Sladić, Dušan

Link to this page

Authority KeyName Variants
orcid::0000-0002-1000-9813
  • Sladić, Dušan (73)
Projects
Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids Biological response modifiers in physiological and pathological conditions
Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200026 (University of Belgrade, Institute of Chemistry, Technology and Metallurgy - IChTM) Interakcije prirodnih proizvoda i njihovih analoga sa proteinima i nukleinskim kiselinama
Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200168 (University of Belgrade, Faculty of Chemistry) Synthesis, modeling, physicochemical and biological properties of organic compounds and related metal complexes
Identification of predictive molecular markers for cancer progression, response to therapy and disease outcome Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200043 (Institute of Oncology and Radiology of Serbia, Belgrade)
Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200288 (Innovation Center of the Faculty of Chemistry) Pharmacodynamic and pharmacogenomic research of new drugs in the treatment of solid tumors
Slovenian Research Agency [P-0175] Sinteza, analiza i aktivnost novih organskih polidentatnih liganada i njihovih kompleksa sa d-metalima
Farmakodinamska i farmakogenetska istraživanja novih lekova i prediktivna/prognostička vrednost farmakoterapije u onkologiji TMMagCat - Tailoring Molecular Magnets and Catalysts Based on Transition Metal Complexes
Italian Ministry for Education, University and Research (MIUR, 2018-2022) Bioactive natural products as potential sources of new pharmaceuticals and food supplements
Project MESTD, br. 1586 Slovenian Research Agency (P1-0175)
COST Action CM1106 StemChem - "Chemical Approaches to Targeting Drug Resistance in Cancer Stem Cells" Deutscher Akademischer Austausch Dienst (DAAD)
European Commission Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research
Modeling and Numerical Simulations of Complex Many-Body Systems Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds
Design, synthesis, characterization and assessment of practical applications of coordination and organometallic compounds Structure-properties relationships of natural and synthetic molecules and their metal complexes
Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology Natural products of wild, cultivated and edible plants: structure and bioactivity determination
Brain plasticity in aging: effect of dietary restriction and anesthesia Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200007 (University of Belgrade, Institute for Biological Research 'Siniša Stanković')

Author's Bibliography

The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone

Stojičkov, Marko; Zlatar, Matija; Mazzeo, Paolo Pio; Bacchi, Alessia; Radanović, Dušanka; Stevanović, Nevena; Jevtović, Mima; Novaković, Irena; Anđelković, Katarina; Sladić, Dušan; Čobeljić, Božidar; Gruden, Maja

(Elsevier, 2023)

TY  - JOUR
AU  - Stojičkov, Marko
AU  - Zlatar, Matija
AU  - Mazzeo, Paolo Pio
AU  - Bacchi, Alessia
AU  - Radanović, Dušanka
AU  - Stevanović, Nevena
AU  - Jevtović, Mima
AU  - Novaković, Irena
AU  - Anđelković, Katarina
AU  - Sladić, Dušan
AU  - Čobeljić, Božidar
AU  - Gruden, Maja
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6041
AB  - Fe(III) and Mn(II) complexes with condensation product of thiosemicarbazide and 2-acetylthiazole (HL1, (E)-2-(1-(thiazol-2-yl)ethylidene)hydrazine-1-carbothioamide) have been synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy, and elemental analysis. In both complexes, the thiosemicarbazone ligand is coordinated in deprotonated form through the NNS donor set of atoms. However, while Fe(III) complex is in the doublet ground state with distorted octahedral geometry, the coordination environment around Mn(II) is distorted trigonal-prismatic, and the sextet state is found to be the ground state. DFT calculations were performed to rationalize spin state preferences, and continuous shape measure describes the deviation from ideal six-coordinated polyhedral geometries in the ground and excited states. Antimicrobial activity (against a panel of Gram-negative and Gram-positive bacteria, two yeast, and one fungal strain), brine shrimp assay, and DPPH radical scavenging activity of both complexes were evaluated, and these results relate to the electronic structure of the complexes.
PB  - Elsevier
T2  - Polyhedron
T1  - The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone
VL  - 237
SP  - 116389
DO  - 10.1016/j.poly.2023.116389
ER  - 
@article{
author = "Stojičkov, Marko and Zlatar, Matija and Mazzeo, Paolo Pio and Bacchi, Alessia and Radanović, Dušanka and Stevanović, Nevena and Jevtović, Mima and Novaković, Irena and Anđelković, Katarina and Sladić, Dušan and Čobeljić, Božidar and Gruden, Maja",
year = "2023",
abstract = "Fe(III) and Mn(II) complexes with condensation product of thiosemicarbazide and 2-acetylthiazole (HL1, (E)-2-(1-(thiazol-2-yl)ethylidene)hydrazine-1-carbothioamide) have been synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy, and elemental analysis. In both complexes, the thiosemicarbazone ligand is coordinated in deprotonated form through the NNS donor set of atoms. However, while Fe(III) complex is in the doublet ground state with distorted octahedral geometry, the coordination environment around Mn(II) is distorted trigonal-prismatic, and the sextet state is found to be the ground state. DFT calculations were performed to rationalize spin state preferences, and continuous shape measure describes the deviation from ideal six-coordinated polyhedral geometries in the ground and excited states. Antimicrobial activity (against a panel of Gram-negative and Gram-positive bacteria, two yeast, and one fungal strain), brine shrimp assay, and DPPH radical scavenging activity of both complexes were evaluated, and these results relate to the electronic structure of the complexes.",
publisher = "Elsevier",
journal = "Polyhedron",
title = "The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone",
volume = "237",
pages = "116389",
doi = "10.1016/j.poly.2023.116389"
}
Stojičkov, M., Zlatar, M., Mazzeo, P. P., Bacchi, A., Radanović, D., Stevanović, N., Jevtović, M., Novaković, I., Anđelković, K., Sladić, D., Čobeljić, B.,& Gruden, M.. (2023). The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone. in Polyhedron
Elsevier., 237, 116389.
https://doi.org/10.1016/j.poly.2023.116389
Stojičkov M, Zlatar M, Mazzeo PP, Bacchi A, Radanović D, Stevanović N, Jevtović M, Novaković I, Anđelković K, Sladić D, Čobeljić B, Gruden M. The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone. in Polyhedron. 2023;237:116389.
doi:10.1016/j.poly.2023.116389 .
Stojičkov, Marko, Zlatar, Matija, Mazzeo, Paolo Pio, Bacchi, Alessia, Radanović, Dušanka, Stevanović, Nevena, Jevtović, Mima, Novaković, Irena, Anđelković, Katarina, Sladić, Dušan, Čobeljić, Božidar, Gruden, Maja, "The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone" in Polyhedron, 237 (2023):116389,
https://doi.org/10.1016/j.poly.2023.116389 . .
1
1
1

The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone

Stojičkov, Marko; Zlatar, Matija; Mazzeo, Paolo Pio; Bacchi, Alessia; Radanović, Dušanka; Stevanović, Nevena; Jevtović, Mima; Novaković, Irena; Anđelković, Katarina; Sladić, Dušan; Čobeljić, Božidar; Gruden, Maja

(Elsevier, 2023)

TY  - JOUR
AU  - Stojičkov, Marko
AU  - Zlatar, Matija
AU  - Mazzeo, Paolo Pio
AU  - Bacchi, Alessia
AU  - Radanović, Dušanka
AU  - Stevanović, Nevena
AU  - Jevtović, Mima
AU  - Novaković, Irena
AU  - Anđelković, Katarina
AU  - Sladić, Dušan
AU  - Čobeljić, Božidar
AU  - Gruden, Maja
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6042
AB  - Fe(III) and Mn(II) complexes with condensation product of thiosemicarbazide and 2-acetylthiazole (HL1, (E)-2-(1-(thiazol-2-yl)ethylidene)hydrazine-1-carbothioamide) have been synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy, and elemental analysis. In both complexes, the thiosemicarbazone ligand is coordinated in deprotonated form through the NNS donor set of atoms. However, while Fe(III) complex is in the doublet ground state with distorted octahedral geometry, the coordination environment around Mn(II) is distorted trigonal-prismatic, and the sextet state is found to be the ground state. DFT calculations were performed to rationalize spin state preferences, and continuous shape measure describes the deviation from ideal six-coordinated polyhedral geometries in the ground and excited states. Antimicrobial activity (against a panel of Gram-negative and Gram-positive bacteria, two yeast, and one fungal strain), brine shrimp assay, and DPPH radical scavenging activity of both complexes were evaluated, and these results relate to the electronic structure of the complexes.
PB  - Elsevier
T2  - Polyhedron
T1  - The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone
VL  - 237
SP  - 116389
DO  - 10.1016/j.poly.2023.116389
ER  - 
@article{
author = "Stojičkov, Marko and Zlatar, Matija and Mazzeo, Paolo Pio and Bacchi, Alessia and Radanović, Dušanka and Stevanović, Nevena and Jevtović, Mima and Novaković, Irena and Anđelković, Katarina and Sladić, Dušan and Čobeljić, Božidar and Gruden, Maja",
year = "2023",
abstract = "Fe(III) and Mn(II) complexes with condensation product of thiosemicarbazide and 2-acetylthiazole (HL1, (E)-2-(1-(thiazol-2-yl)ethylidene)hydrazine-1-carbothioamide) have been synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy, and elemental analysis. In both complexes, the thiosemicarbazone ligand is coordinated in deprotonated form through the NNS donor set of atoms. However, while Fe(III) complex is in the doublet ground state with distorted octahedral geometry, the coordination environment around Mn(II) is distorted trigonal-prismatic, and the sextet state is found to be the ground state. DFT calculations were performed to rationalize spin state preferences, and continuous shape measure describes the deviation from ideal six-coordinated polyhedral geometries in the ground and excited states. Antimicrobial activity (against a panel of Gram-negative and Gram-positive bacteria, two yeast, and one fungal strain), brine shrimp assay, and DPPH radical scavenging activity of both complexes were evaluated, and these results relate to the electronic structure of the complexes.",
publisher = "Elsevier",
journal = "Polyhedron",
title = "The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone",
volume = "237",
pages = "116389",
doi = "10.1016/j.poly.2023.116389"
}
Stojičkov, M., Zlatar, M., Mazzeo, P. P., Bacchi, A., Radanović, D., Stevanović, N., Jevtović, M., Novaković, I., Anđelković, K., Sladić, D., Čobeljić, B.,& Gruden, M.. (2023). The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone. in Polyhedron
Elsevier., 237, 116389.
https://doi.org/10.1016/j.poly.2023.116389
Stojičkov M, Zlatar M, Mazzeo PP, Bacchi A, Radanović D, Stevanović N, Jevtović M, Novaković I, Anđelković K, Sladić D, Čobeljić B, Gruden M. The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone. in Polyhedron. 2023;237:116389.
doi:10.1016/j.poly.2023.116389 .
Stojičkov, Marko, Zlatar, Matija, Mazzeo, Paolo Pio, Bacchi, Alessia, Radanović, Dušanka, Stevanović, Nevena, Jevtović, Mima, Novaković, Irena, Anđelković, Katarina, Sladić, Dušan, Čobeljić, Božidar, Gruden, Maja, "The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone" in Polyhedron, 237 (2023):116389,
https://doi.org/10.1016/j.poly.2023.116389 . .
1
1
1

Electronic Supplementary Information (ESI) for: "The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone"

Stojičkov, Marko; Zlatar, Matija; Mazzeo, Paolo Pio; Bacchi, Alessia; Radanović, Dušanka; Stevanović, Nevena; Jevtović, Mima; Novaković, Irena; Anđelković, Katarina; Sladić, Dušan; Čobeljić, Božidar; Gruden, Maja

(Elsevier, 2023)

TY  - DATA
AU  - Stojičkov, Marko
AU  - Zlatar, Matija
AU  - Mazzeo, Paolo Pio
AU  - Bacchi, Alessia
AU  - Radanović, Dušanka
AU  - Stevanović, Nevena
AU  - Jevtović, Mima
AU  - Novaković, Irena
AU  - Anđelković, Katarina
AU  - Sladić, Dušan
AU  - Čobeljić, Božidar
AU  - Gruden, Maja
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6043
AB  - Fe(III) and Mn(II) complexes with condensation product of thiosemicarbazide and 2-acetylthiazole (HL1, (E)-2-(1-(thiazol-2-yl)ethylidene)hydrazine-1-carbothioamide) have been synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy, and elemental analysis. In both complexes, the thiosemicarbazone ligand is coordinated in deprotonated form through the NNS donor set of atoms. However, while Fe(III) complex is in the doublet ground state with distorted octahedral geometry, the coordination environment around Mn(II) is distorted trigonal-prismatic, and the sextet state is found to be the ground state. DFT calculations were performed to rationalize spin state preferences, and continuous shape measure describes the deviation from ideal six-coordinated polyhedral geometries in the ground and excited states. Antimicrobial activity (against a panel of Gram-negative and Gram-positive bacteria, two yeast, and one fungal strain), brine shrimp assay, and DPPH radical scavenging activity of both complexes were evaluated, and these results relate to the electronic structure of the complexes.
AB  - Additional crystallographic  and computational results, and the Cartesian coordinates of all DFT  optimized structures
PB  - Elsevier
T2  - Polyhedron
T1  - Electronic Supplementary Information (ESI) for: "The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone"
UR  - https://hdl.handle.net/21.15107/rcub_cer_6043
ER  - 
@misc{
author = "Stojičkov, Marko and Zlatar, Matija and Mazzeo, Paolo Pio and Bacchi, Alessia and Radanović, Dušanka and Stevanović, Nevena and Jevtović, Mima and Novaković, Irena and Anđelković, Katarina and Sladić, Dušan and Čobeljić, Božidar and Gruden, Maja",
year = "2023",
abstract = "Fe(III) and Mn(II) complexes with condensation product of thiosemicarbazide and 2-acetylthiazole (HL1, (E)-2-(1-(thiazol-2-yl)ethylidene)hydrazine-1-carbothioamide) have been synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy, and elemental analysis. In both complexes, the thiosemicarbazone ligand is coordinated in deprotonated form through the NNS donor set of atoms. However, while Fe(III) complex is in the doublet ground state with distorted octahedral geometry, the coordination environment around Mn(II) is distorted trigonal-prismatic, and the sextet state is found to be the ground state. DFT calculations were performed to rationalize spin state preferences, and continuous shape measure describes the deviation from ideal six-coordinated polyhedral geometries in the ground and excited states. Antimicrobial activity (against a panel of Gram-negative and Gram-positive bacteria, two yeast, and one fungal strain), brine shrimp assay, and DPPH radical scavenging activity of both complexes were evaluated, and these results relate to the electronic structure of the complexes., Additional crystallographic  and computational results, and the Cartesian coordinates of all DFT  optimized structures",
publisher = "Elsevier",
journal = "Polyhedron",
title = "Electronic Supplementary Information (ESI) for: "The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone"",
url = "https://hdl.handle.net/21.15107/rcub_cer_6043"
}
Stojičkov, M., Zlatar, M., Mazzeo, P. P., Bacchi, A., Radanović, D., Stevanović, N., Jevtović, M., Novaković, I., Anđelković, K., Sladić, D., Čobeljić, B.,& Gruden, M.. (2023). Electronic Supplementary Information (ESI) for: "The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone". in Polyhedron
Elsevier..
https://hdl.handle.net/21.15107/rcub_cer_6043
Stojičkov M, Zlatar M, Mazzeo PP, Bacchi A, Radanović D, Stevanović N, Jevtović M, Novaković I, Anđelković K, Sladić D, Čobeljić B, Gruden M. Electronic Supplementary Information (ESI) for: "The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone". in Polyhedron. 2023;.
https://hdl.handle.net/21.15107/rcub_cer_6043 .
Stojičkov, Marko, Zlatar, Matija, Mazzeo, Paolo Pio, Bacchi, Alessia, Radanović, Dušanka, Stevanović, Nevena, Jevtović, Mima, Novaković, Irena, Anđelković, Katarina, Sladić, Dušan, Čobeljić, Božidar, Gruden, Maja, "Electronic Supplementary Information (ESI) for: "The interplay between spin states, geometries and biological activity of Fe(III) and Mn(II) complexes with thiosemicarbazone"" in Polyhedron (2023),
https://hdl.handle.net/21.15107/rcub_cer_6043 .

