cisneros JA, Robertson MJ, Valhondo M, Jorgensen WL. A fluorescence polarization assay for binding to macrophage migration inhibitory factor and crystal structures for complexes of two potent inhibitors. J Am Chem Soc 2016;138:8630-8638. doi:10.1021\/jacs.6b04910","DOI":"10.1021\/jacs.6b04910"},{"key":"#cr-split#-CIT0062.5","doi-asserted-by":"crossref","unstructured":"(ei) Krimmer SG, Robertson MJ, Jorgensen WL. Macrophage migration inhibitory factor in complex with a Naphthyridinone Inhibitor (3a), 2017. doi:10.2210\/pdb6B1K\/pdb. (eii) Dawson TK, Dziedzic P, Robertson MJ, et al. Adding a hydrogen bond may not help: naphthyridinone vs quinoline inhibitors of macrophage migration inhibitory factor. ACS Med Chem Lett 2017;8:1287-1291. doi:10.1021\/acsmedchemlett.7b00384","DOI":"10.1021\/acsmedchemlett.7b00384"},{"key":"#cr-split#-CIT0063.1","doi-asserted-by":"crossref","unstructured":"(ai) Dziedzic P, Cisneros JA, Robertson MJ, et al . Design, synthesis, and protein crystallography of biaryltriazoles as potent tautomerase inhibitors of macrophage migration inhibitory factor. J Am Chem Soc 2015;137:2996-3003. doi:10.1021\/ja512112j","DOI":"10.1021\/ja512112j"},{"key":"#cr-split#-CIT0063.2","doi-asserted-by":"crossref","unstructured":"(bi) Trivedi-Parmar V, Robertson MJ, Cisneros JA, et al. Optimization of pyrazoles as phenol surrogates to yield potent inhibitors of macrophage migration inhibitory factor. ChemMedChem 2018;13:1092-1097. doi:10.1002\/cmdc.201800158","DOI":"10.1002\/cmdc.201800158"},{"key":"CIT0064","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2010.02.009"},{"key":"CIT0065","doi-asserted-by":"publisher","DOI":"10.1111\/jcmm.12949"},{"key":"CIT0066","doi-asserted-by":"publisher","DOI":"10.1016\/j.pisc.2014.12.007"},{"key":"CIT0067","doi-asserted-by":"publisher","DOI":"10.1021\/bi8014423"},{"key":"CIT0068","unstructured":"Sean E, ed. Computational toxicology. Risk assessment for pharmaceutical and environmental chemicals. Vol. 2, 2nd ed. Boca Raton (FL): CRC Press; 2018:59."},{"key":"CIT0069","doi-asserted-by":"publisher","DOI":"10.1080\/08923973.2018.1424896"},{"key":"CIT0070","doi-asserted-by":"publisher","DOI":"10.1179\/096805100101532414"},{"key":"CIT0071","doi-asserted-by":"publisher","DOI":"10.1042\/BST20150014"},{"key":"CIT0072","doi-asserted-by":"publisher","DOI":"10.1006\/cimm.1996.1061"},{"key":"CIT0073","doi-asserted-by":"publisher","DOI":"10.1007\/s40200-018-0341-y"},{"key":"CIT0074","doi-asserted-by":"publisher","DOI":"10.1016\/B978-0-444-64074-1.00034-3"},{"key":"CIT0075","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2006.05.001"},{"key":"CIT0076","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2009.09.106"},{"key":"CIT0077","first-page":"248","volume":"18","author":"Dimmock JR","year":"1983","journal-title":"Eur J Med Chem"},{"key":"CIT0078","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2006.03.008"},{"key":"CIT0079","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.200900177"},{"key":"CIT0080","doi-asserted-by":"publisher","DOI":"10.1093\/chromsci\/bms099"},{"key":"CIT0081","doi-asserted-by":"publisher","DOI":"10.2741\/1690"},{"key":"CIT0082","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jcim.5b00445"},{"key":"CIT0083","doi-asserted-by":"publisher","DOI":"10.2741\/1381"},{"key":"CIT0084","doi-asserted-by":"publisher","DOI":"10.1186\/cc4899"},{"key":"CIT0085","doi-asserted-by":"publisher","DOI":"10.1186\/1471-2172-11-50"}],"container-title":["Journal of Enzyme Inhibition and Medicinal Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.tandfonline.com\/doi\/pdf\/10.1080\/14756366.2021.1916010","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,1,14]],"date-time":"2022-01-14T08:52:06Z","timestamp":1642150326000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.tandfonline.com\/doi\/full\/10.1080\/14756366.2021.1916010"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,1,1]]},"references-count":90,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2021,1,1]]}},"alternative-id":["10.1080\/14756366.2021.1916010"],"URL":"https:\/\/doi.org\/10.1080\/14756366.2021.1916010","relation":{},"ISSN":["1475-6366","1475-6374"],"issn-type":[{"value":"1475-6366","type":"print"},{"value":"1475-6374","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,1,1]]},"assertion":[{"value":"The publishing and review policy for this title is described in its Aims & Scope.","order":1,"name":"peerreview_statement","label":"Peer Review Statement"},{"value":"http:\/\/www.tandfonline.com\/action\/journalInformation?show=aimsScope&journalCode=ienz20","URL":"http:\/\/www.tandfonline.com\/action\/journalInformation?show=aimsScope&journalCode=ienz20","order":2,"name":"aims_and_scope_url","label":"Aim & Scope"},{"value":"2021-02-01","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-03-30","order":1,"name":"revised","label":"Revised","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-04-06","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-07-06","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}