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@article{2251569,
author = {Rudolfová, Jana and Kryštof, Vladimir and Nečas, Marek and Vicha, Robert and Rouchal, Michal},
article_location = {Basel},
article_number = {23},
doi = {http://dx.doi.org/10.3390/ijms232315143},
keywords = {adamantane; purine; nucleoside; glycosylation; beta-cyclodextrin; antiproliferative activity},
language = {eng},
issn = {1422-0067},
journal = {International Journal of Molecular Sciences},
title = {Adamantane-Substituted Purine Nucleosides: Synthesis, Host-Guest Complexes with beta-Cyclodextrin and Biological Activity},
url = {https://www.mdpi.com/1422-0067/23/23/15143},
volume = {23},
year = {2022}
}
TY - JOUR
ID - 2251569
AU - Rudolfová, Jana - Kryštof, Vladimir - Nečas, Marek - Vicha, Robert - Rouchal, Michal
PY - 2022
TI - Adamantane-Substituted Purine Nucleosides: Synthesis, Host-Guest Complexes with beta-Cyclodextrin and Biological Activity
JF - International Journal of Molecular Sciences
VL - 23
IS - 23
SP - 1-22
EP - 1-22
PB - MDPI
SN - 14220067
KW - adamantane
KW - purine
KW - nucleoside
KW - glycosylation
KW - beta-cyclodextrin
KW - antiproliferative activity
UR - https://www.mdpi.com/1422-0067/23/23/15143
N2 - Purine nucleosides represent an interesting group of nitrogen heterocycles, showing a wide range of biological effects. In this study, we designed and synthesized a series of 6,9-disubstituted and 2,6,9-trisubstituted purine ribonucleosides via consecutive nucleophilic aromatic substitution, glycosylation, and deprotection of the ribofuranose unit. We prepared eight new purine nucleosides bearing unique adamantylated aromatic amines at position 6. Additionally, the ability of the synthesized purine nucleosides to form stable host–guest complexes with β-cyclodextrin (β-CD) was confirmed using nuclear magnetic resonance (NMR) and mass spectrometry (ESI-MS) experiments. The in vitro antiproliferative activity of purine nucleosides and their equimolar mixtures with β-CD was tested against two types of human tumor cell line. Six adamantane-based purine nucleosides showed an antiproliferative activity in the micromolar range. Moreover, their effect was only slightly suppressed by the presence of β-CD, which was probably due to the competitive binding of the corresponding purine nucleoside inside the β-CD cavity.
ER -
RUDOLFOVÁ, Jana, Vladimir KRYŠTOF, Marek NEČAS, Robert VICHA and Michal ROUCHAL. Adamantane-Substituted Purine Nucleosides: Synthesis, Host-Guest Complexes with beta-Cyclodextrin and Biological Activity. \textit{International Journal of Molecular Sciences}. Basel: MDPI, 2022, vol.~23, No~23, p.~1-22. ISSN~1422-0067. Available from: https://dx.doi.org/10.3390/ijms232315143.
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