TY  - JOUR
AU  - Dimitrijević, Jelena
AU  - Solovjova, Natalija
AU  - Bukonjić, Andriana M.
AU  - Tomović, Dušan Lj.
AU  - Milinković, Mirjana
AU  - Caković, Angelina
AU  - Bogojeski, Jovana
AU  - Ratković, Zoran R.
AU  - Janjić, Goran
AU  - Rakić, Aleksandra
AU  - Arsenijević, Nebojša N.
AU  - Milovanović, Marija Z.
AU  - Milovanović, Jelena Z.
AU  - Radić, Gordana P.
AU  - Jevtić, Verica V.
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7060
AB  - The numerous side effects of platinum based chemotherapy has led to the design of new therapeutics with platinum replaced by another transition metal. Here, we investigated the interactions of previously reported copper(II) complexes containing S-isoalkyl derivatives, the salicylic acid with guanosine-5′-monophosphate and calf thymus DNA (CT-DNA) and their antitumor effects, in a colon carcinoma model. All three copper(II) complexes exhibited an affinity for binding to CT-DNA, but there was no indication of intercalation or the displacement of ethidium bromide. Molecular docking studies revealed a significant affinity of the complexes for binding to the minor groove of B-form DNA, which coincided with DNA elongation, and a higher affinity for binding to Z-form DNA, supporting the hypothesis that the complex binding to CT-DNA induces a local transition from B-form to Z-form DNA. These complexes show a moderate, but selective cytotoxic effect toward colon cancer cells in vitro. Binuclear complex of copper(II) with S-isoamyl derivative of thiosalicylic acid showed the highest cytotoxic effect, arrested tumor cells in the G2/M phase of the cell cycle, and significantly reduced the expression of inflammatory molecules pro-IL-1β, TNF-α, ICAM-1, and VCAM-1 in the tissue of primary heterotopic murine colon cancer, which was accompanied by a significantly reduced tumor growth and metastases in the lung and liver.
PB  - MDPI
T2  - International Journal of Molecular Sciences
T1  - Docking studies, cytotoxicity evaluation and interactions of binuclear copper(ii) complexes with s-isoalkyl derivatives of thiosalicylic acid with some relevant biomolecules
VL  - 24
IS  - 15
SP  - 12504
DO  - 10.3390/ijms241512504
ER  - 

@article{
author = "Dimitrijević, Jelena and Solovjova, Natalija and Bukonjić, Andriana M. and Tomović, Dušan Lj. and Milinković, Mirjana and Caković, Angelina and Bogojeski, Jovana and Ratković, Zoran R. and Janjić, Goran and Rakić, Aleksandra and Arsenijević, Nebojša N. and Milovanović, Marija Z. and Milovanović, Jelena Z. and Radić, Gordana P. and Jevtić, Verica V.",
year = "2023",
abstract = "The numerous side effects of platinum based chemotherapy has led to the design of new therapeutics with platinum replaced by another transition metal. Here, we investigated the interactions of previously reported copper(II) complexes containing S-isoalkyl derivatives, the salicylic acid with guanosine-5′-monophosphate and calf thymus DNA (CT-DNA) and their antitumor effects, in a colon carcinoma model. All three copper(II) complexes exhibited an affinity for binding to CT-DNA, but there was no indication of intercalation or the displacement of ethidium bromide. Molecular docking studies revealed a significant affinity of the complexes for binding to the minor groove of B-form DNA, which coincided with DNA elongation, and a higher affinity for binding to Z-form DNA, supporting the hypothesis that the complex binding to CT-DNA induces a local transition from B-form to Z-form DNA. These complexes show a moderate, but selective cytotoxic effect toward colon cancer cells in vitro. Binuclear complex of copper(II) with S-isoamyl derivative of thiosalicylic acid showed the highest cytotoxic effect, arrested tumor cells in the G2/M phase of the cell cycle, and significantly reduced the expression of inflammatory molecules pro-IL-1β, TNF-α, ICAM-1, and VCAM-1 in the tissue of primary heterotopic murine colon cancer, which was accompanied by a significantly reduced tumor growth and metastases in the lung and liver.",
publisher = "MDPI",
journal = "International Journal of Molecular Sciences",
title = "Docking studies, cytotoxicity evaluation and interactions of binuclear copper(ii) complexes with s-isoalkyl derivatives of thiosalicylic acid with some relevant biomolecules",
volume = "24",
number = "15",
pages = "12504",
doi = "10.3390/ijms241512504"
}

