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Biomolecules 2014, 4(1), 140-159; doi:10.3390/biom4010140
Article

Analysis of Guanine Oxidation Products in Double-Stranded DNA and Proposed Guanine Oxidation Pathways in Single-Stranded, Double-Stranded or Quadruplex DNA

1
,
1,* , 2
,
1
,
1
 and
1
1 Kagawa School of Pharmaceutical Sciences, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan 2 Faculty of Science, Department of Chemistry, Shizuoka University, 836 Ohya, Suruga, Shizuoka 422-8529, Japan
* Author to whom correspondence should be addressed.
Received: 25 December 2013 / Revised: 21 January 2014 / Accepted: 23 January 2014 / Published: 10 February 2014
(This article belongs to the Special Issue Focus Update in Biomolecules)
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Abstract

Guanine is the most easily oxidized among the four DNA bases, and some guanine-rich sequences can form quadruplex structures. In a previous study using 6-mer DNA d(TGGGGT), which is the shortest oligomer capable of forming quadruplex structures, we demonstrated that guanine oxidation products of quadruplex DNA differ from those of single-stranded DNA. Therefore, the hotooxidation products of double-stranded DNA (dsDNA) may also differ from that of quadruplex or single-stranded DNA, with the difference likely explaining the influence of DNA structures on guanine oxidation pathways. In this study, the guanine oxidation products of the dsDNA d(TGGGGT)/d(ACCCCA) were analyzed using HPLC and electrospray ionization-mass spectrometry (ESI-MS). As a result, the oxidation products in this dsDNA were identified as 2,5-diamino-4H-imidazol-4-one (Iz), 8-oxo-7,8-dihydroguanine (8oxoG), dehydroguanidinohydantoin (Ghox), and guanidinohydantoin (Gh). The major oxidation products in dsDNA were consistent with a combination of each major oxidation product observed in single-stranded and quadruplex DNA. We previously reported that the kinds of the oxidation products in single-stranded or quadruplex DNA depend on the ease of deprotonation of the guanine radical cation (G•+) at the N1 proton. Similarly, this mechanism was also involved in dsDNA. Deprotonation in dsDNA is easier than in quadruplex DNA and more difficult in single-stranded DNA, which can explain the formation of the four oxidation products in dsDNA.
Keywords: DNA damage; electron transfer; photooxidation; 8-oxo-7,8-dihydroguanine DNA damage; electron transfer; photooxidation; 8-oxo-7,8-dihydroguanine
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Morikawa, M.; Kino, K.; Oyoshi, T.; Suzuki, M.; Kobayashi, T.; Miyazawa, H. Analysis of Guanine Oxidation Products in Double-Stranded DNA and Proposed Guanine Oxidation Pathways in Single-Stranded, Double-Stranded or Quadruplex DNA. Biomolecules 2014, 4, 140-159.

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