Tailoring the Properties of Quadruplex Nucleobases for
Biological and Nanomaterial Applications

J 2014

Tailoring the Properties of Quadruplex Nucleobases for Biological and Nanomaterial Applications

NOVOTNÝ, Jan, Yevgen YURENKO, Petr KULHÁNEK and Radek MAREK

Basic information

Original name

Tailoring the Properties of Quadruplex Nucleobases for Biological and Nanomaterial Applications

Authors

NOVOTNÝ, Jan (203 Czech Republic, belonging to the institution), Yevgen YURENKO (804 Ukraine, belonging to the institution), Petr KULHÁNEK (203 Czech Republic, belonging to the institution) and Radek MAREK (203 Czech Republic, guarantor, belonging to the institution)

Edition

Physical Chemistry Chemical Physics, Cambridge, Royal Society of Chemistry, 2014, 1463-9076

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10403 Physical chemistry

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

DOI: 10.1039/C4CP00541D

Impact factor

Impact factor: 4.493

RIV identification code

RIV/00216224:14740/14:00075618

Organization unit

Central European Institute of Technology

DOI

http://dx.doi.org/10.1039/C4CP00541D

UT WoS

000339173700023

Keywords in English

Quadruplex; DNA; guanine; xanthine; 9-deaza-8-haloxanthine; density-functional theory; hydrogen-bonding; stacking; ion coordination; formation energy

Abstract

V originále

Guanine DNA quadruplexes are interesting and important biological objects because they represent potential targets for regulatory drugs. Their use as building blocks for biomaterial applications is also being investigated. This contribution reports the in silico design of artificial building blocks derived from xanthine. Methods of quantum chemistry were used to evaluate the properties of xanthine structures relative to those containing guanine, the natural reference used. Tailoring the xanthine core showed that the base stacking and the ion coordination were significantly enhanced in the designed systems, while the ion-transport properties were not affected. Our study suggests that the 9-deaza-8-haloxanthine bases (where the halogen is fluorine or chlorine) is highly promising candidate for the development of artificial quadruplexes and quadruplex-active ligands.

Links

ED1.1.00/02.0068, research and development project

Name: CEITEC - central european institute of technology

Files attached

PCCP14_16_15241.pdf

Request the author's version of the file

Citovat

NOVOTNÝ, Jan, Yevgen YURENKO, Petr KULHÁNEK and Radek MAREK. Tailoring the Properties of Quadruplex Nucleobases for Biological and Nanomaterial Applications. Physical Chemistry Chemical Physics. Cambridge: Royal Society of Chemistry, 2014, vol. 16, No 29, p. 15241-15248. ISSN 1463-9076. Available from: https://dx.doi.org/10.1039/C4CP00541D.

@article{1184712,
   author = {Novotný, Jan and Yurenko, Yevgen and Kulhánek, Petr and Marek, Radek},
   article_location = {Cambridge},
   article_number = {29},
   doi = {http://dx.doi.org/10.1039/C4CP00541D},
   keywords = {Quadruplex; DNA; guanine; xanthine; 9-deaza-8-haloxanthine; density-functional theory; hydrogen-bonding; stacking; ion coordination; formation energy},
   language = {eng},
   issn = {1463-9076},
   journal = {Physical Chemistry Chemical Physics},
   title = {Tailoring the Properties of Quadruplex Nucleobases for Biological and Nanomaterial Applications},
   url = {http://dx.doi.org/10.1039/C4CP00541D},
   volume = {16},
   year = {2014}
}

TY  - JOUR
ID  - 1184712
AU  - Novotný, Jan - Yurenko, Yevgen - Kulhánek, Petr - Marek, Radek
PY  - 2014
TI  - Tailoring the Properties of Quadruplex Nucleobases for Biological and Nanomaterial Applications
JF  - Physical Chemistry Chemical Physics
VL  - 16
IS  - 29
SP  - 15241-15248
EP  - 15241-15248
PB  - Royal Society of Chemistry
SN  - 14639076
KW  - Quadruplex
KW  - DNA
KW  - guanine
KW  - xanthine
KW  - 9-deaza-8-haloxanthine
KW  - density-functional theory
KW  - hydrogen-bonding
KW  - stacking
KW  - ion coordination
KW  - formation energy
UR  - http://dx.doi.org/10.1039/C4CP00541D
L2  - http://dx.doi.org/10.1039/C4CP00541D
N2  - Guanine DNA quadruplexes are interesting and important biological objects because they represent potential targets for regulatory drugs. Their use as building blocks for biomaterial applications is also being investigated. This contribution reports the in silico design of artificial building blocks derived from xanthine. Methods of quantum chemistry were used to evaluate the properties of xanthine structures relative to those containing guanine, the natural reference used. Tailoring the xanthine core showed that the base stacking and the ion coordination were significantly enhanced in the designed systems, while the ion-transport properties were not affected. Our study suggests that the 9-deaza-8-haloxanthine bases (where the halogen is fluorine or chlorine) is highly promising candidate for the development of artificial quadruplexes and quadruplex-active ligands.
ER  -

NOVOTNÝ, Jan, Yevgen YURENKO, Petr KULHÁNEK and Radek MAREK. Tailoring the Properties of Quadruplex Nucleobases for Biological and Nanomaterial Applications. \textit{Physical Chemistry Chemical Physics}. Cambridge: Royal Society of Chemistry, 2014, vol.~16, No~29, p.~15241-15248. ISSN~1463-9076. Available from: https://dx.doi.org/10.1039/C4CP00541D.

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