Dimitrijević, J., Solovjova, N., Bukonjić, A. M., Tomović, D. Lj., Milinković, M., Caković, A., Bogojeski, J., Ratković, Z. R., Janjić, G., Rakić, A., Arsenijević, N. N., Milovanović, M. Z., Milovanović, J. Z., Radić, G. P.,& Jevtić, V. V.. (2023). Docking studies, cytotoxicity evaluation and interactions of binuclear copper(ii) complexes with s-isoalkyl derivatives of thiosalicylic acid with some relevant biomolecules. in International Journal of Molecular Sciences
MDPI., 24(15), 12504.
https://doi.org/10.3390/ijms241512504

Dimitrijević J, Solovjova N, Bukonjić AM, Tomović DL, Milinković M, Caković A, Bogojeski J, Ratković ZR, Janjić G, Rakić A, Arsenijević NN, Milovanović MZ, Milovanović JZ, Radić GP, Jevtić VV. Docking studies, cytotoxicity evaluation and interactions of binuclear copper(ii) complexes with s-isoalkyl derivatives of thiosalicylic acid with some relevant biomolecules. in International Journal of Molecular Sciences. 2023;24(15):12504.
doi:10.3390/ijms241512504 .

Dimitrijević, Jelena, Solovjova, Natalija, Bukonjić, Andriana M., Tomović, Dušan Lj., Milinković, Mirjana, Caković, Angelina, Bogojeski, Jovana, Ratković, Zoran R., Janjić, Goran, Rakić, Aleksandra, Arsenijević, Nebojša N., Milovanović, Marija Z., Milovanović, Jelena Z., Radić, Gordana P., Jevtić, Verica V., "Docking studies, cytotoxicity evaluation and interactions of binuclear copper(ii) complexes with s-isoalkyl derivatives of thiosalicylic acid with some relevant biomolecules" in International Journal of Molecular Sciences, 24, no. 15 (2023):12504,
https://doi.org/10.3390/ijms241512504 . .

TY  - JOUR
AU  - Konovalov, Bata
AU  - Đorđević, Ivana
AU  - Franich, Andjela A.
AU  - Šmit, Biljana
AU  - Živković, Marija D.
AU  - Djuran, Miloš I.
AU  - Janjić, Goran
AU  - Rajković, Snežana
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7061
AB  - The hydrolysis of N-acetylated L-methionylglycine dipeptide (Ac-L-Met-Gly) in the presence of dinuclear platinum(II)-aqua complexes with general formula [{Pt(L)(H2O)}2(μ-1,5-nphe)]4+ (1,5-nphe is 1,5-naphthyridine; L is bidentately coordinated ethylenediamine (1w), (±)-1,2-propylenediamine (2w) and 1,3-propylenediamine (3w)) is described in detail. The hydrolytic activity of these complexes was monitored by 1H NMR spectroscopy, which confirmed the regioselective cleavage of the Met-Gly-amide bond in this peptide. Quantum-chemical calculations revealed the primary reaction path with coordination of dipeptide via the terminal amide nitrogen of methionine followed by its coordination for the sulphur atom, in which the decomposition of the resulted platinum(II)-dipeptide complex and the coordination of its glycine residue precedes the hydrolytic cleavage of the Met-Gly amide bond. In the secondary reaction path, in which Ac-L-Met-Gly is coordinated via the methionine sulphur atom, the decomposition of the starting [{Pt(L)(H2O)}2(μ-1,5-nphe)]4+ complex is followed by the regioselective hydrolysis of the investigated dipeptide. The binding affinity of the chloride derivatives of the corresponding dinuclear platinum(II)-aqua complexes, [{Pt(L)Cl}2(μ-1,5-nphe)]2+ (1–3) towards the human serum albumin (HSA), a transport protein, was investigated using electronic absorption and fluorescence emission measurements, and results indicated the static interactions between these complexes and HSA. A docking study revealed a unique binding site on HSA, based on the electrostatic and the hydrogen bonding, which does not have a methionine residue nearby, therefore does not exist danger of HSA hydrolysis by these complexes.
PB  - Elsevier
T2  - Journal of Molecular Structure
T1  - Dinuclear platinum(II) complexes with 1,5-nphe bridging ligand: Spectroscopic and molecular docking study of the interactions with N-acetylated L-methionylglycine and human serum albumin
VL  - 1288
SP  - 135810
DO  - 10.1016/j.molstruc.2023.135810
ER  - 

