Oxidation of eugenol to form DNA adducts and 8-hydroxy-2'-deoxyguanosine: role of quinone methide derivative in DNA adduct formation

Carcinogenesis
W J BodellK Pongracz

Abstract

We have investigated the activation of eugenol to form DNA adducts and oxidative base damage. Treatment of myeloperoxidase containing HL-60 cells with eugenol, produced a dose-dependent formation of three DNA adducts as detected with P1-enhanced 32P-post-labeling. Incubation of HL-60 cells with the combination of 100 microM eugenol and 100 microM H2O2 potentiated the levels of DNA adduct in HL-60 cells by 14-fold, which suggests peroxidase activation in adduct formation. In vitro activation of eugenol with either horseradish peroxidase or myeloperoxidase and H2O2 produced three DNA adducts that were inhibited by the addition of either ascorbic acid or glutathione, by 66 and 90%, respectively. The DNA adducts formed in HL-60 cells treated with eugenol were the same as those formed by in vitro peroxidase activation. In addition to adduct formation, peroxidase activation of eugenol produced a 2- to 3-fold increase in the level of oxidative base damage. Eugenol quinone methide was prepared by Ag(I)oxide oxidation of eugenol. Peroxidase activation of eugenol gave a product that had the same UV spectrum as eugenol quinone methide, which suggests that it was one of the products. Reaction of eugenol quinone methide with either DNA or d...Continue Reading

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