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Article

Importance of Chiral Recognition in Designing Metal-Free Ligands for G-Quadruplex DNA

by
Dora M. Răsădean
,
Samuel W. O. Harrison
,
Isobel R. Owens
,
Aucéanne Miramont
,
Frances M. Bromley
and
G. Dan Pantoș
*
Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UK
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(8), 1473; https://doi.org/10.3390/molecules24081473
Submission received: 21 December 2018 / Revised: 8 April 2019 / Accepted: 11 April 2019 / Published: 15 April 2019
(This article belongs to the Special Issue G-Quadruplex Ligands and Cancer)
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Abstract

Four pairs of amino acid-functionalized naphthalenediimide enantiomers (d- and l-lysine derived NDIs) were screened toward G-quadruplex forming sequences in telomeres (h-TELO) and oncogene promoters: c-KIT1, c-KIT2, k-RAS and BCL-2. This is the first study to address the effect of point chirality toward G-quadruplex DNA stabilization using purely small organic molecules. Enantioselective behavior toward the majority of ligands was observed, particularly in the case of parallel conformations of c-KIT2 and k-RAS. Additionally, Nε-Boc-l-Lys-NDI and Nε-Boc-d-Lys-NDI discriminate between quadruplexes with parallel and hybrid topologies, which has not previously been observed with enantiomeric ligands.
Keywords: circular dichroism; G-quadruplex DNA; chirality; enantioselectivity; chiral recognition circular dichroism; G-quadruplex DNA; chirality; enantioselectivity; chiral recognition

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MDPI and ACS Style

Răsădean, D.M.; Harrison, S.W.O.; Owens, I.R.; Miramont, A.; Bromley, F.M.; Pantoș, G.D. Importance of Chiral Recognition in Designing Metal-Free Ligands for G-Quadruplex DNA. Molecules 2019, 24, 1473. https://doi.org/10.3390/molecules24081473

AMA Style

Răsădean DM, Harrison SWO, Owens IR, Miramont A, Bromley FM, Pantoș GD. Importance of Chiral Recognition in Designing Metal-Free Ligands for G-Quadruplex DNA. Molecules. 2019; 24(8):1473. https://doi.org/10.3390/molecules24081473

Chicago/Turabian Style

Răsădean, Dora M., Samuel W. O. Harrison, Isobel R. Owens, Aucéanne Miramont, Frances M. Bromley, and G. Dan Pantoș. 2019. "Importance of Chiral Recognition in Designing Metal-Free Ligands for G-Quadruplex DNA" Molecules 24, no. 8: 1473. https://doi.org/10.3390/molecules24081473

APA Style

Răsădean, D. M., Harrison, S. W. O., Owens, I. R., Miramont, A., Bromley, F. M., & Pantoș, G. D. (2019). Importance of Chiral Recognition in Designing Metal-Free Ligands for G-Quadruplex DNA. Molecules, 24(8), 1473. https://doi.org/10.3390/molecules24081473

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