TY  - DATA
AU  - Tubić, Biljana K.
AU  - Dobričić, Vladimir
AU  - Poljarević, Jelena
AU  - Savić, Aleksandar
AU  - Sabo, Tibor
AU  - Marković, Bojan D.
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3870
PB  - Elsevier B.V.
T2  - Journal of Pharmaceutical and Biomedical Analysis
T1  - Supplementary data for the article: Tubić, B.; Dobričić, V.; Poljarević, J.; Savić, A.; Sabo, T.; Marković, B. Estimation of Passive Gastrointestinal Absorption and Membrane Retention Using PAMPA Test, Quantitative Structure-Permeability and Quantitative Structure-Retention Relationship Analyses of Ethylenediamine-N,N’-Di-2-(3-Cyclohexyl)Propanoic Acid and 1,3-Propanediamine-N,N’-Di-2-(3-Cyclohexyl)Propanoic Acid Derivatives. Journal of Pharmaceutical and Biomedical Analysis 2020, 184. https://doi.org/10.1016/j.jpba.2020.113213
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3870
ER  - 

@misc{
author = "Tubić, Biljana K. and Dobričić, Vladimir and Poljarević, Jelena and Savić, Aleksandar and Sabo, Tibor and Marković, Bojan D.",
year = "2020",
publisher = "Elsevier B.V.",
journal = "Journal of Pharmaceutical and Biomedical Analysis",
title = "Supplementary data for the article: Tubić, B.; Dobričić, V.; Poljarević, J.; Savić, A.; Sabo, T.; Marković, B. Estimation of Passive Gastrointestinal Absorption and Membrane Retention Using PAMPA Test, Quantitative Structure-Permeability and Quantitative Structure-Retention Relationship Analyses of Ethylenediamine-N,N’-Di-2-(3-Cyclohexyl)Propanoic Acid and 1,3-Propanediamine-N,N’-Di-2-(3-Cyclohexyl)Propanoic Acid Derivatives. Journal of Pharmaceutical and Biomedical Analysis 2020, 184. https://doi.org/10.1016/j.jpba.2020.113213",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3870"
}

Tubić, B. K., Dobričić, V., Poljarević, J., Savić, A., Sabo, T.,& Marković, B. D.. (2020). Supplementary data for the article: Tubić, B.; Dobričić, V.; Poljarević, J.; Savić, A.; Sabo, T.; Marković, B. Estimation of Passive Gastrointestinal Absorption and Membrane Retention Using PAMPA Test, Quantitative Structure-Permeability and Quantitative Structure-Retention Relationship Analyses of Ethylenediamine-N,N’-Di-2-(3-Cyclohexyl)Propanoic Acid and 1,3-Propanediamine-N,N’-Di-2-(3-Cyclohexyl)Propanoic Acid Derivatives. Journal of Pharmaceutical and Biomedical Analysis 2020, 184. https://doi.org/10.1016/j.jpba.2020.113213. in Journal of Pharmaceutical and Biomedical Analysis
Elsevier B.V...
https://hdl.handle.net/21.15107/rcub_cherry_3870

Tubić BK, Dobričić V, Poljarević J, Savić A, Sabo T, Marković BD. Supplementary data for the article: Tubić, B.; Dobričić, V.; Poljarević, J.; Savić, A.; Sabo, T.; Marković, B. Estimation of Passive Gastrointestinal Absorption and Membrane Retention Using PAMPA Test, Quantitative Structure-Permeability and Quantitative Structure-Retention Relationship Analyses of Ethylenediamine-N,N’-Di-2-(3-Cyclohexyl)Propanoic Acid and 1,3-Propanediamine-N,N’-Di-2-(3-Cyclohexyl)Propanoic Acid Derivatives. Journal of Pharmaceutical and Biomedical Analysis 2020, 184. https://doi.org/10.1016/j.jpba.2020.113213. in Journal of Pharmaceutical and Biomedical Analysis. 2020;.
https://hdl.handle.net/21.15107/rcub_cherry_3870 .

Tubić, Biljana K., Dobričić, Vladimir, Poljarević, Jelena, Savić, Aleksandar, Sabo, Tibor, Marković, Bojan D., "Supplementary data for the article: Tubić, B.; Dobričić, V.; Poljarević, J.; Savić, A.; Sabo, T.; Marković, B. Estimation of Passive Gastrointestinal Absorption and Membrane Retention Using PAMPA Test, Quantitative Structure-Permeability and Quantitative Structure-Retention Relationship Analyses of Ethylenediamine-N,N’-Di-2-(3-Cyclohexyl)Propanoic Acid and 1,3-Propanediamine-N,N’-Di-2-(3-Cyclohexyl)Propanoic Acid Derivatives. Journal of Pharmaceutical and Biomedical Analysis 2020, 184. https://doi.org/10.1016/j.jpba.2020.113213" in Journal of Pharmaceutical and Biomedical Analysis (2020),
https://hdl.handle.net/21.15107/rcub_cherry_3870 .

TY  - JOUR
AU  - Tubić, Biljana K.
AU  - Dobričić, Vladimir
AU  - Poljarević, Jelena
AU  - Savić, Aleksandar
AU  - Sabo, Tibor
AU  - Marković, Bojan D.
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3868
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3869
AB  - Passive gastrointestinal absorption and membrane retention of twelve esters of (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid (EDCP) and (S,S)-1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid (PDCP), as well as of these two non-esterified acids were estimated using PAMPA test. Artificial PAMPA membrane used in this study for the simulation of gastrointestinal barrier was solution of egg lecithin in dodecane (1 % w/v). All tested compounds belong to class III (high membrane retention and low permeation), whereas EDCP, dipentyl ester of PDCP (DPE-PDCP) and diisopentyl ester of PDCP (DIPE-PDCP) belong to class I (negligible membrane retention and low permeation). Finally, quantitative structure – permeability and structure – retention relationships models were created in order to find quantitative relationships between physico-chemical properties of tested compounds and PAMPA membrane permeability/membrane retention parameters. Statistically the most reliable models were analysed and used for the design of new compounds for which favourable membrane permeability and retention can be expected.
PB  - Elsevier B.V.
T2  - Journal of Pharmaceutical and Biomedical Analysis
T1  - Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives
VL  - 184
DO  - 10.1016/j.jpba.2020.113213
ER  - 

@article{
author = "Tubić, Biljana K. and Dobričić, Vladimir and Poljarević, Jelena and Savić, Aleksandar and Sabo, Tibor and Marković, Bojan D.",
year = "2020",
abstract = "Passive gastrointestinal absorption and membrane retention of twelve esters of (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid (EDCP) and (S,S)-1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid (PDCP), as well as of these two non-esterified acids were estimated using PAMPA test. Artificial PAMPA membrane used in this study for the simulation of gastrointestinal barrier was solution of egg lecithin in dodecane (1 % w/v). All tested compounds belong to class III (high membrane retention and low permeation), whereas EDCP, dipentyl ester of PDCP (DPE-PDCP) and diisopentyl ester of PDCP (DIPE-PDCP) belong to class I (negligible membrane retention and low permeation). Finally, quantitative structure – permeability and structure – retention relationships models were created in order to find quantitative relationships between physico-chemical properties of tested compounds and PAMPA membrane permeability/membrane retention parameters. Statistically the most reliable models were analysed and used for the design of new compounds for which favourable membrane permeability and retention can be expected.",
publisher = "Elsevier B.V.",
journal = "Journal of Pharmaceutical and Biomedical Analysis",
title = "Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives",
volume = "184",
doi = "10.1016/j.jpba.2020.113213"
}

Tubić, B. K., Dobričić, V., Poljarević, J., Savić, A., Sabo, T.,& Marković, B. D.. (2020). Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives. in Journal of Pharmaceutical and Biomedical Analysis
Elsevier B.V.., 184.
https://doi.org/10.1016/j.jpba.2020.113213

Tubić BK, Dobričić V, Poljarević J, Savić A, Sabo T, Marković BD. Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives. in Journal of Pharmaceutical and Biomedical Analysis. 2020;184.
doi:10.1016/j.jpba.2020.113213 .

Tubić, Biljana K., Dobričić, Vladimir, Poljarević, Jelena, Savić, Aleksandar, Sabo, Tibor, Marković, Bojan D., "Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives" in Journal of Pharmaceutical and Biomedical Analysis, 184 (2020),
https://doi.org/10.1016/j.jpba.2020.113213 . .

TY  - JOUR
AU  - Tubić, Biljana K.
AU  - Dobričić, Vladimir
AU  - Poljarević, Jelena
AU  - Savić, Aleksandar
AU  - Sabo, Tibor
AU  - Marković, Bojan D.
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3868
AB  - Passive gastrointestinal absorption and membrane retention of twelve esters of (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid (EDCP) and (S,S)-1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid (PDCP), as well as of these two non-esterified acids were estimated using PAMPA test. Artificial PAMPA membrane used in this study for the simulation of gastrointestinal barrier was solution of egg lecithin in dodecane (1 % w/v). All tested compounds belong to class III (high membrane retention and low permeation), whereas EDCP, dipentyl ester of PDCP (DPE-PDCP) and diisopentyl ester of PDCP (DIPE-PDCP) belong to class I (negligible membrane retention and low permeation). Finally, quantitative structure – permeability and structure – retention relationships models were created in order to find quantitative relationships between physico-chemical properties of tested compounds and PAMPA membrane permeability/membrane retention parameters. Statistically the most reliable models were analysed and used for the design of new compounds for which favourable membrane permeability and retention can be expected.
PB  - Elsevier B.V.
T2  - Journal of Pharmaceutical and Biomedical Analysis
T1  - Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives
VL  - 184
DO  - 10.1016/j.jpba.2020.113213
ER  - 

@article{
author = "Tubić, Biljana K. and Dobričić, Vladimir and Poljarević, Jelena and Savić, Aleksandar and Sabo, Tibor and Marković, Bojan D.",
year = "2020",
abstract = "Passive gastrointestinal absorption and membrane retention of twelve esters of (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid (EDCP) and (S,S)-1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid (PDCP), as well as of these two non-esterified acids were estimated using PAMPA test. Artificial PAMPA membrane used in this study for the simulation of gastrointestinal barrier was solution of egg lecithin in dodecane (1 % w/v). All tested compounds belong to class III (high membrane retention and low permeation), whereas EDCP, dipentyl ester of PDCP (DPE-PDCP) and diisopentyl ester of PDCP (DIPE-PDCP) belong to class I (negligible membrane retention and low permeation). Finally, quantitative structure – permeability and structure – retention relationships models were created in order to find quantitative relationships between physico-chemical properties of tested compounds and PAMPA membrane permeability/membrane retention parameters. Statistically the most reliable models were analysed and used for the design of new compounds for which favourable membrane permeability and retention can be expected.",
publisher = "Elsevier B.V.",
journal = "Journal of Pharmaceutical and Biomedical Analysis",
title = "Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives",
volume = "184",
doi = "10.1016/j.jpba.2020.113213"
}

Tubić, B. K., Dobričić, V., Poljarević, J., Savić, A., Sabo, T.,& Marković, B. D.. (2020). Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives. in Journal of Pharmaceutical and Biomedical Analysis
Elsevier B.V.., 184.
https://doi.org/10.1016/j.jpba.2020.113213

Tubić BK, Dobričić V, Poljarević J, Savić A, Sabo T, Marković BD. Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives. in Journal of Pharmaceutical and Biomedical Analysis. 2020;184.
doi:10.1016/j.jpba.2020.113213 .

Tubić, Biljana K., Dobričić, Vladimir, Poljarević, Jelena, Savić, Aleksandar, Sabo, Tibor, Marković, Bojan D., "Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives" in Journal of Pharmaceutical and Biomedical Analysis, 184 (2020),
https://doi.org/10.1016/j.jpba.2020.113213 . .

TY  - JOUR
AU  - Misirlić-Denčić, Sonja
AU  - Poljarević, Jelena
AU  - Isaković, Anđelka M.
AU  - Sabo, Tibor
AU  - Marković, Ivanka
AU  - Trajković, Vladimir S.
PY  - 2020
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5072
AB  - Background: The discovery of cisplatin and the subsequent research revealed the importance of dinitrogen-containing moiety for the anticancer action of metal complexes. Moreover, certain diamine ligands alone display cytotoxicity that contributes to the overall activity of corresponding complexes.

Objective: To summarize the current knowledge on the anticancer efficacy, selectivity, and the mechanisms of action of metal complexes with various types of diamine ligands.

Methods: The contribution of aliphatic acyclic, aliphatic cyclic, and aromatic diamine ligands to the anticancer activity and selectivity/toxicity of metal complexes with different metal ions were analyzed by comparison with organic ligand alone and/or conventional platinum-based chemotherapeutics.

Results: The aliphatic acyclic diamine ligands are present mostly in complexes with platinum. Aliphatic cyclic diamines are part of Pt(II), Ru(II) and Au(III) complexes, while aromatic diamine ligands are found in Pt(II), Ru(II), Pd(II) and Ir(III) complexes. The type and oxidation state of metal ions greatly influences the cytotoxicity of metal complexes with aliphatic acyclic diamine ligands. Lipophilicity of organic ligands, dependent on alkyl-side chain length and structure, determines their cellular uptake, with edda and eddp/eddip ligands being most useful in this regard. Aliphatic cyclic diamine ligands improved the activity/toxicity ratio of oxaliplatin-type complexes. The complexes with aromatic diamine ligands remain unexplored regarding their anticancer mechanism. The investigated complexes mainly caused apoptotic or necrotic cell death.

Conclusion: Metal complexes with diamine ligands are promising candidates for efficient and more selective alternatives to conventional platinum-based chemotherapeutics. Further research is required to reveal the chemico-physical properties and molecular mechanisms underlying their biological activity.
PB  - Bentham Science
T2  - Current Medicinal Chemistry
T1  - Current development of metal complexes with diamine ligands as potential anticancer agents
VL  - 27
IS  - 3
SP  - 380
EP  - 410
DO  - 10.2174/0929867325666181031114306
ER  - 

@article{
author = "Misirlić-Denčić, Sonja and Poljarević, Jelena and Isaković, Anđelka M. and Sabo, Tibor and Marković, Ivanka and Trajković, Vladimir S.",
year = "2020",
abstract = "Background: The discovery of cisplatin and the subsequent research revealed the importance of dinitrogen-containing moiety for the anticancer action of metal complexes. Moreover, certain diamine ligands alone display cytotoxicity that contributes to the overall activity of corresponding complexes.

