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

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)...

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Autores principales: Suzuki, Masayo, Kino, Katsuhito, Morikawa, Masayuki, Kobayashi, Takanobu, Komori, Rie, Miyazawa, Hiroshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268328/
https://www.ncbi.nlm.nih.gov/pubmed/22728364
http://dx.doi.org/10.3390/molecules17066705
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author Suzuki, Masayo
Kino, Katsuhito
Morikawa, Masayuki
Kobayashi, Takanobu
Komori, Rie
Miyazawa, Hiroshi
author_facet Suzuki, Masayo
Kino, Katsuhito
Morikawa, Masayuki
Kobayashi, Takanobu
Komori, Rie
Miyazawa, Hiroshi
author_sort Suzuki, Masayo
collection PubMed
description 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.
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spelling pubmed-62683282018-12-12 Calculation of the Stabilization Energies of Oxidatively Damaged Guanine Base Pairs with Guanine Suzuki, Masayo Kino, Katsuhito Morikawa, Masayuki Kobayashi, Takanobu Komori, Rie Miyazawa, Hiroshi Molecules Article 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. MDPI 2012-06-01 /pmc/articles/PMC6268328/ /pubmed/22728364 http://dx.doi.org/10.3390/molecules17066705 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Suzuki, Masayo
Kino, Katsuhito
Morikawa, Masayuki
Kobayashi, Takanobu
Komori, Rie
Miyazawa, Hiroshi
Calculation of the Stabilization Energies of Oxidatively Damaged Guanine Base Pairs with Guanine
title Calculation of the Stabilization Energies of Oxidatively Damaged Guanine Base Pairs with Guanine
title_full Calculation of the Stabilization Energies of Oxidatively Damaged Guanine Base Pairs with Guanine
title_fullStr Calculation of the Stabilization Energies of Oxidatively Damaged Guanine Base Pairs with Guanine
title_full_unstemmed Calculation of the Stabilization Energies of Oxidatively Damaged Guanine Base Pairs with Guanine
title_short Calculation of the Stabilization Energies of Oxidatively Damaged Guanine Base Pairs with Guanine
title_sort calculation of the stabilization energies of oxidatively damaged guanine base pairs with guanine
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268328/
https://www.ncbi.nlm.nih.gov/pubmed/22728364
http://dx.doi.org/10.3390/molecules17066705
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