Issue 18, 2019

G-Quadruplex binding optimization by gold(iii) insertion into the center of a porphyrin

Abstract

Porphyrins represent a valuable class of ligands for G-quadruplex nucleic acids. Herein, we evaluate the binding of cationic porphyrins metallated with gold(III) to G-quadruplex DNA and we compare it with other porphyrin derivatives. The G-quadruplex stabilization capacity and the selectivity of the various porphyrins were evaluated by biophysical and biochemical assays. The porphyrins were also tested as inhibitors of telomerase. It clearly appeared that the insertion of gold(III) ion in the center of the porphyrin increases the binding affinity of the porphyrin for the G-quadruplex target. Together with modelling studies, it is possible to propose that the insertion of the square planar gold(III) ion adds an extra positive charge on the complex and decreases the electron density in the porphyrin aromatic macrocycle, both properties being in favour of stronger electrostatic and π-staking interactions.

Graphical abstract: G-Quadruplex binding optimization by gold(iii) insertion into the center of a porphyrin

Supplementary files

Article information

Article type
Paper
Submitted
28 Nov 2018
Accepted
04 Mar 2019
First published
04 Mar 2019

Dalton Trans., 2019,48, 6091-6099

G-Quadruplex binding optimization by gold(III) insertion into the center of a porphyrin

A. Pipier, A. De Rache, C. Modeste, S. Amrane, E. Mothes-Martin, J. Stigliani, P. Calsou, J. Mergny, G. Pratviel and D. Gomez, Dalton Trans., 2019, 48, 6091 DOI: 10.1039/C8DT04703K

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