Atropisomeric 1-phenylbenzimidazoles affecting microtubule organization: influence of axial chirality
Identifikátory výsledku
Kód výsledku v IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F24%3A00602474" target="_blank" >RIV/61389030:_____/24:00602474 - isvavai.cz</a>
Nalezeny alternativní kódy
RIV/61989592:15310/24:73626671
Výsledek na webu
<a href="https://doi.org/10.1039/d4ob00863d" target="_blank" >https://doi.org/10.1039/d4ob00863d</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d4ob00863d" target="_blank" >10.1039/d4ob00863d</a>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Atropisomeric 1-phenylbenzimidazoles affecting microtubule organization: influence of axial chirality
Popis výsledku v původním jazyce
Benzimidazoles are frequently used in medicinal chemistry. Their anticancer effect is among the most prominent biological activities exhibited by this scaffold. Although numerous benzimidazole derivatives have been synthesized, possible atropisomerism of ortho-substituted 1-phenylbenzimidazoles has been largely overlooked. The aim of this research was to synthesize a small library of novel atropisomeric benzimidazole derivatives and explore their biological activity in various cancer and normal human cell lines. The new unique structural motif provides an interesting 3D architecture with axial chirality, which further contributes to molecular complexity and specificity. Racemates and their separated atropisomers arrested the cell cycle, caused apoptosis, and affected microtubule organization in cancer cells in vitro at different intensities. Moreover, this phenomenon was also verified by the inhibition of endothelial cell migration. These results showed that (+)-atropisomers, especially 5n, exhibit a stronger effect and show promise as agents for cancer therapy.
Název v anglickém jazyce
Atropisomeric 1-phenylbenzimidazoles affecting microtubule organization: influence of axial chirality
Popis výsledku anglicky
Benzimidazoles are frequently used in medicinal chemistry. Their anticancer effect is among the most prominent biological activities exhibited by this scaffold. Although numerous benzimidazole derivatives have been synthesized, possible atropisomerism of ortho-substituted 1-phenylbenzimidazoles has been largely overlooked. The aim of this research was to synthesize a small library of novel atropisomeric benzimidazole derivatives and explore their biological activity in various cancer and normal human cell lines. The new unique structural motif provides an interesting 3D architecture with axial chirality, which further contributes to molecular complexity and specificity. Racemates and their separated atropisomers arrested the cell cycle, caused apoptosis, and affected microtubule organization in cancer cells in vitro at different intensities. Moreover, this phenomenon was also verified by the inhibition of endothelial cell migration. These results showed that (+)-atropisomers, especially 5n, exhibit a stronger effect and show promise as agents for cancer therapy.
Klasifikace
Druh
J<sub>imp</sub> - Článek v periodiku v databázi Web of Science
CEP obor
—
OECD FORD obor
10401 - Organic chemistry
Návaznosti výsledku
Projekt
Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.
Návaznosti
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Ostatní
Rok uplatnění
2024
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
Organic & Biomolecular Chemistry
ISSN
1477-0520
e-ISSN
1477-0539
Svazek periodika
22
Číslo periodika v rámci svazku
34
Stát vydavatele periodika
GB - Spojené království Velké Británie a Severního Irska
Počet stran výsledku
15
Strana od-do
6966-6980
Kód UT WoS článku
001265780200001
EID výsledku v databázi Scopus
2-s2.0-85198663786