TY  - JOUR
AU  - Pavlović, Marijana
AU  - Kahrović, Emira
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Ilich, Predrag-Peter
AU  - Grgurić-Šipka, Sanja
AU  - Ljubijankić, Nevzeta
AU  - Žilić, Dijana
AU  - Jurec, Jurica
PY  - 2023
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5901
AB  - Novel ruthenium(III) complexes of general formula Na[
RuCl2(L1−3-N,O)2] where L(
1–3) denote deprotonated Schiff bases
(
HL1-HL3) derived from 5-substituted salicyladehyde and alkylamine (propyl- or butylamine) were prepared and characterized
based on elemental analysis, mass spectra, infrared, electron spin/paramagnetic resonance (ESR/EPR) spectroscopy,
and cyclovoltammetric study. Optimization of five isomers of complex C1 was done by DFT calculation. The interaction
of C1–C3 complexes with DNA (Deoxyribonucleic acid) and BSA (Bovine serum albumin) was investigated by electron
spectroscopy and fluorescence quenching. The cytotoxic activity of C1–C3 was investigated in a panel of four human cancer
cell lines (K562, A549, EA.hy926, MDA-MB-231) and one human non-tumor cell line (MRC-5). Complexes displayed an
apparent cytoselective profile, with IC50
values in the low micromolar range from 1.6 ± 0.3 to 23.0 ± 0.1 μM. Cisplatinresistant
triple-negative breast cancer cells MDA-MB-231 displayed the highest sensitivity to complexes, with Ru(III)
compound containing two chlorides and two deprotonated N-propyl-5-chloro-salicylidenimine (hereinafter C1) as the most
potent (
IC50 = 1.6 μM), and approximately ten times more active than cisplatin (
IC50 = 21.9 μM). MDA-MB-231 cells treated
for 24 h with C1 presented with apoptotic morphology, as seen by acridine orange/ethidium bromide staining, while 48 h of
treatment induced DNA fragmentation, and necrotic changes in cells, as seen by flow cytometry analysis. Drug-accumulation
study by inductively coupled plasma mass spectrometry (ICP-MS) demonstrated markedly higher intracellular accumulation
of C1 compared with cisplatin.
PB  - Springer
T2  - J. Biol. Inorg. Chem.
T1  - Tumor Selective Ru(III) Schiff Bases Complexes with Strong In Vitro Activity Toward Cisplatin-Resistant MDA-MB-231 Breast Cancer Cells
VL  - 28
SP  - 263
EP  - 284
DO  - 10.1007/s00775-023-01989-0
ER  - 

@article{
author = "Pavlović, Marijana and Kahrović, Emira and Aranđelović, Sandra and Radulović, Siniša and Ilich, Predrag-Peter and Grgurić-Šipka, Sanja and Ljubijankić, Nevzeta and Žilić, Dijana and Jurec, Jurica",
year = "2023",
abstract = "Novel ruthenium(III) complexes of general formula Na[
RuCl2(L1−3-N,O)2] where L(
1–3) denote deprotonated Schiff bases
(
HL1-HL3) derived from 5-substituted salicyladehyde and alkylamine (propyl- or butylamine) were prepared and characterized
based on elemental analysis, mass spectra, infrared, electron spin/paramagnetic resonance (ESR/EPR) spectroscopy,
and cyclovoltammetric study. Optimization of five isomers of complex C1 was done by DFT calculation. The interaction
of C1–C3 complexes with DNA (Deoxyribonucleic acid) and BSA (Bovine serum albumin) was investigated by electron
spectroscopy and fluorescence quenching. The cytotoxic activity of C1–C3 was investigated in a panel of four human cancer
cell lines (K562, A549, EA.hy926, MDA-MB-231) and one human non-tumor cell line (MRC-5). Complexes displayed an
apparent cytoselective profile, with IC50
values in the low micromolar range from 1.6 ± 0.3 to 23.0 ± 0.1 μM. Cisplatinresistant
triple-negative breast cancer cells MDA-MB-231 displayed the highest sensitivity to complexes, with Ru(III)
compound containing two chlorides and two deprotonated N-propyl-5-chloro-salicylidenimine (hereinafter C1) as the most
potent (
IC50 = 1.6 μM), and approximately ten times more active than cisplatin (
IC50 = 21.9 μM). MDA-MB-231 cells treated
for 24 h with C1 presented with apoptotic morphology, as seen by acridine orange/ethidium bromide staining, while 48 h of
treatment induced DNA fragmentation, and necrotic changes in cells, as seen by flow cytometry analysis. Drug-accumulation
study by inductively coupled plasma mass spectrometry (ICP-MS) demonstrated markedly higher intracellular accumulation
of C1 compared with cisplatin.",
publisher = "Springer",
journal = "J. Biol. Inorg. Chem.",
title = "Tumor Selective Ru(III) Schiff Bases Complexes with Strong In Vitro Activity Toward Cisplatin-Resistant MDA-MB-231 Breast Cancer Cells",
volume = "28",
pages = "263-284",
doi = "10.1007/s00775-023-01989-0"
}

Pavlović, M., Kahrović, E., Aranđelović, S., Radulović, S., Ilich, P., Grgurić-Šipka, S., Ljubijankić, N., Žilić, D.,& Jurec, J.. (2023). Tumor Selective Ru(III) Schiff Bases Complexes with Strong In Vitro Activity Toward Cisplatin-Resistant MDA-MB-231 Breast Cancer Cells. in J. Biol. Inorg. Chem.
Springer., 28, 263-284.
https://doi.org/10.1007/s00775-023-01989-0

Pavlović M, Kahrović E, Aranđelović S, Radulović S, Ilich P, Grgurić-Šipka S, Ljubijankić N, Žilić D, Jurec J. Tumor Selective Ru(III) Schiff Bases Complexes with Strong In Vitro Activity Toward Cisplatin-Resistant MDA-MB-231 Breast Cancer Cells. in J. Biol. Inorg. Chem.. 2023;28:263-284.
doi:10.1007/s00775-023-01989-0 .

Pavlović, Marijana, Kahrović, Emira, Aranđelović, Sandra, Radulović, Siniša, Ilich, Predrag-Peter, Grgurić-Šipka, Sanja, Ljubijankić, Nevzeta, Žilić, Dijana, Jurec, Jurica, "Tumor Selective Ru(III) Schiff Bases Complexes with Strong In Vitro Activity Toward Cisplatin-Resistant MDA-MB-231 Breast Cancer Cells" in J. Biol. Inorg. Chem., 28 (2023):263-284,
https://doi.org/10.1007/s00775-023-01989-0 . .

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 .