Carbohydrate binding polypeptide of Savalia Savaglia

Andjelković, Uroš; Sladić, Dušan; Vukasinović, Ivana; Lah, Jurij; Fonovic, Marko

(The World Intellectual Property Organization, 2023)

TY  - PAT
AU  - Andjelković, Uroš
AU  - Sladić, Dušan
AU  - Vukasinović, Ivana
AU  - Lah, Jurij
AU  - Fonovic, Marko
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6941
AB  - The present invention relates to a novel polypeptide which displays specific carbohydrate binding activity, particularly against glycans that contain mannose, and in vivo and ex vivo methods of use thereof. Methods of use comprise administering a polypeptide of the invention, for example to a sample or a subject in which carbohydrate is present, under conditions suitable for the polypeptide to bind the carbohydrate. The carbohydrate may be expressed by a pathogen. The invention relates to polypeptides and compositions thereof with anti-pathogen activity, such as anti-viral, anti-bacterial, anti-fungal or anti-tumour activity. Also provided are methods for the prevention or treatment of diseases and conditions mediated by pathogens which express carbohydrate, for example as glycoproteins.
PB  - The World Intellectual Property Organization
T2  - The World Intellectual Property Organization
T1  - Carbohydrate binding polypeptide of Savalia Savaglia
IS  - WO20230552505A1
UR  - https://hdl.handle.net/21.15107/rcub_cer_6941
ER  - 
@misc{
author = "Andjelković, Uroš and Sladić, Dušan and Vukasinović, Ivana and Lah, Jurij and Fonovic, Marko",
year = "2023",
abstract = "The present invention relates to a novel polypeptide which displays specific carbohydrate binding activity, particularly against glycans that contain mannose, and in vivo and ex vivo methods of use thereof. Methods of use comprise administering a polypeptide of the invention, for example to a sample or a subject in which carbohydrate is present, under conditions suitable for the polypeptide to bind the carbohydrate. The carbohydrate may be expressed by a pathogen. The invention relates to polypeptides and compositions thereof with anti-pathogen activity, such as anti-viral, anti-bacterial, anti-fungal or anti-tumour activity. Also provided are methods for the prevention or treatment of diseases and conditions mediated by pathogens which express carbohydrate, for example as glycoproteins.",
publisher = "The World Intellectual Property Organization",
journal = "The World Intellectual Property Organization",
title = "Carbohydrate binding polypeptide of Savalia Savaglia",
number = "WO20230552505A1",
url = "https://hdl.handle.net/21.15107/rcub_cer_6941"
}
Andjelković, U., Sladić, D., Vukasinović, I., Lah, J.,& Fonovic, M.. (2023). Carbohydrate binding polypeptide of Savalia Savaglia. in The World Intellectual Property Organization
The World Intellectual Property Organization.(WO20230552505A1).
https://hdl.handle.net/21.15107/rcub_cer_6941
Andjelković U, Sladić D, Vukasinović I, Lah J, Fonovic M. Carbohydrate binding polypeptide of Savalia Savaglia. in The World Intellectual Property Organization. 2023;(WO20230552505A1).
https://hdl.handle.net/21.15107/rcub_cer_6941 .
Andjelković, Uroš, Sladić, Dušan, Vukasinović, Ivana, Lah, Jurij, Fonovic, Marko, "Carbohydrate binding polypeptide of Savalia Savaglia" in The World Intellectual Property Organization, no. WO20230552505A1 (2023),
https://hdl.handle.net/21.15107/rcub_cer_6941 .

Evaluation of antitumor potential of Cu(II) complex withhydrazone of 2-acetylthiazole and Girard’s T reagent

Stevanović, Nevena; Jevtović, Mima; Mitić, Dragana; Matić, Ivana Z.; Crnogorac, Marija; Vujčić, Miroslava; Sladić, Dušan; Čobeljić, Božidar; Anđelković, Katarina

(Beograd : Srpsko hemijsko društvo, 2022)

TY  - JOUR
AU  - Stevanović, Nevena
AU  - Jevtović, Mima
AU  - Mitić, Dragana
AU  - Matić, Ivana Z.
AU  - Crnogorac, Marija
AU  - Vujčić, Miroslava
AU  - Sladić, Dušan
AU  - Čobeljić, Božidar
AU  - Anđelković, Katarina
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5230
AB  - In this paper, the previously synthesized Cu(II) complex ([CuL1(N3) (CH3OH)]BF4) with N,N,N-trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride, has been characterized and its biological activity has been studied in detail. The Cu(II) complex consists of ligand coordinated in a deprotonated, formally neutral zwitter-ionic form, via NNO atoms, one azido ligand and one methanol molecule. The Cu(II) complex was selected due to results of the cytotoxic activity, the brine shrimp test and DPPH radical scavenging activity, which were previously performed. The effects of Cu(II) complex on cell cycle phase distribution of cervical adenocarcinoma HeLa cells were investigated in order to examine the mechanisms of its anticancer activity. The measurement of intracellular ROS levels in HeLa and HaCaT cell lines were evaluated in order to explore their possible generation and the role in cytotoxic activity. The possible anti-invasive and anti-angiogenic properties of Cu(II) complex were evaluated. DNA binding experiments, including fluorescence displacement study and DNA cleavage experiments, were performed in order to obtain information on the type of DNA-metal complex interactions. © 2022 Serbian Chemical Society. All rights reserved.
PB  - Beograd : Srpsko hemijsko društvo
T2  - Journal of the Serbian Chemical Society
T1  - Evaluation of antitumor potential of Cu(II) complex withhydrazone of 2-acetylthiazole and Girard’s T reagent
VL  - 87
IS  - 2
SP  - 181
EP  - 192
DO  - 10.2298/JSC211203114S
ER  - 
@article{
author = "Stevanović, Nevena and Jevtović, Mima and Mitić, Dragana and Matić, Ivana Z. and Crnogorac, Marija and Vujčić, Miroslava and Sladić, Dušan and Čobeljić, Božidar and Anđelković, Katarina",
year = "2022",
abstract = "In this paper, the previously synthesized Cu(II) complex ([CuL1(N3) (CH3OH)]BF4) with N,N,N-trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride, has been characterized and its biological activity has been studied in detail. The Cu(II) complex consists of ligand coordinated in a deprotonated, formally neutral zwitter-ionic form, via NNO atoms, one azido ligand and one methanol molecule. The Cu(II) complex was selected due to results of the cytotoxic activity, the brine shrimp test and DPPH radical scavenging activity, which were previously performed. The effects of Cu(II) complex on cell cycle phase distribution of cervical adenocarcinoma HeLa cells were investigated in order to examine the mechanisms of its anticancer activity. The measurement of intracellular ROS levels in HeLa and HaCaT cell lines were evaluated in order to explore their possible generation and the role in cytotoxic activity. The possible anti-invasive and anti-angiogenic properties of Cu(II) complex were evaluated. DNA binding experiments, including fluorescence displacement study and DNA cleavage experiments, were performed in order to obtain information on the type of DNA-metal complex interactions. © 2022 Serbian Chemical Society. All rights reserved.",
publisher = "Beograd : Srpsko hemijsko društvo",
journal = "Journal of the Serbian Chemical Society",
title = "Evaluation of antitumor potential of Cu(II) complex withhydrazone of 2-acetylthiazole and Girard’s T reagent",
volume = "87",
number = "2",
pages = "181-192",
doi = "10.2298/JSC211203114S"
}
Stevanović, N., Jevtović, M., Mitić, D., Matić, I. Z., Crnogorac, M., Vujčić, M., Sladić, D., Čobeljić, B.,& Anđelković, K.. (2022). Evaluation of antitumor potential of Cu(II) complex withhydrazone of 2-acetylthiazole and Girard’s T reagent. in Journal of the Serbian Chemical Society
Beograd : Srpsko hemijsko društvo., 87(2), 181-192.
https://doi.org/10.2298/JSC211203114S
Stevanović N, Jevtović M, Mitić D, Matić IZ, Crnogorac M, Vujčić M, Sladić D, Čobeljić B, Anđelković K. Evaluation of antitumor potential of Cu(II) complex withhydrazone of 2-acetylthiazole and Girard’s T reagent. in Journal of the Serbian Chemical Society. 2022;87(2):181-192.
doi:10.2298/JSC211203114S .
Stevanović, Nevena, Jevtović, Mima, Mitić, Dragana, Matić, Ivana Z., Crnogorac, Marija, Vujčić, Miroslava, Sladić, Dušan, Čobeljić, Božidar, Anđelković, Katarina, "Evaluation of antitumor potential of Cu(II) complex withhydrazone of 2-acetylthiazole and Girard’s T reagent" in Journal of the Serbian Chemical Society, 87, no. 2 (2022):181-192,
https://doi.org/10.2298/JSC211203114S . .
1
1

Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity

Stevanović, Nevena; Zlatar, Matija; Novaković, Irena; Pevec, Andrej; Radanović, Dušanka; Matić, Ivana Z.; Đorđić Crnogorac, Marija; Stanojković, Tatjana; Vujčić, Miroslava; Gruden, Maja; Sladić, Dušan; Anđelković, Katarina; Turel, Iztok; Čobeljić, Božidar

(Royal Society of Chemistry (RSC), 2022)

TY  - JOUR
AU  - Stevanović, Nevena
AU  - Zlatar, Matija
AU  - Novaković, Irena
AU  - Pevec, Andrej
AU  - Radanović, Dušanka
AU  - Matić, Ivana Z.
AU  - Đorđić Crnogorac, Marija
AU  - Stanojković, Tatjana
AU  - Vujčić, Miroslava
AU  - Gruden, Maja
AU  - Sladić, Dušan
AU  - Anđelković, Katarina
AU  - Turel, Iztok
AU  - Čobeljić, Božidar
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4901
AB  - In this paper, Cu(II), Mn(II) and Zn(II) complexes with N,N,N-trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride (HL1Cl) were synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy, elemental analysis and DFT calculations. In all three complexes, a ligand (L1) is coordinated in a deprotonated formally neutral zwitterionic form via NNO donor set atoms. Cu(II) and Zn(II) form mononuclear penta-coordinated complexes [CuL1(N3)(CH3OH)]BF4 and [ZnL1(N3)2], respectively, while Mn(II) forms a binuclear [Mn2L12(μ-1,1-N3)2(N3)2]·2CH3OH complex, with unusual distorted trigonal-prismatic geometry around the metal centers. The antimicrobial activity of these complexes was tested against a panel of Gram-negative and Gram-positive bacteria, two yeasts and one fungal strain. The binuclear Mn(II) complex showed antifungal activity of similar intensity to amphotericin B. Based on the results of the brine shrimp test and DPPH radical scavenging activity, the most active Cu(II) and Mn(II) complexes were selected for evaluation of cytotoxic activity against five malignant cancer cell lines (HeLa, A375, MCF7, PC-3 and A549) and one normal cell line HaCaT. Both complexes showed significant activity. It should be pointed out that the activity of the Mn(II) complex against the MCF7 breast cancer cell line is only slightly weaker than that of cisplatin, but with selectivity to the tumor cell line in comparison to normal HaCaT cells, which is non-existent in the case of cisplatin.
PB  - Royal Society of Chemistry (RSC)
T2  - Dalton Transactions
T1  - Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity
VL  - 51
IS  - 1
SP  - 185
EP  - 196
DO  - 10.1039/D1DT03169D
ER  - 
@article{
author = "Stevanović, Nevena and Zlatar, Matija and Novaković, Irena and Pevec, Andrej and Radanović, Dušanka and Matić, Ivana Z. and Đorđić Crnogorac, Marija and Stanojković, Tatjana and Vujčić, Miroslava and Gruden, Maja and Sladić, Dušan and Anđelković, Katarina and Turel, Iztok and Čobeljić, Božidar",
year = "2022",
abstract = "In this paper, Cu(II), Mn(II) and Zn(II) complexes with N,N,N-trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride (HL1Cl) were synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy, elemental analysis and DFT calculations. In all three complexes, a ligand (L1) is coordinated in a deprotonated formally neutral zwitterionic form via NNO donor set atoms. Cu(II) and Zn(II) form mononuclear penta-coordinated complexes [CuL1(N3)(CH3OH)]BF4 and [ZnL1(N3)2], respectively, while Mn(II) forms a binuclear [Mn2L12(μ-1,1-N3)2(N3)2]·2CH3OH complex, with unusual distorted trigonal-prismatic geometry around the metal centers. The antimicrobial activity of these complexes was tested against a panel of Gram-negative and Gram-positive bacteria, two yeasts and one fungal strain. The binuclear Mn(II) complex showed antifungal activity of similar intensity to amphotericin B. Based on the results of the brine shrimp test and DPPH radical scavenging activity, the most active Cu(II) and Mn(II) complexes were selected for evaluation of cytotoxic activity against five malignant cancer cell lines (HeLa, A375, MCF7, PC-3 and A549) and one normal cell line HaCaT. Both complexes showed significant activity. It should be pointed out that the activity of the Mn(II) complex against the MCF7 breast cancer cell line is only slightly weaker than that of cisplatin, but with selectivity to the tumor cell line in comparison to normal HaCaT cells, which is non-existent in the case of cisplatin.",
publisher = "Royal Society of Chemistry (RSC)",
journal = "Dalton Transactions",
title = "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity",
volume = "51",
number = "1",
pages = "185-196",
doi = "10.1039/D1DT03169D"
}
Stevanović, N., Zlatar, M., Novaković, I., Pevec, A., Radanović, D., Matić, I. Z., Đorđić Crnogorac, M., Stanojković, T., Vujčić, M., Gruden, M., Sladić, D., Anđelković, K., Turel, I.,& Čobeljić, B.. (2022). Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity. in Dalton Transactions
Royal Society of Chemistry (RSC)., 51(1), 185-196.
https://doi.org/10.1039/D1DT03169D
Stevanović N, Zlatar M, Novaković I, Pevec A, Radanović D, Matić IZ, Đorđić Crnogorac M, Stanojković T, Vujčić M, Gruden M, Sladić D, Anđelković K, Turel I, Čobeljić B. Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity. in Dalton Transactions. 2022;51(1):185-196.
doi:10.1039/D1DT03169D .
Stevanović, Nevena, Zlatar, Matija, Novaković, Irena, Pevec, Andrej, Radanović, Dušanka, Matić, Ivana Z., Đorđić Crnogorac, Marija, Stanojković, Tatjana, Vujčić, Miroslava, Gruden, Maja, Sladić, Dušan, Anđelković, Katarina, Turel, Iztok, Čobeljić, Božidar, "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity" in Dalton Transactions, 51, no. 1 (2022):185-196,
https://doi.org/10.1039/D1DT03169D . .
11
15
1
12

