Substituting CF2 for O4' in Components of Nucleic Acids:
Towards Systems with Reduced Propensity to Form Abasic Lesions

J 2015

Substituting CF2 for O4' in Components of Nucleic Acids: Towards Systems with Reduced Propensity to Form Abasic Lesions

YURENKO, Yevgen, Jan NOVOTNÝ, Vladimír SKLENÁŘ a Radek MAREK

Základní údaje

Originální název

Substituting CF2 for O4' in Components of Nucleic Acids: Towards Systems with Reduced Propensity to Form Abasic Lesions

Autoři

YURENKO, Yevgen (804 Ukrajina, domácí), Jan NOVOTNÝ (203 Česká republika, domácí), Vladimír SKLENÁŘ (203 Česká republika, domácí) a Radek MAREK (203 Česká republika, garant, domácí)

Vydání

Chemistry - A European Journal, WEINHEIM, Wiley, 2015, 0947-6539

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10403 Physical chemistry

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

DOI: 10.1002/chem.201502977

Impakt faktor

Impact factor: 5.771

Kód RIV

RIV/00216224:14740/15:00084338

Organizační jednotka

Středoevropský technologický institut

DOI

http://dx.doi.org/10.1002/chem.201502977

UT WoS

000367185700049

Klíčová slova anglicky

density functional calculations; DNA; fluorinated compounds; G-quadruplexes; relaxed force constants

Štítky

rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 10. 3. 2016 12:15, Martina Prášilová

Anotace

V originále

Intrinsic structural features and energetics of nucleotides containing variously fluorinated sugars as potential building blocks of DNA duplexes and quadruplexes are explored systematically using the modern methods of density functional theory (DFT) and quantum chemical topology (QCT). Our results suggest that fluorination at the 2'-B or 2'-A,B positions somewhat stabilizes in vacuo the AI relative to the BI conformations. In contrast, substitution of the CF2 group for the O4' atom (O4'-CF2 modification) leads to a preference of the BI relative to AI DNA-like conformers. All the studied modifications result in a noticeable increase in the stability of the glycosidic bond [estimated by the relaxed force constants (RFC) approach], with particularly encouraging results for the O4'-CF2 derivative. Consequently, the O4'-CF2 modified systems are suggested and explored as promising scaffolds for the development of duplex and quadruplex structures with reduced propensity to form abasic lesions and to undergo DNA damage.

Návaznosti

ED1.1.00/02.0068, projekt VaV

Název: CEITEC - central european institute of technology

286154, interní kód MU

Název: SYLICA - Synergies of Life and Material Sciences to Create a New Future (Akronym: SYLICA)

Investor: Evropská unie, SYLICA - Synergies of Life and Material Sciences to Create a New Future, Kapacity

Přiložené soubory

CEJ15_21_17933.pdf

Požádat o autorskou verzi souboru

Citovat

YURENKO, Yevgen, Jan NOVOTNÝ, Vladimír SKLENÁŘ a Radek MAREK. Substituting CF2 for O4' in Components of Nucleic Acids: Towards Systems with Reduced Propensity to Form Abasic Lesions. Chemistry - A European Journal. WEINHEIM: Wiley, 2015, roč. 21, č. 49, s. 17933-17943. ISSN 0947-6539. Dostupné z: https://dx.doi.org/10.1002/chem.201502977.

@article{1314691,
   author = {Yurenko, Yevgen and Novotný, Jan and Sklenář, Vladimír and Marek, Radek},
   article_location = {WEINHEIM},
   article_number = {49},
   doi = {http://dx.doi.org/10.1002/chem.201502977},
   keywords = {density functional calculations; DNA; fluorinated compounds; G-quadruplexes; relaxed force constants},
   language = {eng},
   issn = {0947-6539},
   journal = {Chemistry - A European Journal},
   title = {Substituting CF2 for O4' in Components of Nucleic Acids: Towards Systems with Reduced Propensity to Form Abasic Lesions},
   url = {http://dx.doi.org/10.1002/chem.201502977},
   volume = {21},
   year = {2015}
}

TY  - JOUR
ID  - 1314691
AU  - Yurenko, Yevgen - Novotný, Jan - Sklenář, Vladimír - Marek, Radek
PY  - 2015
TI  - Substituting CF2 for O4' in Components of Nucleic Acids: Towards Systems with Reduced Propensity to Form Abasic Lesions
JF  - Chemistry - A European Journal
VL  - 21
IS  - 49
SP  - 17933-17943
EP  - 17933-17943
PB  - Wiley
SN  - 09476539
KW  - density functional calculations
KW  - DNA
KW  - fluorinated compounds
KW  - G-quadruplexes
KW  - relaxed force constants
UR  - http://dx.doi.org/10.1002/chem.201502977
L2  - http://dx.doi.org/10.1002/chem.201502977
N2  - Intrinsic structural features and energetics of nucleotides containing variously fluorinated sugars as potential building blocks of DNA duplexes and quadruplexes are explored systematically using the modern methods of density functional theory (DFT) and quantum chemical topology (QCT). Our results suggest that fluorination at the 2'-B or 2'-A,B positions somewhat stabilizes in vacuo the AI relative to the BI conformations. In contrast, substitution of the CF2 group for the O4' atom (O4'-CF2 modification) leads to a preference of the BI relative to AI DNA-like conformers. All the studied modifications result in a noticeable increase in the stability of the glycosidic bond [estimated by the relaxed force constants (RFC) approach], with particularly encouraging results for the O4'-CF2 derivative. Consequently, the O4'-CF2 modified systems are suggested and explored as promising scaffolds for the development of duplex and quadruplex structures with reduced propensity to form abasic lesions and to undergo DNA damage.
ER  -

YURENKO, Yevgen, Jan NOVOTNÝ, Vladimír SKLENÁŘ a Radek MAREK. Substituting CF2 for O4' in Components of Nucleic Acids: Towards Systems with Reduced Propensity to Form Abasic Lesions. \textit{Chemistry - A European Journal}. WEINHEIM: Wiley, 2015, roč.~21, č.~49, s.~17933-17943. ISSN~0947-6539. Dostupné z: https://dx.doi.org/10.1002/chem.201502977.

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