Structural and energetic properties of the potential HIV-1 reverse transcriptase inhibitors d4A and d4G: a comprehensive theoretical investigation
Identifikátory výsledku
Kód výsledku v IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14740%2F14%3A00074813" target="_blank" >RIV/00216224:14740/14:00074813 - isvavai.cz</a>
Výsledek na webu
<a href="http://www.tandfonline.com/doi/full/10.1080/07391102.2013.789401#.UoYzdScXeSk" target="_blank" >http://www.tandfonline.com/doi/full/10.1080/07391102.2013.789401#.UoYzdScXeSk</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1080/07391102.2013.789401" target="_blank" >10.1080/07391102.2013.789401</a>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Structural and energetic properties of the potential HIV-1 reverse transcriptase inhibitors d4A and d4G: a comprehensive theoretical investigation
Popis výsledku v původním jazyce
A comprehensive quantum-chemical investigation of the conformational landscapes of two nucleoside HIV-1 reverse transcriptase inhibitors, d4A and d4G, has been performed. Both nucleosides are shaped by a sophisticated network of specific noncovalent interactions, including conventional OH_O, NH_O and weak CH_O, CH_N hydrogen bonds, as well as dihydrogen CH_HC contacts. For the OH_O, NH_O, and CH_O hydrogen bonds, natural bond orbital analysis revealed hyperconjugative interactions between the oxygen lone pairs and the antibonding orbital of the donor group. For the CH _HC contacts, the electron density migrates from the antibonding orbital, corresponding to the CH group of the sugar residue, to the bonding orbital relative to the same group in the nucleobase. The results confirm the current belief that the biological activity of d4A and d4G is connected with the termination of the DNA chain synthesis. Thus, these nucleosides act as competitive HIV-1 reverse transcriptase inhibitors.
Název v anglickém jazyce
Structural and energetic properties of the potential HIV-1 reverse transcriptase inhibitors d4A and d4G: a comprehensive theoretical investigation
Popis výsledku anglicky
A comprehensive quantum-chemical investigation of the conformational landscapes of two nucleoside HIV-1 reverse transcriptase inhibitors, d4A and d4G, has been performed. Both nucleosides are shaped by a sophisticated network of specific noncovalent interactions, including conventional OH_O, NH_O and weak CH_O, CH_N hydrogen bonds, as well as dihydrogen CH_HC contacts. For the OH_O, NH_O, and CH_O hydrogen bonds, natural bond orbital analysis revealed hyperconjugative interactions between the oxygen lone pairs and the antibonding orbital of the donor group. For the CH _HC contacts, the electron density migrates from the antibonding orbital, corresponding to the CH group of the sugar residue, to the bonding orbital relative to the same group in the nucleobase. The results confirm the current belief that the biological activity of d4A and d4G is connected with the termination of the DNA chain synthesis. Thus, these nucleosides act as competitive HIV-1 reverse transcriptase inhibitors.
Klasifikace
Druh
J<sub>x</sub> - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)
CEP obor
CF - Fyzikální chemie a teoretická chemie
OECD FORD obor
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Návaznosti výsledku
Projekt
<a href="/cs/project/ED1.1.00%2F02.0068" target="_blank" >ED1.1.00/02.0068: CEITEC - central european institute of technology</a><br>
Návaznosti
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Ostatní
Rok uplatnění
2014
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
Journal of Biomolecular Structure and Dynamics
ISSN
0739-1102
e-ISSN
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Svazek periodika
32
Číslo periodika v rámci svazku
5
Stát vydavatele periodika
GB - Spojené království Velké Británie a Severního Irska
Počet stran výsledku
11
Strana od-do
730-740
Kód UT WoS článku
000331525100005
EID výsledku v databázi Scopus
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