title: Adrenaline and noradrenaline: protectors against oxidative stress or molecular targets?
abstract: 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.
authors: Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa , San Rafael Atlixco 186, Col. Vicentina, Iztapalapa, C. P. 09340. México D.F., México.
authors: Ruslán
authors: R
authors: Álvarez-Diduk
authors: Annia
authors: A
authors: Galano
mesh_terms: D002614:Chelating Agents / Q000737:chemistry; D002839:Chromans / Q000737:chemistry; D003198:Computer Simulation; D003300:Copper / Q000737:chemistry; D004583:Electrons; D004837:Epinephrine / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D007477:Ions / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D009638:Norepinephrine / Q000737:chemistry*; D018384:Oxidative Stress / Q000187:drug effects; D010545:Peroxides / Q000737:chemistry; D011522:Protons; D012996:Solutions; D014867:Water / Q000737:chemistry
chemical_list: D002614:Chelating Agents; D002839:Chromans; D016166:Free Radical Scavengers; D007477:Ions; D010545:Peroxides; D011522:Protons; D012996:Solutions; D014867:Water; C049375:perhydroxyl radical; D003300:Copper; D006859:Hydrogen; C010643:6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid; D009638:Norepinephrine; D004837:Epinephrine