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Verfasst von:Scholz, Therese [VerfasserIn]   i
 Heyl, Carina [VerfasserIn]   i
 Zimmermann, Stefan [VerfasserIn]   i
 Klein, Christian D. [VerfasserIn]   i
Titel:Chemical, biochemical and microbiological properties of a brominated nitrovinylfuran with broad-spectrum antibacterial activity
Verf.angabe:Therese Scholz, Carina L. Heyl, Dan Bernardi, Stefan Zimmermann, Lars Kattner, Christian D. Klein
Jahr:2013
Umfang:10 S.
Fussnoten:Available online 24 November 2012 ; Gesehen am 18.07.2018
Titel Quelle:Enthalten in: Bioorganic & medicinal chemistry
Ort Quelle:Amsterdam [u.a.] : Elsevier, 1993
Jahr Quelle:2013
Band/Heft Quelle:21(2013), 3, Seite 795-804
ISSN Quelle:1464-3391
Abstract:A di-bromo substituted nitrovinylfuran with reported broad-spectrum antibacterial activity was found to be a potent inhibitor of MurA, a key enzyme in peptidoglycan biosynthesis. Further characterization of the compound was carried out to assess its reactivity towards thiol nucleophiles, its stability and degradation under aqueous conditions, inhibitory potential at other enzymes, and antibacterial and cytotoxic activity. Our results indicate that the nitrovinylfuran derivative is reactive towards cysteine residues in proteins, as demonstrated by the irreversible inhibition of MurA and bacterial methionine aminopeptidase. Experiments with proteins and model thiols indicate that the compound forms covalent adducts with SH groups and induces intermolecular disulfide bonds, with the intermediate formation of a monobromide derivative. The parent molecule as well as most of its breakdown products are potent antibiotics with MIC values below 4μg/mL and are active against multiresistant strains such as methicillin-resistant Staphylococcus aureus (MRSA). Further development of the bromonitrovinyl scaffold towards antibiotics with clinical relevance, however, requires optimization of the antibiotic-cytotoxic selectivity profile.
DOI:doi:10.1016/j.bmc.2012.11.018
URL:Bitte beachten Sie: Dies ist ein Bibliographieeintrag. Ein Volltextzugriff für Mitglieder der Universität besteht hier nur, falls für die entsprechende Zeitschrift/den entsprechenden Sammelband ein Abonnement besteht oder es sich um einen OpenAccess-Titel handelt.

Volltext ; Verlag: http://dx.doi.org/10.1016/j.bmc.2012.11.018
 Volltext: http://www.sciencedirect.com/science/article/pii/S0968089612009029
 DOI: https://doi.org/10.1016/j.bmc.2012.11.018
Datenträger:Online-Ressource
Sprache:eng
Sach-SW:Antibacterial agent
 Degradation mechanism
 Drug resistance
 HPLC
 Inhibition
 MurA enzyme
 Nitrovinylfuran
 Stability
K10plus-PPN:1577705424
Verknüpfungen:→ Zeitschrift

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