The influence of the phosphorothioate diester bond on the DNA oxidation process

• Autorzy: Boleslaw T. Karwowski
• Języki publikacji: EN

Abstrakty

EN

This study describes the influence of the phosphorothioate internucleotide bond on the deoxyribonucleic acid (DNA) oxidation process. The interaction of an ultraviolet radiation (UVA) with a targeted double-stranded (ds) oligonucleotide, in which one strand contains an antraquinone (AQ) moiety on the 5’-end, may lead to a hole migration process through the double helix. In the end, the migration of theformed radical cation terminates in a suitable place. Usually, this is a guanine-rich sequence. In another experiment, phosphorothioate internucleotide bonds were detected in the bacterial genome as a natural modification. In this study, a polyacrylamide gel electrophoresis (PAGE) autoradiogram analysis of irradiated ds-DNA showed that the oxidation reaction was not inhibited by an isolated guanine. Instead, irrespective of the absence or presence of a phosphorothioate bond, the termination of the ds-DNA oxidation process was predominantly observed on the thymine moieties. Based on the obtained results, it can be concluded that in the discussed case, a hole migration by a hopping mechanism is in competition with an oxidation reaction with a superoxide radical anion. Alternatively, the radical cation migration process is sequence-dependent due to its different ionization potentials. Therefore, the presence of a phosphorothioate internucleotide bond did not change the stability of ds-DNA under UVA irradiation conditions.

EN

Słowa kluczowe

EN

Phosphorothioates; DNA damage; UVA radiation; oxidation; charge transfer

• Czasopismo: Open Chemistry
• Rocznik: 2015
• Tom: 13
• Numer: 1

Daty

otrzymano

2015-06-02

zaakceptowano

2015-08-24

online

2015-10-20

Twórcy

autor

Boleslaw T. Karwowski

• ---

Bibliografia

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Identyfikatory

DOI

10.1515/chem-2015-0136