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.
journal_name
Bioorg Med Chemjournal_title
Bioorganic & medicinal chemistryauthors
Suzuki T,Ida K,Uchibe S,Inukai Mdoi
10.1016/j.bmc.2008.03.007subject
Has Abstractpub_date
2008-05-01 00:00:00pages
5164-70issue
9eissn
0968-0896issn
1464-3391pii
S0968-0896(08)00220-4journal_volume
16pub_type
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