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Molecules 2012, 17(6), 6705-6715; doi:10.3390/molecules17066705

Calculation of the Stabilization Energies of Oxidatively Damaged Guanine Base Pairs with Guanine

Kagawa School of Pharmaceutical Sciences, Tokushima Bunri University, 1314-1, Shido, Sanuki, Kagawa 769-2193, Japan
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Received: 11 May 2012 / Revised: 18 May 2012 / Accepted: 25 May 2012 / Published: 1 June 2012
(This article belongs to the Special Issue ECSOC-15)
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Abstract

DNA is constantly exposed to endogenous and exogenous oxidative stresses. Damaged DNA can cause mutations, which may increase the risk of developing cancer and other diseases. G:C-C:G transversions are caused by various oxidative stresses. 2,2,4-Triamino-5(2H)-oxazolone (Oz), guanidinohydantoin (Gh)/iminoallantoin (Ia) and spiro-imino-dihydantoin (Sp) are known products of oxidative guanine damage. These damaged bases can base pair with guanine and cause G:C-C:G transversions. In this study, the stabilization energies of these bases paired with guanine were calculated in vacuo and in water. The calculated stabilization energies of the Ia:G base pairs were similar to that of the native C:G base pair, and both bases pairs have three hydrogen bonds. By contrast, the calculated stabilization energies of Gh:G, which form two hydrogen bonds, were lower than the Ia:G base pairs, suggesting that the stabilization energy depends on the number of hydrogen bonds. In addition, the Sp:G base pairs were less stable than the Ia:G base pairs. Furthermore, calculations showed that the Oz:G base pairs were less stable than the Ia:G, Gh:G and Sp:G base pairs, even though experimental results showed that incorporation of guanine opposite Oz is more efficient than that opposite Gh/Ia and Sp.
Keywords: oxidative guanine damage; base pair; hydrogen bond; stabilization energy oxidative guanine damage; base pair; hydrogen bond; stabilization energy
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MDPI and ACS Style

Suzuki, M.; Kino, K.; Morikawa, M.; Kobayashi, T.; Komori, R.; Miyazawa, H. Calculation of the Stabilization Energies of Oxidatively Damaged Guanine Base Pairs with Guanine. Molecules 2012, 17, 6705-6715.

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