Supporting information for: "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity"

Stevanović, Nevena; Zlatar, Matija; Novaković, Irena; Pevec, Andrej; Radanović, Dušanka; Matić, Ivana Z.; Đorđić Crnogorac, Marija; Stanojković, Tatjana; Vujčić, Miroslava; Gruden, Maja; Sladić, Dušan; Anđelković, Katarina; Turel, Iztok; Čobeljić, Božidar

(Royal Society of Chemistry (RSC), 2022)

TY  - DATA
AU  - Stevanović, Nevena
AU  - Zlatar, Matija
AU  - Novaković, Irena
AU  - Pevec, Andrej
AU  - Radanović, Dušanka
AU  - Matić, Ivana Z.
AU  - Đorđić Crnogorac, Marija
AU  - Stanojković, Tatjana
AU  - Vujčić, Miroslava
AU  - Gruden, Maja
AU  - Sladić, Dušan
AU  - Anđelković, Katarina
AU  - Turel, Iztok
AU  - Čobeljić, Božidar
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4902
AB  - In this paper, Cu(II), Mn(II) and Zn(II) complexes with N,N,N-trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride (HL1Cl) were synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy, elemental analysis and DFT calculations. In all three complexes, a ligand (L1) is coordinated in a deprotonated formally neutral zwitterionic form via NNO donor set atoms. Cu(II) and Zn(II) form mononuclear penta-coordinated complexes [CuL1(N3)(CH3OH)]BF4 and [ZnL1(N3)2], respectively, while Mn(II) forms a binuclear [Mn2L12(μ-1,1-N3)2(N3)2]·2CH3OH complex, with unusual distorted trigonal-prismatic geometry around the metal centers. The antimicrobial activity of these complexes was tested against a panel of Gram-negative and Gram-positive bacteria, two yeasts and one fungal strain. The binuclear Mn(II) complex showed antifungal activity of similar intensity to amphotericin B. Based on the results of the brine shrimp test and DPPH radical scavenging activity, the most active Cu(II) and Mn(II) complexes were selected for evaluation of cytotoxic activity against five malignant cancer cell lines (HeLa, A375, MCF7, PC-3 and A549) and one normal cell line HaCaT. Both complexes showed significant activity. It should be pointed out that the activity of the Mn(II) complex against the MCF7 breast cancer cell line is only slightly weaker than that of cisplatin, but with selectivity to the tumor cell line in comparison to normal HaCaT cells, which is non-existent in the case of cisplatin.
PB  - Royal Society of Chemistry (RSC)
T2  - Dalton Transactions
T1  - Supporting information for: "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity"
UR  - https://hdl.handle.net/21.15107/rcub_cherry_4858
ER  - 
@misc{
author = "Stevanović, Nevena and Zlatar, Matija and Novaković, Irena and Pevec, Andrej and Radanović, Dušanka and Matić, Ivana Z. and Đorđić Crnogorac, Marija and Stanojković, Tatjana and Vujčić, Miroslava and Gruden, Maja and Sladić, Dušan and Anđelković, Katarina and Turel, Iztok and Čobeljić, Božidar",
year = "2022",
abstract = "In this paper, Cu(II), Mn(II) and Zn(II) complexes with N,N,N-trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride (HL1Cl) were synthesized and characterized by single-crystal X-ray diffraction, IR spectroscopy, elemental analysis and DFT calculations. In all three complexes, a ligand (L1) is coordinated in a deprotonated formally neutral zwitterionic form via NNO donor set atoms. Cu(II) and Zn(II) form mononuclear penta-coordinated complexes [CuL1(N3)(CH3OH)]BF4 and [ZnL1(N3)2], respectively, while Mn(II) forms a binuclear [Mn2L12(μ-1,1-N3)2(N3)2]·2CH3OH complex, with unusual distorted trigonal-prismatic geometry around the metal centers. The antimicrobial activity of these complexes was tested against a panel of Gram-negative and Gram-positive bacteria, two yeasts and one fungal strain. The binuclear Mn(II) complex showed antifungal activity of similar intensity to amphotericin B. Based on the results of the brine shrimp test and DPPH radical scavenging activity, the most active Cu(II) and Mn(II) complexes were selected for evaluation of cytotoxic activity against five malignant cancer cell lines (HeLa, A375, MCF7, PC-3 and A549) and one normal cell line HaCaT. Both complexes showed significant activity. It should be pointed out that the activity of the Mn(II) complex against the MCF7 breast cancer cell line is only slightly weaker than that of cisplatin, but with selectivity to the tumor cell line in comparison to normal HaCaT cells, which is non-existent in the case of cisplatin.",
publisher = "Royal Society of Chemistry (RSC)",
journal = "Dalton Transactions",
title = "Supporting information for: "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity"",
url = "https://hdl.handle.net/21.15107/rcub_cherry_4858"
}
Stevanović, N., Zlatar, M., Novaković, I., Pevec, A., Radanović, D., Matić, I. Z., Đorđić Crnogorac, M., Stanojković, T., Vujčić, M., Gruden, M., Sladić, D., Anđelković, K., Turel, I.,& Čobeljić, B.. (2022). Supporting information for: "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity". in Dalton Transactions
Royal Society of Chemistry (RSC)..
https://hdl.handle.net/21.15107/rcub_cherry_4858
Stevanović N, Zlatar M, Novaković I, Pevec A, Radanović D, Matić IZ, Đorđić Crnogorac M, Stanojković T, Vujčić M, Gruden M, Sladić D, Anđelković K, Turel I, Čobeljić B. Supporting information for: "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity". in Dalton Transactions. 2022;.
https://hdl.handle.net/21.15107/rcub_cherry_4858 .
Stevanović, Nevena, Zlatar, Matija, Novaković, Irena, Pevec, Andrej, Radanović, Dušanka, Matić, Ivana Z., Đorđić Crnogorac, Marija, Stanojković, Tatjana, Vujčić, Miroslava, Gruden, Maja, Sladić, Dušan, Anđelković, Katarina, Turel, Iztok, Čobeljić, Božidar, "Supporting information for: "Cu(II), Mn(II) and Zn(II) complexes of hydrazones with a quaternary ammonium moiety: synthesis, experimental and theoretical characterization and cytotoxic activity"" in Dalton Transactions (2022),
https://hdl.handle.net/21.15107/rcub_cherry_4858 .

Synthesis and biological activity of alkylthio and arylthio derivatives of tert-butylquinone

Djordjević, Jelena; Kolarević, Stoimir; Jovanović-Marić, Jovana; Oaldje-Pavlovic, Mariana; Sladić, Dušan; Novaković, Irena; Vuković-Gačić, Branka

(Serbian chemical society, 2022)

TY  - JOUR
AU  - Djordjević, Jelena
AU  - Kolarević, Stoimir
AU  - Jovanović-Marić, Jovana
AU  - Oaldje-Pavlovic, Mariana
AU  - Sladić, Dušan
AU  - Novaković, Irena
AU  - Vuković-Gačić, Branka
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5609
AB  - Biological activity of 2-tert-butyl-1,4-benzoquinone (TBQ) and its derivatives, 2-tert-butyl-5-(2-propylthio)-1,4-benzoquinone, 2-tert-butyl-5- -(propylthio)-1,4-benzoquinone, 2-tert-butyl-5,6-(ethylenedithio)-1,4-benzoquinone, 2-tert-butyl-5-(phenylthio)-1,4-benzoquinone and 2-tert-butyl-6-(phenylthio)- 1,4-benzoquinone, were tested for their antioxidant, antibacterial, toxic, cytotoxic and genotoxic potential. Using the DPPH test, all derivatives showed good antioxidant activity, better than ascorbic acid, and the 2-tert- -butyl-5-(propylthio)-1,4-benzoquinone derivative showed the strongest effect. Better antibacterial potential was observed against Gram-positive bacteria in the broth microdilution method in which the 2-tert-butyl-5-(phenylthio)-1,4- -benzoquinone derivative showed the strongest activity (MIC = 15.6 μM). The results of toxicity tests, using the Brine shrimp test, indicated that the derivatives lose their toxic potential compared to TBQ, except for 2-tert-butyl-6- -(phenylthio)-1,4-benzoquinone, which showed a 3 times stronger effect. Cytotoxicity was assessed by the MTT assay in 24 and 72 h treatments in MRC-5, HS 294T and A549 cell lines in threefold decreasing gradient (11, 33 and 100 μM). Modifications potentiate the cytotoxic effect, and the strongest effect was observed with the 2-tert-butyl-5,6-(ethylendithio)-1,4-benzoquinone derivative. In addition, the genotoxic potential was examined in the MRC-5 cell line using the comet assay. All tested derivatives of TBQ showed a genotoxic effect at all applied subtoxic concentrations. In general, the chemical modifications of TBQ enhanced its biological activity.
AB  - Испитана је биолошка активност 2-терц-бутил-1,4-бензохинона (TBQ) и његових деривата: 2-терц-бутил-5-(изопропилтио)-1,4-бензохинона, 2-терц-бутил-5-(пропилтио)-1,4-бензохинона, 2-терц-бутил-5,6-(етиленедитио)-1,4-бензохинона, 2-терц-бутил-  -5-(фенилтио)-1,4-бензохинона и 2-терц-бутил-6-(фенилтио)-1,4-бензохинона укључујући њихов антиоксидативни, антибактеријски, токсични, цитотоксични и генотоксични потенцијал. Применом DPPH теста, сви деривати су показали добру антиоксидативну активност, бољу од аскорбинске киселине, а најјаче дејство показао је дериват 2-терц-бутил-5-(пропилтио)-1,4-бензохинон. Бољи антимикробни потенцијал је примећен против Грам-позитивних бактерија методом микродилуције у бујону, где је дериват 2-терц-бутил-5-(фенилтио)-1,4-бензохинон показао најјачу активност (MIC = 15,6  μМ). Резултати испитивања токсичности, применом теста на Artemia salina, показују да деривати губе токсични потенцијал у односу на TBQ, осим 2-терц-бутил-6-(фенилтио)-  -1,4-бензохинона, који је показао 3 пута јачи ефекат. Цитотоксичност је испитана МТТ тестом у третманима од 24 и 72 h на ћелијским линијама MRC-5, HS 294T и A549 у троструко опадајућем градијенту (11, 33 и 100 μМ). Модификације појачавају цитотоксични ефекат, а најјачи ефекат је примећен код деривата 2-терц-бутил-5,6-(етилендитио)-1,4-бензохинона. Поред тога, генотоксични потенцијал је испитан на ћелијској линији MRC-5 комет тестом. Сви испитивани деривати су показали генотоксични ефекат при свим примењеним субтоксичним концентрацијама. Генерално, хемијске модификације побољшавају биолошку активност 2-терц-бутил-1,4-бензохинона.
PB  - Serbian chemical society
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis and biological activity of alkylthio and arylthio derivatives of tert-butylquinone
T1  - Синтеза и биолошка активност алкилтио и арилтио деривата терц-бутилхинона
VL  - 87
IS  - 11
SP  - 1245
EP  - 1258
DO  - 10.2298/JSC220304044D
ER  - 
@article{
author = "Djordjević, Jelena and Kolarević, Stoimir and Jovanović-Marić, Jovana and Oaldje-Pavlovic, Mariana and Sladić, Dušan and Novaković, Irena and Vuković-Gačić, Branka",
year = "2022",
abstract = "Biological activity of 2-tert-butyl-1,4-benzoquinone (TBQ) and its derivatives, 2-tert-butyl-5-(2-propylthio)-1,4-benzoquinone, 2-tert-butyl-5- -(propylthio)-1,4-benzoquinone, 2-tert-butyl-5,6-(ethylenedithio)-1,4-benzoquinone, 2-tert-butyl-5-(phenylthio)-1,4-benzoquinone and 2-tert-butyl-6-(phenylthio)- 1,4-benzoquinone, were tested for their antioxidant, antibacterial, toxic, cytotoxic and genotoxic potential. Using the DPPH test, all derivatives showed good antioxidant activity, better than ascorbic acid, and the 2-tert- -butyl-5-(propylthio)-1,4-benzoquinone derivative showed the strongest effect. Better antibacterial potential was observed against Gram-positive bacteria in the broth microdilution method in which the 2-tert-butyl-5-(phenylthio)-1,4- -benzoquinone derivative showed the strongest activity (MIC = 15.6 μM). The results of toxicity tests, using the Brine shrimp test, indicated that the derivatives lose their toxic potential compared to TBQ, except for 2-tert-butyl-6- -(phenylthio)-1,4-benzoquinone, which showed a 3 times stronger effect. Cytotoxicity was assessed by the MTT assay in 24 and 72 h treatments in MRC-5, HS 294T and A549 cell lines in threefold decreasing gradient (11, 33 and 100 μM). Modifications potentiate the cytotoxic effect, and the strongest effect was observed with the 2-tert-butyl-5,6-(ethylendithio)-1,4-benzoquinone derivative. In addition, the genotoxic potential was examined in the MRC-5 cell line using the comet assay. All tested derivatives of TBQ showed a genotoxic effect at all applied subtoxic concentrations. In general, the chemical modifications of TBQ enhanced its biological activity., Испитана је биолошка активност 2-терц-бутил-1,4-бензохинона (TBQ) и његових деривата: 2-терц-бутил-5-(изопропилтио)-1,4-бензохинона, 2-терц-бутил-5-(пропилтио)-1,4-бензохинона, 2-терц-бутил-5,6-(етиленедитио)-1,4-бензохинона, 2-терц-бутил-  -5-(фенилтио)-1,4-бензохинона и 2-терц-бутил-6-(фенилтио)-1,4-бензохинона укључујући њихов антиоксидативни, антибактеријски, токсични, цитотоксични и генотоксични потенцијал. Применом DPPH теста, сви деривати су показали добру антиоксидативну активност, бољу од аскорбинске киселине, а најјаче дејство показао је дериват 2-терц-бутил-5-(пропилтио)-1,4-бензохинон. Бољи антимикробни потенцијал је примећен против Грам-позитивних бактерија методом микродилуције у бујону, где је дериват 2-терц-бутил-5-(фенилтио)-1,4-бензохинон показао најјачу активност (MIC = 15,6  μМ). Резултати испитивања токсичности, применом теста на Artemia salina, показују да деривати губе токсични потенцијал у односу на TBQ, осим 2-терц-бутил-6-(фенилтио)-  -1,4-бензохинона, који је показао 3 пута јачи ефекат. Цитотоксичност је испитана МТТ тестом у третманима од 24 и 72 h на ћелијским линијама MRC-5, HS 294T и A549 у троструко опадајућем градијенту (11, 33 и 100 μМ). Модификације појачавају цитотоксични ефекат, а најјачи ефекат је примећен код деривата 2-терц-бутил-5,6-(етилендитио)-1,4-бензохинона. Поред тога, генотоксични потенцијал је испитан на ћелијској линији MRC-5 комет тестом. Сви испитивани деривати су показали генотоксични ефекат при свим примењеним субтоксичним концентрацијама. Генерално, хемијске модификације побољшавају биолошку активност 2-терц-бутил-1,4-бензохинона.",
publisher = "Serbian chemical society",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis and biological activity of alkylthio and arylthio derivatives of tert-butylquinone, Синтеза и биолошка активност алкилтио и арилтио деривата терц-бутилхинона",
volume = "87",
number = "11",
pages = "1245-1258",
doi = "10.2298/JSC220304044D"
}
Djordjević, J., Kolarević, S., Jovanović-Marić, J., Oaldje-Pavlovic, M., Sladić, D., Novaković, I.,& Vuković-Gačić, B.. (2022). Synthesis and biological activity of alkylthio and arylthio derivatives of tert-butylquinone. in Journal of the Serbian Chemical Society
Serbian chemical society., 87(11), 1245-1258.
https://doi.org/10.2298/JSC220304044D
Djordjević J, Kolarević S, Jovanović-Marić J, Oaldje-Pavlovic M, Sladić D, Novaković I, Vuković-Gačić B. Synthesis and biological activity of alkylthio and arylthio derivatives of tert-butylquinone. in Journal of the Serbian Chemical Society. 2022;87(11):1245-1258.
doi:10.2298/JSC220304044D .
Djordjević, Jelena, Kolarević, Stoimir, Jovanović-Marić, Jovana, Oaldje-Pavlovic, Mariana, Sladić, Dušan, Novaković, Irena, Vuković-Gačić, Branka, "Synthesis and biological activity of alkylthio and arylthio derivatives of tert-butylquinone" in Journal of the Serbian Chemical Society, 87, no. 11 (2022):1245-1258,
https://doi.org/10.2298/JSC220304044D . .

