Next Article in Journal
Next Article in Special Issue
Previous Article in Journal
Previous Article in Special Issue
Molecules 2012, 17(6), 6705-6715; doi:10.3390/molecules17066705
Article

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

, * , , ,  and
Received: 11 May 2012; in revised form: 18 May 2012 / Accepted: 25 May 2012 / Published: 1 June 2012
(This article belongs to the Special Issue ECSOC-15)
Download PDF [469 KB, uploaded 18 June 2014]
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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


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.

AMA 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(6):6705-6715.

Chicago/Turabian Style

Suzuki, Masayo; Kino, Katsuhito; Morikawa, Masayuki; Kobayashi, Takanobu; Komori, Rie; Miyazawa, Hiroshi. 2012. "Calculation of the Stabilization Energies of Oxidatively Damaged Guanine Base Pairs with Guanine." Molecules 17, no. 6: 6705-6715.



Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert