Synthesis and biological activity of amino acid derivatives of avarone and its model compound
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2015
Authors
Vilipić, JovanaNovaković, Irena T.
Stanojković, Tatjana
Matić, Ivana Z.
Šegan, Dejan M.
Kljajić, Zoran
Sladić, Dušan
Article (Published 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 activitySource:
Bioorganic and Medicinal Chemistry, 2015, 23, 21, 6930-6942Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Funding / projects:
- Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids (RS-MESTD-Basic Research (BR or ON)-172055)
Note:
- Peer-reviewed manuscript: http://cherry.chem.bg.ac.rs/handle/123456789/3438
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3439
DOI: 10.1016/j.bmc.2015.09.044
ISSN: 0968-0896
PubMed: 26476666
WoS: 000364437400016
Scopus: 2-s2.0-84946147820
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Vilipić, Jovana AU - Novaković, Irena T. AU - Stanojković, Tatjana AU - Matić, Ivana Z. AU - Šegan, Dejan M. AU - Kljajić, Zoran AU - Sladić, Dušan PY - 2015 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1997 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 T. and Stanojković, Tatjana and Matić, Ivana Z. and Šegan, Dejan M. and Kljajić, Zoran and Sladić, Dušan", year = "2015", 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. T., Stanojković, T., Matić, I. Z., Šegan, D. M., Kljajić, Z.,& Sladić, D.. (2015). Synthesis and biological activity of amino acid derivatives of avarone and its model compound. in 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 IT, Stanojković T, Matić IZ, Šegan DM, Kljajić Z, Sladić D. Synthesis and biological activity of amino acid derivatives of avarone and its model compound. in Bioorganic and Medicinal Chemistry. 2015;23(21):6930-6942. doi:10.1016/j.bmc.2015.09.044 .
Vilipić, Jovana, Novaković, Irena T., Stanojković, Tatjana, Matić, Ivana Z., Šegan, Dejan M., Kljajić, Zoran, Sladić, Dušan, "Synthesis and biological activity of amino acid derivatives of avarone and its model compound" in Bioorganic and Medicinal Chemistry, 23, no. 21 (2015):6930-6942, https://doi.org/10.1016/j.bmc.2015.09.044 . .