Sinteza i ispitivanje biološke aktivnosti ariltio i aralkiltio derivata 2-terc-butil-1,4-benzohinona

Kovačević, Andrej; Novaković, Irena; Sladić, Dušan

(Belgrade: Serbian Chemical Society, 2022)

TY  - CONF
AU  - Kovačević, Andrej
AU  - Novaković, Irena
AU  - Sladić, Dušan
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5782
AB  - Sintetisana su dva ariltio i dva aralkiltio derivata 2-terc-butil-1,4-benzohinona reakcijom  Michael-ove adicije tiola na hinonsko jezgro u etanolu. Dobijenim derivatima je ispitana antimikrobna i antioksidativna aktivnost, kao i toksinost  na raie Artemia salina. Najjau antimikrobnu aktivnost je pokazao derivat 4, najveu  antioksidativnu aktivnost je imao derivat 2 (IC50=0,0526 mM), dok je toksinost prema  raiima ispoljio samo derivat 4 (LC50=0,032 mM).
AB  - Two arylthio and aralkylthio derivatives of 2-tert-butyl-1.4-benzoquinone were  synthesized by Michael addition of thiols on quionone moiety in ethanol. For all compounds antimicrobial and antioxidant activity was investigated, as well as  toxicity towards nauplii of Artemia salina. Derivative 4 showed the strongest antimicrobial  activity, derivative 2 showed the most intense antioxidant activity (IC50=0.0526 mM),  while only derivative 4 showed toxicity against nauplii of A. salina (LC50=0.032 mM).
PB  - Belgrade: Serbian Chemical Society
C3  - Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine
T1  - Sinteza i ispitivanje biološke aktivnosti ariltio i aralkiltio derivata  2-terc-butil-1,4-benzohinona
T1  - Synthesis and investigation of biological activity of arylthio and aralkylthio derivatives of 2-tert-butyl-1.4-benzoquinone
SP  - 90
EP  - 90
UR  - https://hdl.handle.net/21.15107/rcub_cer_5782
ER  - 
@conference{
author = "Kovačević, Andrej and Novaković, Irena and Sladić, Dušan",
year = "2022",
abstract = "Sintetisana su dva ariltio i dva aralkiltio derivata 2-terc-butil-1,4-benzohinona reakcijom  Michael-ove adicije tiola na hinonsko jezgro u etanolu. Dobijenim derivatima je ispitana antimikrobna i antioksidativna aktivnost, kao i toksinost  na raie Artemia salina. Najjau antimikrobnu aktivnost je pokazao derivat 4, najveu  antioksidativnu aktivnost je imao derivat 2 (IC50=0,0526 mM), dok je toksinost prema  raiima ispoljio samo derivat 4 (LC50=0,032 mM)., Two arylthio and aralkylthio derivatives of 2-tert-butyl-1.4-benzoquinone were  synthesized by Michael addition of thiols on quionone moiety in ethanol. For all compounds antimicrobial and antioxidant activity was investigated, as well as  toxicity towards nauplii of Artemia salina. Derivative 4 showed the strongest antimicrobial  activity, derivative 2 showed the most intense antioxidant activity (IC50=0.0526 mM),  while only derivative 4 showed toxicity against nauplii of A. salina (LC50=0.032 mM).",
publisher = "Belgrade: Serbian Chemical Society",
journal = "Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine",
title = "Sinteza i ispitivanje biološke aktivnosti ariltio i aralkiltio derivata  2-terc-butil-1,4-benzohinona, Synthesis and investigation of biological activity of arylthio and aralkylthio derivatives of 2-tert-butyl-1.4-benzoquinone",
pages = "90-90",
url = "https://hdl.handle.net/21.15107/rcub_cer_5782"
}
Kovačević, A., Novaković, I.,& Sladić, D.. (2022). Sinteza i ispitivanje biološke aktivnosti ariltio i aralkiltio derivata  2-terc-butil-1,4-benzohinona. in Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine
Belgrade: Serbian Chemical Society., 90-90.
https://hdl.handle.net/21.15107/rcub_cer_5782
Kovačević A, Novaković I, Sladić D. Sinteza i ispitivanje biološke aktivnosti ariltio i aralkiltio derivata  2-terc-butil-1,4-benzohinona. in Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine. 2022;:90-90.
https://hdl.handle.net/21.15107/rcub_cer_5782 .
Kovačević, Andrej, Novaković, Irena, Sladić, Dušan, "Sinteza i ispitivanje biološke aktivnosti ariltio i aralkiltio derivata  2-terc-butil-1,4-benzohinona" in Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine (2022):90-90,
https://hdl.handle.net/21.15107/rcub_cer_5782 .

Citotoksičnost novog steroidnog bis(karbazatnog) estra

Živković, Marijana; Novaković, Irena; Matić, Ivana; Sladić, Dušan; Krstić, Natalija

(Belgrade: Serbian Chemical Society, 2022)

TY  - CONF
AU  - Živković, Marijana
AU  - Novaković, Irena
AU  - Matić, Ivana
AU  - Sladić, Dušan
AU  - Krstić, Natalija
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5783
AB  - Usled stalne potrebe za novim antitumorskim lekovima, počevši od androstanskog  bis(semikarbazona), sintetisan je novi bis(karbazatni) estar (bisKBZ) za koji je određena  antimikrobna aktivnost, citotoksična aktivnost na tri maligne ćelijske linije, i urađen je  brine shrimp test toksičnosti. Novo jedinjenje se nije pokazalo kao dobar antimikrobni  agens, ispoljilo je umerenu citotoksičnost prema testiranim ćelijskim linijama i pokazalo se  kao pet puta manje toksično od cisplatina za račiće Artemia salina što je u dobroj korelaciji  sa citotoksičnošću prema HeLa ćelijskoj liniji.
AB  - Due to the constant need for new antitumor drugs, starting from androstane  bis(semicarbazone), a new bis(carbazate) ester (bis-KBZ) was synthesized; antimicrobial  activity and cytotoxicity against three malignant cell lines were determined, and the brine  shrimp toxicity test was performed. The new compound did not prove to be a good  antimicrobial agent, it showed moderate cytotoxicity to the tested cell lines, and proved to  be five times less toxic than cisplatin to Artemia salina, which correlates well with the  cytotoxicity to HeLa cell line.
PB  - Belgrade: Serbian Chemical Society
C3  - Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine
T1  - Citotoksičnost novog steroidnog bis(karbazatnog) estra
T1  - Cytotoxicity of a new steroidal bis(carbazate) ester
SP  - 93
EP  - 93
UR  - https://hdl.handle.net/21.15107/rcub_cer_5783
ER  - 
@conference{
author = "Živković, Marijana and Novaković, Irena and Matić, Ivana and Sladić, Dušan and Krstić, Natalija",
year = "2022",
abstract = "Usled stalne potrebe za novim antitumorskim lekovima, počevši od androstanskog  bis(semikarbazona), sintetisan je novi bis(karbazatni) estar (bisKBZ) za koji je određena  antimikrobna aktivnost, citotoksična aktivnost na tri maligne ćelijske linije, i urađen je  brine shrimp test toksičnosti. Novo jedinjenje se nije pokazalo kao dobar antimikrobni  agens, ispoljilo je umerenu citotoksičnost prema testiranim ćelijskim linijama i pokazalo se  kao pet puta manje toksično od cisplatina za račiće Artemia salina što je u dobroj korelaciji  sa citotoksičnošću prema HeLa ćelijskoj liniji., Due to the constant need for new antitumor drugs, starting from androstane  bis(semicarbazone), a new bis(carbazate) ester (bis-KBZ) was synthesized; antimicrobial  activity and cytotoxicity against three malignant cell lines were determined, and the brine  shrimp toxicity test was performed. The new compound did not prove to be a good  antimicrobial agent, it showed moderate cytotoxicity to the tested cell lines, and proved to  be five times less toxic than cisplatin to Artemia salina, which correlates well with the  cytotoxicity to HeLa cell line.",
publisher = "Belgrade: Serbian Chemical Society",
journal = "Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine",
title = "Citotoksičnost novog steroidnog bis(karbazatnog) estra, Cytotoxicity of a new steroidal bis(carbazate) ester",
pages = "93-93",
url = "https://hdl.handle.net/21.15107/rcub_cer_5783"
}
Živković, M., Novaković, I., Matić, I., Sladić, D.,& Krstić, N.. (2022). Citotoksičnost novog steroidnog bis(karbazatnog) estra. in Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine
Belgrade: Serbian Chemical Society., 93-93.
https://hdl.handle.net/21.15107/rcub_cer_5783
Živković M, Novaković I, Matić I, Sladić D, Krstić N. Citotoksičnost novog steroidnog bis(karbazatnog) estra. in Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine. 2022;:93-93.
https://hdl.handle.net/21.15107/rcub_cer_5783 .
Živković, Marijana, Novaković, Irena, Matić, Ivana, Sladić, Dušan, Krstić, Natalija, "Citotoksičnost novog steroidnog bis(karbazatnog) estra" in Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine (2022):93-93,
https://hdl.handle.net/21.15107/rcub_cer_5783 .

Synthesis, characterization, antimicrobial and cytotoxic activity and DNA-binding properties of d-metal complexes with hydrazones of Girard’s T and P reagents

Stevanović, Nevena; Mazzeo, Paolo Pio; Bacchi, Alessia; Matić, Ivana Z.; Đorđić Crnogorac, Marija; Stanojković, Tatjana; Vujčić, Miroslava; Novaković, Irena; Radanović, Dušanka; Šumar‑Ristović, Maja; Sladić, Dušan; Čobeljić, Božidar; Anđelković, Katarina

(Springer Science and Business Media Deutschland GmbH, 2021)

