Unemoto T, Shimada H, Hayashi M
Laboratory of Membrane Biochemistry, Faculty of Pharmaceutical Sciences, Chiba University, Japan.
Biochim Biophys Acta. 1992 Feb 21;1099(2):170-4.
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.
在甲萘醌（2-甲基-1,4-萘醌）存在的条件下培养大肠杆菌，可诱导其产生一种依赖黄素单核苷酸的NADH-醌还原酶。由于诱导酶的性质与动物细胞中已知的NAD(P)H：（醌受体）氧化还原酶（EC 1.6.99.2）即DT-黄递酶的性质非常相似，因此研究了醌衍生物作为大肠杆菌中NADH-醌还原酶诱导剂的结构要求。在所研究的醌衍生物中，发现具有未被取代或被Br取代的C-3的2-烷基-1,4-醌结构作为常见的诱导信号至关重要。据报道，在小鼠肝癌细胞中作为DT-黄递酶强诱导剂的迈克尔反应受体在大肠杆菌中并不总是有效的诱导剂。然而，一些化合物，如2-亚甲基-4-丁内酯、丙烯酸甲酯和甲基乙烯基酮，表现出轻微的诱导活性。大肠杆菌中NADH-醌还原酶的有效诱导剂含有1,4-醌结构作为诱导信号的一部分。这些化合物属于迈克尔受体，可能与谷胱甘肽等硫醇化合物结合。
