Assessment of the prooxidant activity of beta-amino alcohols via luminol chemiluminescence
2012
Gabriel, J. J.
Recently, extensive research has been conducted to explore and develop synthetic pathways for an efficient production of beta-aminoalcohols, considering their interesting chemical and biological properties. Nevertheless the behaviour and effect of beta-aminoalcohols towards oxidation is not well investigated yet. In fact, they are believed to have prooxidant activity under certain conditions. To evaluate this hypothesis and with a view to understand and to develop possible explanations for the mechanism of action of beta-aminoalcohols, their effect on luminol oxidation was evaluated by chemiluminescnence. In addition, their behaviour in the presence of a free radical like DPPH and a transition metal like iron were evaluated. It was shown that these compounds enhance the oxidation of luminol and cause an increase in light production whereas they do not have any important reducing effect on the free-radical DPPH. For the FRAP experiment, the absorbance remains approximately the same after the addition of beta-aminoalcohols indicating that Fe(III) was not reduced. The results of the three experiments conducted in this study give clear evidence of the prooxidant activity of beta-aminoalcohols which depends on the compound concentration and on the analytical conditions, especially the pH of the solution. 2-amino-3-phenyl-1-propanol, 2-amino-1-methyl-1-propanol and 2-amino-2-phenylethanol showed the highest prooxidant activity, while ethanolamine and serinol revealed a lower prooxidant activity; furthermore a certain antioxidant activity was noticed for low concentrations of the samples. Moreover the enhancement effect of beta-aminolacohols can have several interpretations, but the more probable one is the ability of these compounds to stabilize free radicals.
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