Objective: To summarize the current knowledge on the anticancer efficacy, selectivity, and the mechanisms of action of metal complexes with various types of diamine ligands.

Methods: The contribution of aliphatic acyclic, aliphatic cyclic, and aromatic diamine ligands to the anticancer activity and selectivity/toxicity of metal complexes with different metal ions were analyzed by comparison with organic ligand alone and/or conventional platinum-based chemotherapeutics.

Results: The aliphatic acyclic diamine ligands are present mostly in complexes with platinum. Aliphatic cyclic diamines are part of Pt(II), Ru(II) and Au(III) complexes, while aromatic diamine ligands are found in Pt(II), Ru(II), Pd(II) and Ir(III) complexes. The type and oxidation state of metal ions greatly influences the cytotoxicity of metal complexes with aliphatic acyclic diamine ligands. Lipophilicity of organic ligands, dependent on alkyl-side chain length and structure, determines their cellular uptake, with edda and eddp/eddip ligands being most useful in this regard. Aliphatic cyclic diamine ligands improved the activity/toxicity ratio of oxaliplatin-type complexes. The complexes with aromatic diamine ligands remain unexplored regarding their anticancer mechanism. The investigated complexes mainly caused apoptotic or necrotic cell death.

Conclusion: Metal complexes with diamine ligands are promising candidates for efficient and more selective alternatives to conventional platinum-based chemotherapeutics. Further research is required to reveal the chemico-physical properties and molecular mechanisms underlying their biological activity.",
publisher = "Bentham Science",
journal = "Current Medicinal Chemistry",
title = "Current development of metal complexes with diamine ligands as potential anticancer agents",
volume = "27",
number = "3",
pages = "380-410",
doi = "10.2174/0929867325666181031114306"
}

Misirlić-Denčić, S., Poljarević, J., Isaković, A. M., Sabo, T., Marković, I.,& Trajković, V. S.. (2020). Current development of metal complexes with diamine ligands as potential anticancer agents. in Current Medicinal Chemistry
Bentham Science., 27(3), 380-410.
https://doi.org/10.2174/0929867325666181031114306

Misirlić-Denčić S, Poljarević J, Isaković AM, Sabo T, Marković I, Trajković VS. Current development of metal complexes with diamine ligands as potential anticancer agents. in Current Medicinal Chemistry. 2020;27(3):380-410.
doi:10.2174/0929867325666181031114306 .

Misirlić-Denčić, Sonja, Poljarević, Jelena, Isaković, Anđelka M., Sabo, Tibor, Marković, Ivanka, Trajković, Vladimir S., "Current development of metal complexes with diamine ligands as potential anticancer agents" in Current Medicinal Chemistry, 27, no. 3 (2020):380-410,
https://doi.org/10.2174/0929867325666181031114306 . .

TY  - JOUR
AU  - Jurišević, Milena
AU  - Jagić, Nikola
AU  - Gajović, Nevena
AU  - Arsenijević, Aleksandar
AU  - Jovanović, Milan
AU  - Milovanović, Marija
AU  - Pantić, Jelena
AU  - Jovanović, Ivan
AU  - Sabo, Tibor
AU  - Radosavljević, Gordana
AU  - Arsenijević, Nebojša
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4238
AB  - Background/Aim. O,O'-diethyl-(S,S)-ethylenediamineN,N'-di-2-(3-cyclohexyl)propanoate dihydrochloride (DE-EDCP) has been found to possess promising cytotoxic activity against various tumor cell lines. Also, DE-EDCP reduces tumor progression by several mechanisms such as triggering tumor cell death and inhibition of cell proliferation. The aim of present study was to further evaluate antitumor activity of DE-EDCP by investigating effects on migratory potential of tumor cells and anti-tumor immune response. Methods. Migratory potential of DE-EDCP was evaluated by scratch wound assay. Female BALB/c mice were inoculated with 4T1 breast cancer cells and treatment with DE-EDCP started five days following orthotopic tumor implantation. The frequency and phenotype of tumor-infiltrating natural killer (NK) and natural killer T (NKT) cells were analyzed by flow cytometry. Results. DE-EDCP inhibited migratory potential of highly metastatic 4T1 cells. DE-EDCP facilitated accumulation of CD3+CD49+ NKT cells and CD3-CD49+ NK cells in tumor microenvironment. DE-EDCP treatment led to significant decrement of tumor infiltrating anergic NKT cells expressing cytotoxic T-lymphocyte-associated protein 4 (CTLA-4), killer cell lectin like receptor G1 (KLRG-1) and programmed cell death protein-1 (PD-1). Mice given DE-EDCP had significantly increased percentages of tumoricidal fas ligand (FasL) positive NK cells. Conclusion. DE-EDCP inhibits murine breast cancer progression through direct effects on tumor cells and by facilitating anti-tumor immunity. DE-EDCP enhances accumulation, promotes tumoricidal phenotype and maintenances responsiveness of NK and NKT cells in 4T1 murine breast cancer.
PB  - Military Medical Academy, INI
T2  - Vojnosanitetski pregled
T1  - O,O'-diethyl-(S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate dihydrochloride enhances influx of effective NK and NKT cells in murine breast cancer
VL  - 77
IS  - 7
SP  - 715
EP  - 723
DO  - 10.2298/VSP180723149J
ER  - 

@article{
author = "Jurišević, Milena and Jagić, Nikola and Gajović, Nevena and Arsenijević, Aleksandar and Jovanović, Milan and Milovanović, Marija and Pantić, Jelena and Jovanović, Ivan and Sabo, Tibor and Radosavljević, Gordana and Arsenijević, Nebojša",
year = "2020",
abstract = "Background/Aim. O,O'-diethyl-(S,S)-ethylenediamineN,N'-di-2-(3-cyclohexyl)propanoate dihydrochloride (DE-EDCP) has been found to possess promising cytotoxic activity against various tumor cell lines. Also, DE-EDCP reduces tumor progression by several mechanisms such as triggering tumor cell death and inhibition of cell proliferation. The aim of present study was to further evaluate antitumor activity of DE-EDCP by investigating effects on migratory potential of tumor cells and anti-tumor immune response. Methods. Migratory potential of DE-EDCP was evaluated by scratch wound assay. Female BALB/c mice were inoculated with 4T1 breast cancer cells and treatment with DE-EDCP started five days following orthotopic tumor implantation. The frequency and phenotype of tumor-infiltrating natural killer (NK) and natural killer T (NKT) cells were analyzed by flow cytometry. Results. DE-EDCP inhibited migratory potential of highly metastatic 4T1 cells. DE-EDCP facilitated accumulation of CD3+CD49+ NKT cells and CD3-CD49+ NK cells in tumor microenvironment. DE-EDCP treatment led to significant decrement of tumor infiltrating anergic NKT cells expressing cytotoxic T-lymphocyte-associated protein 4 (CTLA-4), killer cell lectin like receptor G1 (KLRG-1) and programmed cell death protein-1 (PD-1). Mice given DE-EDCP had significantly increased percentages of tumoricidal fas ligand (FasL) positive NK cells. Conclusion. DE-EDCP inhibits murine breast cancer progression through direct effects on tumor cells and by facilitating anti-tumor immunity. DE-EDCP enhances accumulation, promotes tumoricidal phenotype and maintenances responsiveness of NK and NKT cells in 4T1 murine breast cancer.",
publisher = "Military Medical Academy, INI",
journal = "Vojnosanitetski pregled",
title = "O,O'-diethyl-(S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate dihydrochloride enhances influx of effective NK and NKT cells in murine breast cancer",
volume = "77",
number = "7",
pages = "715-723",
doi = "10.2298/VSP180723149J"
}

Jurišević, M., Jagić, N., Gajović, N., Arsenijević, A., Jovanović, M., Milovanović, M., Pantić, J., Jovanović, I., Sabo, T., Radosavljević, G.,& Arsenijević, N.. (2020). O,O'-diethyl-(S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate dihydrochloride enhances influx of effective NK and NKT cells in murine breast cancer. in Vojnosanitetski pregled
Military Medical Academy, INI., 77(7), 715-723.
https://doi.org/10.2298/VSP180723149J

Jurišević M, Jagić N, Gajović N, Arsenijević A, Jovanović M, Milovanović M, Pantić J, Jovanović I, Sabo T, Radosavljević G, Arsenijević N. O,O'-diethyl-(S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate dihydrochloride enhances influx of effective NK and NKT cells in murine breast cancer. in Vojnosanitetski pregled. 2020;77(7):715-723.
doi:10.2298/VSP180723149J .

Jurišević, Milena, Jagić, Nikola, Gajović, Nevena, Arsenijević, Aleksandar, Jovanović, Milan, Milovanović, Marija, Pantić, Jelena, Jovanović, Ivan, Sabo, Tibor, Radosavljević, Gordana, Arsenijević, Nebojša, "O,O'-diethyl-(S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate dihydrochloride enhances influx of effective NK and NKT cells in murine breast cancer" in Vojnosanitetski pregled, 77, no. 7 (2020):715-723,
https://doi.org/10.2298/VSP180723149J . .

TY  - JOUR
AU  - Šmigić, Jelena
AU  - Sabo, Tibor
AU  - Vranić, Aleksandra
AU  - Živković, Vladimir
AU  - Srejović, Ivan
AU  - Turnić, Tamara N.
AU  - Milosavljević, Isidora
AU  - Poljarević, Jelena
AU  - Krivokapić, Miloš
AU  - Bolevich, Sergey
AU  - Jakovljević, Vladimir
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3721
AB  - The aim of the present study was to compare the cardiodynamic parameters in the isolated rat heart in animals chronically treated with cisplatin, platinum(IV) complex and its diamine ligand. Sixty Wistar albino rats (8 weeks old) were divided into five groups: three experimental and two control groups. Animals in all groups were treated with a dose of 4 mg/kg body weight once a week for 4 weeks with different substances; experimental groups received cisplatin, ligand and octahedral platinum(IV) complex, and control groups received saline and dimethyl sulfoxide. After sacrificing the animals, hearts were isolated and perfused according to the Langendorff technique at gradually increased coronary perfusion pressures (40–120 cmH2O). The following parameters of cardiac function were continuously recorded: maximum and minimum rate of change of pressure in the left ventricle, systolic and diastolic left ventricular pressure, heart rate and coronary flow. The results showed statistically significant differences between all experimental groups in maximum and minimum rate of pressure development as well as in systolic pressure of the left ventricle, whereas cisplatin, ligand and the platinum(IV) complex had effects on heart contractility without significant influences on coronary circulation. The findings of the present study could be important for a better understanding of anticancer drug cardiac side effects. Our results indicate that compared to cisplatin as a “gold standard”, novel platinum complexes and ligands do not possess fewer negative effects on the heart, indicating insufficient safety for their usage in terms of affecting cardiac function, a result that can be of great interest for further investigations.
PB  - Springer Science+Business Media, LLC
T2  - Molecular and Cellular Biochemistry
T1  - Chronic effects of platinum(IV) complex and its diamine ligand on rat heart function: comparison with cisplatin
VL  - 458
IS  - 1-2
SP  - 89
EP  - 98
DO  - 10.1007/s11010-019-03533-8
ER  - 

@article{
author = "Šmigić, Jelena and Sabo, Tibor and Vranić, Aleksandra and Živković, Vladimir and Srejović, Ivan and Turnić, Tamara N. and Milosavljević, Isidora and Poljarević, Jelena and Krivokapić, Miloš and Bolevich, Sergey and Jakovljević, Vladimir",
year = "2019",
abstract = "The aim of the present study was to compare the cardiodynamic parameters in the isolated rat heart in animals chronically treated with cisplatin, platinum(IV) complex and its diamine ligand. Sixty Wistar albino rats (8 weeks old) were divided into five groups: three experimental and two control groups. Animals in all groups were treated with a dose of 4 mg/kg body weight once a week for 4 weeks with different substances; experimental groups received cisplatin, ligand and octahedral platinum(IV) complex, and control groups received saline and dimethyl sulfoxide. After sacrificing the animals, hearts were isolated and perfused according to the Langendorff technique at gradually increased coronary perfusion pressures (40–120 cmH2O). The following parameters of cardiac function were continuously recorded: maximum and minimum rate of change of pressure in the left ventricle, systolic and diastolic left ventricular pressure, heart rate and coronary flow. The results showed statistically significant differences between all experimental groups in maximum and minimum rate of pressure development as well as in systolic pressure of the left ventricle, whereas cisplatin, ligand and the platinum(IV) complex had effects on heart contractility without significant influences on coronary circulation. The findings of the present study could be important for a better understanding of anticancer drug cardiac side effects. Our results indicate that compared to cisplatin as a “gold standard”, novel platinum complexes and ligands do not possess fewer negative effects on the heart, indicating insufficient safety for their usage in terms of affecting cardiac function, a result that can be of great interest for further investigations.",
publisher = "Springer Science+Business Media, LLC",
journal = "Molecular and Cellular Biochemistry",
title = "Chronic effects of platinum(IV) complex and its diamine ligand on rat heart function: comparison with cisplatin",
volume = "458",
number = "1-2",
pages = "89-98",
doi = "10.1007/s11010-019-03533-8"
}

Šmigić, J., Sabo, T., Vranić, A., Živković, V., Srejović, I., Turnić, T. N., Milosavljević, I., Poljarević, J., Krivokapić, M., Bolevich, S.,& Jakovljević, V.. (2019). Chronic effects of platinum(IV) complex and its diamine ligand on rat heart function: comparison with cisplatin. in Molecular and Cellular Biochemistry
Springer Science+Business Media, LLC., 458(1-2), 89-98.
https://doi.org/10.1007/s11010-019-03533-8

Šmigić J, Sabo T, Vranić A, Živković V, Srejović I, Turnić TN, Milosavljević I, Poljarević J, Krivokapić M, Bolevich S, Jakovljević V. Chronic effects of platinum(IV) complex and its diamine ligand on rat heart function: comparison with cisplatin. in Molecular and Cellular Biochemistry. 2019;458(1-2):89-98.
doi:10.1007/s11010-019-03533-8 .

