2. Academic Validation
  3. Synthesis and biological activity of amino acid derivatives of avarone and its model compound

Synthesis and biological activity of amino acid derivatives of avarone and its model compound

  • Bioorg Med Chem. 2015 Nov 1;23(21):6930-42. doi: 10.1016/j.bmc.2015.09.044.
Jovana Vilipić 1,  Irena Novaković 2,  Tatjana Stanojković 3,  Ivana Matić 3,  Dejan Šegan 1,  Zoran Kljajić 4,  Dušan Sladić 5
Affiliations

Affiliations

  • 1 Faculty of Chemistry, University of Belgrade, Studentski trg 12-16, 11000 Belgrade, Serbia.
  • 2 Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Njegoševa 12, PO Box 815, 11000 Belgrade, Serbia.
  • 3 Institute of Oncology and Radiology, Pasterova 14, 11000 Belgrade, Serbia.
  • 4 Institute of Marine Biology-Kotor, University of Montenegro, Dobrota bb, 85330 Kotor, Montenegro.
  • 5 Faculty of Chemistry, University of Belgrade, Studentski trg 12-16, 11000 Belgrade, Serbia. Electronic address: dsladic@chem.bg.ac.rs.
PMID: 26476666 DOI: 10.1016/j.bmc.2015.09.044
Abstract

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, K562, MDA-MB-453) and normal MRC-5 cell line was determined. Several compounds showed very strong inhibitory activity with IC50 values less than 10 μM. 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-negative bacteria were determined, as well as Antifungal activity against three Fungal species.

Keywords

Amino acids; Antimicrobial activity; Apoptosis; Avarone; Caspase; Cytotoxicity.

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