YURENKO, Yevgen, Jan NOVOTNÝ, Vladimír SKLENÁŘ and 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, vol. 21, No 49, p. 17933-17943. ISSN 0947-6539. doi:10.1002/chem.201502977.
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Basic information
Original name Substituting CF2 for O4' in Components of Nucleic Acids: Towards Systems with Reduced Propensity to Form Abasic Lesions
Authors YURENKO, Yevgen (804 Ukraine, belonging to the institution), Jan NOVOTNÝ (203 Czech Republic, belonging to the institution), Vladimír SKLENÁŘ (203 Czech Republic, belonging to the institution) and Radek MAREK (203 Czech Republic, guarantor, belonging to the institution).
Edition Chemistry - A European Journal, WEINHEIM, Wiley, 2015, 0947-6539.
Other information
Original language English
Type of outcome Article in a journal
Field of Study 10403 Physical chemistry
Country of publisher Germany
Confidentiality degree is not subject to a state or trade secret
WWW DOI: 10.1002/chem.201502977
Impact factor Impact factor: 5.771
RIV identification code RIV/00216224:14740/15:00084338
Organization unit Central European Institute of Technology
Doi http://dx.doi.org/10.1002/chem.201502977
UT WoS 000367185700049
Keywords in English density functional calculations; DNA; fluorinated compounds; G-quadruplexes; relaxed force constants
Tags rivok
Tags International impact, Reviewed
Changed by Changed by: Martina Prášilová, učo 342282. Changed: 10. 3. 2016 12:15.
Abstract
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.
Links
ED1.1.00/02.0068, research and development projectName: CEITEC - central european institute of technology
286154, interní kód MUName: SYLICA - Synergies of Life and Material Sciences to Create a New Future (Acronym: SYLICA)
Investor: European Union, Capacities
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