Šmigić, Jelena, Sabo, Tibor, Vranić, Aleksandra, Živković, Vladimir, Srejović, Ivan, Turnić, Tamara N., Milosavljević, Isidora, Poljarević, Jelena, Krivokapić, Miloš, Bolevich, Sergey, Jakovljević, Vladimir, "Chronic effects of platinum(IV) complex and its diamine ligand on rat heart function: comparison with cisplatin" in Molecular and Cellular Biochemistry, 458, no. 1-2 (2019):89-98,
https://doi.org/10.1007/s11010-019-03533-8 . .

TY  - JOUR
AU  - Stanković, Dalibor
AU  - Ristić, Slavica M.
AU  - Vukadinović, Aleksandar
AU  - Mirković, Marija D.
AU  - Vladimirov, Sandra S.
AU  - Milanović, Zorana
AU  - Radović, Magdalena
AU  - Mijović, Milica
AU  - Stanković, Dalibor
AU  - Sabo, Tibor
AU  - Vranješ-Đurić, Sanja
AU  - Janković, Drina
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2894
AB  - It was reported that novel O,O′-diethyl-(S, S)-ethylenediamine-N,N′-di-2-(3-cyclohexyl) propanoate dihydrochloride (DE-EDCP) displayed in vitro antiproliferative activity on several human and mouse cancer cell lines, which was comparable to that of the prototypical anticancer drug cisplatin. In order to reveal its toxicity profile, acute and repeated-dose toxicity studies were performed in Naval Medical Research Institute (NMRI) Han mice. The intravenous LD 50 values of DE-EDCP were found to be 95.3 and 101.3 mg/kg body weight in female and male mice, respectively. In the subacute toxicity study, DE-EDCP was administered intravenously at the doses of 15, 25, and 40 mg/kg/day for a period of 28 days. There were no adverse effects on general condition, growth, feed and water consumption, and hematological parameters. There was a significant increase in urea and alanine aminotransferase in female mice and aspartate aminotransferase and alkaline phosphatase in both genders in 40 mg/kg/day dose-treated group. The histopathological changes confined to the liver and kidney, but in other organs were not found. Satellite group revealed that changes in the kidney and liver were less pronounced, suggesting their reversibility. Interactions with DNA could also be of importance for understanding DE-EDCP toxic side effects. Hyperchromic effect obtained with ultraviolet–visible, suggested electrostatic interactions between DE-EDCP and calf thymus DNA. The toxicity testing of DE-EDCP was conducted to predict human outcomes.
PB  - SAGE PUBLICATIONS LTD
T2  - Human and Experimental Toxicology
T1  - Toxicity study of DE-EDCP as a potential drug for cancer therapy: Toxicity profile of DE-EDCP
VL  - 38
IS  - 4
SP  - 466
EP  - 481
DO  - 10.1177/0960327118819047
ER  - 

@article{
author = "Stanković, Dalibor and Ristić, Slavica M. and Vukadinović, Aleksandar and Mirković, Marija D. and Vladimirov, Sandra S. and Milanović, Zorana and Radović, Magdalena and Mijović, Milica and Stanković, Dalibor and Sabo, Tibor and Vranješ-Đurić, Sanja and Janković, Drina",
year = "2019",
abstract = "It was reported that novel O,O′-diethyl-(S, S)-ethylenediamine-N,N′-di-2-(3-cyclohexyl) propanoate dihydrochloride (DE-EDCP) displayed in vitro antiproliferative activity on several human and mouse cancer cell lines, which was comparable to that of the prototypical anticancer drug cisplatin. In order to reveal its toxicity profile, acute and repeated-dose toxicity studies were performed in Naval Medical Research Institute (NMRI) Han mice. The intravenous LD 50 values of DE-EDCP were found to be 95.3 and 101.3 mg/kg body weight in female and male mice, respectively. In the subacute toxicity study, DE-EDCP was administered intravenously at the doses of 15, 25, and 40 mg/kg/day for a period of 28 days. There were no adverse effects on general condition, growth, feed and water consumption, and hematological parameters. There was a significant increase in urea and alanine aminotransferase in female mice and aspartate aminotransferase and alkaline phosphatase in both genders in 40 mg/kg/day dose-treated group. The histopathological changes confined to the liver and kidney, but in other organs were not found. Satellite group revealed that changes in the kidney and liver were less pronounced, suggesting their reversibility. Interactions with DNA could also be of importance for understanding DE-EDCP toxic side effects. Hyperchromic effect obtained with ultraviolet–visible, suggested electrostatic interactions between DE-EDCP and calf thymus DNA. The toxicity testing of DE-EDCP was conducted to predict human outcomes.",
publisher = "SAGE PUBLICATIONS LTD",
journal = "Human and Experimental Toxicology",
title = "Toxicity study of DE-EDCP as a potential drug for cancer therapy: Toxicity profile of DE-EDCP",
volume = "38",
number = "4",
pages = "466-481",
doi = "10.1177/0960327118819047"
}

Stanković, D., Ristić, S. M., Vukadinović, A., Mirković, M. D., Vladimirov, S. S., Milanović, Z., Radović, M., Mijović, M., Stanković, D., Sabo, T., Vranješ-Đurić, S.,& Janković, D.. (2019). Toxicity study of DE-EDCP as a potential drug for cancer therapy: Toxicity profile of DE-EDCP. in Human and Experimental Toxicology
SAGE PUBLICATIONS LTD., 38(4), 466-481.
https://doi.org/10.1177/0960327118819047

Stanković D, Ristić SM, Vukadinović A, Mirković MD, Vladimirov SS, Milanović Z, Radović M, Mijović M, Stanković D, Sabo T, Vranješ-Đurić S, Janković D. Toxicity study of DE-EDCP as a potential drug for cancer therapy: Toxicity profile of DE-EDCP. in Human and Experimental Toxicology. 2019;38(4):466-481.
doi:10.1177/0960327118819047 .

Stanković, Dalibor, Ristić, Slavica M., Vukadinović, Aleksandar, Mirković, Marija D., Vladimirov, Sandra S., Milanović, Zorana, Radović, Magdalena, Mijović, Milica, Stanković, Dalibor, Sabo, Tibor, Vranješ-Đurić, Sanja, Janković, Drina, "Toxicity study of DE-EDCP as a potential drug for cancer therapy: Toxicity profile of DE-EDCP" in Human and Experimental Toxicology, 38, no. 4 (2019):466-481,
https://doi.org/10.1177/0960327118819047 . .

TY  - CONF
AU  - Tubić, Biljana K.
AU  - Marković, Bojan D.
AU  - Sabo, Tibor
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3136
AB  - In previously in vitro studies on different cell lines and in vivo on melanoma and 4T1 murine breast cancer and metastasis it was shown antiproliferative activity for ester derivatives of (S,S)-ethylenediamine-N,N′-di-2-(3-cyclohexyl)propanoic acid, and (S,S)-1,3-propanediamine-N,N′-di-2-(3-cyclohexyl)propanoic acid. The aim of this study was to predict membrane permeability by parallel artificial membrane permeability assay (PAMPA), molecular mechanism of action, metabolites and absorption, distribution, metabolism, toxicity—ADMET properties for observed substances using in vitro and in silico methods. Obtained results of PAMPA show the best membrane permeability of ethyl esters analogs (DE-EDCP and DE-PDCP) and refer to the hypothesis that the retention in cell membrane is important for cytotoxic activity of investigated substances. Prediction of main metabolic pathways was performed by the Metabolizer software and it was obtained that the major metabolic reactions were the hydrolyses of ester and subsequently intramolecular cyclization. Toxicity of investigated substances and their potential metabolites are lower than toxicity of observed official cytotoxic drugs. Based on the results obtained by the Molecular docking, it can be assumed that the antiproliferative effects of the investigated substances were realized through the multiple mechanisms by potential metabolites: acids, lactam carboxylate and lactam alkyl esters, while the esters are probably a prodrug substance with favorable properties to provide sufficient bioavailability at the target of action. Based on obtained results it can be proposed there to be investigated the existence of the metabolites: lactam carboxylate and lactam alkyl esters in biological materials.
C3  - IFMBE Proceedings
T1  - Discovery of membrane permeability, pharmacokinetics properties and mechanism of action for analogs of ethylenediamine-n,n′-di-2-(3-cyclohexyl)propionic acid and 1,3-propandiamine-n,n′-di-2-(3-cyclohexyl)propionic acid with antiproliferative activity using in vitro and in silico methods
VL  - 73
SP  - 357
EP  - 369
DO  - 10.1007/978-3-030-17971-7_55
ER  - 

@conference{
author = "Tubić, Biljana K. and Marković, Bojan D. and Sabo, Tibor",
year = "2019",
abstract = "In previously in vitro studies on different cell lines and in vivo on melanoma and 4T1 murine breast cancer and metastasis it was shown antiproliferative activity for ester derivatives of (S,S)-ethylenediamine-N,N′-di-2-(3-cyclohexyl)propanoic acid, and (S,S)-1,3-propanediamine-N,N′-di-2-(3-cyclohexyl)propanoic acid. The aim of this study was to predict membrane permeability by parallel artificial membrane permeability assay (PAMPA), molecular mechanism of action, metabolites and absorption, distribution, metabolism, toxicity—ADMET properties for observed substances using in vitro and in silico methods. Obtained results of PAMPA show the best membrane permeability of ethyl esters analogs (DE-EDCP and DE-PDCP) and refer to the hypothesis that the retention in cell membrane is important for cytotoxic activity of investigated substances. Prediction of main metabolic pathways was performed by the Metabolizer software and it was obtained that the major metabolic reactions were the hydrolyses of ester and subsequently intramolecular cyclization. Toxicity of investigated substances and their potential metabolites are lower than toxicity of observed official cytotoxic drugs. Based on the results obtained by the Molecular docking, it can be assumed that the antiproliferative effects of the investigated substances were realized through the multiple mechanisms by potential metabolites: acids, lactam carboxylate and lactam alkyl esters, while the esters are probably a prodrug substance with favorable properties to provide sufficient bioavailability at the target of action. Based on obtained results it can be proposed there to be investigated the existence of the metabolites: lactam carboxylate and lactam alkyl esters in biological materials.",
journal = "IFMBE Proceedings",
title = "Discovery of membrane permeability, pharmacokinetics properties and mechanism of action for analogs of ethylenediamine-n,n′-di-2-(3-cyclohexyl)propionic acid and 1,3-propandiamine-n,n′-di-2-(3-cyclohexyl)propionic acid with antiproliferative activity using in vitro and in silico methods",
volume = "73",
pages = "357-369",
doi = "10.1007/978-3-030-17971-7_55"
}

Tubić, B. K., Marković, B. D.,& Sabo, T.. (2019). Discovery of membrane permeability, pharmacokinetics properties and mechanism of action for analogs of ethylenediamine-n,n′-di-2-(3-cyclohexyl)propionic acid and 1,3-propandiamine-n,n′-di-2-(3-cyclohexyl)propionic acid with antiproliferative activity using in vitro and in silico methods. in IFMBE Proceedings, 73, 357-369.
https://doi.org/10.1007/978-3-030-17971-7_55

Tubić BK, Marković BD, Sabo T. Discovery of membrane permeability, pharmacokinetics properties and mechanism of action for analogs of ethylenediamine-n,n′-di-2-(3-cyclohexyl)propionic acid and 1,3-propandiamine-n,n′-di-2-(3-cyclohexyl)propionic acid with antiproliferative activity using in vitro and in silico methods. in IFMBE Proceedings. 2019;73:357-369.
doi:10.1007/978-3-030-17971-7_55 .

Tubić, Biljana K., Marković, Bojan D., Sabo, Tibor, "Discovery of membrane permeability, pharmacokinetics properties and mechanism of action for analogs of ethylenediamine-n,n′-di-2-(3-cyclohexyl)propionic acid and 1,3-propandiamine-n,n′-di-2-(3-cyclohexyl)propionic acid with antiproliferative activity using in vitro and in silico methods" in IFMBE Proceedings, 73 (2019):357-369,
https://doi.org/10.1007/978-3-030-17971-7_55 . .

