Investigation of the reaction of peroxynitrite with propofol at acid pH: predominant production of oxidized, nitrated, and halogenated derivatives.

We reported here the reaction, in acidic conditions, of peroxynitrite (ONOO(-)) with the anaesthetic agent propofol (2,6-diisopropylphenol, PPF). The most interesting finding is that peroxynitrite is able to nitrate and to oxidize propofol leading to 4-nitropropofol, quinone, and diphenylquinone as the major products. More surprisingly, we also found that peroxynitrite is capable of halogenating propofol in the presence of halide ions, suggesting the formation of nitrosyl chloride (NOCl) or nitryl chloride (NO(2)Cl) from the reaction of peroxynitrite with chloride ions.