Diarylpropane-1,3-dione Derivatives as TetR-Inducing Tetracycline Mimetics: Synthesis and Biological Investigations. Chembiochem : a European journal of chemical biology [Chembiochem] Journal article | | Title | Diarylpropane-1,3-dione Derivatives as TetR-Inducing Tetracycline Mimetics: Synthesis and Biological Investigations. | | Author(s) | Kormann C, Pimenta I, Löber S, Wimmer C, Lanig H, Clark T, Hillen W, Gmeiner P | | Institution | Department of Chemistry and Pharmacy, Emil Fischer Center, Friedrich Alexander University, Schuhstrasse 19, 91052 Erlangen (Germany), Fax: (+49) 9131-8522585. | | Source | Chembiochem 2009 Nov 2. | | Abstract | Synthesis, biological investigations and molecular docking studies of nonantibiotic and nontetracyclic inducers that feature a minimal key motif of the natural lead tetracycline are presented. The diarylpropane-1,3-dione 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-substituted beta-diketone 31 displayed the highest activity. Interestingly, antibiotic activity could not be detected for 31. Homology modeling based on the X-ray structure of 7-chlorotetracycline bound to TetR indicated analogous binding modes for the natural inducer and the synthetic diarylpropane-1,3-dione derivatives. | | Language | ENG | | Pub Type(s) | JOURNAL ARTICLE
| | PubMed ID | 19885899 |
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