TY  - JOUR
AU  - Jurisevic, M.
AU  - Arsenijevic, A.
AU  - Pantic, J.
AU  - Gajovic, N.
AU  - Milovanović, Jelena
AU  - Milovanovic, M.
AU  - Poljarević, Jelena
AU  - Sabo, Tibor
AU  - Vojvodic, D.
AU  - Radosavljevic, G.D.
AU  - Arsenijevic, N.
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/335
AB  - Pharmacological treatment of cancer is mostly limited by drug-toxicity and resistance. It has been noticed that new organic ester ligand, O,O'-diethyl-(S,S)- ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate dihydrochloride (named DEEDCP) showed effective cytotoxic capacities against several human and mouse cancer cell lines. However, its effects on tumor growth and metastasis are unexplored. The aim of present study was to examine the ability of DE-EDCP to inhibit 4T1 murine breast cancer growth and progression and to explore possible molecular mechanisms. DE-EDCP exhibited significant tumoricidal activity on human and murine breast cancer cell lines. Further, marked reduction of murine breast cancer growth and progression by DE-EDCP was shown. DE-EDCP exhibits fewer side-effects compared to cisplatin as a conventional chemotherapeutic. Results obtained from in vivo and in vitro experiments indicate that DE-EDCP induces apoptosis and inhibits proliferation of 4T1 cells. DE-EDCP increases percentage of 4T1 cells in late apoptosis, expression of pro-apoptotic Bax and caspase-3, while decreases expression of anti-apoptotic Bcl-2. DE-EDCP treatment increased the percentage of TUNEL-positive nuclei and reduced Ki-67 expression in breast cancer tissue. DE-EDCP decreased expression of cyclin D3 and Ki-67, increased expression of cyclin-dependent kinase inhibitors p16, p21 and p27 and arrested 4T1 cells in G0/G1 cell cycle phase. Expression of STAT3 and downstream regulated molecules, NANOG and SOX2, was reduced in 4T1 cells after DE-EDCP treatment. In conclusion, DE-EDCP impairs breast cancer growth and progression by triggering cancer cell death and inhibition of cancer cell proliferation. DE-EDCP might be of interest in the development of the new anticancer agent. ©Jurisevic et al.
T2  - Oncotarget
T1  - The organic ester O,O'-diethyl-(S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate dihydrochloride attenuates murine breast cancer growth and metastasis
VL  - 9
IS  - 46
SP  - 28195
EP  - 28212
DO  - 10.18632/oncotarget.25610
ER  - 

@article{
author = "Jurisevic, M. and Arsenijevic, A. and Pantic, J. and Gajovic, N. and Milovanović, Jelena and Milovanovic, M. and Poljarević, Jelena and Sabo, Tibor and Vojvodic, D. and Radosavljevic, G.D. and Arsenijevic, N.",
year = "2018",
abstract = "Pharmacological treatment of cancer is mostly limited by drug-toxicity and resistance. It has been noticed that new organic ester ligand, O,O'-diethyl-(S,S)- ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate dihydrochloride (named DEEDCP) showed effective cytotoxic capacities against several human and mouse cancer cell lines. However, its effects on tumor growth and metastasis are unexplored. The aim of present study was to examine the ability of DE-EDCP to inhibit 4T1 murine breast cancer growth and progression and to explore possible molecular mechanisms. DE-EDCP exhibited significant tumoricidal activity on human and murine breast cancer cell lines. Further, marked reduction of murine breast cancer growth and progression by DE-EDCP was shown. DE-EDCP exhibits fewer side-effects compared to cisplatin as a conventional chemotherapeutic. Results obtained from in vivo and in vitro experiments indicate that DE-EDCP induces apoptosis and inhibits proliferation of 4T1 cells. DE-EDCP increases percentage of 4T1 cells in late apoptosis, expression of pro-apoptotic Bax and caspase-3, while decreases expression of anti-apoptotic Bcl-2. DE-EDCP treatment increased the percentage of TUNEL-positive nuclei and reduced Ki-67 expression in breast cancer tissue. DE-EDCP decreased expression of cyclin D3 and Ki-67, increased expression of cyclin-dependent kinase inhibitors p16, p21 and p27 and arrested 4T1 cells in G0/G1 cell cycle phase. Expression of STAT3 and downstream regulated molecules, NANOG and SOX2, was reduced in 4T1 cells after DE-EDCP treatment. In conclusion, DE-EDCP impairs breast cancer growth and progression by triggering cancer cell death and inhibition of cancer cell proliferation. DE-EDCP might be of interest in the development of the new anticancer agent. ©Jurisevic et al.",
journal = "Oncotarget",
title = "The organic ester O,O'-diethyl-(S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate dihydrochloride attenuates murine breast cancer growth and metastasis",
volume = "9",
number = "46",
pages = "28195-28212",
doi = "10.18632/oncotarget.25610"
}

Jurisevic, M., Arsenijevic, A., Pantic, J., Gajovic, N., Milovanović, J., Milovanovic, M., Poljarević, J., Sabo, T., Vojvodic, D., Radosavljevic, G.D.,& Arsenijevic, N.. (2018). The organic ester O,O'-diethyl-(S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate dihydrochloride attenuates murine breast cancer growth and metastasis. in Oncotarget, 9(46), 28195-28212.
https://doi.org/10.18632/oncotarget.25610

Jurisevic M, Arsenijevic A, Pantic J, Gajovic N, Milovanović J, Milovanovic M, Poljarević J, Sabo T, Vojvodic D, Radosavljevic G, Arsenijevic N. The organic ester O,O'-diethyl-(S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate dihydrochloride attenuates murine breast cancer growth and metastasis. in Oncotarget. 2018;9(46):28195-28212.
doi:10.18632/oncotarget.25610 .

Jurisevic, M., Arsenijevic, A., Pantic, J., Gajovic, N., Milovanović, Jelena, Milovanovic, M., Poljarević, Jelena, Sabo, Tibor, Vojvodic, D., Radosavljevic, G.D., Arsenijevic, N., "The organic ester O,O'-diethyl-(S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate dihydrochloride attenuates murine breast cancer growth and metastasis" in Oncotarget, 9, no. 46 (2018):28195-28212,
https://doi.org/10.18632/oncotarget.25610 . .

TY  - JOUR
AU  - Mihajlović-Lalić, Ljiljana
AU  - Stanković, Dalibor
AU  - Poljarević, Jelena
AU  - Sabo, Tibor
AU  - Manojlović, Dragan D.
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2196
AB  - The electrochemical behavior of four dialkyl esters (methyl, ethyl, n-propyl and n-butyl) of (S,S)-alpha,alpha'-(1,2-ethanediyldiimino)-bis[cyclohexanepropanoic acid] with moderate antitumor activity has been studied by cyclic voltammetry. I-E curves recorded at boron-doped diamond electrode in -2.00  lt  E-p  lt  0.00 V range show a single oxidative peak located in the -0.95  lt  E-p,E-a  lt  -0.52 V region in a form of one-electron wave. The electrochemical processes appear to be irreversible for all compounds except for the compound with methyl substituent which demonstrates well-defined reversible electron transfer. Derivatives with bulkier moieties are easier to oxidize. For all investigated compounds an amine-centered redox process is dominant. Further investigation indicates that electrochemical reaction is diffusion controlled, chemically irreversible process. The results are discussed in terms of linking their electrochemical activity to antitumor effect. (C) 2018 The Electrochemical Society.
PB  - Electrochemical Soc Inc, Pennington
T2  - Journal of the Electrochemical Society
T1  - Voltammetric Study of Antitumor Efficient Ethylenediamine-Type of Ligands
VL  - 165
IS  - 10
DO  - 10.1149/2.1121810jes
ER  - 

@article{
author = "Mihajlović-Lalić, Ljiljana and Stanković, Dalibor and Poljarević, Jelena and Sabo, Tibor and Manojlović, Dragan D.",
year = "2018",
abstract = "The electrochemical behavior of four dialkyl esters (methyl, ethyl, n-propyl and n-butyl) of (S,S)-alpha,alpha'-(1,2-ethanediyldiimino)-bis[cyclohexanepropanoic acid] with moderate antitumor activity has been studied by cyclic voltammetry. I-E curves recorded at boron-doped diamond electrode in -2.00  lt  E-p  lt  0.00 V range show a single oxidative peak located in the -0.95  lt  E-p,E-a  lt  -0.52 V region in a form of one-electron wave. The electrochemical processes appear to be irreversible for all compounds except for the compound with methyl substituent which demonstrates well-defined reversible electron transfer. Derivatives with bulkier moieties are easier to oxidize. For all investigated compounds an amine-centered redox process is dominant. Further investigation indicates that electrochemical reaction is diffusion controlled, chemically irreversible process. The results are discussed in terms of linking their electrochemical activity to antitumor effect. (C) 2018 The Electrochemical Society.",
publisher = "Electrochemical Soc Inc, Pennington",
journal = "Journal of the Electrochemical Society",
title = "Voltammetric Study of Antitumor Efficient Ethylenediamine-Type of Ligands",
volume = "165",
number = "10",
doi = "10.1149/2.1121810jes"
}

Mihajlović-Lalić, L., Stanković, D., Poljarević, J., Sabo, T.,& Manojlović, D. D.. (2018). Voltammetric Study of Antitumor Efficient Ethylenediamine-Type of Ligands. in Journal of the Electrochemical Society
Electrochemical Soc Inc, Pennington., 165(10).
https://doi.org/10.1149/2.1121810jes

Mihajlović-Lalić L, Stanković D, Poljarević J, Sabo T, Manojlović DD. Voltammetric Study of Antitumor Efficient Ethylenediamine-Type of Ligands. in Journal of the Electrochemical Society. 2018;165(10).
doi:10.1149/2.1121810jes .

Mihajlović-Lalić, Ljiljana, Stanković, Dalibor, Poljarević, Jelena, Sabo, Tibor, Manojlović, Dragan D., "Voltammetric Study of Antitumor Efficient Ethylenediamine-Type of Ligands" in Journal of the Electrochemical Society, 165, no. 10 (2018),
https://doi.org/10.1149/2.1121810jes . .

TY  - JOUR
AU  - Isaković, Anđelka M.
AU  - Petričević, Saša
AU  - Ristić, Slavica M.
AU  - Popadić, Dušan
AU  - Kravić-Stevović, Tamara
AU  - Zogović, Nevena
AU  - Poljarević, Jelena
AU  - Živanović-Radnić, Tatjana
AU  - Sabo, Tibor
AU  - Isaković, Aleksandra J.
AU  - Marković, Ivanka
AU  - Trajković, Vladimir S.
AU  - Misirlić-Denčić, Sonja
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2086
AB  - Melanoma, an aggressive skin tumor with high metastatic potential, is associated with high mortality and increasing morbidity. Multiple available chemotherapeutic and immunotherapeutic modalities failed to improve survival in advanced disease, and the search for new agents is ongoing. The aim of this study was to investigate antimelanoma effects of O, O-diethyl-(S, S)-ethylenediamineN, N'di-2-(3-cyclohexyl) propanoate dihydrochloride (EE), a previously synthesized and characterized organic compound. Mouse melanoma B16 cell viability was assessed using acid phosphatase, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide, sulforhodamine B, and lactate dehydrogenase assays. Apoptosis and autophagy were investigated using flow cytometry, fluorescence and electron microscopy, and western blotting. In vivo antitumor potential was assessed in subcutaneous mouse melanoma model after 14 days of treatment with EE. Tumor mass and volume were measured, and RT-PCR was used for investigating the expression of autophagy-related, proapoptotic, and antiapoptotic molecules in tumor tissue. Investigated organic compound exerts significant cytotoxic effect against B16 cells. EE induced apoptosis, as confirmed by phosphatidyl serine externalisation, caspase activation, and ultrastructural features typical for apoptosis seen on fluorescence and electron microscopes. The apoptotic mechanism included prompt disruption of mitochondrial membrane potential and oxidative stress. No autophagy was observed. Antimelanoma action and apoptosis induction were confirmed in vivo, as EE decreased mass and volume of tumors, and increased expression of several proapoptotic genes. EE possesses significant antimelanoma action and causes caspasedependent apoptosis mediated by mitochondrial damage and reactive oxygen species production. Decrease in tumor growth and increase in expression of proapoptotic genes in tumor tissue suggest that EE warrants further investigation as a candidate agent in treating melanoma. Copyright (C) 2018 Wolters Kluwer Health, Inc. All rights reserved.
PB  - Lippincott Williams & Wilkins, Philadelphia
T2  - Melanoma Research
T1  - In vitro and in vivo antimelanoma effect of ethyl ester cyclohexyl analog of ethylenediamine dipropanoic acid
VL  - 28
IS  - 1
SP  - 8
EP  - 20
DO  - 10.1097/CMR.0000000000000409
ER  - 

@article{
author = "Isaković, Anđelka M. and Petričević, Saša and Ristić, Slavica M. and Popadić, Dušan and Kravić-Stevović, Tamara and Zogović, Nevena and Poljarević, Jelena and Živanović-Radnić, Tatjana and Sabo, Tibor and Isaković, Aleksandra J. and Marković, Ivanka and Trajković, Vladimir S. and Misirlić-Denčić, Sonja",
year = "2018",
abstract = "Melanoma, an aggressive skin tumor with high metastatic potential, is associated with high mortality and increasing morbidity. Multiple available chemotherapeutic and immunotherapeutic modalities failed to improve survival in advanced disease, and the search for new agents is ongoing. The aim of this study was to investigate antimelanoma effects of O, O-diethyl-(S, S)-ethylenediamineN, N'di-2-(3-cyclohexyl) propanoate dihydrochloride (EE), a previously synthesized and characterized organic compound. Mouse melanoma B16 cell viability was assessed using acid phosphatase, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide, sulforhodamine B, and lactate dehydrogenase assays. Apoptosis and autophagy were investigated using flow cytometry, fluorescence and electron microscopy, and western blotting. In vivo antitumor potential was assessed in subcutaneous mouse melanoma model after 14 days of treatment with EE. Tumor mass and volume were measured, and RT-PCR was used for investigating the expression of autophagy-related, proapoptotic, and antiapoptotic molecules in tumor tissue. Investigated organic compound exerts significant cytotoxic effect against B16 cells. EE induced apoptosis, as confirmed by phosphatidyl serine externalisation, caspase activation, and ultrastructural features typical for apoptosis seen on fluorescence and electron microscopes. The apoptotic mechanism included prompt disruption of mitochondrial membrane potential and oxidative stress. No autophagy was observed. Antimelanoma action and apoptosis induction were confirmed in vivo, as EE decreased mass and volume of tumors, and increased expression of several proapoptotic genes. EE possesses significant antimelanoma action and causes caspasedependent apoptosis mediated by mitochondrial damage and reactive oxygen species production. Decrease in tumor growth and increase in expression of proapoptotic genes in tumor tissue suggest that EE warrants further investigation as a candidate agent in treating melanoma. Copyright (C) 2018 Wolters Kluwer Health, Inc. All rights reserved.",
publisher = "Lippincott Williams & Wilkins, Philadelphia",
journal = "Melanoma Research",
title = "In vitro and in vivo antimelanoma effect of ethyl ester cyclohexyl analog of ethylenediamine dipropanoic acid",
volume = "28",
number = "1",
pages = "8-20",
doi = "10.1097/CMR.0000000000000409"
}

Isaković, A. M., Petričević, S., Ristić, S. M., Popadić, D., Kravić-Stevović, T., Zogović, N., Poljarević, J., Živanović-Radnić, T., Sabo, T., Isaković, A. J., Marković, I., Trajković, V. S.,& Misirlić-Denčić, S.. (2018). In vitro and in vivo antimelanoma effect of ethyl ester cyclohexyl analog of ethylenediamine dipropanoic acid. in Melanoma Research
Lippincott Williams & Wilkins, Philadelphia., 28(1), 8-20.
https://doi.org/10.1097/CMR.0000000000000409

Isaković AM, Petričević S, Ristić SM, Popadić D, Kravić-Stevović T, Zogović N, Poljarević J, Živanović-Radnić T, Sabo T, Isaković AJ, Marković I, Trajković VS, Misirlić-Denčić S. In vitro and in vivo antimelanoma effect of ethyl ester cyclohexyl analog of ethylenediamine dipropanoic acid. in Melanoma Research. 2018;28(1):8-20.
doi:10.1097/CMR.0000000000000409 .

