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.
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
TY - JOUR
AU - Vilipić, Jovana
AU - Novaković, Irena
AU - Stanojković, Tatjana
AU - Matić, Ivana Z.
AU - Šegan, Dejan
AU - Kljajić, Zoran
AU - Sladić, Dušan
PY - 2015
UR - http://cherry.chem.bg.ac.rs/handle/123456789/3438
UR - http://cer.ihtm.bg.ac.rs/handle/123456789/3141
AB - 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-negative bacteria were determined, as well as antifungal activity against three fungal species.
PB - Pergamon-Elsevier Science Ltd, Oxford
T2 - Bioorganic and Medicinal Chemistry
T1 - Synthesis and biological activity of amino acid derivatives of avarone and its model compound
VL - 23
IS - 21
SP - 6930
EP - 6942
DO - 10.1016/j.bmc.2015.09.044
ER -
@article{
author = "Vilipić, Jovana and Novaković, Irena and Stanojković, Tatjana and Matić, Ivana Z. and Šegan, Dejan and Kljajić, Zoran and Sladić, Dušan",
year = "2015",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3438, http://cer.ihtm.bg.ac.rs/handle/123456789/3141",
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, 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-negative bacteria were determined, as well as antifungal activity against three fungal species.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Bioorganic and Medicinal Chemistry",
title = "Synthesis and biological activity of amino acid derivatives of avarone and its model compound",
volume = "23",
number = "21",
pages = "6930-6942",
doi = "10.1016/j.bmc.2015.09.044"
}
Vilipić, J., Novaković, I., Stanojković, T., Matić, I. Z., Šegan, D., Kljajić, Z.,& Sladić, D. (2015). Synthesis and biological activity of amino acid derivatives of avarone and its model compound.
Bioorganic and Medicinal Chemistry
Pergamon-Elsevier Science Ltd, Oxford., 23(21), 6930-6942.
https://doi.org/10.1016/j.bmc.2015.09.044
Vilipić J, Novaković I, Stanojković T, Matić IZ, 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
Vilipić Jovana, Novaković Irena, Stanojković Tatjana, Matić Ivana Z., Šegan Dejan, Kljajić Zoran, Sladić Dušan, "Synthesis and biological activity of amino acid derivatives of avarone and its model compound" Bioorganic and Medicinal Chemistry, 23, no. 21 (2015):6930-6942,
https://doi.org/10.1016/j.bmc.2015.09.044 .
