Diarylpropane-1,3-dione derivatives as TetR-inducing tetracycline mimetics: Synthesis and biological investigations

Kormann C, Pimenta I, Löber S, Wimmer C, Lanig H, Clark T, Hillen W, Gmeiner P (2009)

Publication Type: Journal article, Original article

Publication year: 2009

Journal

Original Authors: Kormann C., Pimenta I., Lober S., Wimmer C., Lanig H., Clark T., Hillen W., Gmeiner P.

Publisher: Wiley-VCH Verlag

Book Volume: 10

Pages Range: 2924-2933

Journal Issue: 18

DOI: 10.1002/cbic.200900564

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 β-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. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

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APA:

Kormann, C., Pimenta, I., Löber, S., Wimmer, C., Lanig, H., Clark, T.,... Gmeiner, P. (2009). Diarylpropane-1,3-dione derivatives as TetR-inducing tetracycline mimetics: Synthesis and biological investigations. ChemBioChem, 10(18), 2924-2933. https://doi.org/10.1002/cbic.200900564

MLA:

Kormann, Christian, et al. "Diarylpropane-1,3-dione derivatives as TetR-inducing tetracycline mimetics: Synthesis and biological investigations." ChemBioChem 10.18 (2009): 2924-2933.

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