@article{
author = "Konovalov, Bata and Đorđević, Ivana and Franich, Andjela A. and Šmit, Biljana and Živković, Marija D. and Djuran, Miloš I. and Janjić, Goran and Rajković, Snežana",
year = "2023",
abstract = "The hydrolysis of N-acetylated L-methionylglycine dipeptide (Ac-L-Met-Gly) in the presence of dinuclear platinum(II)-aqua complexes with general formula [{Pt(L)(H2O)}2(μ-1,5-nphe)]4+ (1,5-nphe is 1,5-naphthyridine; L is bidentately coordinated ethylenediamine (1w), (±)-1,2-propylenediamine (2w) and 1,3-propylenediamine (3w)) is described in detail. The hydrolytic activity of these complexes was monitored by 1H NMR spectroscopy, which confirmed the regioselective cleavage of the Met-Gly-amide bond in this peptide. Quantum-chemical calculations revealed the primary reaction path with coordination of dipeptide via the terminal amide nitrogen of methionine followed by its coordination for the sulphur atom, in which the decomposition of the resulted platinum(II)-dipeptide complex and the coordination of its glycine residue precedes the hydrolytic cleavage of the Met-Gly amide bond. In the secondary reaction path, in which Ac-L-Met-Gly is coordinated via the methionine sulphur atom, the decomposition of the starting [{Pt(L)(H2O)}2(μ-1,5-nphe)]4+ complex is followed by the regioselective hydrolysis of the investigated dipeptide. The binding affinity of the chloride derivatives of the corresponding dinuclear platinum(II)-aqua complexes, [{Pt(L)Cl}2(μ-1,5-nphe)]2+ (1–3) towards the human serum albumin (HSA), a transport protein, was investigated using electronic absorption and fluorescence emission measurements, and results indicated the static interactions between these complexes and HSA. A docking study revealed a unique binding site on HSA, based on the electrostatic and the hydrogen bonding, which does not have a methionine residue nearby, therefore does not exist danger of HSA hydrolysis by these complexes.",
publisher = "Elsevier",
journal = "Journal of Molecular Structure",
title = "Dinuclear platinum(II) complexes with 1,5-nphe bridging ligand: Spectroscopic and molecular docking study of the interactions with N-acetylated L-methionylglycine and human serum albumin",
volume = "1288",
pages = "135810",
doi = "10.1016/j.molstruc.2023.135810"
}

Konovalov, B., Đorđević, I., Franich, A. A., Šmit, B., Živković, M. D., Djuran, M. I., Janjić, G.,& Rajković, S.. (2023). Dinuclear platinum(II) complexes with 1,5-nphe bridging ligand: Spectroscopic and molecular docking study of the interactions with N-acetylated L-methionylglycine and human serum albumin. in Journal of Molecular Structure
Elsevier., 1288, 135810.
https://doi.org/10.1016/j.molstruc.2023.135810

Konovalov B, Đorđević I, Franich AA, Šmit B, Živković MD, Djuran MI, Janjić G, Rajković S. Dinuclear platinum(II) complexes with 1,5-nphe bridging ligand: Spectroscopic and molecular docking study of the interactions with N-acetylated L-methionylglycine and human serum albumin. in Journal of Molecular Structure. 2023;1288:135810.
doi:10.1016/j.molstruc.2023.135810 .

Konovalov, Bata, Đorđević, Ivana, Franich, Andjela A., Šmit, Biljana, Živković, Marija D., Djuran, Miloš I., Janjić, Goran, Rajković, Snežana, "Dinuclear platinum(II) complexes with 1,5-nphe bridging ligand: Spectroscopic and molecular docking study of the interactions with N-acetylated L-methionylglycine and human serum albumin" in Journal of Molecular Structure, 1288 (2023):135810,
https://doi.org/10.1016/j.molstruc.2023.135810 . .

TY  - JOUR
AU  - Franich, Andjela
AU  - Đorđević, Ivana S.
AU  - Živković, Marija D.
AU  - Rajković, Snežana
AU  - Janjić, Goran
AU  - Đuran, Miloš
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4832
AB  - The mechanism of action of most approved drugs in use today is based on their binding to specific proteins or DNA. One
of the achievements of this research is a new perspective for recognition of binding modes to DNA by monitoring of
changes in measured and stoichiometric values of absorbance at 260 nm. UV–Vis and IR spectroscopy, gel electrophoresis
and docking study were used for investigation of binding properties of three dinuclear platinum(II) complexes containing
different pyridine-based bridging ligands, [{Pt(en)Cl}2(μ-4,4’-bipy)]Cl2・2H2O (Pt1), [{Pt(en)Cl}2(μ-bpa)]Cl2・4H2O (Pt2)
and [{Pt(en)Cl}2(μ-bpe)]Cl2・4H2O (Pt3) to DNA (4,4’-bipy, bpa and bpe are 4,4′-bipyridine, 1,2-bis(4-pyridyl)ethane and
1,2-bis(4-pyridyl)ethene, respectively). In contrast to the system with well-known intercalated ligand (EtBr), covalently bound
ligand (cis-Pt) and with minor groove binder (Hoechst 33258), which do not have significant differences in measured and
stoichiometric values, the most pronounced deviations are recorded for two dinuclear platinum(II) complexes (Pt1 and Pt2),
as a consequence of complex binding to the phosphate backbone and bending of DNA helix. The hydrolysis of complexes
and changes in DNA conformation were also analysed as phenomena that may have an impact on the changes in absorbance.
PB  - Springer
T2  - Journal of Biological Inorganic Chemistry
T1  - Dinuclear platinum(II) complexes as the pattern for phosphate backbone binding: a new perspective for recognition of binding modes to DNA
VL  - 27
SP  - 65
EP  - 79
DO  - 10.1007/s00775-021-01911-6
ER  - 

