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Bioorg Med Chem. 2013 Jul 1;21(13):3674-9. doi: 10.1016/j.bmc.2013.04.060. Epub 2013 May 1.

Reaction of 3',5'-di-O-acetyl-2'-deoxyguansoine with hypobromous acid.

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  • 1School of Pharmacy, Shujitsu University, 1-6-1 Nishigawara, Okayama 703-8516, Japan.


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.

Copyright © 2013 The Authors. Published by Elsevier Ltd.. All rights reserved.

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