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@article{1299450,
author = {Bazzi, Sophia and Novotný, Jan and Yurenko, Yevgen and Marek, Radek},
article_location = {Weinheim},
article_number = {26},
doi = {http://dx.doi.org/10.1002/chem.201500743},
keywords = {Density functional calculations; DNA; G-quadruplexes; ligand design; nucleobases},
language = {eng},
issn = {0947-6539},
journal = {Chemistry - A European Journal},
title = {Designing a New Class of Bases for Nucleic Acid Quadruplexes and Quadruplex-Active Ligands},
url = {http://dx.doi.org/10.1002/chem.201500743},
volume = {21},
year = {2015}
}
TY - JOUR
ID - 1299450
AU - Bazzi, Sophia - Novotný, Jan - Yurenko, Yevgen - Marek, Radek
PY - 2015
TI - Designing a New Class of Bases for Nucleic Acid Quadruplexes and Quadruplex-Active Ligands
JF - Chemistry - A European Journal
VL - 21
IS - 26
SP - 9414-9425
EP - 9414-9425
PB - Wiley-VCH
SN - 09476539
KW - Density functional calculations
KW - DNA
KW - G-quadruplexes
KW - ligand design
KW - nucleobases
UR - http://dx.doi.org/10.1002/chem.201500743
L2 - http://dx.doi.org/10.1002/chem.201500743
N2 - A new class of quadruplex nucleobases, derived from 3-deazaguanine, has been designed for various applications as smart quadruplex ligands as well as quadruplex-based aptamers, receptors, and sensors. An efficient strategy for modifying the guanine quadruplex core has been developed and tested by using quantum chemistry methods. Several potential guanine derivatives modified at the 3- or 8-position or both are analyzed, and the results compared to reference systems containing natural guanine. Analysis of the formation energies (BLYP-D3(BJ)/def2-TZVPP level of theory, in combination with the COSMO model for water) in model systems consisting of two and three stacked tetrads with Na+/K+ ion(s) inside the internal channel indicates that the formation of structures with 3-halo-3-deazaguanine bases leads to a substantial gain in energy, as compared to the corresponding reference guanine complexes. The results cast light on changes in the noncovalent interactions (hydrogen bonding, stacking, and ion coordination) in a quadruplex stem upon modification of the guanine core. In particular, the enhanced stability of the modified quadruplexes was shown to originate mainly from increased pi–pi stacking. Our study suggests the 3-halo-3-deazaguanine skeleton as a potential building unit for quadruplex systems and smart G-quadruplex ligands.
ER -
BAZZI, Sophia, Jan NOVOTNÝ, Yevgen YURENKO and Radek MAREK. Designing a New Class of Bases for Nucleic Acid Quadruplexes and Quadruplex-Active Ligands. \textit{Chemistry - A European Journal}. Weinheim: Wiley-VCH, 2015, vol.~21, No~26, p.~9414-9425. ISSN~0947-6539. Available from: https://dx.doi.org/10.1002/chem.201500743.
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