Isaković, Anđelka M., Petričević, Saša, Ristić, Slavica M., Popadić, Dušan, Kravić-Stevović, Tamara, Zogović, Nevena, Poljarević, Jelena, Živanović-Radnić, Tatjana, Sabo, Tibor, Isaković, Aleksandra J., Marković, Ivanka, Trajković, Vladimir S., Misirlić-Denčić, Sonja, "In vitro and in vivo antimelanoma effect of ethyl ester cyclohexyl analog of ethylenediamine dipropanoic acid" in Melanoma Research, 28, no. 1 (2018):8-20,
https://doi.org/10.1097/CMR.0000000000000409 . .

TY  - JOUR
AU  - Šmigić, Jelena
AU  - Stojić, I.
AU  - Živković, Vladimir
AU  - Srejović, Ivan
AU  - Nikolić, Tanja
AU  - Jeremić, J.
AU  - Sabo, Tibor
AU  - Jakovljević, Violeta D.
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/330
AB  - Taken into consideration that molecular and cellular mechanisms involved in cardiotoxicity are still not clear the aim of this study was to compare the production of oxidative stress parameters in the isolated rat heart between animals chronically treated with cisplatin and saline. The hearts of male Wistar albino rats (n = 24, 12 per group, age 8 weeks, body mass 250±50 g) were excised and perfused according to the Langendorff technique at gradually increased coronary perfusion pressures (40-120 cmH2O). We followed the production of superoxide anion radicals, hydrogen peroxide, and nitrites and also index of lipid peroxidation during the changes of coronary perfusion pressure (CPP) (from 40 to 120 cm H2O) in coronary venous effluent. Modifications CPP were performed in order to determined if oxidative stress is involved in coronary endothelium response in conditions of hypoxia (lower than 60 cm H2O) and hyperoxia (higher than 80 cm H2O). Based on the results of this research we can conclude that with enhancement of CPP the values of oxidative stress statistically increased. However, this increment is more prominent in control group as a result of preserved endothelium and its more powerful response to hyperoxia. On the other hand, damaged endothelium of cisplatin-treated animals had weaker response to hyperoxia, and also lower antioxidant capacity. © 2018, University of Kragujevac, Faculty of Science. All rights reserved.
T2  - Serbian Journal of Experimental and Clinical Research (ranije: Medicus)
T1  - The effects of chronic administration of cisplatin on oxidative stress in the isolated rat heart [Efekti hronične primene cisplatine na oksidacioni stres izolovanog srca pacova]
VL  - 19
IS  - 1
SP  - 11
EP  - 16
DO  - 10.1515/SJECR-2017-0003
ER  - 

@article{
author = "Šmigić, Jelena and Stojić, I. and Živković, Vladimir and Srejović, Ivan and Nikolić, Tanja and Jeremić, J. and Sabo, Tibor and Jakovljević, Violeta D.",
year = "2018",
abstract = "Taken into consideration that molecular and cellular mechanisms involved in cardiotoxicity are still not clear the aim of this study was to compare the production of oxidative stress parameters in the isolated rat heart between animals chronically treated with cisplatin and saline. The hearts of male Wistar albino rats (n = 24, 12 per group, age 8 weeks, body mass 250±50 g) were excised and perfused according to the Langendorff technique at gradually increased coronary perfusion pressures (40-120 cmH2O). We followed the production of superoxide anion radicals, hydrogen peroxide, and nitrites and also index of lipid peroxidation during the changes of coronary perfusion pressure (CPP) (from 40 to 120 cm H2O) in coronary venous effluent. Modifications CPP were performed in order to determined if oxidative stress is involved in coronary endothelium response in conditions of hypoxia (lower than 60 cm H2O) and hyperoxia (higher than 80 cm H2O). Based on the results of this research we can conclude that with enhancement of CPP the values of oxidative stress statistically increased. However, this increment is more prominent in control group as a result of preserved endothelium and its more powerful response to hyperoxia. On the other hand, damaged endothelium of cisplatin-treated animals had weaker response to hyperoxia, and also lower antioxidant capacity. © 2018, University of Kragujevac, Faculty of Science. All rights reserved.",
journal = "Serbian Journal of Experimental and Clinical Research (ranije: Medicus)",
title = "The effects of chronic administration of cisplatin on oxidative stress in the isolated rat heart [Efekti hronične primene cisplatine na oksidacioni stres izolovanog srca pacova]",
volume = "19",
number = "1",
pages = "11-16",
doi = "10.1515/SJECR-2017-0003"
}

Šmigić, J., Stojić, I., Živković, V., Srejović, I., Nikolić, T., Jeremić, J., Sabo, T.,& Jakovljević, V. D.. (2018). The effects of chronic administration of cisplatin on oxidative stress in the isolated rat heart [Efekti hronične primene cisplatine na oksidacioni stres izolovanog srca pacova]. in Serbian Journal of Experimental and Clinical Research (ranije: Medicus), 19(1), 11-16.
https://doi.org/10.1515/SJECR-2017-0003

Šmigić J, Stojić I, Živković V, Srejović I, Nikolić T, Jeremić J, Sabo T, Jakovljević VD. The effects of chronic administration of cisplatin on oxidative stress in the isolated rat heart [Efekti hronične primene cisplatine na oksidacioni stres izolovanog srca pacova]. in Serbian Journal of Experimental and Clinical Research (ranije: Medicus). 2018;19(1):11-16.
doi:10.1515/SJECR-2017-0003 .

Šmigić, Jelena, Stojić, I., Živković, Vladimir, Srejović, Ivan, Nikolić, Tanja, Jeremić, J., Sabo, Tibor, Jakovljević, Violeta D., "The effects of chronic administration of cisplatin on oxidative stress in the isolated rat heart [Efekti hronične primene cisplatine na oksidacioni stres izolovanog srca pacova]" in Serbian Journal of Experimental and Clinical Research (ranije: Medicus), 19, no. 1 (2018):11-16,
https://doi.org/10.1515/SJECR-2017-0003 . .

TY  - JOUR
AU  - Tubić, Biljana K.
AU  - Vladimirov, Sandra S.
AU  - Marković, Bojan D.
AU  - Sabo, Tibor
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2113
AB  - O,O'-diethyl-(S, S)-ethylenediamine-N, N'-di-2-(3-cyclohexyl) propanoate (DE-EDCP) is novel substance with cytotoxic activity in human leukemic cells. The aim of this study has been to predict in vivo bioavailability of the DE-EDCP and its potential metabolite (S, S)-ethylenediamine-N, N'-di-2-(3-cyclohexyl) propanoic acid (EDCP) by in vitro characterization which includes determination of lipophilicity and passive membrane permeability. There has also been evaluated inter-laboratory reproducibility of the bio-analytical method which was previously developed and validated for non-clinical study of the DE-EDCP and EDCP. Distribution coefficient n-octanol/water was 1.68 and 0.03, and apparent permeability coefficient was 4 x 10(-4) cm/s and 20 x 10(-4) cm/s, for the DE-EDCP and EDCP, respectively. Observed results have shown that the DE-EDCP is more lipophilic with better membrane retention, but the EDCP has better pass through the membrane. Also, there has been demonstrated a reproducibility and robustness of the proposed bio-analytical method.
PB  - Slovensko Kemijsko Drustvo, Ljubljana
T2  - Acta Chimica Slovenica
T1  - Prediction of in vivo Bioavailibility by in vitro Characterization of Ethylenediamine Dipropanoic Acid Derivatives with Cytotoxic Activity
VL  - 65
IS  - 1
SP  - 59
EP  - 64
DO  - 10.17344/acsi.2017.3477
ER  - 

@article{
author = "Tubić, Biljana K. and Vladimirov, Sandra S. and Marković, Bojan D. and Sabo, Tibor",
year = "2018",
abstract = "O,O'-diethyl-(S, S)-ethylenediamine-N, N'-di-2-(3-cyclohexyl) propanoate (DE-EDCP) is novel substance with cytotoxic activity in human leukemic cells. The aim of this study has been to predict in vivo bioavailability of the DE-EDCP and its potential metabolite (S, S)-ethylenediamine-N, N'-di-2-(3-cyclohexyl) propanoic acid (EDCP) by in vitro characterization which includes determination of lipophilicity and passive membrane permeability. There has also been evaluated inter-laboratory reproducibility of the bio-analytical method which was previously developed and validated for non-clinical study of the DE-EDCP and EDCP. Distribution coefficient n-octanol/water was 1.68 and 0.03, and apparent permeability coefficient was 4 x 10(-4) cm/s and 20 x 10(-4) cm/s, for the DE-EDCP and EDCP, respectively. Observed results have shown that the DE-EDCP is more lipophilic with better membrane retention, but the EDCP has better pass through the membrane. Also, there has been demonstrated a reproducibility and robustness of the proposed bio-analytical method.",
publisher = "Slovensko Kemijsko Drustvo, Ljubljana",
journal = "Acta Chimica Slovenica",
title = "Prediction of in vivo Bioavailibility by in vitro Characterization of Ethylenediamine Dipropanoic Acid Derivatives with Cytotoxic Activity",
volume = "65",
number = "1",
pages = "59-64",
doi = "10.17344/acsi.2017.3477"
}

Tubić, B. K., Vladimirov, S. S., Marković, B. D.,& Sabo, T.. (2018). Prediction of in vivo Bioavailibility by in vitro Characterization of Ethylenediamine Dipropanoic Acid Derivatives with Cytotoxic Activity. in Acta Chimica Slovenica
Slovensko Kemijsko Drustvo, Ljubljana., 65(1), 59-64.
https://doi.org/10.17344/acsi.2017.3477

Tubić BK, Vladimirov SS, Marković BD, Sabo T. Prediction of in vivo Bioavailibility by in vitro Characterization of Ethylenediamine Dipropanoic Acid Derivatives with Cytotoxic Activity. in Acta Chimica Slovenica. 2018;65(1):59-64.
doi:10.17344/acsi.2017.3477 .

Tubić, Biljana K., Vladimirov, Sandra S., Marković, Bojan D., Sabo, Tibor, "Prediction of in vivo Bioavailibility by in vitro Characterization of Ethylenediamine Dipropanoic Acid Derivatives with Cytotoxic Activity" in Acta Chimica Slovenica, 65, no. 1 (2018):59-64,
https://doi.org/10.17344/acsi.2017.3477 . .

TY  - JOUR
AU  - Pantelić, Nebojša Đ.
AU  - Stanojković, Tatjana
AU  - Zmejkovski, Bojana B.
AU  - Kaluđerović, Goran N.
AU  - Sabo, Tibor
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/325
AB  - Six gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N’-diacetate, general formula [AuCl2{(S,S)-R2eddch}]PF6, [(S,S)-eddch = (S,S)-ethylenediamine-N,N’-di-2-(3-cyclohexyl)propanoate, R = Me, Et, n-Pr, n-Bu, i-Bu, i-Am, 1-6, respectively], were tested against cancer cell lines such as human melanoma Fem-x, human colon carcinoma LS174T and non-small cell lung carcinoma A549 as well as a non-cancerous human embryonic lung fibroblasts MRC-5 using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay with the aim of assessing in vitro antitumoral activity and selectivity. All investigated complexes showed lower cytotoxicity and better or similar selectivity in comparison to cisplatin, used as reference compound. Complex [AuCl2{(S,S)-(i-Am)2eddch}]PF6 (6) demonstrated the highest activity against Fem-x (IC50 = 14.98 ± 0.34 µM). Additionally, the same complex expressed 4.5 times higher selectivity than cisplatin. © 2017, University of Kragujevac, Faculty of Science. All rights reserved.
T2  - Serbian Journal of Experimental and Clinical Research (ranije: Medicus)
T1  - Antiproliferative activity of gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N’-diacetate [Antiproliferativna aktivnost zlato(III) kompleksa sa cikloheksil-funkcionalizovanim estrima etilendiamin-N,N’-diacetata]
VL  - 18
IS  - 4
SP  - 289
EP  - 294
DO  - 10.1515/SJECR-2017-0067
ER  - 

@article{
author = "Pantelić, Nebojša Đ. and Stanojković, Tatjana and Zmejkovski, Bojana B. and Kaluđerović, Goran N. and Sabo, Tibor",
year = "2017",
abstract = "Six gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N’-diacetate, general formula [AuCl2{(S,S)-R2eddch}]PF6, [(S,S)-eddch = (S,S)-ethylenediamine-N,N’-di-2-(3-cyclohexyl)propanoate, R = Me, Et, n-Pr, n-Bu, i-Bu, i-Am, 1-6, respectively], were tested against cancer cell lines such as human melanoma Fem-x, human colon carcinoma LS174T and non-small cell lung carcinoma A549 as well as a non-cancerous human embryonic lung fibroblasts MRC-5 using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay with the aim of assessing in vitro antitumoral activity and selectivity. All investigated complexes showed lower cytotoxicity and better or similar selectivity in comparison to cisplatin, used as reference compound. Complex [AuCl2{(S,S)-(i-Am)2eddch}]PF6 (6) demonstrated the highest activity against Fem-x (IC50 = 14.98 ± 0.34 µM). Additionally, the same complex expressed 4.5 times higher selectivity than cisplatin. © 2017, University of Kragujevac, Faculty of Science. All rights reserved.",
journal = "Serbian Journal of Experimental and Clinical Research (ranije: Medicus)",
title = "Antiproliferative activity of gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N’-diacetate [Antiproliferativna aktivnost zlato(III) kompleksa sa cikloheksil-funkcionalizovanim estrima etilendiamin-N,N’-diacetata]",
volume = "18",
number = "4",
pages = "289-294",
doi = "10.1515/SJECR-2017-0067"
}

Pantelić, N. Đ., Stanojković, T., Zmejkovski, B. B., Kaluđerović, G. N.,& Sabo, T.. (2017). Antiproliferative activity of gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N’-diacetate [Antiproliferativna aktivnost zlato(III) kompleksa sa cikloheksil-funkcionalizovanim estrima etilendiamin-N,N’-diacetata]. in Serbian Journal of Experimental and Clinical Research (ranije: Medicus), 18(4), 289-294.
https://doi.org/10.1515/SJECR-2017-0067

Pantelić NĐ, Stanojković T, Zmejkovski BB, Kaluđerović GN, Sabo T. Antiproliferative activity of gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N’-diacetate [Antiproliferativna aktivnost zlato(III) kompleksa sa cikloheksil-funkcionalizovanim estrima etilendiamin-N,N’-diacetata]. in Serbian Journal of Experimental and Clinical Research (ranije: Medicus). 2017;18(4):289-294.
doi:10.1515/SJECR-2017-0067 .

