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

Journal article
(Original article)


Publication Details

Author(s): Kormann C, Pimenta I, Löber S, Wimmer C, Lanig H, Clark T, Hillen W, Gmeiner P
Journal: ChemBioChem
Publisher: Wiley-VCH Verlag
Publication year: 2009
Volume: 10
Journal issue: 18
Pages range: 2924-2933
ISSN: 1439-4227


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.



FAU Authors / FAU Editors

Clark, Timothy apl. Prof. Dr.
Computer-Chemie-Centrum
Gmeiner, Peter Prof. Dr.
Lehrstuhl für Pharmazeutische Chemie
Lanig, Harald PD Dr.
Computer-Chemie-Centrum
Löber, Stefan Dr.
Lehrstuhl für Pharmazeutische Chemie
Wimmer, Cornelius
Professur für Mikrobiologie


Additional Organisation
Emil-Fischer-Zentrum (Emil Fischer Center)


How to cite

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://dx.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.

BibTeX: 

Last updated on 2018-09-08 at 01:55