TY  - 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/123456789/3438
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 . .

TY  - DATA
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/123456789/3439
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Bioorganic and Medicinal Chemistry
T1  - Supplementary data for 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
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3439
ER  - 

@misc{
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",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Bioorganic and Medicinal Chemistry",
title = "Supplementary data for 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",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3439"
}

Vilipić, J., Novaković, I. T., Stanojković, T., Matić, I. Z., Šegan, D. M., Kljajić, Z.,& Sladić, D.. (2015). Supplementary data for 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. in Bioorganic and Medicinal Chemistry
Pergamon-Elsevier Science Ltd, Oxford..
https://hdl.handle.net/21.15107/rcub_cherry_3439

Vilipić J, Novaković IT, Stanojković T, Matić IZ, Šegan DM, Kljajić Z, Sladić D. Supplementary data for 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. in Bioorganic and Medicinal Chemistry. 2015;.
https://hdl.handle.net/21.15107/rcub_cherry_3439 .

Vilipić, Jovana, Novaković, Irena T., Stanojković, Tatjana, Matić, Ivana Z., Šegan, Dejan M., Kljajić, Zoran, Sladić, Dušan, "Supplementary data for 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" in Bioorganic and Medicinal Chemistry (2015),
https://hdl.handle.net/21.15107/rcub_cherry_3439 .

TY  - 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 . .

TY  - JOUR
AU  - Božić, Tatjana T.
AU  - Novaković, Irena T.
AU  - Gasic, Miroslav J.
AU  - Juranić, Zorica D.
AU  - Stanojković, Tatjana
AU  - Tufegdžić, Srđan
AU  - Kljajić, Zoran
AU  - Sladić, Dušan
PY  - 2010
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1057
AB  - Nine alkyl(aryl)thio derivatives of the marine sesquiterpene quinone avarone were synthesized by nucleophilic addition of thiols or thiophenol to avarone. In most cases only one regioisomer was obtained. Their cytotoxic activities, brine shrimp lethality and antibacterial activity were evaluated, as well as those of some previously synthesized avarone derivatives. Anti-HIV activity of two derivatives was tested. Electrochemical properties were determined for all the derivatives in Order to obtain more accurate information on structure-activity relationships. Most derivatives showed cytotoxic activity against tumor cell lines, with IC(50) values less than 10 mu M for some of them, in particular those with electron-donating substituents. The most active Compound was 4'-(methylamino)avarone, with IC(50) value of 2.4 mu M to melanoma Fem-X cells, and no cytotoxicity to normal lymphocytes. (C) 2009 Elsevier Masson SAS. All Fights reserved.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Synthesis and biological activity of derivatives of the marine quinone avarone
VL  - 45
IS  - 3
SP  - 923
EP  - 929
DO  - 10.1016/j.ejmech.2009.11.033
ER  - 

@article{
author = "Božić, Tatjana T. and Novaković, Irena T. and Gasic, Miroslav J. and Juranić, Zorica D. and Stanojković, Tatjana and Tufegdžić, Srđan and Kljajić, Zoran and Sladić, Dušan",
year = "2010",
abstract = "Nine alkyl(aryl)thio derivatives of the marine sesquiterpene quinone avarone were synthesized by nucleophilic addition of thiols or thiophenol to avarone. In most cases only one regioisomer was obtained. Their cytotoxic activities, brine shrimp lethality and antibacterial activity were evaluated, as well as those of some previously synthesized avarone derivatives. Anti-HIV activity of two derivatives was tested. Electrochemical properties were determined for all the derivatives in Order to obtain more accurate information on structure-activity relationships. Most derivatives showed cytotoxic activity against tumor cell lines, with IC(50) values less than 10 mu M for some of them, in particular those with electron-donating substituents. The most active Compound was 4'-(methylamino)avarone, with IC(50) value of 2.4 mu M to melanoma Fem-X cells, and no cytotoxicity to normal lymphocytes. (C) 2009 Elsevier Masson SAS. All Fights reserved.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Synthesis and biological activity of derivatives of the marine quinone avarone",
volume = "45",
number = "3",
pages = "923-929",
doi = "10.1016/j.ejmech.2009.11.033"
}

Božić, T. T., Novaković, I. T., Gasic, M. J., Juranić, Z. D., Stanojković, T., Tufegdžić, S., Kljajić, Z.,& Sladić, D.. (2010). Synthesis and biological activity of derivatives of the marine quinone avarone. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 45(3), 923-929.
https://doi.org/10.1016/j.ejmech.2009.11.033

Božić TT, Novaković IT, Gasic MJ, Juranić ZD, Stanojković T, Tufegdžić S, Kljajić Z, Sladić D. Synthesis and biological activity of derivatives of the marine quinone avarone. in European Journal of Medicinal Chemistry. 2010;45(3):923-929.
doi:10.1016/j.ejmech.2009.11.033 .

Božić, Tatjana T., Novaković, Irena T., Gasic, Miroslav J., Juranić, Zorica D., Stanojković, Tatjana, Tufegdžić, Srđan, Kljajić, Zoran, Sladić, Dušan, "Synthesis and biological activity of derivatives of the marine quinone avarone" in European Journal of Medicinal Chemistry, 45, no. 3 (2010):923-929,
https://doi.org/10.1016/j.ejmech.2009.11.033 . .