TY  - JOUR
AU  - Stevanović, Nevena
AU  - Mazzeo, Paolo Pio
AU  - Bacchi, Alessia
AU  - Matić, Ivana Z.
AU  - Đorđić Crnogorac, Marija
AU  - Stanojković, Tatjana
AU  - Vujčić, Miroslava
AU  - Novaković, Irena
AU  - Radanović, Dušanka
AU  - Šumar‑Ristović, Maja
AU  - Sladić, Dušan
AU  - Čobeljić, Božidar
AU  - Anđelković, Katarina
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4769
AB  - In this work synthesis, characterization and crystal structures of 1, Zn(II) complex ([ZnL1(NCS)2]), with (E)-1-(2-oxo-2-(2-(quinolin-2-ylmethylene)hydrazinyl)ethyl)pyridin-1-ium chloride (HL1Cl) and 2, Bi(III) complex ([BiHL2Cl4] × 1/2CH3OH), with (E)-N,N,N-trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride (HL2Cl), have been reported. Zn(II) complex possesses a distorted trigonal bipyramidal geometry while surroundings around Bi(III) ion are extended pentagonal bipyramidal. Antimicrobial activity, brine shrimp assay and DPPH radical scavenging activity of both complexes, including previously synthesized complexes with HL2Cl ligand (Zn(II) and Ni(II)) and complexes with (E)-N,N,N-trimethyl-2-oxo-2-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride (HL3Cl) (Zn(II), Cu(II), Cd(II), Co(II), Fe(III), Ni(II)), were evaluated. For the most active complexes, cytotoxic activity against five malignant cancer cell lines (HeLa, A375, MCF7, PC-3 and A549) and normal cell line HaCaT, as well as generation of reactive oxygen species (ROS), was tested. Graphic abstract: [Figure not available: see fulltext.]
PB  - Springer Science and Business Media Deutschland GmbH
T2  - Journal of Biological Inorganic Chemistry
T1  - Synthesis, characterization, antimicrobial and cytotoxic activity and DNA-binding properties of d-metal complexes with hydrazones of Girard’s T and P reagents
DO  - 10.1007/s00775-021-01893-5
ER  - 
@article{
author = "Stevanović, Nevena and Mazzeo, Paolo Pio and Bacchi, Alessia and Matić, Ivana Z. and Đorđić Crnogorac, Marija and Stanojković, Tatjana and Vujčić, Miroslava and Novaković, Irena and Radanović, Dušanka and Šumar‑Ristović, Maja and Sladić, Dušan and Čobeljić, Božidar and Anđelković, Katarina",
year = "2021",
abstract = "In this work synthesis, characterization and crystal structures of 1, Zn(II) complex ([ZnL1(NCS)2]), with (E)-1-(2-oxo-2-(2-(quinolin-2-ylmethylene)hydrazinyl)ethyl)pyridin-1-ium chloride (HL1Cl) and 2, Bi(III) complex ([BiHL2Cl4] × 1/2CH3OH), with (E)-N,N,N-trimethyl-2-oxo-2-(2-(1-(thiazol-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride (HL2Cl), have been reported. Zn(II) complex possesses a distorted trigonal bipyramidal geometry while surroundings around Bi(III) ion are extended pentagonal bipyramidal. Antimicrobial activity, brine shrimp assay and DPPH radical scavenging activity of both complexes, including previously synthesized complexes with HL2Cl ligand (Zn(II) and Ni(II)) and complexes with (E)-N,N,N-trimethyl-2-oxo-2-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)ethan-1-aminium chloride (HL3Cl) (Zn(II), Cu(II), Cd(II), Co(II), Fe(III), Ni(II)), were evaluated. For the most active complexes, cytotoxic activity against five malignant cancer cell lines (HeLa, A375, MCF7, PC-3 and A549) and normal cell line HaCaT, as well as generation of reactive oxygen species (ROS), was tested. Graphic abstract: [Figure not available: see fulltext.]",
publisher = "Springer Science and Business Media Deutschland GmbH",
journal = "Journal of Biological Inorganic Chemistry",
title = "Synthesis, characterization, antimicrobial and cytotoxic activity and DNA-binding properties of d-metal complexes with hydrazones of Girard’s T and P reagents",
doi = "10.1007/s00775-021-01893-5"
}
Stevanović, N., Mazzeo, P. P., Bacchi, A., Matić, I. Z., Đorđić Crnogorac, M., Stanojković, T., Vujčić, M., Novaković, I., Radanović, D., Šumar‑Ristović, M., Sladić, D., Čobeljić, B.,& Anđelković, K.. (2021). Synthesis, characterization, antimicrobial and cytotoxic activity and DNA-binding properties of d-metal complexes with hydrazones of Girard’s T and P reagents. in Journal of Biological Inorganic Chemistry
Springer Science and Business Media Deutschland GmbH..
https://doi.org/10.1007/s00775-021-01893-5
Stevanović N, Mazzeo PP, Bacchi A, Matić IZ, Đorđić Crnogorac M, Stanojković T, Vujčić M, Novaković I, Radanović D, Šumar‑Ristović M, Sladić D, Čobeljić B, Anđelković K. Synthesis, characterization, antimicrobial and cytotoxic activity and DNA-binding properties of d-metal complexes with hydrazones of Girard’s T and P reagents. in Journal of Biological Inorganic Chemistry. 2021;.
doi:10.1007/s00775-021-01893-5 .
Stevanović, Nevena, Mazzeo, Paolo Pio, Bacchi, Alessia, Matić, Ivana Z., Đorđić Crnogorac, Marija, Stanojković, Tatjana, Vujčić, Miroslava, Novaković, Irena, Radanović, Dušanka, Šumar‑Ristović, Maja, Sladić, Dušan, Čobeljić, Božidar, Anđelković, Katarina, "Synthesis, characterization, antimicrobial and cytotoxic activity and DNA-binding properties of d-metal complexes with hydrazones of Girard’s T and P reagents" in Journal of Biological Inorganic Chemistry (2021),
https://doi.org/10.1007/s00775-021-01893-5 . .
6
2
7

Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives

Živković, Marijana B.; Novaković, Irena; Matić, Ivana Z.; Sladić, Dušan; Krstić, Natalija

(Elsevier, 2019)

TY  - JOUR
AU  - Živković, Marijana B.
AU  - Novaković, Irena
AU  - Matić, Ivana Z.
AU  - Sladić, Dušan
AU  - Krstić, Natalija
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2947
AB  - Eleven new steroidal mono- and bis(semicarbazones) 2a–e, 4d and 3a–e have been prepared starting from various 3-oxo-α,β-unsaturated steroids. Mono-semicarbazones 2a–e were further subjected to ethyl chloroacetate in boiling absolute ethanol but, instead of expected intramolecular cyclocondensation reaction products, the new carbazate esters 5a-e were obtained. The structures of all synthesized compounds and identification of each E/Z isomer were deduced by elemental analysis, HRMS, NMR, and IR spectroscopy. Preliminary screening for the cytotoxic activity in vitro of the new compounds has been conducted against three cancer cell lines, K562, Jurkat and HeLa cells. HeLa cells were the most sensitive while K562 cells were the least sensitive to the cytotoxic action of the novel steroid derivatives. Compounds 2e, 3c and 5e were found to have the best but still moderate cytotoxic effects. All tested compounds showed very weak antimicrobial activities. These results demonstrate that the replacement of thioxo group with carbonyl group in steroidal hydrazone derivatives resulted in decrease in their biological activity.
PB  - Elsevier
T2  - Steroids
T1  - Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives
VL  - 148
SP  - 36
EP  - 46
DO  - 10.1016/j.steroids.2019.04.010
ER  - 
@article{
author = "Živković, Marijana B. and Novaković, Irena and Matić, Ivana Z. and Sladić, Dušan and Krstić, Natalija",
year = "2019",
abstract = "Eleven new steroidal mono- and bis(semicarbazones) 2a–e, 4d and 3a–e have been prepared starting from various 3-oxo-α,β-unsaturated steroids. Mono-semicarbazones 2a–e were further subjected to ethyl chloroacetate in boiling absolute ethanol but, instead of expected intramolecular cyclocondensation reaction products, the new carbazate esters 5a-e were obtained. The structures of all synthesized compounds and identification of each E/Z isomer were deduced by elemental analysis, HRMS, NMR, and IR spectroscopy. Preliminary screening for the cytotoxic activity in vitro of the new compounds has been conducted against three cancer cell lines, K562, Jurkat and HeLa cells. HeLa cells were the most sensitive while K562 cells were the least sensitive to the cytotoxic action of the novel steroid derivatives. Compounds 2e, 3c and 5e were found to have the best but still moderate cytotoxic effects. All tested compounds showed very weak antimicrobial activities. These results demonstrate that the replacement of thioxo group with carbonyl group in steroidal hydrazone derivatives resulted in decrease in their biological activity.",
publisher = "Elsevier",
journal = "Steroids",
title = "Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives",
volume = "148",
pages = "36-46",
doi = "10.1016/j.steroids.2019.04.010"
}
Živković, M. B., Novaković, I., Matić, I. Z., Sladić, D.,& Krstić, N.. (2019). Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives. in Steroids
Elsevier., 148, 36-46.
https://doi.org/10.1016/j.steroids.2019.04.010
Živković MB, Novaković I, Matić IZ, Sladić D, Krstić N. Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives. in Steroids. 2019;148:36-46.
doi:10.1016/j.steroids.2019.04.010 .
Živković, Marijana B., Novaković, Irena, Matić, Ivana Z., Sladić, Dušan, Krstić, Natalija, "Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives" in Steroids, 148 (2019):36-46,
https://doi.org/10.1016/j.steroids.2019.04.010 . .
2
5
2
5

Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives

Živković, Marijana B.; Novaković, Irena; Matić, Ivana Z.; Sladić, Dušan; Krstić, Natalija

(Elsevier, 2019)

TY  - JOUR
AU  - Živković, Marijana B.
AU  - Novaković, Irena
AU  - Matić, Ivana Z.
AU  - Sladić, Dušan
AU  - Krstić, Natalija
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2948
AB  - Eleven new steroidal mono- and bis(semicarbazones) 2a–e, 4d and 3a–e have been prepared starting from various 3-oxo-α,β-unsaturated steroids. Mono-semicarbazones 2a–e were further subjected to ethyl chloroacetate in boiling absolute ethanol but, instead of expected intramolecular cyclocondensation reaction products, the new carbazate esters 5a-e were obtained. The structures of all synthesized compounds and identification of each E/Z isomer were deduced by elemental analysis, HRMS, NMR, and IR spectroscopy. Preliminary screening for the cytotoxic activity in vitro of the new compounds has been conducted against three cancer cell lines, K562, Jurkat and HeLa cells. HeLa cells were the most sensitive while K562 cells were the least sensitive to the cytotoxic action of the novel steroid derivatives. Compounds 2e, 3c and 5e were found to have the best but still moderate cytotoxic effects. All tested compounds showed very weak antimicrobial activities. These results demonstrate that the replacement of thioxo group with carbonyl group in steroidal hydrazone derivatives resulted in decrease in their biological activity.
PB  - Elsevier
T2  - Steroids
T1  - Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives
VL  - 148
SP  - 36
EP  - 46
DO  - 10.1016/j.steroids.2019.04.010
ER  - 
@article{
author = "Živković, Marijana B. and Novaković, Irena and Matić, Ivana Z. and Sladić, Dušan and Krstić, Natalija",
year = "2019",
abstract = "Eleven new steroidal mono- and bis(semicarbazones) 2a–e, 4d and 3a–e have been prepared starting from various 3-oxo-α,β-unsaturated steroids. Mono-semicarbazones 2a–e were further subjected to ethyl chloroacetate in boiling absolute ethanol but, instead of expected intramolecular cyclocondensation reaction products, the new carbazate esters 5a-e were obtained. The structures of all synthesized compounds and identification of each E/Z isomer were deduced by elemental analysis, HRMS, NMR, and IR spectroscopy. Preliminary screening for the cytotoxic activity in vitro of the new compounds has been conducted against three cancer cell lines, K562, Jurkat and HeLa cells. HeLa cells were the most sensitive while K562 cells were the least sensitive to the cytotoxic action of the novel steroid derivatives. Compounds 2e, 3c and 5e were found to have the best but still moderate cytotoxic effects. All tested compounds showed very weak antimicrobial activities. These results demonstrate that the replacement of thioxo group with carbonyl group in steroidal hydrazone derivatives resulted in decrease in their biological activity.",
publisher = "Elsevier",
journal = "Steroids",
title = "Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives",
volume = "148",
pages = "36-46",
doi = "10.1016/j.steroids.2019.04.010"
}
Živković, M. B., Novaković, I., Matić, I. Z., Sladić, D.,& Krstić, N.. (2019). Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives. in Steroids
Elsevier., 148, 36-46.
https://doi.org/10.1016/j.steroids.2019.04.010
Živković MB, Novaković I, Matić IZ, Sladić D, Krstić N. Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives. in Steroids. 2019;148:36-46.
doi:10.1016/j.steroids.2019.04.010 .
Živković, Marijana B., Novaković, Irena, Matić, Ivana Z., Sladić, Dušan, Krstić, Natalija, "Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives" in Steroids, 148 (2019):36-46,
https://doi.org/10.1016/j.steroids.2019.04.010 . .
2
5
2
5

Antitumor and antimicrobial properties of isothiocyanato pentagonal-bipyramidal d metal complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent

Milenković, Milica R.; Anđelković, Katarina; Matić, Ivana Z.; Vujčić, Miroslava; Sladić, Dušan; Čobeljić, Božidar; Romanović, Mima

(Serbian Biochemical Society, 2018)

