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Molecules 2018, 23(5), 1134; https://doi.org/10.3390/molecules23051134

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

1
Laboratory of Bioanalytical Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Umultowska Street 89b, 61-614 Poznań, Poland
2
Laboratory of Quantum Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Umultowska Street 89b, 61-614 Poznań, Poland
3
School of Pharmacy, University College London, London WC1N 1AX, UK
*
Author to whom correspondence should be addressed.
Received: 9 April 2018 / Revised: 25 April 2018 / Accepted: 7 May 2018 / Published: 10 May 2018
(This article belongs to the Section Medicinal Chemistry)
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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. View Full-Text
Keywords: c-KIT; G-quadruplex; 2O3M; carbazole derivatives; spectroscopy; molecular modeling c-KIT; G-quadruplex; 2O3M; carbazole derivatives; spectroscopy; molecular modeling
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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).

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Głuszyńska, A.; Juskowiak, B.; Kuta-Siejkowska, M.; Hoffmann, M.; Haider, S. Carbazole Derivatives’ Binding to c-KIT G-Quadruplex DNA. Molecules 2018, 23, 1134.

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