Next Article in Journal
Synthetic Development of New 3-(4-Arylmethylamino)butyl-5-arylidene-rhodanines under Microwave Irradiation and Their Effects on Tumor Cell Lines and against Protein Kinases
Next Article in Special Issue
Synthesis and Enzymatic Incorporation of Modified Deoxyuridine Triphosphates
Previous Article in Journal
Relationship of Structure and Function of DNA-Binding Domain in Vitamin D Receptor
Previous Article in Special Issue
Modulation of the RNA Interference Activity Using Central Mismatched siRNAs and Acyclic Threoninol Nucleic Acids (aTNA) Units
Article Menu

Export Article

Open AccessArticle
Molecules 2015, 20(7), 12400-12411; doi:10.3390/molecules200712400

The Influence of the Terminal Phosphorothioate Diester Bond on the DNA Oxidation Process. An Experimental and Theoretical Approach

Food Science Department, Medical University of Lodz, ul. Muszynskiego 1, 90-151 Lodz, Poland
Academic Editor: Ramon Eritja
Received: 6 March 2015 / Revised: 12 June 2015 / Accepted: 24 June 2015 / Published: 8 July 2015
(This article belongs to the Special Issue Frontiers in Nucleic Acid Chemistry)
View Full-Text   |   Download PDF [1546 KB, uploaded 8 July 2015]   |  

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. View Full-Text
Keywords: phosphorothioate; DNA damage; UVA radiation; oxidation process; charge transfer phosphorothioate; DNA damage; UVA radiation; oxidation process; charge transfer
Figures

Figure 1

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. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Karwowski, B.T. The Influence of the Terminal Phosphorothioate Diester Bond on the DNA Oxidation Process. An Experimental and Theoretical Approach. Molecules 2015, 20, 12400-12411.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

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