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

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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

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Publication details

The article was received on 28 Nov 2018, accepted on 04 Mar 2019 and first published on 04 Mar 2019


Article type: Paper
DOI: 10.1039/C8DT04703K
Citation: Dalton Trans., 2019, Advance Article

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    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, Advance Article , DOI: 10.1039/C8DT04703K

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