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首页> 外文期刊>Biochemistry >Pivotal Role of Electrophilicity in Glutathione S-Transferase Induction by tert-Butylhydroquinone.
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Pivotal Role of Electrophilicity in Glutathione S-Transferase Induction by tert-Butylhydroquinone.

机译：亲电性在叔丁基对苯二酚谷胱甘肽S-转移酶诱导中的关键作用。

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摘要

Although the induction of glutathione S-transferase (GST) activity by tert-butylhydroquinone (tBHQ) has been well-documented in several cell culture systems and rodent experiments, the exact mechanism responsible for its inducibility is still not thoroughly understood. To more precisely define the molecular mechanism of GST induction by tBHQ, we examined the one-electron oxidation and glutathione (GSH) reaction potentials of tBHQ as compared to its analogue, 2,5-di-tert-butylhydroquinone (DtBHQ). tBHQ and DtBHQ showed similar one-electron oxidation potentials, including free radical quenching (antioxidant), oxidative conversion of both compounds to a benzoquinone form, and Cu(2+)-dependent superoxide generation. On the other hand, the reduced GSH level was observed by the addition of tBHQ, but not DtBHQ, suggesting that tBHQ acts as an electrophile while DtBHQ does not. The data were consistent with the observation that tBHQ more potently induced the GSTP1 gene expression in RL34 cells than DtBHQ did. Moreover, we indeed detected the GSH-tBHQ conjugates in the cells exposed to tBHQ using an electrochemical detector-high-performance liquid chromatography technique. Thus, we conclude that an electrophilic quinone oxidation product that reacts with intracellular nucleophiles including protein thiol or GSH plays a major role in the GSTP1 gene expression.
机译：尽管叔丁基对苯二酚（tBHQ）诱导谷胱甘肽S-转移酶（GST）活性已在许多细胞培养系统和啮齿动物实验中得到了充分证明，但对其诱导性的确切机制仍未完全了解。为了更精确地定义tBHQ诱导GST的分子机制，我们研究了tBHQ与类似物2,5-二叔丁基对苯二酚（DtBHQ）相比的单电子氧化和谷胱甘肽（GSH）反应电势。 tBHQ和DtBHQ显示相似的单电子氧化电位，包括自由基猝灭（抗氧化剂），两种化合物氧化转化为苯醌形式以及依赖Cu（2+）的超氧化物生成。另一方面，通过添加tBHQ而不是DtBHQ可以观察到GSH含量降低，这表明tBHQ充当了亲电试剂，而DtBHQ却没有。数据与以下观察结果一致：tBHQ比DtBHQ更有效地诱导RL34细胞中GSTP1基因表达。此外，我们确实使用电化学检测器-高效液相色谱技术在暴露于tBHQ的细胞中检测到GSH-tBHQ缀合物。因此，我们得出结论，与细胞内亲核试剂（包括蛋白质硫醇或GSH）反应的亲电子醌氧化产物在GSTP1基因表达中起主要作用。

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