TY  - JOUR
AU  - Glamočlija, Una
AU  - Padhye, Subhash
AU  - Špirtović-Halilović, Selma
AU  - Osmanović, Amar
AU  - Veljović, Elma
AU  - Roca, Sunčica
AU  - Novaković, Irena T.
AU  - Mandić, Boris
AU  - Turel, Iztok
AU  - Kljun, Jakob
AU  - Trifunović, Snežana S.
AU  - Kahrović, Emira
AU  - Pavelić-Kraljević, Sandra
AU  - Harej, Anja
AU  - Klobučar, Marko
AU  - Završnik, Davorka
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2807
AB  - Thymoquinone (TQ), a natural compound with antimicrobial and antitumor activity, was used as the starting molecule for the preparation of 3-aminothymoquinone (ATQ) from which ten novel benzoxazole derivatives were prepared and characterized by elemental analysis, IR spectroscopy, mass spectrometry and NMR (1H,13C) spectroscopy in solution. The crystal structure of 4-methyl-2-phenyl-7-isopropyl-1,3-benzoxazole-5-ol (1a) has been determined by X-ray diffraction. All compounds were tested for their antibacterial, antifungal and antitumor activities. TQ and ATQ showed better antibacterial activity against tested Gram-positive and Gram-negative bacterial strains than benzoxazoles. ATQ had the most potent antifungal effect against Candida albicans, Saccharomyces cerevisiae and Aspergillus brasiliensis. Three benzoxazole derivatives and ATQ showed the highest antitumor activities. The most potent was 2-(4-fluorophenyl)-4-methyl-7-isopropyl-1,3-benzoxazole-5-ol (1f). Western blot analyses have shown that this compound inhibited phosphorylation of protein kinase B (Akt) and Insulin-like Growth Factor-1 Receptor (IGF1R β) in HeLa and HepG2 cells. The least toxic compound against normal fibroblast cells, which maintains similar antitumor activities as TQ, was 2-(4-chlorophenyl)-4-methyl-7-isopropyl-1,3-benzoxazole-5-ol (1e). Docking studies indicated that 1e and 1f have significant effects against selected receptors playing important roles in tumour survival.
PB  - MDPI
T2  - Molecules
T1  - Synthesis, biological evaluation and docking studies of benzoxazoles derived from thymoquinone
VL  - 23
IS  - 12
DO  - 10.3390/molecules23123297
ER  - 

@article{
author = "Glamočlija, Una and Padhye, Subhash and Špirtović-Halilović, Selma and Osmanović, Amar and Veljović, Elma and Roca, Sunčica and Novaković, Irena T. and Mandić, Boris and Turel, Iztok and Kljun, Jakob and Trifunović, Snežana S. and Kahrović, Emira and Pavelić-Kraljević, Sandra and Harej, Anja and Klobučar, Marko and Završnik, Davorka",
year = "2018",
abstract = "Thymoquinone (TQ), a natural compound with antimicrobial and antitumor activity, was used as the starting molecule for the preparation of 3-aminothymoquinone (ATQ) from which ten novel benzoxazole derivatives were prepared and characterized by elemental analysis, IR spectroscopy, mass spectrometry and NMR (1H,13C) spectroscopy in solution. The crystal structure of 4-methyl-2-phenyl-7-isopropyl-1,3-benzoxazole-5-ol (1a) has been determined by X-ray diffraction. All compounds were tested for their antibacterial, antifungal and antitumor activities. TQ and ATQ showed better antibacterial activity against tested Gram-positive and Gram-negative bacterial strains than benzoxazoles. ATQ had the most potent antifungal effect against Candida albicans, Saccharomyces cerevisiae and Aspergillus brasiliensis. Three benzoxazole derivatives and ATQ showed the highest antitumor activities. The most potent was 2-(4-fluorophenyl)-4-methyl-7-isopropyl-1,3-benzoxazole-5-ol (1f). Western blot analyses have shown that this compound inhibited phosphorylation of protein kinase B (Akt) and Insulin-like Growth Factor-1 Receptor (IGF1R β) in HeLa and HepG2 cells. The least toxic compound against normal fibroblast cells, which maintains similar antitumor activities as TQ, was 2-(4-chlorophenyl)-4-methyl-7-isopropyl-1,3-benzoxazole-5-ol (1e). Docking studies indicated that 1e and 1f have significant effects against selected receptors playing important roles in tumour survival.",
publisher = "MDPI",
journal = "Molecules",
title = "Synthesis, biological evaluation and docking studies of benzoxazoles derived from thymoquinone",
volume = "23",
number = "12",
doi = "10.3390/molecules23123297"
}

