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首页> 外文期刊>Canadian Journal of Physiology and Pharmacology >The interaction of diamines and polyamines with the peroxidase-catalyzed metabolism of aromatic amines: A potential mechanism for the modulation of aniline toxicity
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The interaction of diamines and polyamines with the peroxidase-catalyzed metabolism of aromatic amines: A potential mechanism for the modulation of aniline toxicity

机译：二胺和多胺与过氧化物酶催化的芳香胺代谢的相互作用：调节苯胺毒性的潜在机制

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摘要

Synthetic and biological amines such as ethylenediamine (EDA), spermine, and spermidine have not been previously investigated in free-radical biochemical systems involving aniline-based drugs or xenobiotics. We aimed to study the influence of polyamines in the modulation of aromatic amine radical metabolites in peroxidase-mediated free radical reactions. The aniline compounds tested caused a relatively low oxidation rate of glutathione in the presence of horseradish peroxidase (HRP), and H2O2; however, they demonstrated marked oxygen consumption when a polyamine molecule was present. Next, we characterized the free-radical products generated by these reactions using spin-trapping and electron paramagnetic resonance (EPR) spectrometry. Primary and secondary but not tertiary polyamines dose-dependently enhanced the N-centered radicals of different aniline compounds catalyzed by either HRP or myeloperoxidase, which we believe occurred via charge transfer intermediates and subsequent stabilization of aniline-derived radical species as suggested by isotopically labeled aniline. Aniline/peroxidase reaction product(s) were monitored at 435 nm by kinetic spectrophotometry in the presence and absence of a polyamine additive. Using gas chromatography - mass spectrometry, the dimerziation product of aniline, azobenzene, was significantly amplified when EDA was present. In conclusion, di-and poly-amines are capable of enhancing the formation of aromatic-amine-derived free radicals, a fact that is expected to have toxicological consequences.
机译：合成和生物胺，例如乙二胺（EDA），亚精胺和亚精胺，以前尚未在涉及苯胺基药物或异生物素的自由基生化系统中进行过研究。我们旨在研究多胺对过氧化物酶介导的自由基反应中芳香胺自由基代谢物调节的影响。在存在辣根过氧化物酶（HRP）和H2O2的情况下，所测试的苯胺化合物引起了相对较低的谷胱甘肽氧化速率。然而，当存在多胺分子时，他们证明了明显的耗氧量。接下来，我们使用自旋俘获和电子顺磁共振（EPR）光谱对由这些反应产生的自由基产物进行了表征。伯多胺和仲多胺而不是叔叔多胺剂量依赖性地增强了HRP或髓过氧化物酶催化的不同苯胺化合物的N中心自由基，我们认为这是通过电荷转移中间体和随后苯胺衍生的自由基物种的稳定而发生的，如同位素标记的苯胺所示。在存在和不存在多胺添加剂的情况下，通过动力学分光光度法在435nm下监测苯胺/过氧化物酶反应产物。使用气相色谱-质谱法，当存在EDA时，苯胺，偶氮苯的二聚产物被显着放大。总之，二胺和多胺能够增强芳香族胺衍生的自由基的形成，这一事实预计会产生毒理学后果。

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