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Naturally occurring quaternary benzo[c]phenanthridine alkaloids selectively stabilize G-quadruplexes

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Abstract

In this work, the interaction of six natural benzo[c]phenanthridine alkaloids (macarpine, sanguilutine, sanguirubine, chelerythrine, sanguinarine and chelirubine) with parallel and antiparallel G-quadruplex DNA structures was studied. HT22 corresponding to the end of human telomeres and the modified promoter oncogene c-kit21 and Pu22 sequences have been used. Spectroscopically-monitored melting experiments and fluorescence titrations, competitive dialysis and nuclear magnetic resonance spectroscopy were used for this purpose. The results showed that these alkaloids stabilized G-quadruplex structures in terms of increments of Tm values (from 15 to 25 °C) with high selectivity over duplexes and unfolded DNA. The mode of binding was mainly by stacking on the terminal G-tetrads with stoichiometries of 1 : 2 (DNA : ligand). The presence of non-specific electrostatic interactions was also observed. Overall, the results pointed to a strong stabilization of G-quadruplex structures by these alkaloids.

Graphical abstract: Naturally occurring quaternary benzo[c]phenanthridine alkaloids selectively stabilize G-quadruplexes

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Publication details

The article was received on 27 Apr 2018, accepted on 05 Aug 2018 and first published on 06 Aug 2018


Article type: Paper
DOI: 10.1039/C8CP02681E
Citation: Phys. Chem. Chem. Phys., 2018, Advance Article
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    Naturally occurring quaternary benzo[c]phenanthridine alkaloids selectively stabilize G-quadruplexes

    P. Jarosova, P. Paroulek, M. Rajecky, V. Rajecka, E. Taborska, R. Eritja, A. Aviñó, S. Mazzini, R. Gargallo and P. Taborsky, Phys. Chem. Chem. Phys., 2018, Advance Article , DOI: 10.1039/C8CP02681E

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