Glamočlija, U., Padhye, S., Špirtović-Halilović, S., Osmanović, A., Veljović, E., Roca, S., Novaković, I. T., Mandić, B., Turel, I., Kljun, J., Trifunović, S. S., Kahrović, E., Pavelić-Kraljević, S., Harej, A., Klobučar, M.,& Završnik, D.. (2018). Synthesis, biological evaluation and docking studies of benzoxazoles derived from thymoquinone. in Molecules
MDPI., 23(12).
https://doi.org/10.3390/molecules23123297

Glamočlija U, Padhye S, Špirtović-Halilović S, Osmanović A, Veljović E, Roca S, Novaković IT, Mandić B, Turel I, Kljun J, Trifunović SS, Kahrović E, Pavelić-Kraljević S, Harej A, Klobučar M, Završnik D. Synthesis, biological evaluation and docking studies of benzoxazoles derived from thymoquinone. in Molecules. 2018;23(12).
doi:10.3390/molecules23123297 .

Glamočlija, Una, Padhye, Subhash, Špirtović-Halilović, Selma, Osmanović, Amar, Veljović, Elma, Roca, Sunčica, Novaković, Irena T., Mandić, Boris, Turel, Iztok, Kljun, Jakob, Trifunović, Snežana S., Kahrović, Emira, Pavelić-Kraljević, Sandra, Harej, Anja, Klobučar, Marko, Završnik, Davorka, "Synthesis, biological evaluation and docking studies of benzoxazoles derived from thymoquinone" in Molecules, 23, no. 12 (2018),
https://doi.org/10.3390/molecules23123297 . .

TY  - DATA
AU  - Glamočlija, Una
AU  - Padhye, Subhash
AU  - Špirtović-Halilović, Selma
AU  - Osmanović, Amar
AU  - Veljović, Elma
AU  - Roca, Sunčica
AU  - Novaković, Irena T.
AU  - Mandić, Boris
AU  - Turel, Iztok
AU  - Kljun, Jakob
AU  - Trifunović, Snežana S.
AU  - Kahrović, Emira
AU  - Pavelić-Kraljević, Sandra
AU  - Harej, Anja
AU  - Klobučar, Marko
AU  - Završnik, Davorka
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3004
PB  - MDPI
T2  - Molecules
T1  - Supplementary material for the article: Glamočlija, U.; Padhye, S.; Špirtović-Halilović, S.; Osmanović, A.; Veljović, E.; Roca, S.;  Novaković, I.; Mandić, B.; Turel, I.; Kljun, J.; et al. Synthesis, Biological Evaluation and  Docking Studies of Benzoxazoles Derived from Thymoquinone. Molecules 2018, 23 (12).  https://doi.org/10.3390/molecules23123297
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3004
ER  - 

@misc{
author = "Glamočlija, Una and Padhye, Subhash and Špirtović-Halilović, Selma and Osmanović, Amar and Veljović, Elma and Roca, Sunčica and Novaković, Irena T. and Mandić, Boris and Turel, Iztok and Kljun, Jakob and Trifunović, Snežana S. and Kahrović, Emira and Pavelić-Kraljević, Sandra and Harej, Anja and Klobučar, Marko and Završnik, Davorka",
year = "2018",
publisher = "MDPI",
journal = "Molecules",
title = "Supplementary material for the article: Glamočlija, U.; Padhye, S.; Špirtović-Halilović, S.; Osmanović, A.; Veljović, E.; Roca, S.;  Novaković, I.; Mandić, B.; Turel, I.; Kljun, J.; et al. Synthesis, Biological Evaluation and  Docking Studies of Benzoxazoles Derived from Thymoquinone. Molecules 2018, 23 (12).  https://doi.org/10.3390/molecules23123297",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3004"
}

