Ton-Seng Chen, M. Platz, M. Robert
Mar 13, 1997
Citations
0
Influential Citations
12
Citations
Journal
Journal of Physical Chemistry A
Abstract
Bromopsoralens and bromocoumarins have been used to sensitize the inactivation of viruses. The bromine substituent increased the antiviral potency of the sensitizer, an effect attributed to cleavage of the C−Br bond of the aromatic radical anion produced by a light-induced electron transfer reaction with nucleic acids. This hypothesis was tested by a detailed mechanistic electrochemical investigation in acetonitrile and N,N-dimethylformamide of 5-bromo-8-methoxypsoralen, 8-methoxypsoralen, 3-bromocoumarin, and coumarin. A one-electron reduction process involves the formation of a radical anion, a step coupled with the cleavage of the carbon−bromine bond in the case of the brominated compounds, leading to the formation of an aryl radical moiety and a bromide anion. These experiments were further confirmed by radiolytic preparation coupled with UV−vis detection of the radical anions in glassy 2-methyltetrahydrofuran at 77 K and in ether, acetonitrile, and alcohol solutions at ambient temperature. This allow...