Pantelić, Nebojša Đ., Stanojković, Tatjana, Zmejkovski, Bojana B., Kaluđerović, Goran N., Sabo, Tibor, "Antiproliferative activity of gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N’-diacetate [Antiproliferativna aktivnost zlato(III) kompleksa sa cikloheksil-funkcionalizovanim estrima etilendiamin-N,N’-diacetata]" in Serbian Journal of Experimental and Clinical Research (ranije: Medicus), 18, no. 4 (2017):289-294,
https://doi.org/10.1515/SJECR-2017-0067 . .

TY  - JOUR
AU  - Pantelić, Nebojša Đ.
AU  - Zmejkovski, Bojana B.
AU  - Kolundžija, Branka
AU  - Crnogorac, Marija Đorđić
AU  - Vujić, Jelena M.
AU  - Dojčinović, Biljana P.
AU  - Trifunović, Srećko R.
AU  - Stanojković, Tatjana
AU  - Sabo, Tibor
AU  - Kaluđerović, Goran N.
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2478
AB  - Four novel gold(III) complexes of general formulae [AuCl2{(S,S)-R(2)eddl}]PF6 (R(2)eddl = O,O'-dialkyl-(S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoate, R= n-Pr, n-Bu, n-Pe, i-Bu; 1-4, respectively), were synthesized and characterized by elemental analysis, UV/Vis, IR, and NMR spectroscopy, as well as high resolution mass spectrometry. Density functional theory calculations pointed out that (R,R)-N,N'-configuration diastereoisomers were energetically the most favorable. Duo to high cytotoxic activity complex 3 was chosen for stability study in DMSO, no decomposition occurs within 24 h, and for the reaction with ascorbic acid in which was reduced immediately. Additionally, 3 interacts with bovine serum albumin (BSA) as proven by UV/Vis spectroscopy. In vitro antitumor activity was determined against human cervix adenocarcinoma (HeLa), human myelogenous leukemia (K562), and human melanoma (Fem-x) cancer cell lines, as well as against non-cancerous human embryonic lung fibroblast cells MRC-5. The highest activity was observed against K562 cells (IC50: 5.04-6.51 mu M). Selectivity indices showed that these complexes are less toxic than cisplatin. 3 had a similar viability kinetics on HeLa cells as cisplatin. Drug accumulation studies in HeLa cells showed that the total gold uptake increased much faster than that of cisplatin pointing out that 3 more efficiently enters the cells than cisplatin. Furthermore, morphological and cell cycle analysis reveal that gold(III) complexes induced apoptosis in time- and dose-dependent manner.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N '-ethylenediamine bidentate ester ligands
VL  - 172
SP  - 55
EP  - 66
DO  - 10.1016/j.jinorgbio.2017.04.001
ER  - 

@article{
author = "Pantelić, Nebojša Đ. and Zmejkovski, Bojana B. and Kolundžija, Branka and Crnogorac, Marija Đorđić and Vujić, Jelena M. and Dojčinović, Biljana P. and Trifunović, Srećko R. and Stanojković, Tatjana and Sabo, Tibor and Kaluđerović, Goran N.",
year = "2017",
abstract = "Four novel gold(III) complexes of general formulae [AuCl2{(S,S)-R(2)eddl}]PF6 (R(2)eddl = O,O'-dialkyl-(S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoate, R= n-Pr, n-Bu, n-Pe, i-Bu; 1-4, respectively), were synthesized and characterized by elemental analysis, UV/Vis, IR, and NMR spectroscopy, as well as high resolution mass spectrometry. Density functional theory calculations pointed out that (R,R)-N,N'-configuration diastereoisomers were energetically the most favorable. Duo to high cytotoxic activity complex 3 was chosen for stability study in DMSO, no decomposition occurs within 24 h, and for the reaction with ascorbic acid in which was reduced immediately. Additionally, 3 interacts with bovine serum albumin (BSA) as proven by UV/Vis spectroscopy. In vitro antitumor activity was determined against human cervix adenocarcinoma (HeLa), human myelogenous leukemia (K562), and human melanoma (Fem-x) cancer cell lines, as well as against non-cancerous human embryonic lung fibroblast cells MRC-5. The highest activity was observed against K562 cells (IC50: 5.04-6.51 mu M). Selectivity indices showed that these complexes are less toxic than cisplatin. 3 had a similar viability kinetics on HeLa cells as cisplatin. Drug accumulation studies in HeLa cells showed that the total gold uptake increased much faster than that of cisplatin pointing out that 3 more efficiently enters the cells than cisplatin. Furthermore, morphological and cell cycle analysis reveal that gold(III) complexes induced apoptosis in time- and dose-dependent manner.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N '-ethylenediamine bidentate ester ligands",
volume = "172",
pages = "55-66",
doi = "10.1016/j.jinorgbio.2017.04.001"
}

Pantelić, N. Đ., Zmejkovski, B. B., Kolundžija, B., Crnogorac, M. Đ., Vujić, J. M., Dojčinović, B. P., Trifunović, S. R., Stanojković, T., Sabo, T.,& Kaluđerović, G. N.. (2017). In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N '-ethylenediamine bidentate ester ligands. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 172, 55-66.
https://doi.org/10.1016/j.jinorgbio.2017.04.001

Pantelić NĐ, Zmejkovski BB, Kolundžija B, Crnogorac MĐ, Vujić JM, Dojčinović BP, Trifunović SR, Stanojković T, Sabo T, Kaluđerović GN. In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N '-ethylenediamine bidentate ester ligands. in Journal of Inorganic Biochemistry. 2017;172:55-66.
doi:10.1016/j.jinorgbio.2017.04.001 .

Pantelić, Nebojša Đ., Zmejkovski, Bojana B., Kolundžija, Branka, Crnogorac, Marija Đorđić, Vujić, Jelena M., Dojčinović, Biljana P., Trifunović, Srećko R., Stanojković, Tatjana, Sabo, Tibor, Kaluđerović, Goran N., "In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N '-ethylenediamine bidentate ester ligands" in Journal of Inorganic Biochemistry, 172 (2017):55-66,
https://doi.org/10.1016/j.jinorgbio.2017.04.001 . .

TY  - JOUR
AU  - Zmejkovski, Bojana B.
AU  - Pantelić, Nebojša Đ.
AU  - Filipović, Lana
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Sabo, Tibor
AU  - Kaluđerović, Goran N.
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2501
AB  - Aims: Platinum(II) and platinum(IV) complexes [PtCln{(S,S)-(i-Am)(2)eddip}] (n = 2, 4: 1, 2, respectively; (S,S)-(i-Am)(2)eddip = O,O'-diisoamyl-(S,S)-ethylenediamine-N,N'-di-2-propanoate) were synthesized and characterized by elemental analysis, IR, H-1 and C-13 NMR spectroscopy and mass spectrometry. Method: Quantum chemical calculations were used to predict formed isomers of 1 and 2. Furthermore, reduction of 2 with ascorbic acid was followed by time-dependant C-13 NMR spectroscopy in order to enable assignation of the formed isomers for complex 1. In vitro cytotoxic activity was determined for 1 and 2 on a panel of five human tumor cell lines derived from cervix adenocarcinoma (HeLa), alveolar basal adenocarcinoma (A549), breast adenocarcinoma (MDA-453), colorectal cancer (LS 174), erythromyeloblastoid leukemia (K562), as well as one non-malignant human lung fibroblast cell line (MRC-5), using MTT assay. Result: Both complexes exhibited high (2 against K562: IC50 = 5.4 mu M), more active than cisplatin, to moderate activity (1). Both complexes caused considerable decrease of cell number in K562 cells in G1, S and G2 phases, concordantly increasing subpopulation in sub-G1 fraction. Morphological analysis of K562 cell death induced by platinum(II/IV) complexes indicate apoptosis.
PB  - Bentham Science Publ Ltd, Sharjah
T2  - Anti-Cancer Agents in Medicinal Chemistry
T1  - In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid
VL  - 17
IS  - 8
SP  - 1136
EP  - 1143
DO  - 10.2174/1871520616666161207155634
ER  - 

@article{
author = "Zmejkovski, Bojana B. and Pantelić, Nebojša Đ. and Filipović, Lana and Aranđelović, Sandra and Radulović, Siniša and Sabo, Tibor and Kaluđerović, Goran N.",
year = "2017",
abstract = "Aims: Platinum(II) and platinum(IV) complexes [PtCln{(S,S)-(i-Am)(2)eddip}] (n = 2, 4: 1, 2, respectively; (S,S)-(i-Am)(2)eddip = O,O'-diisoamyl-(S,S)-ethylenediamine-N,N'-di-2-propanoate) were synthesized and characterized by elemental analysis, IR, H-1 and C-13 NMR spectroscopy and mass spectrometry. Method: Quantum chemical calculations were used to predict formed isomers of 1 and 2. Furthermore, reduction of 2 with ascorbic acid was followed by time-dependant C-13 NMR spectroscopy in order to enable assignation of the formed isomers for complex 1. In vitro cytotoxic activity was determined for 1 and 2 on a panel of five human tumor cell lines derived from cervix adenocarcinoma (HeLa), alveolar basal adenocarcinoma (A549), breast adenocarcinoma (MDA-453), colorectal cancer (LS 174), erythromyeloblastoid leukemia (K562), as well as one non-malignant human lung fibroblast cell line (MRC-5), using MTT assay. Result: Both complexes exhibited high (2 against K562: IC50 = 5.4 mu M), more active than cisplatin, to moderate activity (1). Both complexes caused considerable decrease of cell number in K562 cells in G1, S and G2 phases, concordantly increasing subpopulation in sub-G1 fraction. Morphological analysis of K562 cell death induced by platinum(II/IV) complexes indicate apoptosis.",
publisher = "Bentham Science Publ Ltd, Sharjah",
journal = "Anti-Cancer Agents in Medicinal Chemistry",
title = "In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid",
volume = "17",
number = "8",
pages = "1136-1143",
doi = "10.2174/1871520616666161207155634"
}

Zmejkovski, B. B., Pantelić, N. Đ., Filipović, L., Aranđelović, S., Radulović, S., Sabo, T.,& Kaluđerović, G. N.. (2017). In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid. in Anti-Cancer Agents in Medicinal Chemistry
Bentham Science Publ Ltd, Sharjah., 17(8), 1136-1143.
https://doi.org/10.2174/1871520616666161207155634

Zmejkovski BB, Pantelić NĐ, Filipović L, Aranđelović S, Radulović S, Sabo T, Kaluđerović GN. In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid. in Anti-Cancer Agents in Medicinal Chemistry. 2017;17(8):1136-1143.
doi:10.2174/1871520616666161207155634 .

Zmejkovski, Bojana B., Pantelić, Nebojša Đ., Filipović, Lana, Aranđelović, Sandra, Radulović, Siniša, Sabo, Tibor, Kaluđerović, Goran N., "In Vitro Anticancer Evaluation of Platinum(II/IV) Complexes with Diisoamyl Ester of (S,S)-ethylenediamine-N,N'-di-2-propanoic Acid" in Anti-Cancer Agents in Medicinal Chemistry, 17, no. 8 (2017):1136-1143,
https://doi.org/10.2174/1871520616666161207155634 . .