Glamočlija, U., Padhye, S., Špirtović-Halilović, S., Osmanović, A., Veljović, E., Roca, S., Novaković, I. T., Mandić, B., Turel, I., Kljun, J., Trifunović, S. S., Kahrović, E., Pavelić-Kraljević, S., Harej, A., Klobučar, M.,& Završnik, D.. (2018). Supplementary material for the article: Glamočlija, U.; Padhye, S.; Špirtović-Halilović, S.; Osmanović, A.; Veljović, E.; Roca, S.;  Novaković, I.; Mandić, B.; Turel, I.; Kljun, J.; et al. Synthesis, Biological Evaluation and  Docking Studies of Benzoxazoles Derived from Thymoquinone. Molecules 2018, 23 (12).  https://doi.org/10.3390/molecules23123297. in Molecules
MDPI..
https://hdl.handle.net/21.15107/rcub_cherry_3004

Glamočlija U, Padhye S, Špirtović-Halilović S, Osmanović A, Veljović E, Roca S, Novaković IT, Mandić B, Turel I, Kljun J, Trifunović SS, Kahrović E, Pavelić-Kraljević S, Harej A, Klobučar M, Završnik D. Supplementary material for the article: Glamočlija, U.; Padhye, S.; Špirtović-Halilović, S.; Osmanović, A.; Veljović, E.; Roca, S.;  Novaković, I.; Mandić, B.; Turel, I.; Kljun, J.; et al. Synthesis, Biological Evaluation and  Docking Studies of Benzoxazoles Derived from Thymoquinone. Molecules 2018, 23 (12).  https://doi.org/10.3390/molecules23123297. in Molecules. 2018;.
https://hdl.handle.net/21.15107/rcub_cherry_3004 .

Glamočlija, Una, Padhye, Subhash, Špirtović-Halilović, Selma, Osmanović, Amar, Veljović, Elma, Roca, Sunčica, Novaković, Irena T., Mandić, Boris, Turel, Iztok, Kljun, Jakob, Trifunović, Snežana S., Kahrović, Emira, Pavelić-Kraljević, Sandra, Harej, Anja, Klobučar, Marko, Završnik, Davorka, "Supplementary material for the article: Glamočlija, U.; Padhye, S.; Špirtović-Halilović, S.; Osmanović, A.; Veljović, E.; Roca, S.;  Novaković, I.; Mandić, B.; Turel, I.; Kljun, J.; et al. Synthesis, Biological Evaluation and  Docking Studies of Benzoxazoles Derived from Thymoquinone. Molecules 2018, 23 (12).  https://doi.org/10.3390/molecules23123297" in Molecules (2018),
https://hdl.handle.net/21.15107/rcub_cherry_3004 .

TY  - JOUR
AU  - Živković, Marija
AU  - Kljun, Jakob
AU  - Ilić-Tomić, Tatjana
AU  - Pavić, Aleksandar
AU  - Veselinovic, A.
AU  - Manojlović, Dragan D.
AU  - Nikodinović-Runić, Jasmina
AU  - Turel, Iztok
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2071
AB  - The anticancer potential of sixteen platinum(II) complexes with general formulae [PtCl(hq)(S-dmso)] (1a-8a) and [PtCl(hq)(pta)] (1b-8b) (where hq is 5-chloro-7-iodo-8-quinolinol (clioquinol; cqH) (1a, 1b), 8-hydroxy-5-nitroquinoline (nitroxoline; nxH) (2a, 2b), 5,7-dichloro-8-quinolinol (3a, 3b), 5,7-diiodo-8-quinolinol (4a, 4b), 5,7-dibromo-8-quinolinol (5a, 5b), 5,7-dichloro-8-hydroxy-2-methyl-quinoline (6a, 6b), 8-hydroxyquinoline (7a, 7b) and 8-quinolinethiol (8a, 8b); dmso is dimethyl sulfoxide and pta is 1,3,5triaza- 7-phosphaadamantane) was determined through in vitro cytotoxicity assay in human fibroblasts (MRC5) and two carcinoma cell lines (A375 and A549) and embryotoxicity assay in a zebrafish model. Interactions with double stranded DNA through in vitro assay and a molecular docking study were examined. All complexes, except 6a, exhibited a high cytotoxic effect on MRC5 cells at a concentration of 10 mu g mL(-1) while 1b, 5a, 6a and 3b showed selective toxicity towards carcinoma cell lines. In general, pta-based complexes (series b) were more toxic according to the results of a MTT screen and the LC50 values obtained in zebrafish (Danio rerio) assay; they also induced higher oxidative stress in this model. Successful cellular uptake of complexes was shown by the ICP-MS methodology. The binding propensity of the complex with DNA obtained in in silico studies can be correlated with those from the experimental investigation. Compounds with the highest binding potential, according to the interaction energy value, were 1b, 3b, 6b and 5b. From observations of the DNA interaction ability and of the in silico assessment, no apparent DNA fragmentation was observed either on DNA extracted from the treated cancer cell line or from the zebrafish embryos.
PB  - Royal Soc Chemistry, Cambridge
T2  - INORGANIC CHEMISTRY FRONTIERS
T1  - A new class of platinum(II) complexes with the phosphine ligand pta which show potent anticancer activity
VL  - 5
IS  - 1
SP  - 39
EP  - 53
DO  - 10.1039/c7qi00299h
ER  - 