TY  - CONF
AU  - Milenković, Milica R.
AU  - Anđelković, Katarina
AU  - Matić, Ivana Z.
AU  - Vujčić, Miroslava
AU  - Sladić, Dušan
AU  - Čobeljić, Božidar
AU  - Romanović, Mima
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3542
AB  - Pentagonal-bipyramidal complexes of 2,6-diacetylpyridine bis(acylhydrazone) ligands
are attractive field of research not only in structural inorganic chemistry and magnetochemistry, but also in bioinorganic chemistry since they exhibit cytotoxic, antimicrobial, SOD mimetic, DNA/RNA binding and nuclease activity. In this work we investigated antitumor and antimicrobial activity of pentagonal-bipyramidal isothiocyanato complexes of Mn(II) ([Mn(H2L)(NCS)2](SCN)2·CH3OH) (1), Ni(II)([Ni(H2L)(NCS)2](SCN)2·2H2O) (2), Co(II) ([Co(H2L)(NCS)2](SCN)2·2H2O (3) and
[Co(H2L)(NCS)2][Co(NCS)4]·2H2O) (4), Zn(II) ([Zn(H2L)(NCS)2][Zn(NCS)4]·2H2O) (5), Cd(II) ([Cd(H2L)(NCS)2][Cd(NCS)4]·2H2O) (6) and Fe(III) ([Fe(L)(NCS)2](SCN)·2H2O (7) and [Fe(L)(NCS)2][Fe(NCS)5(H2O)]·4H2O) (8), with the condensation product of 2,6-diacetylpyridine and Girard’s T reagent (H2LCl2). The complexes showed moderate to low cytotoxic activities towards five tested human cancer cell lines (HeLa, MDA-MB-453, K562, LS174 and A549), while the ligand was inactive. The best activity was observed in the case of complexes 8, 4 and 6. The potential of the most active complexes to induce HeLa and K562 cell cycle perturbations was also studied. Cd(II) complex (6) caused significant increase of apoptotic subG1 cells in both cell lines. Fe(III) complex (8) induced significant changes in cell cycle phase distribution only in HeLa cells. Morphological changes in HeLa cells treated with complexes 8, 4 and 6 were also indicative of apoptosis, with complex 6 having again the most pronounced effect. Complexes 8, 4 and 6 bind to
DNA, most probably by electrostatic interactions, and perturb DNA structure. Complexes 4 and 8 cause cleavage of plasmid DNA in vitro. Iron (III) complexes showed better antimicrobial activity than complexes of other metals with this ligand, but lower than activity of standard antimicrobial drugs.
PB  - Serbian Biochemical Society
C3  - Serbian Biochemical Society Eighth Conference with international participation, “Coordination in Biochemistry and Life”, University of Novi Sad – Rectorate Hall, 16.11.2018. Novi Sad, Serbia
T1  - Antitumor and antimicrobial properties of isothiocyanato pentagonal-bipyramidal d metal complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent
SP  - 33
EP  - 40
UR  - https://hdl.handle.net/21.15107/rcub_cer_3542
ER  - 
@conference{
author = "Milenković, Milica R. and Anđelković, Katarina and Matić, Ivana Z. and Vujčić, Miroslava and Sladić, Dušan and Čobeljić, Božidar and Romanović, Mima",
year = "2018",
abstract = "Pentagonal-bipyramidal complexes of 2,6-diacetylpyridine bis(acylhydrazone) ligands
are attractive field of research not only in structural inorganic chemistry and magnetochemistry, but also in bioinorganic chemistry since they exhibit cytotoxic, antimicrobial, SOD mimetic, DNA/RNA binding and nuclease activity. In this work we investigated antitumor and antimicrobial activity of pentagonal-bipyramidal isothiocyanato complexes of Mn(II) ([Mn(H2L)(NCS)2](SCN)2·CH3OH) (1), Ni(II)([Ni(H2L)(NCS)2](SCN)2·2H2O) (2), Co(II) ([Co(H2L)(NCS)2](SCN)2·2H2O (3) and
[Co(H2L)(NCS)2][Co(NCS)4]·2H2O) (4), Zn(II) ([Zn(H2L)(NCS)2][Zn(NCS)4]·2H2O) (5), Cd(II) ([Cd(H2L)(NCS)2][Cd(NCS)4]·2H2O) (6) and Fe(III) ([Fe(L)(NCS)2](SCN)·2H2O (7) and [Fe(L)(NCS)2][Fe(NCS)5(H2O)]·4H2O) (8), with the condensation product of 2,6-diacetylpyridine and Girard’s T reagent (H2LCl2). The complexes showed moderate to low cytotoxic activities towards five tested human cancer cell lines (HeLa, MDA-MB-453, K562, LS174 and A549), while the ligand was inactive. The best activity was observed in the case of complexes 8, 4 and 6. The potential of the most active complexes to induce HeLa and K562 cell cycle perturbations was also studied. Cd(II) complex (6) caused significant increase of apoptotic subG1 cells in both cell lines. Fe(III) complex (8) induced significant changes in cell cycle phase distribution only in HeLa cells. Morphological changes in HeLa cells treated with complexes 8, 4 and 6 were also indicative of apoptosis, with complex 6 having again the most pronounced effect. Complexes 8, 4 and 6 bind to
DNA, most probably by electrostatic interactions, and perturb DNA structure. Complexes 4 and 8 cause cleavage of plasmid DNA in vitro. Iron (III) complexes showed better antimicrobial activity than complexes of other metals with this ligand, but lower than activity of standard antimicrobial drugs.",
publisher = "Serbian Biochemical Society",
journal = "Serbian Biochemical Society Eighth Conference with international participation, “Coordination in Biochemistry and Life”, University of Novi Sad – Rectorate Hall, 16.11.2018. Novi Sad, Serbia",
title = "Antitumor and antimicrobial properties of isothiocyanato pentagonal-bipyramidal d metal complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent",
pages = "33-40",
url = "https://hdl.handle.net/21.15107/rcub_cer_3542"
}
Milenković, M. R., Anđelković, K., Matić, I. Z., Vujčić, M., Sladić, D., Čobeljić, B.,& Romanović, M.. (2018). Antitumor and antimicrobial properties of isothiocyanato pentagonal-bipyramidal d metal complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent. in Serbian Biochemical Society Eighth Conference with international participation, “Coordination in Biochemistry and Life”, University of Novi Sad – Rectorate Hall, 16.11.2018. Novi Sad, Serbia
Serbian Biochemical Society., 33-40.
https://hdl.handle.net/21.15107/rcub_cer_3542
Milenković MR, Anđelković K, Matić IZ, Vujčić M, Sladić D, Čobeljić B, Romanović M. Antitumor and antimicrobial properties of isothiocyanato pentagonal-bipyramidal d metal complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent. in Serbian Biochemical Society Eighth Conference with international participation, “Coordination in Biochemistry and Life”, University of Novi Sad – Rectorate Hall, 16.11.2018. Novi Sad, Serbia. 2018;:33-40.
https://hdl.handle.net/21.15107/rcub_cer_3542 .
Milenković, Milica R., Anđelković, Katarina, Matić, Ivana Z., Vujčić, Miroslava, Sladić, Dušan, Čobeljić, Božidar, Romanović, Mima, "Antitumor and antimicrobial properties of isothiocyanato pentagonal-bipyramidal d metal complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent" in Serbian Biochemical Society Eighth Conference with international participation, “Coordination in Biochemistry and Life”, University of Novi Sad – Rectorate Hall, 16.11.2018. Novi Sad, Serbia (2018):33-40,
https://hdl.handle.net/21.15107/rcub_cer_3542 .

Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies

Jakovljević, Katarina; Joksovic, Milan D.; Matić, Ivana Z.; Petrovic, Nina; Stanojković, Tatjana; Sladić, Dušan; Vujčić, Miroslava; Janović, Barbara; Joksovic, Ljubinka; Trifunović, Snežana; Markovic, Violeta

(Royal Soc Chemistry, Cambridge, 2018)

TY  - JOUR
AU  - Jakovljević, Katarina
AU  - Joksovic, Milan D.
AU  - Matić, Ivana Z.
AU  - Petrovic, Nina
AU  - Stanojković, Tatjana
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Joksovic, Ljubinka
AU  - Trifunović, Snežana
AU  - Markovic, Violeta
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2379
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3136
AB  - Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.
PB  - Royal Soc Chemistry, Cambridge
T2  - Medchemcomm
T1  - Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies
VL  - 9
IS  - 10
SP  - 1679
EP  - 1697
DO  - 10.1039/c8md00316e
ER  - 
@article{
author = "Jakovljević, Katarina and Joksovic, Milan D. and Matić, Ivana Z. and Petrovic, Nina and Stanojković, Tatjana and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Joksovic, Ljubinka and Trifunović, Snežana and Markovic, Violeta",
year = "2018",
abstract = "Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Medchemcomm",
title = "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies",
volume = "9",
number = "10",
pages = "1679-1697",
doi = "10.1039/c8md00316e"
}
Jakovljević, K., Joksovic, M. D., Matić, I. Z., Petrovic, N., Stanojković, T., Sladić, D., Vujčić, M., Janović, B., Joksovic, L., Trifunović, S.,& Markovic, V.. (2018). Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. in Medchemcomm
Royal Soc Chemistry, Cambridge., 9(10), 1679-1697.
https://doi.org/10.1039/c8md00316e
Jakovljević K, Joksovic MD, Matić IZ, Petrovic N, Stanojković T, Sladić D, Vujčić M, Janović B, Joksovic L, Trifunović S, Markovic V. Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. in Medchemcomm. 2018;9(10):1679-1697.
doi:10.1039/c8md00316e .
Jakovljević, Katarina, Joksovic, Milan D., Matić, Ivana Z., Petrovic, Nina, Stanojković, Tatjana, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Joksovic, Ljubinka, Trifunović, Snežana, Markovic, Violeta, "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies" in Medchemcomm, 9, no. 10 (2018):1679-1697,
https://doi.org/10.1039/c8md00316e . .
4
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Supplementary material to: "Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential"

Jeremić, Marko; Dinić, Jelena; Pešić, Milica; Stepanovic, Marija; Novaković, Irena; Šegan, Dejan; Sladić, Dušan

(Serbian Chemical Society, 2018)

TY  - DATA
AU  - Jeremić, Marko
AU  - Dinić, Jelena
AU  - Pešić, Milica
AU  - Stepanovic, Marija
AU  - Novaković, Irena
AU  - Šegan, Dejan
AU  - Sladić, Dušan
PY  - 2018
UR  - https://www.shd-pub.org.rs/index.php/JSCS/article/view/7014
UR  - https://www.shd-pub.org.rs/index.php/JSCS/article/view/7014/735
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4521
AB  - Additional experimental results, as well as spectroscopic and analytical data
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Supplementary material to: "Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential"
UR  - https://hdl.handle.net/21.15107/rcub_cer_4521
ER  - 
@misc{
author = "Jeremić, Marko and Dinić, Jelena and Pešić, Milica and Stepanovic, Marija and Novaković, Irena and Šegan, Dejan and Sladić, Dušan",
year = "2018",
abstract = "Additional experimental results, as well as spectroscopic and analytical data",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Supplementary material to: "Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential"",
url = "https://hdl.handle.net/21.15107/rcub_cer_4521"
}
Jeremić, M., Dinić, J., Pešić, M., Stepanovic, M., Novaković, I., Šegan, D.,& Sladić, D.. (2018). Supplementary material to: "Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential". in Journal of the Serbian Chemical Society
Serbian Chemical Society..
https://hdl.handle.net/21.15107/rcub_cer_4521
Jeremić M, Dinić J, Pešić M, Stepanovic M, Novaković I, Šegan D, Sladić D. Supplementary material to: "Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential". in Journal of the Serbian Chemical Society. 2018;.
https://hdl.handle.net/21.15107/rcub_cer_4521 .
Jeremić, Marko, Dinić, Jelena, Pešić, Milica, Stepanovic, Marija, Novaković, Irena, Šegan, Dejan, Sladić, Dušan, "Supplementary material to: "Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential"" in Journal of the Serbian Chemical Society (2018),
https://hdl.handle.net/21.15107/rcub_cer_4521 .

Supplementary Information for: "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies"

Jakovljević, Katarina; Joksovic, Milan D.; Matić, Ivana Z.; Petrovic, Nina; Stanojković, Tatjana; Sladić, Dušan; Vujčić, Miroslava; Janović, Barbara; Joksovic, Ljubinka; Trifunović, Snežana; Markovic, Violeta

(Royal Society of Chemistry, Cambridge, 2018)

TY  - DATA
AU  - Jakovljević, Katarina
AU  - Joksovic, Milan D.
AU  - Matić, Ivana Z.
AU  - Petrovic, Nina
AU  - Stanojković, Tatjana
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Joksovic, Ljubinka
AU  - Trifunović, Snežana
AU  - Markovic, Violeta
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4534
AB  - Copies of 1H and 13C NMR spectra for 5a-m
PB  - Royal Society of Chemistry, Cambridge
T2  - Medchemcomm
T1  - Supplementary Information for: "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies"
UR  - https://hdl.handle.net/21.15107/rcub_cer_4534
ER  - 
@misc{
author = "Jakovljević, Katarina and Joksovic, Milan D. and Matić, Ivana Z. and Petrovic, Nina and Stanojković, Tatjana and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Joksovic, Ljubinka and Trifunović, Snežana and Markovic, Violeta",
year = "2018",
abstract = "Copies of 1H and 13C NMR spectra for 5a-m",
publisher = "Royal Society of Chemistry, Cambridge",
journal = "Medchemcomm",
title = "Supplementary Information for: "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies"",
url = "https://hdl.handle.net/21.15107/rcub_cer_4534"
}
Jakovljević, K., Joksovic, M. D., Matić, I. Z., Petrovic, N., Stanojković, T., Sladić, D., Vujčić, M., Janović, B., Joksovic, L., Trifunović, S.,& Markovic, V.. (2018). Supplementary Information for: "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies". in Medchemcomm
Royal Society of Chemistry, Cambridge..
https://hdl.handle.net/21.15107/rcub_cer_4534
Jakovljević K, Joksovic MD, Matić IZ, Petrovic N, Stanojković T, Sladić D, Vujčić M, Janović B, Joksovic L, Trifunović S, Markovic V. Supplementary Information for: "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies". in Medchemcomm. 2018;.
https://hdl.handle.net/21.15107/rcub_cer_4534 .
Jakovljević, Katarina, Joksovic, Milan D., Matić, Ivana Z., Petrovic, Nina, Stanojković, Tatjana, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Joksovic, Ljubinka, Trifunović, Snežana, Markovic, Violeta, "Supplementary Information for: "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies"" in Medchemcomm (2018),
https://hdl.handle.net/21.15107/rcub_cer_4534 .

Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies

Jakovljević, Katarina; Joksovic, Milan D.; Matić, Ivana Z.; Petrovic, Nina; Stanojković, Tatjana; Sladić, Dušan; Vujčić, Miroslava; Janović, Barbara; Joksovic, Ljubinka; Trifunović, Snežana; Markovic, Violeta

(Royal Soc Chemistry, Cambridge, 2018)

TY  - JOUR
AU  - Jakovljević, Katarina
AU  - Joksovic, Milan D.
AU  - Matić, Ivana Z.
AU  - Petrovic, Nina
AU  - Stanojković, Tatjana
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Joksovic, Ljubinka
AU  - Trifunović, Snežana
AU  - Markovic, Violeta
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2379
AB  - Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.
PB  - Royal Soc Chemistry, Cambridge
T2  - Medchemcomm
T1  - Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies
VL  - 9
IS  - 10
SP  - 1679
EP  - 1697
DO  - 10.1039/c8md00316e
ER  - 
@article{
author = "Jakovljević, Katarina and Joksovic, Milan D. and Matić, Ivana Z. and Petrovic, Nina and Stanojković, Tatjana and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Joksovic, Ljubinka and Trifunović, Snežana and Markovic, Violeta",
year = "2018",
abstract = "Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Medchemcomm",
title = "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies",
volume = "9",
number = "10",
pages = "1679-1697",
doi = "10.1039/c8md00316e"
}
Jakovljević, K., Joksovic, M. D., Matić, I. Z., Petrovic, N., Stanojković, T., Sladić, D., Vujčić, M., Janović, B., Joksovic, L., Trifunović, S.,& Markovic, V.. (2018). Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. in Medchemcomm
Royal Soc Chemistry, Cambridge., 9(10), 1679-1697.
https://doi.org/10.1039/c8md00316e
Jakovljević K, Joksovic MD, Matić IZ, Petrovic N, Stanojković T, Sladić D, Vujčić M, Janović B, Joksovic L, Trifunović S, Markovic V. Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. in Medchemcomm. 2018;9(10):1679-1697.
doi:10.1039/c8md00316e .
Jakovljević, Katarina, Joksovic, Milan D., Matić, Ivana Z., Petrovic, Nina, Stanojković, Tatjana, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Joksovic, Ljubinka, Trifunović, Snežana, Markovic, Violeta, "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies" in Medchemcomm, 9, no. 10 (2018):1679-1697,
https://doi.org/10.1039/c8md00316e . .
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24
15
28

Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential

Jeremić, Marko; Dinić, Jelena; Pešić, Milica; Stepanovic, Marija; Novaković, Irena; Šegan, Dejan; Sladić, Dušan

(Serbian Chemical Society, 2018)