TY  - JOUR
AU  - Pantelić, Nebojša Đ.
AU  - Zmejkovski, Bojana B.
AU  - Kolundžija, Branka
AU  - Crnogorac, Marija Đorđić
AU  - Vujić, Jelena M.
AU  - Dojčinović, Biljana P.
AU  - Trifunović, Srećko R.
AU  - Stanojković, Tatjana
AU  - Sabo, Tibor
AU  - Kaluđerović, Goran N.
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3070
AB  - Four novel gold(III) complexes of general formulae [AuCl2{(S,S)-R(2)eddl}]PF6 (R(2)eddl = O,O'-dialkyl-(S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoate, R= n-Pr, n-Bu, n-Pe, i-Bu; 1-4, respectively), were synthesized and characterized by elemental analysis, UV/Vis, IR, and NMR spectroscopy, as well as high resolution mass spectrometry. Density functional theory calculations pointed out that (R,R)-N,N'-configuration diastereoisomers were energetically the most favorable. Duo to high cytotoxic activity complex 3 was chosen for stability study in DMSO, no decomposition occurs within 24 h, and for the reaction with ascorbic acid in which was reduced immediately. Additionally, 3 interacts with bovine serum albumin (BSA) as proven by UV/Vis spectroscopy. In vitro antitumor activity was determined against human cervix adenocarcinoma (HeLa), human myelogenous leukemia (K562), and human melanoma (Fem-x) cancer cell lines, as well as against non-cancerous human embryonic lung fibroblast cells MRC-5. The highest activity was observed against K562 cells (IC50: 5.04-6.51 mu M). Selectivity indices showed that these complexes are less toxic than cisplatin. 3 had a similar viability kinetics on HeLa cells as cisplatin. Drug accumulation studies in HeLa cells showed that the total gold uptake increased much faster than that of cisplatin pointing out that 3 more efficiently enters the cells than cisplatin. Furthermore, morphological and cell cycle analysis reveal that gold(III) complexes induced apoptosis in time- and dose-dependent manner.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N′-ethylenediamine bidentate ester ligands
VL  - 172
SP  - 55
EP  - 66
DO  - 10.1016/j.jinorgbio.2017.04.001
ER  - 

@article{
author = "Pantelić, Nebojša Đ. and Zmejkovski, Bojana B. and Kolundžija, Branka and Crnogorac, Marija Đorđić and Vujić, Jelena M. and Dojčinović, Biljana P. and Trifunović, Srećko R. and Stanojković, Tatjana and Sabo, Tibor and Kaluđerović, Goran N.",
year = "2017",
abstract = "Four novel gold(III) complexes of general formulae [AuCl2{(S,S)-R(2)eddl}]PF6 (R(2)eddl = O,O'-dialkyl-(S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoate, R= n-Pr, n-Bu, n-Pe, i-Bu; 1-4, respectively), were synthesized and characterized by elemental analysis, UV/Vis, IR, and NMR spectroscopy, as well as high resolution mass spectrometry. Density functional theory calculations pointed out that (R,R)-N,N'-configuration diastereoisomers were energetically the most favorable. Duo to high cytotoxic activity complex 3 was chosen for stability study in DMSO, no decomposition occurs within 24 h, and for the reaction with ascorbic acid in which was reduced immediately. Additionally, 3 interacts with bovine serum albumin (BSA) as proven by UV/Vis spectroscopy. In vitro antitumor activity was determined against human cervix adenocarcinoma (HeLa), human myelogenous leukemia (K562), and human melanoma (Fem-x) cancer cell lines, as well as against non-cancerous human embryonic lung fibroblast cells MRC-5. The highest activity was observed against K562 cells (IC50: 5.04-6.51 mu M). Selectivity indices showed that these complexes are less toxic than cisplatin. 3 had a similar viability kinetics on HeLa cells as cisplatin. Drug accumulation studies in HeLa cells showed that the total gold uptake increased much faster than that of cisplatin pointing out that 3 more efficiently enters the cells than cisplatin. Furthermore, morphological and cell cycle analysis reveal that gold(III) complexes induced apoptosis in time- and dose-dependent manner.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N′-ethylenediamine bidentate ester ligands",
volume = "172",
pages = "55-66",
doi = "10.1016/j.jinorgbio.2017.04.001"
}

Pantelić, N. Đ., Zmejkovski, B. B., Kolundžija, B., Crnogorac, M. Đ., Vujić, J. M., Dojčinović, B. P., Trifunović, S. R., Stanojković, T., Sabo, T.,& Kaluđerović, G. N.. (2017). In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N′-ethylenediamine bidentate ester ligands. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 172, 55-66.
https://doi.org/10.1016/j.jinorgbio.2017.04.001

Pantelić NĐ, Zmejkovski BB, Kolundžija B, Crnogorac MĐ, Vujić JM, Dojčinović BP, Trifunović SR, Stanojković T, Sabo T, Kaluđerović GN. In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N′-ethylenediamine bidentate ester ligands. in Journal of Inorganic Biochemistry. 2017;172:55-66.
doi:10.1016/j.jinorgbio.2017.04.001 .

Pantelić, Nebojša Đ., Zmejkovski, Bojana B., Kolundžija, Branka, Crnogorac, Marija Đorđić, Vujić, Jelena M., Dojčinović, Biljana P., Trifunović, Srećko R., Stanojković, Tatjana, Sabo, Tibor, Kaluđerović, Goran N., "In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N′-ethylenediamine bidentate ester ligands" in Journal of Inorganic Biochemistry, 172 (2017):55-66,
https://doi.org/10.1016/j.jinorgbio.2017.04.001 . .

TY  - DATA
AU  - Pantelić, Nebojša Đ.
AU  - Zmejkovski, Bojana B.
AU  - Kolundžija, Branka
AU  - Crnogorac, Marija Đorđić
AU  - Vujić, Jelena M.
AU  - Dojčinović, Biljana P.
AU  - Trifunović, Srećko R.
AU  - Stanojković, Tatjana
AU  - Sabo, Tibor
AU  - Kaluđerović, Goran N.
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3071
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - Supplementary data for article:          Pantelić, N.; Zmejkovski, B. B.; Kolundžija, B.; Crnogorac, M. Đ.; Vujić, J. M.; Dojčinović, B.; Trifunović, S. R.; Stanojković, T. P.; Sabo, T. J.; Kaluđerović, G. N. In Vitro Antitumor Activity, Metal Uptake and Reactivity with Ascorbic Acid and BSA of Some Gold(III) Complexes with N,N′-Ethylenediamine Bidentate Ester Ligands. Journal of Inorganic Biochemistry 2017, 172, 55–66. https://doi.org/10.1016/j.jinorgbio.2017.04.001
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3071
ER  - 

@misc{
author = "Pantelić, Nebojša Đ. and Zmejkovski, Bojana B. and Kolundžija, Branka and Crnogorac, Marija Đorđić and Vujić, Jelena M. and Dojčinović, Biljana P. and Trifunović, Srećko R. and Stanojković, Tatjana and Sabo, Tibor and Kaluđerović, Goran N.",
year = "2017",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "Supplementary data for article:          Pantelić, N.; Zmejkovski, B. B.; Kolundžija, B.; Crnogorac, M. Đ.; Vujić, J. M.; Dojčinović, B.; Trifunović, S. R.; Stanojković, T. P.; Sabo, T. J.; Kaluđerović, G. N. In Vitro Antitumor Activity, Metal Uptake and Reactivity with Ascorbic Acid and BSA of Some Gold(III) Complexes with N,N′-Ethylenediamine Bidentate Ester Ligands. Journal of Inorganic Biochemistry 2017, 172, 55–66. https://doi.org/10.1016/j.jinorgbio.2017.04.001",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3071"
}

Pantelić, N. Đ., Zmejkovski, B. B., Kolundžija, B., Crnogorac, M. Đ., Vujić, J. M., Dojčinović, B. P., Trifunović, S. R., Stanojković, T., Sabo, T.,& Kaluđerović, G. N.. (2017). Supplementary data for article:          Pantelić, N.; Zmejkovski, B. B.; Kolundžija, B.; Crnogorac, M. Đ.; Vujić, J. M.; Dojčinović, B.; Trifunović, S. R.; Stanojković, T. P.; Sabo, T. J.; Kaluđerović, G. N. In Vitro Antitumor Activity, Metal Uptake and Reactivity with Ascorbic Acid and BSA of Some Gold(III) Complexes with N,N′-Ethylenediamine Bidentate Ester Ligands. Journal of Inorganic Biochemistry 2017, 172, 55–66. https://doi.org/10.1016/j.jinorgbio.2017.04.001. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York..
https://hdl.handle.net/21.15107/rcub_cherry_3071

Pantelić NĐ, Zmejkovski BB, Kolundžija B, Crnogorac MĐ, Vujić JM, Dojčinović BP, Trifunović SR, Stanojković T, Sabo T, Kaluđerović GN. Supplementary data for article:          Pantelić, N.; Zmejkovski, B. B.; Kolundžija, B.; Crnogorac, M. Đ.; Vujić, J. M.; Dojčinović, B.; Trifunović, S. R.; Stanojković, T. P.; Sabo, T. J.; Kaluđerović, G. N. In Vitro Antitumor Activity, Metal Uptake and Reactivity with Ascorbic Acid and BSA of Some Gold(III) Complexes with N,N′-Ethylenediamine Bidentate Ester Ligands. Journal of Inorganic Biochemistry 2017, 172, 55–66. https://doi.org/10.1016/j.jinorgbio.2017.04.001. in Journal of Inorganic Biochemistry. 2017;.
https://hdl.handle.net/21.15107/rcub_cherry_3071 .

Pantelić, Nebojša Đ., Zmejkovski, Bojana B., Kolundžija, Branka, Crnogorac, Marija Đorđić, Vujić, Jelena M., Dojčinović, Biljana P., Trifunović, Srećko R., Stanojković, Tatjana, Sabo, Tibor, Kaluđerović, Goran N., "Supplementary data for article:          Pantelić, N.; Zmejkovski, B. B.; Kolundžija, B.; Crnogorac, M. Đ.; Vujić, J. M.; Dojčinović, B.; Trifunović, S. R.; Stanojković, T. P.; Sabo, T. J.; Kaluđerović, G. N. In Vitro Antitumor Activity, Metal Uptake and Reactivity with Ascorbic Acid and BSA of Some Gold(III) Complexes with N,N′-Ethylenediamine Bidentate Ester Ligands. Journal of Inorganic Biochemistry 2017, 172, 55–66. https://doi.org/10.1016/j.jinorgbio.2017.04.001" in Journal of Inorganic Biochemistry (2017),
https://hdl.handle.net/21.15107/rcub_cherry_3071 .

TY  - CONF
AU  - Tubić, Biljana K.
AU  - Marković, Bojan D.
AU  - Vladimirov, S.
AU  - Savić, Aleksandar
AU  - Poljarević, Jelena
AU  - Sabo, Tibor
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/307
AB  - During the early stages of drug discovery, it is very important to determine lipophilicity and to investigate and predict processes of drug distribution and resorption in human body, i.e. their bioavailability. Novel fourteen compounds representing ester derivatives of (S,S')-1,2- ethanediamme-N,N'-di-2-(3-cyclohexyl)propanoic and (S,S)- 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acids, expressing antiproliferative activity in vitro were examined. The objective of this study was to estimation a lipophilicity data of observed fourteen compounds by ultra-high performance liquid chromatographic tandem mass spectrometry (UHPLC-MS) method. It was used gradient and isocratic method to obtain chromatographic parameters of lipophilicity/ hydrophobicity, which are needed for calculated logP values. Results of lipophilicity data for observed 14 compounds, which were obtained by UHPLC-MS method and presented in this paper, are showed that the derivatives of 1,2 ethandiamine-N,N'-di-2-(3-cyclohexyl) propanoic acid have higer values of logP, than derivatives of 1,3-propanediamine- N,N'-di-2-(3-cyclohexyl) propanoic acid. Also, value of lipophilicity data for each of investigated compounds depends on the length of the alkyl chain on the esters bounds. Branching of the alkyl chain on the esters bounds has insignificant influence on the values of lipophilicity/ hydrophobicity.
PB  - Springer Nature Singapore Pte Ltd.
C3  - IFMBE Proceedings
T1  - Estimation of lipophilicity data for derivatives of alkandiamine-N,N’-di-2-(3-cyclohexyl) propanoic acid with potential antineoplastic activity, by UHPLC-MS method
VL  - 62
SP  - 402
EP  - 409
DO  - 10.1007/978-981-10-4166-2_62
ER  - 

@conference{
author = "Tubić, Biljana K. and Marković, Bojan D. and Vladimirov, S. and Savić, Aleksandar and Poljarević, Jelena and Sabo, Tibor",
year = "2017",
abstract = "During the early stages of drug discovery, it is very important to determine lipophilicity and to investigate and predict processes of drug distribution and resorption in human body, i.e. their bioavailability. Novel fourteen compounds representing ester derivatives of (S,S')-1,2- ethanediamme-N,N'-di-2-(3-cyclohexyl)propanoic and (S,S)- 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acids, expressing antiproliferative activity in vitro were examined. The objective of this study was to estimation a lipophilicity data of observed fourteen compounds by ultra-high performance liquid chromatographic tandem mass spectrometry (UHPLC-MS) method. It was used gradient and isocratic method to obtain chromatographic parameters of lipophilicity/ hydrophobicity, which are needed for calculated logP values. Results of lipophilicity data for observed 14 compounds, which were obtained by UHPLC-MS method and presented in this paper, are showed that the derivatives of 1,2 ethandiamine-N,N'-di-2-(3-cyclohexyl) propanoic acid have higer values of logP, than derivatives of 1,3-propanediamine- N,N'-di-2-(3-cyclohexyl) propanoic acid. Also, value of lipophilicity data for each of investigated compounds depends on the length of the alkyl chain on the esters bounds. Branching of the alkyl chain on the esters bounds has insignificant influence on the values of lipophilicity/ hydrophobicity.",
publisher = "Springer Nature Singapore Pte Ltd.",
journal = "IFMBE Proceedings",
title = "Estimation of lipophilicity data for derivatives of alkandiamine-N,N’-di-2-(3-cyclohexyl) propanoic acid with potential antineoplastic activity, by UHPLC-MS method",
volume = "62",
pages = "402-409",
doi = "10.1007/978-981-10-4166-2_62"
}

Tubić, B. K., Marković, B. D., Vladimirov, S., Savić, A., Poljarević, J.,& Sabo, T.. (2017). Estimation of lipophilicity data for derivatives of alkandiamine-N,N’-di-2-(3-cyclohexyl) propanoic acid with potential antineoplastic activity, by UHPLC-MS method. in IFMBE Proceedings
Springer Nature Singapore Pte Ltd.., 62, 402-409.
https://doi.org/10.1007/978-981-10-4166-2_62

Tubić BK, Marković BD, Vladimirov S, Savić A, Poljarević J, Sabo T. Estimation of lipophilicity data for derivatives of alkandiamine-N,N’-di-2-(3-cyclohexyl) propanoic acid with potential antineoplastic activity, by UHPLC-MS method. in IFMBE Proceedings. 2017;62:402-409.
doi:10.1007/978-981-10-4166-2_62 .

Tubić, Biljana K., Marković, Bojan D., Vladimirov, S., Savić, Aleksandar, Poljarević, Jelena, Sabo, Tibor, "Estimation of lipophilicity data for derivatives of alkandiamine-N,N’-di-2-(3-cyclohexyl) propanoic acid with potential antineoplastic activity, by UHPLC-MS method" in IFMBE Proceedings, 62 (2017):402-409,
https://doi.org/10.1007/978-981-10-4166-2_62 . .

