Álvarez-Diduk Ruslán, Galano Annia
Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa , San Rafael Atlixco 186, Col. Vicentina, Iztapalapa, C. P. 09340. México D.F., México.
J Phys Chem B. 2015 Feb 26;119(8):3479-91. doi: 10.1021/acs.jpcb.5b00052. Epub 2015 Feb 16.
Density functional theory was used to investigate the potential role of neurotransmitters adrenaline and noradrenaline regarding oxidative stress. It is predicted that they can be efficient as free radical scavengers both in lipid and aqueous media, with the main reaction mechanism being the hydrogen transfer and the sequential proton loss electron transfer, respectively. Despite the polarity of the environment, adrenaline and noradrenaline react with (•)OOH faster than Trolox, which suggests that they are better peroxyl radical scavengers than the reference compound. Both catecholamines are also proposed to be capable of efficiently inhibiting the oxidative stress induced by copper(II)-ascorbate mixtures, and the (•)OH production via Haber-Weiss reaction, albeit the effects on the later are only partial. They exert such beneficial effects by sequestering Cu(II) ions. In summary, these catecholamines can be capable of reducing oxidative stress, by scavenging free radicals and by sequestering metal ions. However, at the same time they might lose their functions in the process due to the associated structural modifications. Consequently, adrenaline and noradrenaline can be considered as both protectors and molecular targets of oxidative stress. Fortunately, under the proper conditions, both catecholamines can be regenerated to their original form so their functions are restored.
采用密度泛函理论研究神经递质肾上腺素和去甲肾上腺素在氧化应激方面的潜在作用。据预测，它们在脂质和水性介质中均可作为有效的自由基清除剂，主要反应机制分别为氢转移和顺序质子损失电子转移。尽管环境具有极性，但肾上腺素和去甲肾上腺素与（•）OOH的反应速度比Trolox快，这表明它们作为过氧自由基清除剂比参考化合物更有效。还提出两种儿茶酚胺均能够有效抑制铜（II）-抗坏血酸混合物诱导的氧化应激以及通过哈伯-韦斯反应产生（•）OH，尽管对后者的影响只是部分的。它们通过螯合铜（II）离子发挥这种有益作用。总之，这些儿茶酚胺能够通过清除自由基和螯合金属离子来减轻氧化应激。然而，与此同时，它们可能会由于相关的结构修饰而在这个过程中失去其功能。因此，肾上腺素和去甲肾上腺素可被视为氧化应激的保护剂和分子靶点。幸运的是，在适当条件下，两种儿茶酚胺均可再生为其原始形式，从而恢复其功能。
