title: Chemical structures critical for the induction of FMN-dependent NADH-quinone reductase in Escherichia coli.
abstract: An FMN-dependent NADH-quinone reductase is induced in Escherichia coli by growing the cells in the presence of menadione (2-methyl-1,4-naphthoquinone). Since the properties of induced enzyme are very similar to those of NAD(P)H: (quinone-acceptor) oxidoreductase (EC 1.6.99.2), known as DT-diaphorase, from animal cells, structural requirements of quinone derivatives as an inducer of NADH-quinone reductase in E. coli were examined. Among quinone derivatives examined, it was found that 2-alkyl-1,4-quinone structure with C-3 unsubstituted or substituted with Br is critical as a common inductive signal. Michael reaction acceptors which have been reported to be strong inducers of DT-diaphorase in mouse hepatoma cells were not always effective inducers in E. coli. However, several compounds, such as 2-methylene-4-butyrolactone, methylacrylate and methyl vinyl ketone, showed a slight inductive activity. The efficient inducers of NADH-quinone reductase in E. coli contain 1,4-quinone structure as a part of the inductive signal. These compounds belong to Michael acceptors and are likely to conjugate with thiol compounds such as glutathione.
authors.affiliation: Laboratory of Membrane Biochemistry, Faculty of Pharmaceutical Sciences, Chiba University, Japan.
authors.forename: T
authors.initials: T
authors.lastname: Unemoto
authors.forename: H
authors.initials: H
authors.lastname: Shimada
authors.forename: M
authors.initials: M
authors.lastname: Hayashi
mesh_terms: D016227:Benzoquinones / Q000494:pharmacology; D004790:Enzyme Induction / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects / Q000201:enzymology*; D038181:FMN Reductase; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000096:biosynthesis*; D009247:NADH, NADPH Oxidoreductases / Q000096:biosynthesis*; D009285:Naphthoquinones / Q000494:pharmacology; D013482:Superoxide Dismutase / Q000096:biosynthesis; D014812:Vitamin K / Q000494:pharmacology
chemical_list: D016227:Benzoquinones; D009285:Naphthoquinones; D014812:Vitamin K; D013482:Superoxide Dismutase; D038181:FMN Reductase; D009247:NADH, NADPH Oxidoreductases; D016660:NAD(P)H Dehydrogenase (Quinone)