TY  - JOUR
AU  - Vilipić, Jovana P.
AU  - Novaković, Irena
AU  - Zlatović, Mario
AU  - Vujčić, Miroslava
AU  - Tufegdžić, Srđan
AU  - Sladić, Dušan
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2049
AB  - The interactions of nine amino acid derivatives of tert-butylquinone with biomacromolecules were studied. Sodium dodecyl sulphate (SDS) gel electrophoresis and mass spectrometry confirmed the absence of modifications of lysozyme by any of the synthesized compounds. Spectrophotometric studies demonstrated hyperchromism, i.e., the existence of interactions between the quinones and calf thymus DNA (CT-DNA). Determination of the binding constants by absorption titration indicated weak interactions between the quinone derivatives and CT-DNA. The quenching of fluorescence of the intercalator ethidium bromide (EB) from the EB-CT-DNA system and of the minor groove binder Hoechst 33258 (H) from the H-CT-DNA system by the synthesized derivatives indicated interactions of the compounds and CT-DNA. Circular dichroism (CD) spectra demonstrated a non-intercalative binding mode of the quinone derivatives to CT-DNA. Molecular docking results confirmed binding to the minor groove. The electrophoretic pattern showed no cleavage of the pUC19 plasmid in the presence of any of the synthesized compounds. The ability of the derivatives to scavenge radicals was confirmed by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) test. All the presented results suggest that the DNA minor groove binding is the principal mechanism of action of the examined amino acid derivatives.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Interactions of cytotoxic amino acid derivatives of tert-butylquinone with DNA and lysozyme
VL  - 81
IS  - 12
SP  - 1345
EP  - 1358
DO  - 10.2298/JSC160725101V
ER  - 

@article{
author = "Vilipić, Jovana P. and Novaković, Irena and Zlatović, Mario and Vujčić, Miroslava and Tufegdžić, Srđan and Sladić, Dušan",
year = "2016",
abstract = "The interactions of nine amino acid derivatives of tert-butylquinone with biomacromolecules were studied. Sodium dodecyl sulphate (SDS) gel electrophoresis and mass spectrometry confirmed the absence of modifications of lysozyme by any of the synthesized compounds. Spectrophotometric studies demonstrated hyperchromism, i.e., the existence of interactions between the quinones and calf thymus DNA (CT-DNA). Determination of the binding constants by absorption titration indicated weak interactions between the quinone derivatives and CT-DNA. The quenching of fluorescence of the intercalator ethidium bromide (EB) from the EB-CT-DNA system and of the minor groove binder Hoechst 33258 (H) from the H-CT-DNA system by the synthesized derivatives indicated interactions of the compounds and CT-DNA. Circular dichroism (CD) spectra demonstrated a non-intercalative binding mode of the quinone derivatives to CT-DNA. Molecular docking results confirmed binding to the minor groove. The electrophoretic pattern showed no cleavage of the pUC19 plasmid in the presence of any of the synthesized compounds. The ability of the derivatives to scavenge radicals was confirmed by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) test. All the presented results suggest that the DNA minor groove binding is the principal mechanism of action of the examined amino acid derivatives.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Interactions of cytotoxic amino acid derivatives of tert-butylquinone with DNA and lysozyme",
volume = "81",
number = "12",
pages = "1345-1358",
doi = "10.2298/JSC160725101V"
}

Vilipić, J. P., Novaković, I., Zlatović, M., Vujčić, M., Tufegdžić, S.,& Sladić, D.. (2016). Interactions of cytotoxic amino acid derivatives of tert-butylquinone with DNA and lysozyme. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 81(12), 1345-1358.
https://doi.org/10.2298/JSC160725101V

Vilipić JP, Novaković I, Zlatović M, Vujčić M, Tufegdžić S, Sladić D. Interactions of cytotoxic amino acid derivatives of tert-butylquinone with DNA and lysozyme. in Journal of the Serbian Chemical Society. 2016;81(12):1345-1358.
doi:10.2298/JSC160725101V .

Vilipić, Jovana P., Novaković, Irena, Zlatović, Mario, Vujčić, Miroslava, Tufegdžić, Srđan, Sladić, Dušan, "Interactions of cytotoxic amino acid derivatives of tert-butylquinone with DNA and lysozyme" in Journal of the Serbian Chemical Society, 81, no. 12 (2016):1345-1358,
https://doi.org/10.2298/JSC160725101V . .

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  - https://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  - Oxford : Pergamon-Elsevier Science Ltd
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",
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 = "Oxford : Pergamon-Elsevier Science Ltd",
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. in Bioorganic and Medicinal Chemistry
Oxford : Pergamon-Elsevier Science Ltd., 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. in Bioorganic and Medicinal Chemistry. 2015;23(21):6930-6942.
doi:10.1016/j.bmc.2015.09.044 .

