Abstract
Electrochemical experiments (CV, DPV, SWV, CPE) with methyl 2- [p-nitrophenyl(hydroxy) methyl] acrylate (1) were performed in protic (EtOH + phosphate buffer 1:9, 0.1 mol L-1, pH 6.9 and EtOH + phosphate buffer: 1:9, 0.1 mol L-1, pH 9.4) and aprotic (DMF + TBAP, 0.1 mol L-1) media. The reduction behaviours were typical of nitroaromatics, with an additional wave, in aprotic medium, related to the reduction of the olefin. Electrolysis, in protic media, furnished a reduced dimer. The incubation of 1 into a dsDNA biosensor revealed, that, after reduction of the nitroaromatic function, diagnostic oxidation peaks of the nucleobases were observed, indicative of interaction between them. GSH influenced the reduction behaviour of 1. Direct reduction of 1, in phosphate buffer, pH 9.38, to a stable nitroso/GSH adduct is facilitated. These electrochemical results help in the understanding of the anticancer activity of 1 that can be considered a hypoxia targeted bioreductive agent with a glutathione depleting function.
Published Version
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call