@article{
author = "Živković, Marija and Kljun, Jakob and Ilić-Tomić, Tatjana and Pavić, Aleksandar and Veselinovic, A. and Manojlović, Dragan D. and Nikodinović-Runić, Jasmina and Turel, Iztok",
year = "2018",
abstract = "The anticancer potential of sixteen platinum(II) complexes with general formulae [PtCl(hq)(S-dmso)] (1a-8a) and [PtCl(hq)(pta)] (1b-8b) (where hq is 5-chloro-7-iodo-8-quinolinol (clioquinol; cqH) (1a, 1b), 8-hydroxy-5-nitroquinoline (nitroxoline; nxH) (2a, 2b), 5,7-dichloro-8-quinolinol (3a, 3b), 5,7-diiodo-8-quinolinol (4a, 4b), 5,7-dibromo-8-quinolinol (5a, 5b), 5,7-dichloro-8-hydroxy-2-methyl-quinoline (6a, 6b), 8-hydroxyquinoline (7a, 7b) and 8-quinolinethiol (8a, 8b); dmso is dimethyl sulfoxide and pta is 1,3,5triaza- 7-phosphaadamantane) was determined through in vitro cytotoxicity assay in human fibroblasts (MRC5) and two carcinoma cell lines (A375 and A549) and embryotoxicity assay in a zebrafish model. Interactions with double stranded DNA through in vitro assay and a molecular docking study were examined. All complexes, except 6a, exhibited a high cytotoxic effect on MRC5 cells at a concentration of 10 mu g mL(-1) while 1b, 5a, 6a and 3b showed selective toxicity towards carcinoma cell lines. In general, pta-based complexes (series b) were more toxic according to the results of a MTT screen and the LC50 values obtained in zebrafish (Danio rerio) assay; they also induced higher oxidative stress in this model. Successful cellular uptake of complexes was shown by the ICP-MS methodology. The binding propensity of the complex with DNA obtained in in silico studies can be correlated with those from the experimental investigation. Compounds with the highest binding potential, according to the interaction energy value, were 1b, 3b, 6b and 5b. From observations of the DNA interaction ability and of the in silico assessment, no apparent DNA fragmentation was observed either on DNA extracted from the treated cancer cell line or from the zebrafish embryos.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "INORGANIC CHEMISTRY FRONTIERS",
title = "A new class of platinum(II) complexes with the phosphine ligand pta which show potent anticancer activity",
volume = "5",
number = "1",
pages = "39-53",
doi = "10.1039/c7qi00299h"
}

Živković, M., Kljun, J., Ilić-Tomić, T., Pavić, A., Veselinovic, A., Manojlović, D. D., Nikodinović-Runić, J.,& Turel, I.. (2018). A new class of platinum(II) complexes with the phosphine ligand pta which show potent anticancer activity. in INORGANIC CHEMISTRY FRONTIERS
Royal Soc Chemistry, Cambridge., 5(1), 39-53.
https://doi.org/10.1039/c7qi00299h

Živković M, Kljun J, Ilić-Tomić T, Pavić A, Veselinovic A, Manojlović DD, Nikodinović-Runić J, Turel I. A new class of platinum(II) complexes with the phosphine ligand pta which show potent anticancer activity. in INORGANIC CHEMISTRY FRONTIERS. 2018;5(1):39-53.
doi:10.1039/c7qi00299h .

Živković, Marija, Kljun, Jakob, Ilić-Tomić, Tatjana, Pavić, Aleksandar, Veselinovic, A., Manojlović, Dragan D., Nikodinović-Runić, Jasmina, Turel, Iztok, "A new class of platinum(II) complexes with the phosphine ligand pta which show potent anticancer activity" in INORGANIC CHEMISTRY FRONTIERS, 5, no. 1 (2018):39-53,
https://doi.org/10.1039/c7qi00299h . .