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" in Bioorganic and Medicinal Chemistry, 23, no. 21 (2015):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  - https://cer.ihtm.bg.ac.rs/handle/123456789/1822
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  - Oxford : Pergamon-Elsevier Science Ltd
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",
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 = "Oxford : Pergamon-Elsevier Science Ltd",
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. in Bioorganic and Medicinal Chemistry
Oxford : Pergamon-Elsevier Science Ltd., 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. in Bioorganic and Medicinal Chemistry. 2015;23(21):6930-6942.
doi:10.1016/j.bmc.2015.09.044 .

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" in Bioorganic and Medicinal Chemistry, 23, no. 21 (2015):6930-6942,
https://doi.org/10.1016/j.bmc.2015.09.044 . .

TY  - JOUR
AU  - Milenković, Milica R.
AU  - Bacchi, Alessia
AU  - Cantoni, Giulia
AU  - Vilipić, Jovana
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Gligorijević, Nevenka
AU  - Jovanovic, Katarina
AU  - Radulovic, Sinisa
AU  - Anđelković, Katarina
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1266
AB  - Three square-planar complexes of nickel(II) with the tridentate condensation derivative of 2-(diphenylphosphino)benzaldehyde and ethyl carbazate, and monodentate pseudohalides, have been synthesized. Their crystal structures have been determined. All the complexes showed a significant antifungal activity, while only the azido complex displayed antibacterial activity. All the complexes were cytotoxic to a panel of six tumor cell lines, the azido complex showing a similar activity as cisplatin to leukemia cell line K562 and lower toxicity to normal MRC-5 cells than that anticancer agent. The complexes interfered with cell cycle of tumor cells and induced plasmid DNA cleavage.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Synthesis, characterization and biological activity of three square-planar complexes of Ni(II) with ethyl (2E)-2-[2-(diphenylphosphino) benzylidene]hydrazinecarboxylate and monodentate pseudohalides
VL  - 68
SP  - 111
EP  - 120
DO  - 10.1016/j.ejmech.2013.07.039
ER  - 

@article{
author = "Milenković, Milica R. and Bacchi, Alessia and Cantoni, Giulia and Vilipić, Jovana and Sladić, Dušan and Vujčić, Miroslava and Gligorijević, Nevenka and Jovanovic, Katarina and Radulovic, Sinisa and Anđelković, Katarina",
year = "2013",
abstract = "Three square-planar complexes of nickel(II) with the tridentate condensation derivative of 2-(diphenylphosphino)benzaldehyde and ethyl carbazate, and monodentate pseudohalides, have been synthesized. Their crystal structures have been determined. All the complexes showed a significant antifungal activity, while only the azido complex displayed antibacterial activity. All the complexes were cytotoxic to a panel of six tumor cell lines, the azido complex showing a similar activity as cisplatin to leukemia cell line K562 and lower toxicity to normal MRC-5 cells than that anticancer agent. The complexes interfered with cell cycle of tumor cells and induced plasmid DNA cleavage.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Synthesis, characterization and biological activity of three square-planar complexes of Ni(II) with ethyl (2E)-2-[2-(diphenylphosphino) benzylidene]hydrazinecarboxylate and monodentate pseudohalides",
volume = "68",
pages = "111-120",
doi = "10.1016/j.ejmech.2013.07.039"
}

Milenković, M. R., Bacchi, A., Cantoni, G., Vilipić, J., Sladić, D., Vujčić, M., Gligorijević, N., Jovanovic, K., Radulovic, S.,& Anđelković, K.. (2013). Synthesis, characterization and biological activity of three square-planar complexes of Ni(II) with ethyl (2E)-2-[2-(diphenylphosphino) benzylidene]hydrazinecarboxylate and monodentate pseudohalides. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 68, 111-120.
https://doi.org/10.1016/j.ejmech.2013.07.039

Milenković MR, Bacchi A, Cantoni G, Vilipić J, Sladić D, Vujčić M, Gligorijević N, Jovanovic K, Radulovic S, Anđelković K. Synthesis, characterization and biological activity of three square-planar complexes of Ni(II) with ethyl (2E)-2-[2-(diphenylphosphino) benzylidene]hydrazinecarboxylate and monodentate pseudohalides. in European Journal of Medicinal Chemistry. 2013;68:111-120.
doi:10.1016/j.ejmech.2013.07.039 .

Milenković, Milica R., Bacchi, Alessia, Cantoni, Giulia, Vilipić, Jovana, Sladić, Dušan, Vujčić, Miroslava, Gligorijević, Nevenka, Jovanovic, Katarina, Radulovic, Sinisa, Anđelković, Katarina, "Synthesis, characterization and biological activity of three square-planar complexes of Ni(II) with ethyl (2E)-2-[2-(diphenylphosphino) benzylidene]hydrazinecarboxylate and monodentate pseudohalides" in European Journal of Medicinal Chemistry, 68 (2013):111-120,
https://doi.org/10.1016/j.ejmech.2013.07.039 . .