Under physiologically relevant conditions, malondialdehyde reacts smoothly with amine neurotransmitters, i.e. dopamine, norepinephrine and serotonin, to give the fluorescent dihydropyridines 1, 4 and 5, respectively, as the relatively most abundant products. Small amounts of enaminal derivatives, such as 2 and 6, could also be obtained in the reactions with dopamine and serotonin. Oxidation of 1 with hydrogen peroxide/peroxidase leads to a complex pattern of unstable products, the major of which has been isolated and identified as the o-quinone epoxide 7. Similar oxidation of 4 and 5 affords mainly the dihydropyridine 8 and the 4,4'-biindolyl 9, respectively. These results provide new clues to the role of malondialdehyde in neuronal degeneration and lipofuscin formation
Reaction of malondialdehyde with amine neurotransmitters. Formation and oxidation chemistry of fluorescent 1,4-dihydropyridine adducts
M. D'ISCHIA;
1995
Abstract
Under physiologically relevant conditions, malondialdehyde reacts smoothly with amine neurotransmitters, i.e. dopamine, norepinephrine and serotonin, to give the fluorescent dihydropyridines 1, 4 and 5, respectively, as the relatively most abundant products. Small amounts of enaminal derivatives, such as 2 and 6, could also be obtained in the reactions with dopamine and serotonin. Oxidation of 1 with hydrogen peroxide/peroxidase leads to a complex pattern of unstable products, the major of which has been isolated and identified as the o-quinone epoxide 7. Similar oxidation of 4 and 5 affords mainly the dihydropyridine 8 and the 4,4'-biindolyl 9, respectively. These results provide new clues to the role of malondialdehyde in neuronal degeneration and lipofuscin formationI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