TY  - JOUR
AU  - Jeremić, Marko
AU  - Dinić, Jelena
AU  - Pešić, Milica
AU  - Stepanovic, Marija
AU  - Novaković, Irena
AU  - Šegan, Dejan
AU  - Sladić, Dušan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2361
UR  - https://www.shd-pub.org.rs/index.php/JSCS/article/view/7014
AB  - In this paper, the synthesis of fourteen alkylamino and arylamino derivatives of sesquiterpene quinone avarone and its model compound tert-butylquinone is described. Branched, cyclic, allylic and benzylic alkylamino/arylamino groups were introduced into the quinone moiety. For all the obtained derivatives, their biological activity and redox properties were studied. The cytotoxic activity of the synthesized derivatives towards multidrug resistant (MDR) human non-small cell lung carcinoma NCI-H460/R cells, their sensitive counterpart NCI-H460 and human normal keratinocytes (HaCaT) was investigated. The antimicrobial activity towards Gram-positive and Gram-negative bacteria, and fungal cultures was determined. Some of the synthesized derivatives showed selectivity for cancer cells, including MDR cells. Regarding their cell death induction potential, the most promising compounds were allylamino derivatives, preferentially triggering apoptosis, with high selectivity for cancer cells, including MDR cells. Several compounds showed promising antimicrobial activity, comparable to those of commercial antibiotic and antimycotic agents.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential
T1  - Aлкиламино и аралкиламино деривати аварона и његовог миметика као селективни агенси према ћелијама неситноћелијског карцинома плућа, њихов антибактеријски и антифунгални потенцијал
VL  - 83
IS  - 11
SP  - 1193
EP  - 1207
DO  - 10.2298/JSC180627062J
ER  - 
@article{
author = "Jeremić, Marko and Dinić, Jelena and Pešić, Milica and Stepanovic, Marija and Novaković, Irena and Šegan, Dejan and Sladić, Dušan",
year = "2018",
abstract = "In this paper, the synthesis of fourteen alkylamino and arylamino derivatives of sesquiterpene quinone avarone and its model compound tert-butylquinone is described. Branched, cyclic, allylic and benzylic alkylamino/arylamino groups were introduced into the quinone moiety. For all the obtained derivatives, their biological activity and redox properties were studied. The cytotoxic activity of the synthesized derivatives towards multidrug resistant (MDR) human non-small cell lung carcinoma NCI-H460/R cells, their sensitive counterpart NCI-H460 and human normal keratinocytes (HaCaT) was investigated. The antimicrobial activity towards Gram-positive and Gram-negative bacteria, and fungal cultures was determined. Some of the synthesized derivatives showed selectivity for cancer cells, including MDR cells. Regarding their cell death induction potential, the most promising compounds were allylamino derivatives, preferentially triggering apoptosis, with high selectivity for cancer cells, including MDR cells. Several compounds showed promising antimicrobial activity, comparable to those of commercial antibiotic and antimycotic agents.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential, Aлкиламино и аралкиламино деривати аварона и његовог миметика као селективни агенси према ћелијама неситноћелијског карцинома плућа, њихов антибактеријски и антифунгални потенцијал",
volume = "83",
number = "11",
pages = "1193-1207",
doi = "10.2298/JSC180627062J"
}
Jeremić, M., Dinić, J., Pešić, M., Stepanovic, M., Novaković, I., Šegan, D.,& Sladić, D.. (2018). Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 83(11), 1193-1207.
https://doi.org/10.2298/JSC180627062J
Jeremić M, Dinić J, Pešić M, Stepanovic M, Novaković I, Šegan D, Sladić D. Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential. in Journal of the Serbian Chemical Society. 2018;83(11):1193-1207.
doi:10.2298/JSC180627062J .
Jeremić, Marko, Dinić, Jelena, Pešić, Milica, Stepanovic, Marija, Novaković, Irena, Šegan, Dejan, Sladić, Dušan, "Alkylamino and aralkylamino derivatives of avarone and its mimetic as selective agents against non-small cell lung cancer cells, their antibacterial and antifungal potential" in Journal of the Serbian Chemical Society, 83, no. 11 (2018):1193-1207,
https://doi.org/10.2298/JSC180627062J . .
1
2

Novel silver(I) compounds with 1-adamantanamine

Jeremić, Dejan; Dordevic, Milena; Miletić, Srđan; Anđelković, Ljubica; Sladić, Dušan; Brčeski, Ilija

(Serbian Chemical Soc, Belgrade, 2018)

TY  - JOUR
AU  - Jeremić, Dejan
AU  - Dordevic, Milena
AU  - Miletić, Srđan
AU  - Anđelković, Ljubica
AU  - Sladić, Dušan
AU  - Brčeski, Ilija
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2436
AB  - In this work, three novel silver(I) complexes with an almost completely rigid and bulky monodentate ligand, 1-adamantanamine, were synthesized. The aliphatic amine, 1-adamantanamine, is the sole electron donor ligand in these complexes. In addition to spectroscopic characterization, the basic biological activities of the new compounds were investigated and their minimum inhibitory concentrations were determined. The antifungal and antibacterial activities indicate that these compounds could potentially be applied as new therapeutics.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Novel silver(I) compounds with 1-adamantanamine
VL  - 83
IS  - 6
SP  - 699
EP  - 705
DO  - 10.2298/JSC171114041J
ER  - 
@article{
author = "Jeremić, Dejan and Dordevic, Milena and Miletić, Srđan and Anđelković, Ljubica and Sladić, Dušan and Brčeski, Ilija",
year = "2018",
abstract = "In this work, three novel silver(I) complexes with an almost completely rigid and bulky monodentate ligand, 1-adamantanamine, were synthesized. The aliphatic amine, 1-adamantanamine, is the sole electron donor ligand in these complexes. In addition to spectroscopic characterization, the basic biological activities of the new compounds were investigated and their minimum inhibitory concentrations were determined. The antifungal and antibacterial activities indicate that these compounds could potentially be applied as new therapeutics.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Novel silver(I) compounds with 1-adamantanamine",
volume = "83",
number = "6",
pages = "699-705",
doi = "10.2298/JSC171114041J"
}
Jeremić, D., Dordevic, M., Miletić, S., Anđelković, L., Sladić, D.,& Brčeski, I.. (2018). Novel silver(I) compounds with 1-adamantanamine. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 83(6), 699-705.
https://doi.org/10.2298/JSC171114041J
Jeremić D, Dordevic M, Miletić S, Anđelković L, Sladić D, Brčeski I. Novel silver(I) compounds with 1-adamantanamine. in Journal of the Serbian Chemical Society. 2018;83(6):699-705.
doi:10.2298/JSC171114041J .
Jeremić, Dejan, Dordevic, Milena, Miletić, Srđan, Anđelković, Ljubica, Sladić, Dušan, Brčeski, Ilija, "Novel silver(I) compounds with 1-adamantanamine" in Journal of the Serbian Chemical Society, 83, no. 6 (2018):699-705,
https://doi.org/10.2298/JSC171114041J . .
3
3
4

Evaluation of genotoxic potential of tert-butylquinone and its derivatives in prokaryotic and eukaryotic test models

Đorđević, J.; Kolarević, S.; Jovanović, J.; Kostić-Vuković, J.; Novaković, Irena; Jeremić, M.; Sladić, Dušan; Vuković-Gačić, Branka

(Taylor and Francis Ltd, 2018)

TY  - JOUR
AU  - Đorđević, J.
AU  - Kolarević, S.
AU  - Jovanović, J.
AU  - Kostić-Vuković, J.
AU  - Novaković, Irena
AU  - Jeremić, M.
AU  - Sladić, Dušan
AU  - Vuković-Gačić, Branka
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2415
AB  - Tert-butylquinone (TBQ) and its alkylamino and aralkylamino derivatives are of high interest as a potential antitumor agent. Therefore, it was necessary to investigate if the compounds exert undesirable activities such as interaction with DNA molecule which could result in negative side effects in the case of their use in the diseases treatment. The major aim of this study was to investigate genotoxic potential of TBQ and selected derivatives in an acellular model by using plasmid DNA, in the prokaryotic model by the SOS/umuC assay in Salmonella typhimurium TA1535/pSK1002 and in eukaryotic models by using comet assay in human fetal lung cell line (MRC-5) and human liver cancer cell line (HepG2). Results indicated that in the acellular model TBQ and its derivatives do not interact with plasmid pUC19. In the prokaryotic model, only TBQ exerted weak genotoxic potential and only at highly cytotoxic concentrations. In eukaryotic models, genotoxic potential was detected mainly at the highest concentrations of the tested substances but the effect was lower in both cell lines in comparison with benzo[a]pyrene and etoposide which were used as positive controls. Weak genotoxic potential of tested compounds recommends them as good candidates for further testing in development of new antitumor agents.
PB  - Taylor and Francis Ltd
T2  - Drug and Chemical Toxicology
T1  - Evaluation of genotoxic potential of tert-butylquinone and its derivatives in prokaryotic and eukaryotic test models
SP  - 522
EP  - 530
DO  - 10.1080/01480545.2018.1514043
ER  - 
@article{
author = "Đorđević, J. and Kolarević, S. and Jovanović, J. and Kostić-Vuković, J. and Novaković, Irena and Jeremić, M. and Sladić, Dušan and Vuković-Gačić, Branka",
year = "2018",
abstract = "Tert-butylquinone (TBQ) and its alkylamino and aralkylamino derivatives are of high interest as a potential antitumor agent. Therefore, it was necessary to investigate if the compounds exert undesirable activities such as interaction with DNA molecule which could result in negative side effects in the case of their use in the diseases treatment. The major aim of this study was to investigate genotoxic potential of TBQ and selected derivatives in an acellular model by using plasmid DNA, in the prokaryotic model by the SOS/umuC assay in Salmonella typhimurium TA1535/pSK1002 and in eukaryotic models by using comet assay in human fetal lung cell line (MRC-5) and human liver cancer cell line (HepG2). Results indicated that in the acellular model TBQ and its derivatives do not interact with plasmid pUC19. In the prokaryotic model, only TBQ exerted weak genotoxic potential and only at highly cytotoxic concentrations. In eukaryotic models, genotoxic potential was detected mainly at the highest concentrations of the tested substances but the effect was lower in both cell lines in comparison with benzo[a]pyrene and etoposide which were used as positive controls. Weak genotoxic potential of tested compounds recommends them as good candidates for further testing in development of new antitumor agents.",
publisher = "Taylor and Francis Ltd",
journal = "Drug and Chemical Toxicology",
title = "Evaluation of genotoxic potential of tert-butylquinone and its derivatives in prokaryotic and eukaryotic test models",
pages = "522-530",
doi = "10.1080/01480545.2018.1514043"
}
Đorđević, J., Kolarević, S., Jovanović, J., Kostić-Vuković, J., Novaković, I., Jeremić, M., Sladić, D.,& Vuković-Gačić, B.. (2018). Evaluation of genotoxic potential of tert-butylquinone and its derivatives in prokaryotic and eukaryotic test models. in Drug and Chemical Toxicology
Taylor and Francis Ltd., 522-530.
https://doi.org/10.1080/01480545.2018.1514043
Đorđević J, Kolarević S, Jovanović J, Kostić-Vuković J, Novaković I, Jeremić M, Sladić D, Vuković-Gačić B. Evaluation of genotoxic potential of tert-butylquinone and its derivatives in prokaryotic and eukaryotic test models. in Drug and Chemical Toxicology. 2018;:522-530.
doi:10.1080/01480545.2018.1514043 .
Đorđević, J., Kolarević, S., Jovanović, J., Kostić-Vuković, J., Novaković, Irena, Jeremić, M., Sladić, Dušan, Vuković-Gačić, Branka, "Evaluation of genotoxic potential of tert-butylquinone and its derivatives in prokaryotic and eukaryotic test models" in Drug and Chemical Toxicology (2018):522-530,
https://doi.org/10.1080/01480545.2018.1514043 . .
4
1
4

Synthesis, characterization and crystal structures of two pentagonal-bipyramidal Fe(III) complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent. Anticancer properties of various metal complexes of the same ligand

Anđelković, Katarina; Milenković, Milica R.; Pevec, Andrej; Turel, Iztok; Matić, Ivana Z.; Vujčić, Miroslava; Sladić, Dušan; Radanović, Dušanka; Bradan, Gabrijela; Belosevic, Svetlana; Čobeljić, Božidar

(Elsevier Science Inc, New York, 2017)

TY  - JOUR
AU  - Anđelković, Katarina
AU  - Milenković, Milica R.
AU  - Pevec, Andrej
AU  - Turel, Iztok
AU  - Matić, Ivana Z.
AU  - Vujčić, Miroslava
AU  - Sladić, Dušan
AU  - Radanović, Dušanka
AU  - Bradan, Gabrijela
AU  - Belosevic, Svetlana
AU  - Čobeljić, Božidar
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2137
AB  - In this work synthesis, characterization and crystal structures of two isothiocyanato Fe(III) complexes with 2,2'[2,6-pyridinediylbis(ethylidyne-1-hydraziny1-2-ylidene)]bis[N,N,N-trimethyl-2-oxoethanaminium] dichloride (H2LCl2) ligand, with composition [FeL(NCS)(2)]SCN center dot 2H(2)O and [FeL(NCS)(2)](2)[Fe(H2O)(NCS)(5)}4H(2)O, has been reported. Both iron(III) complexes possess the same pentagonal-bipyramidal complex cation, while the nature of their anions depends on mole ratio of NH4SCN and FeCl3 center dot 6H(2)O used in reaction. Cytotoxic activity of new Fe(III) complexes, as well as of previously synthesized isothiocyanato Co(II), Ni(II), Mn(II), Zn(II) and Cd(II) complexes with the same ligand, was tested against five human cancer cell lines (HeLa, MDA-MB-453, K562, LS174 and A549) and normal cell line MRC-5. The best activity was observed in the case of Fe(III), Co(II) and Cd(II) complexes. The investigation of potential of these complexes to induce HeLa and K562 cell cycle perturbations was also evaluated. Mechanism of cell death mode was elucidated on the basis of morphological changes of HeLa cells as well as identification of target caspases. It was established that DNA damage could be responsible for the activity of Fe(III) and Co(II) complexes. Synopsis: Pentagonal-bipyramidal Fe(III) complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent have been synthesized and characterized. Cytotoxic activity of Fe(III) complexes and Co(II), Ni(II), Mn (II), Zn(II) and Cd(II) complexes with the same ligand was tested. The best activity was observed in the case of Fe (III), Co(II) and Cd(II) complexes.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Synthesis, characterization and crystal structures of two pentagonal-bipyramidal Fe(III) complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent. Anticancer properties of various metal complexes of the same ligand
VL  - 174
SP  - 137
EP  - 149
DO  - 10.1016/j.jinorgbio.2017.06.011
ER  - 
@article{
author = "Anđelković, Katarina and Milenković, Milica R. and Pevec, Andrej and Turel, Iztok and Matić, Ivana Z. and Vujčić, Miroslava and Sladić, Dušan and Radanović, Dušanka and Bradan, Gabrijela and Belosevic, Svetlana and Čobeljić, Božidar",
year = "2017",
abstract = "In this work synthesis, characterization and crystal structures of two isothiocyanato Fe(III) complexes with 2,2'[2,6-pyridinediylbis(ethylidyne-1-hydraziny1-2-ylidene)]bis[N,N,N-trimethyl-2-oxoethanaminium] dichloride (H2LCl2) ligand, with composition [FeL(NCS)(2)]SCN center dot 2H(2)O and [FeL(NCS)(2)](2)[Fe(H2O)(NCS)(5)}4H(2)O, has been reported. Both iron(III) complexes possess the same pentagonal-bipyramidal complex cation, while the nature of their anions depends on mole ratio of NH4SCN and FeCl3 center dot 6H(2)O used in reaction. Cytotoxic activity of new Fe(III) complexes, as well as of previously synthesized isothiocyanato Co(II), Ni(II), Mn(II), Zn(II) and Cd(II) complexes with the same ligand, was tested against five human cancer cell lines (HeLa, MDA-MB-453, K562, LS174 and A549) and normal cell line MRC-5. The best activity was observed in the case of Fe(III), Co(II) and Cd(II) complexes. The investigation of potential of these complexes to induce HeLa and K562 cell cycle perturbations was also evaluated. Mechanism of cell death mode was elucidated on the basis of morphological changes of HeLa cells as well as identification of target caspases. It was established that DNA damage could be responsible for the activity of Fe(III) and Co(II) complexes. Synopsis: Pentagonal-bipyramidal Fe(III) complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent have been synthesized and characterized. Cytotoxic activity of Fe(III) complexes and Co(II), Ni(II), Mn (II), Zn(II) and Cd(II) complexes with the same ligand was tested. The best activity was observed in the case of Fe (III), Co(II) and Cd(II) complexes.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Synthesis, characterization and crystal structures of two pentagonal-bipyramidal Fe(III) complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent. Anticancer properties of various metal complexes of the same ligand",
volume = "174",
pages = "137-149",
doi = "10.1016/j.jinorgbio.2017.06.011"
}
Anđelković, K., Milenković, M. R., Pevec, A., Turel, I., Matić, I. Z., Vujčić, M., Sladić, D., Radanović, D., Bradan, G., Belosevic, S.,& Čobeljić, B.. (2017). Synthesis, characterization and crystal structures of two pentagonal-bipyramidal Fe(III) complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent. Anticancer properties of various metal complexes of the same ligand. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 174, 137-149.
https://doi.org/10.1016/j.jinorgbio.2017.06.011
Anđelković K, Milenković MR, Pevec A, Turel I, Matić IZ, Vujčić M, Sladić D, Radanović D, Bradan G, Belosevic S, Čobeljić B. Synthesis, characterization and crystal structures of two pentagonal-bipyramidal Fe(III) complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent. Anticancer properties of various metal complexes of the same ligand. in Journal of Inorganic Biochemistry. 2017;174:137-149.
doi:10.1016/j.jinorgbio.2017.06.011 .
Anđelković, Katarina, Milenković, Milica R., Pevec, Andrej, Turel, Iztok, Matić, Ivana Z., Vujčić, Miroslava, Sladić, Dušan, Radanović, Dušanka, Bradan, Gabrijela, Belosevic, Svetlana, Čobeljić, Božidar, "Synthesis, characterization and crystal structures of two pentagonal-bipyramidal Fe(III) complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent. Anticancer properties of various metal complexes of the same ligand" in Journal of Inorganic Biochemistry, 174 (2017):137-149,
https://doi.org/10.1016/j.jinorgbio.2017.06.011 . .
20
13
20

