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Carbazole Derivatives' Binding to c-KIT G-Quadruplex DNA

Głuszyńska, A; Juskowiak, B; Kuta-Siejkowska, M; Hoffmann, M; Haider, S; (2018) Carbazole Derivatives' Binding to c-KIT G-Quadruplex DNA. Molecules , 23 (5) , Article 1134. 10.3390/molecules23051134. Green open access

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Abstract

The binding affinities of three carbazole derivatives to the intramolecular G-quadruplex (GQ) DNA formed by the sequence 5′-AGGGAGGGCGCTGGGAGGAGGG-3′, derived from the c-KIT 1 oncogene region, were investigated. All carbazole cationic ligands that differed in the substituents on the nitrogen atom were able to stabilize G-quadruplex, as demonstrated using UV-Vis, fluorescence and CD spectroscopic techniques as well as molecular modeling. The spectrophotometric titration results showed spectral features characteristic of these ligands-bathochromic shifts and initial hypochromicity followed by hyperchromicity at higher GQ concentrations. All free carbazole ligands exhibited modest fluorescent properties, but after binding to the DNA the fluorescence intensity increased significantly. The binding affinities of carbazole ligands to the c-KIT 1 DNA were comparable showing values in the order of 105 M−1. Molecular modeling highlights the differences in interactions between each particular ligand and studied G-quadruplex, which potentially influenced binding strength. Obtained results relevant that all three investigated ligands have stabilization properties on studied G-quadruplex.

Type: Article
Title: Carbazole Derivatives' Binding to c-KIT G-Quadruplex DNA
Location: Switzerland
Open access status: An open access version is available from UCL Discovery
DOI: 10.3390/molecules23051134
Publisher version: http://dx.doi.org/10.3390/molecules23051134
Language: English
Additional information: 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).
Keywords: 2O3M, G-quadruplex, c-KIT, carbazole derivatives, molecular modeling, spectroscopy
UCL classification: UCL
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10048674
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