Possible DNA damage by oxidation products of guanine: A density functional and electron propagator theoretical study

• Published in: International journal of quantum chemistry 2012-08, Vol.112 (16), p.2840-2847
• Main Authors: Pacheco-Ortín, Sandy, Gaitán Lozano, Ricardo, Agacino Valdés, Esther
• Format: Article
• Language: English
• Subjects: DNA damage; electron propagator theory; nucleobases; oxidation products of guanine; reactivity analysis
• ISSN: 0020-7608; 1097-461X
• DOI: 10.1002/qua.24001

The stability and reactivity of seven guanine oxidation products (GOP), which contain 8‐oxo‐7,8‐dihydroguanine (8‐oxoG) have been studied and compared with the four nucleobases, such as adenine, cytosine, guanine, and thymine. It has been possible with the use of density functional theory and electron propagator theory (EPT), to evaluate their relation with certain ionization induced process, which produce damage to DNA. Using the application of Koopmans's theorem, EPT provides alternatively a reliable way to calculate the vertical ionization potential (VIP) and vertical electron affinity (VEA). This process has been used to obtain other reactivity indexes, such as: electronegativity and hardness. In the nucleobases and the GOP studies, we observed the following: guanine and 8‐oxo‐7,8‐dihydroguanine were the lowest VIP, and 8‐oxoG was the lowest hardness. This let us confirm that these species are the most susceptible to change their electron densities and transform in other GOP. Particularly, the GOP, Sp(R), Sp(S), and Z were the highest VIP. It allows us to say that they are the most stable. Z and Iz were the highest VEA; this suggests that they have a big capacity to accept electrons and form anionic centers in DNA. The GOP, which was considered in this study, showed hardness values between 9.1 and 10.4 because of π‐conjugation; therefore, these GOP could be good candidates to participate in DNA transversions. © 2012 Wiley Periodicals, Inc.