Adamantane-Substituted Purine Nucleosides: Synthesis,
Host-Guest Complexes with beta-Cyclodextrin and Biological
Activity

J 2022

Adamantane-Substituted Purine Nucleosides: Synthesis, Host-Guest Complexes with beta-Cyclodextrin and Biological Activity

RUDOLFOVÁ, Jana; Vladimir KRYŠTOF; Marek NEČAS; Robert VICHA; Michal ROUCHAL et. al.

Základní údaje

Originální název

Adamantane-Substituted Purine Nucleosides: Synthesis, Host-Guest Complexes with beta-Cyclodextrin and Biological Activity

Autoři

RUDOLFOVÁ, Jana; Vladimir KRYŠTOF; Marek NEČAS; Robert VICHA a Michal ROUCHAL

Vydání

International Journal of Molecular Sciences, Basel, MDPI, 2022, 1422-0067

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

30107 Medicinal chemistry

Stát vydavatele

Švýcarsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Kód RIV

RIV/00216224:14310/22:00128464

Organizační jednotka

Přírodovědecká fakulta

DOI

https://doi.org/10.3390/ijms232315143

UT WoS

000898072900001

EID Scopus

2-s2.0-85143705019

Klíčová slova anglicky

adamantane; purine; nucleoside; glycosylation; beta-cyclodextrin; antiproliferative activity

Štítky

14313010, CF SAXS, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 25. 2. 2025 09:34, Mgr. Marie Novosadová Šípková, DiS.

Anotace

V originále

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.

Návaznosti

EF18_046/0015974, projekt VaV

Název: Modernizace České infrastruktury pro integrativní strukturní biologii

90127, velká výzkumná infrastruktura

Název: CIISB II

Citovat

RUDOLFOVÁ, Jana; Vladimir KRYŠTOF; Marek NEČAS; Robert VICHA a Michal ROUCHAL. Adamantane-Substituted Purine Nucleosides: Synthesis, Host-Guest Complexes with beta-Cyclodextrin and Biological Activity. International Journal of Molecular Sciences. Basel: MDPI, 2022, roč. 23, č. 23, s. 1-22. ISSN 1422-0067. Dostupné z: https://doi.org/10.3390/ijms232315143.

@article{2251569,
   author = {Rudolfová, Jana and Kryštof, Vladimir and Nečas, Marek and Vicha, Robert and Rouchal, Michal},
   article_location = {Basel},
   article_number = {23},
   doi = {https://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 a 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, roč.~23, č.~23, s.~1-22. ISSN~1422-0067. Dostupné z: https://doi.org/10.3390/ijms232315143.

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