@article{
author = "Franich, Andjela and Đorđević, Ivana S. and Živković, Marija D. and Rajković, Snežana and Janjić, Goran and Đuran, Miloš",
year = "2022",
abstract = "The mechanism of action of most approved drugs in use today is based on their binding to specific proteins or DNA. One
of the achievements of this research is a new perspective for recognition of binding modes to DNA by monitoring of
changes in measured and stoichiometric values of absorbance at 260 nm. UV–Vis and IR spectroscopy, gel electrophoresis
and docking study were used for investigation of binding properties of three dinuclear platinum(II) complexes containing
different pyridine-based bridging ligands, [{Pt(en)Cl}2(μ-4,4’-bipy)]Cl2・2H2O (Pt1), [{Pt(en)Cl}2(μ-bpa)]Cl2・4H2O (Pt2)
and [{Pt(en)Cl}2(μ-bpe)]Cl2・4H2O (Pt3) to DNA (4,4’-bipy, bpa and bpe are 4,4′-bipyridine, 1,2-bis(4-pyridyl)ethane and
1,2-bis(4-pyridyl)ethene, respectively). In contrast to the system with well-known intercalated ligand (EtBr), covalently bound
ligand (cis-Pt) and with minor groove binder (Hoechst 33258), which do not have significant differences in measured and
stoichiometric values, the most pronounced deviations are recorded for two dinuclear platinum(II) complexes (Pt1 and Pt2),
as a consequence of complex binding to the phosphate backbone and bending of DNA helix. The hydrolysis of complexes
and changes in DNA conformation were also analysed as phenomena that may have an impact on the changes in absorbance.",
publisher = "Springer",
journal = "Journal of Biological Inorganic Chemistry",
title = "Dinuclear platinum(II) complexes as the pattern for phosphate backbone binding: a new perspective for recognition of binding modes to DNA",
volume = "27",
pages = "65-79",
doi = "10.1007/s00775-021-01911-6"
}

Franich, A., Đorđević, I. S., Živković, M. D., Rajković, S., Janjić, G.,& Đuran, M.. (2022). Dinuclear platinum(II) complexes as the pattern for phosphate backbone binding: a new perspective for recognition of binding modes to DNA. in Journal of Biological Inorganic Chemistry
Springer., 27, 65-79.
https://doi.org/10.1007/s00775-021-01911-6

Franich A, Đorđević IS, Živković MD, Rajković S, Janjić G, Đuran M. Dinuclear platinum(II) complexes as the pattern for phosphate backbone binding: a new perspective for recognition of binding modes to DNA. in Journal of Biological Inorganic Chemistry. 2022;27:65-79.
doi:10.1007/s00775-021-01911-6 .

Franich, Andjela, Đorđević, Ivana S., Živković, Marija D., Rajković, Snežana, Janjić, Goran, Đuran, Miloš, "Dinuclear platinum(II) complexes as the pattern for phosphate backbone binding: a new perspective for recognition of binding modes to DNA" in Journal of Biological Inorganic Chemistry, 27 (2022):65-79,
https://doi.org/10.1007/s00775-021-01911-6 . .

