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Reaction of 2'-deoxycytidine With Peroxynitrite in the Presence of Ammonium Bromide

Reaction of 2'-deoxycytidine With Peroxynitrite in the Presence of Ammonium Bromide

Toshinori Suzuki, Kazuya Ida, Shinya Uchibe, Michiyo Inukai

Bioorg Med Chem. 2008 May 1;16(9):5164-70.

PMID: 18358730

Abstract:

Peroxynitrite, a reactive nitrogen species generated from nitric oxide and superoxide anion radical, is an endogenous potential risk factor for human cancer. When 2'-deoxycytidine was incubated with peroxynitrite at neutral pH and 37 degrees C, the reaction was greatly enhanced by the addition of ammonium bromide. Both ammonium ion and bromide ion were required to exert the enhancing effect. In addition to ammonium ion, methylamine and dimethylamine exerted the enhancing effect in the presence of bromide ion. Two major products were identified as 5-hydroxy-2'-deoxycytidine and 5-bromo-2'-deoxycytidine. Hypochlorite solution and bromine water reacted with 2'-deoxycytidine generating 5-hydroxy-2'-deoxycytidine and 5-bromo-2'-deoxycytidine in the presence of ammonium bromide with the yields similar to those of the reaction of peroxynitrite with ammonium bromide. Fenton reaction of 2'-deoxycytidine was suppressed by the addition of ammonium bromide. Nitrogen dioxide gas did not react with 2'-deoxycytidine in the presence or the absence of ammonium bromide. These results suggest that in the presence of ammonium ion or amines, bromide ion interacts with peroxynitrous acid, which is a protonated form of peroxynitrite, but not with hydroxyl radical or nitrogen dioxide generated by homolysis of peroxynitrous acid, to form hypobromous acid. In the presence of ammonium ion or amines, bromide ion may play a role in enhancing the genotoxic effects of peroxynitrite in humans.

Chemicals Related in the Paper:

Catalog Number	Product Name	CAS Number	Price
AP111762302	5-Chloro-2-thienylmagnesium bromide	111762-30-2	Price
AP12265064	Ammonium-d4 bromide	12265-06-4	Price
AP30897860	2,5-Dimethylphenylmagnesium bromide	30897-86-0	Price

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