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The diarylpropane\u20101,3\u2010dione motif was identified as the minimal substructure responsible for TetR induction by tetracyclines. The first nontetracyclic surrogates of the natural tetracyclines displayed significant inducing effects for TetR(BD)S135L, whereby the chlorohydroxyphenyl\u2010substituted \u03b2\u2010diketone <jats:bold>31<\/jats:bold> displayed the highest activity. Interestingly, antibiotic activity could not be detected for <jats:bold>31<\/jats:bold>. Homology modeling based on the X\u2010ray structure of 7\u2010chlorotetracycline bound to TetR indicated analogous binding modes for the natural inducer and the synthetic diarylpropane\u20101,3\u2010dione derivatives.<\/jats:italic><\/jats:p>","DOI":"10.1002\/cbic.200900564","type":"journal-article","created":{"date-parts":[[2009,11,2]],"date-time":"2009-11-02T10:54:48Z","timestamp":1257159288000},"page":"2924-2933","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Diarylpropane\u20101,3\u2010dione Derivatives as TetR\u2010Inducing Tetracycline Mimetics: Synthesis and Biological Investigations"],"prefix":"10.1002","volume":"10","author":[{"given":"Christian","family":"Kormann","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Irina","family":"Pimenta","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Stefan","family":"L\u00f6ber","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Cornelius","family":"Wimmer","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Harald","family":"Lanig","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Timothy","family":"Clark","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Wolfgang","family":"Hillen","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Peter","family":"Gmeiner","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2009,12,4]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20000616)112:12<2122::AID-ANGE2122>3.0.CO;2-8"},{"key":"e_1_2_6_1_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20000616)39:12<2042::AID-ANIE2042>3.0.CO;2-C"},{"key":"e_1_2_6_2_2","unstructured":"\u00a0"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1074-5521(98)90167-3"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1369-5266(03)00005-0"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.semcancer.2003.11.002"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1038\/sj.gt.3302251"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200503339"},{"key":"e_1_2_6_7_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200503339"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja983988u"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1074-5521(01)00006-0"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0164632"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi049682j"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/jgm.932"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200600226"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmb.2006.04.014"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm060289g"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2006.04.092"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.8153629"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1006\/jmbi.1994.0138"},{"key":"e_1_2_6_19_2","first-page":"117","volume":"110","author":"Giri S.","year":"1983","journal-title":"Acta Chim. 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