TY  - JOUR
AU  - Maksimović, Jelena
AU  - Čupić, Željko
AU  - Manojlović, Nedeljko
AU  - Đerić, Aleksandra
AU  - Anić, Slobodan
AU  - Kolar-Anić, Ljiljana
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3603
AB  - Two hydroxyanthraquinones, alizarin and purpurin, that have been used throughout
history as a natural pigment, were extracted from roots of Rubia tinctorum from
Serbia. As substances with important chemical activities and, therefore, with wide
applications (for example in dyeing textile fabrics as well as in pharmacy because of
their anti-inflammatory, anti-cancer, antiviral, antimicrobial and antioxidant activities,
etc.) they were analyzed in the kinetically very sensitive Bray–Liebhafsky (BL)
oscillatory reaction. However, although they are both, hydroxyanthraquinones it is
shown that their interactions with BL nonlinear reaction system differ significantly.
Consequently, two different reactions were used to explain the mechanism of their
chemical activities. The numerical simulations based on a standard model of the BL
oscillatory reaction together with proposed reactions due to alizarin/purpurin interactions
with a matrix are correlated with experimental investigations. Moreover, it
is shown that very small amounts of alizarin and purpurin (from about 1 × 10–7 M)
produce the response of the BL matrix such that micro-quantitative analysis based
on the BL oscillatory reaction can be successfully performed in this reaction system.
The linear response of the BL matrix on the presence of alizarin and purpurin
(necessary for microquantitative determination) is analyzed as a function of two
concentration sensitive parameters: pre-oscillatory period τ1 and potential shift after
perturbation ΔE.
PB  - Springer Nature Switzerland AG 2020
T2  - Reaction Kinetics, Mechanisms and Catalysis
T1  - Bray–Liebhafsky oscillatory reaction as the matrix system for the kinetic determination of microquantities of alizarin and purpurin
VL  - 130
SP  - 655
EP  - 688
DO  - 10.1007/s11144-020-01798-5
ER  - 

@article{
author = "Maksimović, Jelena and Čupić, Željko and Manojlović, Nedeljko and Đerić, Aleksandra and Anić, Slobodan and Kolar-Anić, Ljiljana",
year = "2020",
abstract = "Two hydroxyanthraquinones, alizarin and purpurin, that have been used throughout
history as a natural pigment, were extracted from roots of Rubia tinctorum from
Serbia. As substances with important chemical activities and, therefore, with wide
applications (for example in dyeing textile fabrics as well as in pharmacy because of
their anti-inflammatory, anti-cancer, antiviral, antimicrobial and antioxidant activities,
etc.) they were analyzed in the kinetically very sensitive Bray–Liebhafsky (BL)
oscillatory reaction. However, although they are both, hydroxyanthraquinones it is
shown that their interactions with BL nonlinear reaction system differ significantly.
Consequently, two different reactions were used to explain the mechanism of their
chemical activities. The numerical simulations based on a standard model of the BL
oscillatory reaction together with proposed reactions due to alizarin/purpurin interactions
with a matrix are correlated with experimental investigations. Moreover, it
is shown that very small amounts of alizarin and purpurin (from about 1 × 10–7 M)
produce the response of the BL matrix such that micro-quantitative analysis based
on the BL oscillatory reaction can be successfully performed in this reaction system.
The linear response of the BL matrix on the presence of alizarin and purpurin
(necessary for microquantitative determination) is analyzed as a function of two
concentration sensitive parameters: pre-oscillatory period τ1 and potential shift after
perturbation ΔE.",
publisher = "Springer Nature Switzerland AG 2020",
journal = "Reaction Kinetics, Mechanisms and Catalysis",
title = "Bray–Liebhafsky oscillatory reaction as the matrix system for the kinetic determination of microquantities of alizarin and purpurin",
volume = "130",
pages = "655-688",
doi = "10.1007/s11144-020-01798-5"
}

Maksimović, J., Čupić, Ž., Manojlović, N., Đerić, A., Anić, S.,& Kolar-Anić, L.. (2020). Bray–Liebhafsky oscillatory reaction as the matrix system for the kinetic determination of microquantities of alizarin and purpurin. in Reaction Kinetics, Mechanisms and Catalysis
Springer Nature Switzerland AG 2020., 130, 655-688.
https://doi.org/10.1007/s11144-020-01798-5

Maksimović J, Čupić Ž, Manojlović N, Đerić A, Anić S, Kolar-Anić L. Bray–Liebhafsky oscillatory reaction as the matrix system for the kinetic determination of microquantities of alizarin and purpurin. in Reaction Kinetics, Mechanisms and Catalysis. 2020;130:655-688.
doi:10.1007/s11144-020-01798-5 .

Maksimović, Jelena, Čupić, Željko, Manojlović, Nedeljko, Đerić, Aleksandra, Anić, Slobodan, Kolar-Anić, Ljiljana, "Bray–Liebhafsky oscillatory reaction as the matrix system for the kinetic determination of microquantities of alizarin and purpurin" in Reaction Kinetics, Mechanisms and Catalysis, 130 (2020):655-688,
https://doi.org/10.1007/s11144-020-01798-5 . .