HYBRIDS OF OLEANOLIC ACID WITH NORBORNENE-2,3-DICARBOXIMIDE-N- CARBOXYLIC ACIDS AS POTENTIAL ANTICANCER AGENTS.
Barbara Bednarczyk-CwynarPiotr RuszkowskpDmytro AtamanyukRoman LesykLucjusz ZaprutkoPublished in: Acta poloniae pharmaceutica (2018)
The synthesis and cytotoxic activity of new oleanolic acid derivatives (8a-c and 9a-c) are presented. The obtained compounds are hybrids of oleanolic acid oximes and carboxylic acids containing short alkyl chains linked with nitrogen atom of norbomene-2,3-dicarboximide moieties via the nitrogen atom. The structures of the obtained new compounds (8a-c and 9a-c) were confinmed by spectral data. The derivatives 8a-c and 9a-c were subjected to the MTT assay in order to evaluate their cytotoxic activity towards HeLa, KB, MCF-7, HepG2 and HDF cell lines in comparison to mother compound (oleanolic acid, 1). Among the tested oximes acylated with carboxylic acids containing norbomene-imide moieties, the derivative 8b, with a propionoxyimino linker, exhibited the most advantageous level of cytotoxicity, with IC50 values from 2.75 pM (for MCF-7 cells) to 4.36 pM (for HDF cells).
Keyphrases
- induced apoptosis
- cell cycle arrest
- air pollution
- particulate matter
- ionic liquid
- molecular dynamics
- heavy metals
- cell death
- endoplasmic reticulum stress
- high throughput
- polycyclic aromatic hydrocarbons
- high resolution
- oxidative stress
- signaling pathway
- mass spectrometry
- anti inflammatory
- data analysis
- visible light
- dual energy