Synthesis and biological activity of amino acid derivatives of avarone and its model compound
Matić, Ivana Z.
Article (Accepted Version)
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A series of eighteen derivatives of marine sesquiterpene quinone avarone and its model system tert-butylquinone with amino acids has been synthesized by nucleophilic addition of amino acids to the quinones. In vitro cytotoxic activity toward human cancer cell lines (HeLa, A549, Fem-X, 1(562, MDA-MB-453) and normal MRC-5 cell line was determined. Several compounds showed very strong inhibitory activity with IC50 values less than 10 mu M. Avarone derivatives were more active than the corresponding tert-butylquinone derivatives. The results of the cytofluorimetric analysis of cell cycle of HeLa cells showed that apoptosis might be one of possible mechanism of action of these compounds in cancer cells. In order to examine the influence of caspases on cell death, the apoptotic mechanisms induced by the tested compounds were determined using specific caspases 3, 8 and 9 inhibitors. For all compounds antibacterial activities against six strains of Gram-positive and four strains of Gram-negati...ve bacteria were determined, as well as antifungal activity against three fungal species.
Keywords:Avarone / Amino acids / Cytotoxicity / Caspase / Apoptosis / Antimicrobial activity
Source:Bioorganic and Medicinal Chemistry, 2015, 23, 21, 6930-6942
- Pergamon-Elsevier Science Ltd, Oxford
- Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids (RS-172055)
- This is the peer-reviewed version of the following article: Vilipić, J.; Novaković, I.; Stanojković, T.; Matić, I.; Šegan, D.; Kljajić, Z.; Sladić, D. Synthesis and Biological Activity of Amino Acid Derivatives of Avarone and Its Model Compound. Bioorganic and Medicinal Chemistry 2015, 23 (21), 6930–6942. https://doi.org/10.1016/j.bmc.2015.09.044