Atropisomeric 1-phenylbenzimidazoles affecting microtubule organization: influence of axial chirality
Jazyk angličtina Země Anglie, Velká Británie Médium electronic
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
38988246
DOI
10.1039/d4ob00863d
Knihovny.cz E-zdroje
- MeSH
- benzimidazoly * chemie farmakologie MeSH
- buněčné linie MeSH
- buněčný cyklus účinky léků MeSH
- lidé MeSH
- mikrotubuly * účinky léků metabolismus MeSH
- molekulární struktura MeSH
- protinádorové látky chemie farmakologie MeSH
- stereoizomerie MeSH
- viabilita buněk účinky léků MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- benzimidazoly * MeSH
- protinádorové látky MeSH
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.
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