Effects of Halides on Reaction of Nucleosides with Ozone

Abstract

GRAPHICAL ABSTRACT

Ozone (O₃), a major component of photochemical oxidants, is used recently as a deodorizer in living spaces. It has been reported that O₃ can directly react with DNA, causing mutagenesis in human cells and carcinogenesis in mice. However, little is known about the effects of coexistent ions in the reaction of O₃. In the present study, we analyzed the effects of halides on the reaction of O₃ with nucleosides using reversed-phase high-performance liquid chromatography with ultraviolet detection. When aqueous O₃ solution was added to a nucleoside mixture in potassium phosphate buffer (pH 7.3), the nucleosides were consumed with the following decreasing order of importance: dGuo > Thd > dCyd > dAdo. The effects of addition of fluoride and chloride in the system were slight. Bromide suppressed the reactions of dGuo, Thd, and dAdo but enhanced the reaction of dCyd. The major products were 5-hydroxy-2′-deoxycytidine, 5-bromo-2′-deoxycytidine, and 8-bromo-2′-deoxyguanosine. The time course and pH dependence of the product yield indicated formation of hypobromous acid as the reactive agent. Iodide suppressed all the reactions effectively. The results suggest that bromide may alter the mutation spectrum by O₃ in humans.

Keywords:

• Ozone
• nucleoside
• halide; hypobromous acid