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Abstract
In this study, the influence of the terminal phosphorothioate (PT) internucleotide bond in ds-DNA on the oxidation process was taken into consideration. The interaction of UV with the targeted oligonucleotide leads to an electron ejection and radical cation “hole” migration through the ds-DNA until it is trapped irreversibly in a suitable place. Phosphorothiate internucleotide bonds were detected in the bacterial genome; however, their role is still unclear. In this study a PAGE analysis of irradiated ds-DNA showed that the degradation rea ction was slowed down by the presence PT next to the anthraquinone moiety. Further, theoretical study shows that [RP] AQ-PS-dG can adopt a slightly lower ionisation potential energy and triplet excited state with a subsequent slightly higher adiabatic electron affinity value in comparison with [SP] AQ-PS-dG and AQ-PO-dG. Moreover, the energy gap between HOMO and LUMO, indicated the radical stabilisation properties of [RP] AQ-PS-dG, which can hinder the charge transfer through ds-DNA.
Highlights
Genetic information is preserved in cellular DNA in every living organism [1]
In 2007, Wang et al showed that phosphorothiate (PT) modification in an internucleotide bond can naturally appear in the bacterial genome [9]
Following the mechanisms proposed by Schuster, the oligonucleotides were irridiated in their double-stranded form by UVA (350 nm) and rapidly formed a triplet excited state of anthraquinone (AQ*3) with one-electron DNA oxidation [12,13]
Summary
Genetic information is preserved in cellular DNA in every living organism [1]. This storage medium is continuously exposed to oxidative stress, which can lead to a variety of DNA lesions [2]. In 2007, Wang et al showed that phosphorothiate (PT) modification in an internucleotide bond can naturally appear in the bacterial genome [9]. This modification was not detected in other cells of living organisms. The influence of the phosphorothioate internucelotide bond on the light-induced oxidation process was examined
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