Issue 25, 2017

Effects of oxygenation on the intercalation of 1,10-phenanthroline-5,6/4,7-dione between DNA base pairs: a computational study

Abstract

The effects of oxygen in positions 4,7 and 5,6 of phenanthroline when this ligand intercalates between guanine–cytosine and adenine–thymine DNA base pairs (GC/CG and AT/TA) have been studied at the M06-2X/6-31+G(d,p) level of calculation. We focused on the changes in the structure, stabilization and energy contributions in the analysis of the interaction. The obtained trends in stabilization are explained by a model including repulsive Pauli (ΔEPauli) contributions, and attractive dispersion (ΔEdisp), orbital (ΔEorb) and electrostatic (ΔEelstat) contributions to energy. When no solvation is considered, the intrinsic ΔEelstat contribution results are crucial for the stabilization of the system. However, the inclusion of the solvation energy ΔEsolv can reverse the final stability trend of the systems becoming, thus, the driving force of the process. Therefore, the solvent will have a relevant influence in the potential cytotoxicity of the intercalation drugs.

Graphical abstract: Effects of oxygenation on the intercalation of 1,10-phenanthroline-5,6/4,7-dione between DNA base pairs: a computational study

Supplementary files

Article information

Article type
Paper
Submitted
24 Jan 2017
Accepted
05 Jun 2017
First published
05 Jun 2017

Phys. Chem. Chem. Phys., 2017,19, 16638-16649

Effects of oxygenation on the intercalation of 1,10-phenanthroline-5,6/4,7-dione between DNA base pairs: a computational study

A. Galliot, A. Gil and M. J. Calhorda, Phys. Chem. Chem. Phys., 2017, 19, 16638 DOI: 10.1039/C7CP00532F

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