title: Reaction of 3',5'-di-O-acetyl-2'-deoxyguansoine with hypobromous acid.
abstract: Hypobromous acid (HOBr) is formed by eosinophil peroxidase and myeloperoxidase in the presence of H2O2, Cl(-), and Br(-) in the host defense system of humans, protecting against invading bacteria. However, the formed HOBr may cause damage to DNA and its components in the host. When a guanine nucleoside (3',5'-di-O-acetyl-2'-deoxyguansoine) was treated with HOBr at pH 7.4, spiroiminodihydantoin, guanidinohydantoin/iminoallantoin, dehydro-iminoallantoin, diimino-imidazole, amino-imidazolone, and diamino-oxazolone nucleosides were generated in addition to an 8-bromoguanine nucleoside. The major products were spiroiminodihydantoin under neutral conditions and guanidinohydantoin/iminoallantoin under mildly acidic conditions. All the products were formed in the reaction with HOCl in the presence of Br(-). These products were also produced by eosinophil peroxidase or myeloperoxidase in the presence of H2O2, Cl(-), and Br(-). The results suggest that the products other than 8-bromoguanine may also have importance for mutagenesis by the reaction of HOBr with guanine residues in nucleotides and DNA.
authors.affiliation: School of Pharmacy, Shujitsu University, 1-6-1 Nishigawara, Okayama 703-8516, Japan. tsuzuki@shujitsu.ac.jp
authors.forename: Toshinori
authors.initials: T
authors.lastname: Suzuki
authors.forename: Asuka
authors.initials: A
authors.lastname: Nakamura
authors.forename: Michiyo
authors.initials: M
authors.lastname: Inukai
mesh_terms: D000107:Acetylation; D000481:Allantoin / Q000031:analogs & derivatives / Q000378:metabolism; D001959:Bromates / Q000378:metabolism*; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism*; D047209:Eosinophil Peroxidase / Q000378:metabolism*; D006151:Guanosine / Q000031:analogs & derivatives / Q000378:metabolism; D006801:Humans; D006861:Hydrogen Peroxide / Q000378:metabolism; D009195:Peroxidase / Q000378:metabolism*; D013141:Spiro Compounds / Q000378:metabolism
chemical_list: D001959:Bromates; D013141:Spiro Compounds; C408822:spiroiminodihydantoin; D006151:Guanosine; D000481:Allantoin; D006861:Hydrogen Peroxide; D047209:Eosinophil Peroxidase; D009195:Peroxidase; D003849:Deoxyguanosine; C027664:hypobromous acid