Synthesis, characterization and crystal structures of two pentagonal-bipyramidal Fe(III) complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent. Anticancer properties of various metal complexes of the same ligand

Anđelković, Katarina; Milenković, Milica R.; Pevec, Andrej; Turel, Iztok; Matić, Ivana Z.; Vujčić, Miroslava; Sladić, Dušan; Radanović, Dušanka; Bradan, Gabrijela; Belosevic, Svetlana; Čobeljić, Božidar

(Elsevier Science Inc, New York, 2017)

TY  - JOUR
AU  - Anđelković, Katarina
AU  - Milenković, Milica R.
AU  - Pevec, Andrej
AU  - Turel, Iztok
AU  - Matić, Ivana Z.
AU  - Vujčić, Miroslava
AU  - Sladić, Dušan
AU  - Radanović, Dušanka
AU  - Bradan, Gabrijela
AU  - Belosevic, Svetlana
AU  - Čobeljić, Božidar
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2940
AB  - In this work synthesis, characterization and crystal structures of two isothiocyanato Fe(III) complexes with 2,2'[2,6-pyridinediylbis(ethylidyne-1-hydraziny1-2-ylidene)]bis[N,N,N-trimethyl-2-oxoethanaminium] dichloride (H2LCl2) ligand, with composition [FeL(NCS)(2)]SCN center dot 2H(2)O and [FeL(NCS)(2)](2)[Fe(H2O)(NCS)(5)}4H(2)O, has been reported. Both iron(III) complexes possess the same pentagonal-bipyramidal complex cation, while the nature of their anions depends on mole ratio of NH4SCN and FeCl3 center dot 6H(2)O used in reaction. Cytotoxic activity of new Fe(III) complexes, as well as of previously synthesized isothiocyanato Co(II), Ni(II), Mn(II), Zn(II) and Cd(II) complexes with the same ligand, was tested against five human cancer cell lines (HeLa, MDA-MB-453, K562, LS174 and A549) and normal cell line MRC-5. The best activity was observed in the case of Fe(III), Co(II) and Cd(II) complexes. The investigation of potential of these complexes to induce HeLa and K562 cell cycle perturbations was also evaluated. Mechanism of cell death mode was elucidated on the basis of morphological changes of HeLa cells as well as identification of target caspases. It was established that DNA damage could be responsible for the activity of Fe(III) and Co(II) complexes. Synopsis: Pentagonal-bipyramidal Fe(III) complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent have been synthesized and characterized. Cytotoxic activity of Fe(III) complexes and Co(II), Ni(II), Mn (II), Zn(II) and Cd(II) complexes with the same ligand was tested. The best activity was observed in the case of Fe (III), Co(II) and Cd(II) complexes.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Synthesis, characterization and crystal structures of two pentagonal-bipyramidal Fe(III) complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent. Anticancer properties of various metal complexes of the same ligand
VL  - 174
SP  - 137
EP  - 149
DO  - 10.1016/j.jinorgbio.2017.06.011
ER  - 
@article{
author = "Anđelković, Katarina and Milenković, Milica R. and Pevec, Andrej and Turel, Iztok and Matić, Ivana Z. and Vujčić, Miroslava and Sladić, Dušan and Radanović, Dušanka and Bradan, Gabrijela and Belosevic, Svetlana and Čobeljić, Božidar",
year = "2017",
abstract = "In this work synthesis, characterization and crystal structures of two isothiocyanato Fe(III) complexes with 2,2'[2,6-pyridinediylbis(ethylidyne-1-hydraziny1-2-ylidene)]bis[N,N,N-trimethyl-2-oxoethanaminium] dichloride (H2LCl2) ligand, with composition [FeL(NCS)(2)]SCN center dot 2H(2)O and [FeL(NCS)(2)](2)[Fe(H2O)(NCS)(5)}4H(2)O, has been reported. Both iron(III) complexes possess the same pentagonal-bipyramidal complex cation, while the nature of their anions depends on mole ratio of NH4SCN and FeCl3 center dot 6H(2)O used in reaction. Cytotoxic activity of new Fe(III) complexes, as well as of previously synthesized isothiocyanato Co(II), Ni(II), Mn(II), Zn(II) and Cd(II) complexes with the same ligand, was tested against five human cancer cell lines (HeLa, MDA-MB-453, K562, LS174 and A549) and normal cell line MRC-5. The best activity was observed in the case of Fe(III), Co(II) and Cd(II) complexes. The investigation of potential of these complexes to induce HeLa and K562 cell cycle perturbations was also evaluated. Mechanism of cell death mode was elucidated on the basis of morphological changes of HeLa cells as well as identification of target caspases. It was established that DNA damage could be responsible for the activity of Fe(III) and Co(II) complexes. Synopsis: Pentagonal-bipyramidal Fe(III) complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent have been synthesized and characterized. Cytotoxic activity of Fe(III) complexes and Co(II), Ni(II), Mn (II), Zn(II) and Cd(II) complexes with the same ligand was tested. The best activity was observed in the case of Fe (III), Co(II) and Cd(II) complexes.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Synthesis, characterization and crystal structures of two pentagonal-bipyramidal Fe(III) complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent. Anticancer properties of various metal complexes of the same ligand",
volume = "174",
pages = "137-149",
doi = "10.1016/j.jinorgbio.2017.06.011"
}
Anđelković, K., Milenković, M. R., Pevec, A., Turel, I., Matić, I. Z., Vujčić, M., Sladić, D., Radanović, D., Bradan, G., Belosevic, S.,& Čobeljić, B.. (2017). Synthesis, characterization and crystal structures of two pentagonal-bipyramidal Fe(III) complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent. Anticancer properties of various metal complexes of the same ligand. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 174, 137-149.
https://doi.org/10.1016/j.jinorgbio.2017.06.011
Anđelković K, Milenković MR, Pevec A, Turel I, Matić IZ, Vujčić M, Sladić D, Radanović D, Bradan G, Belosevic S, Čobeljić B. Synthesis, characterization and crystal structures of two pentagonal-bipyramidal Fe(III) complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent. Anticancer properties of various metal complexes of the same ligand. in Journal of Inorganic Biochemistry. 2017;174:137-149.
doi:10.1016/j.jinorgbio.2017.06.011 .
Anđelković, Katarina, Milenković, Milica R., Pevec, Andrej, Turel, Iztok, Matić, Ivana Z., Vujčić, Miroslava, Sladić, Dušan, Radanović, Dušanka, Bradan, Gabrijela, Belosevic, Svetlana, Čobeljić, Božidar, "Synthesis, characterization and crystal structures of two pentagonal-bipyramidal Fe(III) complexes with dihydrazone of 2,6-diacetylpyridine and Girard's T reagent. Anticancer properties of various metal complexes of the same ligand" in Journal of Inorganic Biochemistry, 174 (2017):137-149,
https://doi.org/10.1016/j.jinorgbio.2017.06.011 . .
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Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro

Živković, Marijana; Matić, Ivana Z.; Rodić, Marko V.; Novaković, Irena; Krivokuca, Ana M.; Sladić, Dušan; Krstić, Natalija

(Oxford : Pergamon-Elsevier Science Ltd, 2017)

TY  - JOUR
AU  - Živković, Marijana
AU  - Matić, Ivana Z.
AU  - Rodić, Marko V.
AU  - Novaković, Irena
AU  - Krivokuca, Ana M.
AU  - Sladić, Dušan
AU  - Krstić, Natalija
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2089
AB  - The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (5)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC50 values from 8.5 mu M to 14.9 mu M), eight on HeLa cells (IC50 values ranging from 8.9 mu M to 15.1 mu M) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC50 values from 12.7 mu M to 25.6 mu M) than cisplatin (21.5 mu M) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Journal of Steroid Biochemistry and Molecular Biology
T1  - Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro
VL  - 174
SP  - 72
EP  - 85
DO  - 10.1016/j.jsbmb.2017.07.031
ER  - 
@article{
author = "Živković, Marijana and Matić, Ivana Z. and Rodić, Marko V. and Novaković, Irena and Krivokuca, Ana M. and Sladić, Dušan and Krstić, Natalija",
year = "2017",
abstract = "The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (5)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC50 values from 8.5 mu M to 14.9 mu M), eight on HeLa cells (IC50 values ranging from 8.9 mu M to 15.1 mu M) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC50 values from 12.7 mu M to 25.6 mu M) than cisplatin (21.5 mu M) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Journal of Steroid Biochemistry and Molecular Biology",
title = "Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro",
volume = "174",
pages = "72-85",
doi = "10.1016/j.jsbmb.2017.07.031"
}
Živković, M., Matić, I. Z., Rodić, M. V., Novaković, I., Krivokuca, A. M., Sladić, D.,& Krstić, N.. (2017). Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro. in Journal of Steroid Biochemistry and Molecular Biology
Oxford : Pergamon-Elsevier Science Ltd., 174, 72-85.
https://doi.org/10.1016/j.jsbmb.2017.07.031
Živković M, Matić IZ, Rodić MV, Novaković I, Krivokuca AM, Sladić D, Krstić N. Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro. in Journal of Steroid Biochemistry and Molecular Biology. 2017;174:72-85.
doi:10.1016/j.jsbmb.2017.07.031 .
Živković, Marijana, Matić, Ivana Z., Rodić, Marko V., Novaković, Irena, Krivokuca, Ana M., Sladić, Dušan, Krstić, Natalija, "Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro" in Journal of Steroid Biochemistry and Molecular Biology, 174 (2017):72-85,
https://doi.org/10.1016/j.jsbmb.2017.07.031 . .
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Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro

Živković, Marijana; Matić, Ivana Z.; Rodić, Marko V.; Novaković, Irena; Krivokuca, Ana M.; Sladić, Dušan; Krstić, Natalija

(Oxford : Pergamon-Elsevier Science Ltd, 2017)

TY  - JOUR
AU  - Živković, Marijana
AU  - Matić, Ivana Z.
AU  - Rodić, Marko V.
AU  - Novaković, Irena
AU  - Krivokuca, Ana M.
AU  - Sladić, Dušan
AU  - Krstić, Natalija
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3009
AB  - The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (5)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC50 values from 8.5 mu M to 14.9 mu M), eight on HeLa cells (IC50 values ranging from 8.9 mu M to 15.1 mu M) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC50 values from 12.7 mu M to 25.6 mu M) than cisplatin (21.5 mu M) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Journal of Steroid Biochemistry and Molecular Biology
T1  - Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro
VL  - 174
SP  - 72
EP  - 85
DO  - 10.1016/j.jsbmb.2017.07.031
ER  - 
@article{
author = "Živković, Marijana and Matić, Ivana Z. and Rodić, Marko V. and Novaković, Irena and Krivokuca, Ana M. and Sladić, Dušan and Krstić, Natalija",
year = "2017",
abstract = "The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (5)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC50 values from 8.5 mu M to 14.9 mu M), eight on HeLa cells (IC50 values ranging from 8.9 mu M to 15.1 mu M) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC50 values from 12.7 mu M to 25.6 mu M) than cisplatin (21.5 mu M) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Journal of Steroid Biochemistry and Molecular Biology",
title = "Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro",
volume = "174",
pages = "72-85",
doi = "10.1016/j.jsbmb.2017.07.031"
}
Živković, M., Matić, I. Z., Rodić, M. V., Novaković, I., Krivokuca, A. M., Sladić, D.,& Krstić, N.. (2017). Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro. in Journal of Steroid Biochemistry and Molecular Biology
Oxford : Pergamon-Elsevier Science Ltd., 174, 72-85.
https://doi.org/10.1016/j.jsbmb.2017.07.031
Živković M, Matić IZ, Rodić MV, Novaković I, Krivokuca AM, Sladić D, Krstić N. Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro. in Journal of Steroid Biochemistry and Molecular Biology. 2017;174:72-85.
doi:10.1016/j.jsbmb.2017.07.031 .
Živković, Marijana, Matić, Ivana Z., Rodić, Marko V., Novaković, Irena, Krivokuca, Ana M., Sladić, Dušan, Krstić, Natalija, "Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro" in Journal of Steroid Biochemistry and Molecular Biology, 174 (2017):72-85,
https://doi.org/10.1016/j.jsbmb.2017.07.031 . .
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