TY  - JOUR
AU  - Misirlić-Denčić, Sonja
AU  - Poljarević, Jelena
AU  - Isaković, Anđelka M.
AU  - Marković, Ivanka
AU  - Sabo, Tibor
AU  - Grgurić-Šipka, Sanja
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3120
AB  - This study presents the synthesis, characterization, and antitumor action of five new Pt(II) halogenido, chlorido, and iodido complexes with edda type of ligands. (S,S)-Ethylenediamine-N,N-di-2-(3-cyclohexyl)propanoic acid dihydrochloride and its methyl, ethyl, and n-propyl esters were prepared according to the previously reported procedure. All investigated complexes were characterized by IR, ESI-MS (H-1, C-13, and HMBC) NMR spectroscopy, and elemental analysis. Their cytotoxic action was investigated in four human tumor cell lines: promyelocytic (HL-60) and lymphocytic (REH) leukemia, glioma (U251), and lung carcinoma (H460). Cell viability was assessed by acid phosphatase and LDH assay, while oxidative stress and cell death parameters were analyzed by flow cytometry. The results showed that novel Pt(II) complexes exhibited antitumor action superior to precursor ligands, with iodido complexes being more efficient than corresponding chlorido complexes. Human promyelocytic cell line (HL-60) was the most sensitive to antitumor action of all investigated substances and was used for investigation of the underlying mode of antileukemic action. The investigated Pt(II) complexes showed more potent antileukemic action than corresponding Pt(IV) complex, through induction of oxidative stress and apoptosis, evidenced by caspase (8, 9, and 3) activation and phosphatidylserine externalization.
PB  - Wiley, Hoboken
T2  - Chemical Biology and Drug Design
T1  - Antileukemic action of novel diamine Pt(II) halogenido complexes: Comparison of the representative novel Pt(II) with corresponding Pt(IV) complex
VL  - 90
IS  - 2
SP  - 262
EP  - 271
DO  - 10.1111/cbdd.12945
ER  - 

@article{
author = "Misirlić-Denčić, Sonja and Poljarević, Jelena and Isaković, Anđelka M. and Marković, Ivanka and Sabo, Tibor and Grgurić-Šipka, Sanja",
year = "2017",
abstract = "This study presents the synthesis, characterization, and antitumor action of five new Pt(II) halogenido, chlorido, and iodido complexes with edda type of ligands. (S,S)-Ethylenediamine-N,N-di-2-(3-cyclohexyl)propanoic acid dihydrochloride and its methyl, ethyl, and n-propyl esters were prepared according to the previously reported procedure. All investigated complexes were characterized by IR, ESI-MS (H-1, C-13, and HMBC) NMR spectroscopy, and elemental analysis. Their cytotoxic action was investigated in four human tumor cell lines: promyelocytic (HL-60) and lymphocytic (REH) leukemia, glioma (U251), and lung carcinoma (H460). Cell viability was assessed by acid phosphatase and LDH assay, while oxidative stress and cell death parameters were analyzed by flow cytometry. The results showed that novel Pt(II) complexes exhibited antitumor action superior to precursor ligands, with iodido complexes being more efficient than corresponding chlorido complexes. Human promyelocytic cell line (HL-60) was the most sensitive to antitumor action of all investigated substances and was used for investigation of the underlying mode of antileukemic action. The investigated Pt(II) complexes showed more potent antileukemic action than corresponding Pt(IV) complex, through induction of oxidative stress and apoptosis, evidenced by caspase (8, 9, and 3) activation and phosphatidylserine externalization.",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology and Drug Design",
title = "Antileukemic action of novel diamine Pt(II) halogenido complexes: Comparison of the representative novel Pt(II) with corresponding Pt(IV) complex",
volume = "90",
number = "2",
pages = "262-271",
doi = "10.1111/cbdd.12945"
}

Misirlić-Denčić, S., Poljarević, J., Isaković, A. M., Marković, I., Sabo, T.,& Grgurić-Šipka, S.. (2017). Antileukemic action of novel diamine Pt(II) halogenido complexes: Comparison of the representative novel Pt(II) with corresponding Pt(IV) complex. in Chemical Biology and Drug Design
Wiley, Hoboken., 90(2), 262-271.
https://doi.org/10.1111/cbdd.12945

Misirlić-Denčić S, Poljarević J, Isaković AM, Marković I, Sabo T, Grgurić-Šipka S. Antileukemic action of novel diamine Pt(II) halogenido complexes: Comparison of the representative novel Pt(II) with corresponding Pt(IV) complex. in Chemical Biology and Drug Design. 2017;90(2):262-271.
doi:10.1111/cbdd.12945 .

Misirlić-Denčić, Sonja, Poljarević, Jelena, Isaković, Anđelka M., Marković, Ivanka, Sabo, Tibor, Grgurić-Šipka, Sanja, "Antileukemic action of novel diamine Pt(II) halogenido complexes: Comparison of the representative novel Pt(II) with corresponding Pt(IV) complex" in Chemical Biology and Drug Design, 90, no. 2 (2017):262-271,
https://doi.org/10.1111/cbdd.12945 . .

TY  - DATA
AU  - Misirlić-Denčić, Sonja
AU  - Poljarević, Jelena
AU  - Isaković, Anđelka M.
AU  - Marković, Ivanka
AU  - Sabo, Tibor
AU  - Grgurić-Šipka, Sanja
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3121
PB  - Wiley, Hoboken
T2  - Chemical Biology and Drug Design
T1  - Supplementary data for article:           Misirlić Denčić, S.; Poljarević, J.; Isakovic, A. M.; Marković, I.; Sabo, T. J.; Grgurić-Šipka, S. Antileukemic Action of Novel Diamine Pt(II) Halogenido Complexes: Comparison of the Representative Novel Pt(II) with Corresponding Pt(IV) Complex. Chemical Biology and Drug Design 2017, 90 (2), 262–271. https://doi.org/10.1111/cbdd.12945
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3121
ER  - 

@misc{
author = "Misirlić-Denčić, Sonja and Poljarević, Jelena and Isaković, Anđelka M. and Marković, Ivanka and Sabo, Tibor and Grgurić-Šipka, Sanja",
year = "2017",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology and Drug Design",
title = "Supplementary data for article:           Misirlić Denčić, S.; Poljarević, J.; Isakovic, A. M.; Marković, I.; Sabo, T. J.; Grgurić-Šipka, S. Antileukemic Action of Novel Diamine Pt(II) Halogenido Complexes: Comparison of the Representative Novel Pt(II) with Corresponding Pt(IV) Complex. Chemical Biology and Drug Design 2017, 90 (2), 262–271. https://doi.org/10.1111/cbdd.12945",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3121"
}

Misirlić-Denčić, S., Poljarević, J., Isaković, A. M., Marković, I., Sabo, T.,& Grgurić-Šipka, S.. (2017). Supplementary data for article:           Misirlić Denčić, S.; Poljarević, J.; Isakovic, A. M.; Marković, I.; Sabo, T. J.; Grgurić-Šipka, S. Antileukemic Action of Novel Diamine Pt(II) Halogenido Complexes: Comparison of the Representative Novel Pt(II) with Corresponding Pt(IV) Complex. Chemical Biology and Drug Design 2017, 90 (2), 262–271. https://doi.org/10.1111/cbdd.12945. in Chemical Biology and Drug Design
Wiley, Hoboken..
https://hdl.handle.net/21.15107/rcub_cherry_3121

Misirlić-Denčić S, Poljarević J, Isaković AM, Marković I, Sabo T, Grgurić-Šipka S. Supplementary data for article:           Misirlić Denčić, S.; Poljarević, J.; Isakovic, A. M.; Marković, I.; Sabo, T. J.; Grgurić-Šipka, S. Antileukemic Action of Novel Diamine Pt(II) Halogenido Complexes: Comparison of the Representative Novel Pt(II) with Corresponding Pt(IV) Complex. Chemical Biology and Drug Design 2017, 90 (2), 262–271. https://doi.org/10.1111/cbdd.12945. in Chemical Biology and Drug Design. 2017;.
https://hdl.handle.net/21.15107/rcub_cherry_3121 .

Misirlić-Denčić, Sonja, Poljarević, Jelena, Isaković, Anđelka M., Marković, Ivanka, Sabo, Tibor, Grgurić-Šipka, Sanja, "Supplementary data for article:           Misirlić Denčić, S.; Poljarević, J.; Isakovic, A. M.; Marković, I.; Sabo, T. J.; Grgurić-Šipka, S. Antileukemic Action of Novel Diamine Pt(II) Halogenido Complexes: Comparison of the Representative Novel Pt(II) with Corresponding Pt(IV) Complex. Chemical Biology and Drug Design 2017, 90 (2), 262–271. https://doi.org/10.1111/cbdd.12945" in Chemical Biology and Drug Design (2017),
https://hdl.handle.net/21.15107/rcub_cherry_3121 .

TY  - JOUR
AU  - Tubić, Biljana K.
AU  - Marković, Bojan D.
AU  - Vladimirov, Sandra S.
AU  - Ristić, Slavica M.
AU  - Ivković, Branka
AU  - Savić, Miroslav M.
AU  - Poljarević, Jelena
AU  - Sabo, Tibor
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2459
AB  - A series of new (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate esters has shown cytotoxic activity towards human leukemic cell lines. The aim of this study was to develop and validate a bioanalytical method for quantification of (S,S)-O,O-diethyl-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate dihydrochlorides (DE-EDCP) and its metabolite, substituted propanoic acid (EDCP), in mouse serum by ultra high-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS). Structural analog, derivative of 1,3-propanediamine, was used as an internal standard (IS). Sample preparation employed protein precipitation by acetonitrile and subsequent centrifugation. Optimal UHPLC separation conditions were set to achieve simultaneous determination of both compounds in a short run time of 6 min. Additionally, the selected reaction monitoring (SRM) mode developed in this method allowed a highly sensitive, accurate, and precise identification of compounds of interest. The lower limit of quantitation (LOQ) was 1.3 ng mL(-1) for DE-EDCP and 0.3 mu g mL(-1) for EDCP. The calibration curves were linear over the concentration range of 1.3-26.7 ng mL(-1) and 0.3-6.7 mu g mL(-1) for DE-EDCP and EDCP, respectively. Precision (%CV) and accuracy (% RE) for DE-EDCP and EDCP ranged from 3.5% to 16.0% and from 1.8% to 14.4%, respectively. The validation process was performed in accordance with the regulatory guidance/guideline, and all of the obtained results met the established acceptance criteria. The newly developed and validated UHPLC-MS/MS method is rapid, sensitive, and selective, and it can be successfully applied to drug monitoring in nonclinical studies.
PB  - Akademiai Kiado Rt, Budapest
T2  - Acta Chromatographica
T1  - Highly Sensitive UHPLC-MS/MS Method for Quantification of Ethylenediamine-N,N '-di-2-(3-cyclohexyl) Propanoic Acid Derivatives in Mouse Serum
VL  - 29
IS  - 2
SP  - 235
EP  - 252
DO  - 10.1556/1326.2017.29.2.7
ER  - 

@article{
author = "Tubić, Biljana K. and Marković, Bojan D. and Vladimirov, Sandra S. and Ristić, Slavica M. and Ivković, Branka and Savić, Miroslav M. and Poljarević, Jelena and Sabo, Tibor",
year = "2017",
abstract = "A series of new (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate esters has shown cytotoxic activity towards human leukemic cell lines. The aim of this study was to develop and validate a bioanalytical method for quantification of (S,S)-O,O-diethyl-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoate dihydrochlorides (DE-EDCP) and its metabolite, substituted propanoic acid (EDCP), in mouse serum by ultra high-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS). Structural analog, derivative of 1,3-propanediamine, was used as an internal standard (IS). Sample preparation employed protein precipitation by acetonitrile and subsequent centrifugation. Optimal UHPLC separation conditions were set to achieve simultaneous determination of both compounds in a short run time of 6 min. Additionally, the selected reaction monitoring (SRM) mode developed in this method allowed a highly sensitive, accurate, and precise identification of compounds of interest. The lower limit of quantitation (LOQ) was 1.3 ng mL(-1) for DE-EDCP and 0.3 mu g mL(-1) for EDCP. The calibration curves were linear over the concentration range of 1.3-26.7 ng mL(-1) and 0.3-6.7 mu g mL(-1) for DE-EDCP and EDCP, respectively. Precision (%CV) and accuracy (% RE) for DE-EDCP and EDCP ranged from 3.5% to 16.0% and from 1.8% to 14.4%, respectively. The validation process was performed in accordance with the regulatory guidance/guideline, and all of the obtained results met the established acceptance criteria. The newly developed and validated UHPLC-MS/MS method is rapid, sensitive, and selective, and it can be successfully applied to drug monitoring in nonclinical studies.",
publisher = "Akademiai Kiado Rt, Budapest",
journal = "Acta Chromatographica",
title = "Highly Sensitive UHPLC-MS/MS Method for Quantification of Ethylenediamine-N,N '-di-2-(3-cyclohexyl) Propanoic Acid Derivatives in Mouse Serum",
volume = "29",
number = "2",
pages = "235-252",
doi = "10.1556/1326.2017.29.2.7"
}

Tubić, B. K., Marković, B. D., Vladimirov, S. S., Ristić, S. M., Ivković, B., Savić, M. M., Poljarević, J.,& Sabo, T.. (2017). Highly Sensitive UHPLC-MS/MS Method for Quantification of Ethylenediamine-N,N '-di-2-(3-cyclohexyl) Propanoic Acid Derivatives in Mouse Serum. in Acta Chromatographica
Akademiai Kiado Rt, Budapest., 29(2), 235-252.
https://doi.org/10.1556/1326.2017.29.2.7

Tubić BK, Marković BD, Vladimirov SS, Ristić SM, Ivković B, Savić MM, Poljarević J, Sabo T. Highly Sensitive UHPLC-MS/MS Method for Quantification of Ethylenediamine-N,N '-di-2-(3-cyclohexyl) Propanoic Acid Derivatives in Mouse Serum. in Acta Chromatographica. 2017;29(2):235-252.
doi:10.1556/1326.2017.29.2.7 .

Tubić, Biljana K., Marković, Bojan D., Vladimirov, Sandra S., Ristić, Slavica M., Ivković, Branka, Savić, Miroslav M., Poljarević, Jelena, Sabo, Tibor, "Highly Sensitive UHPLC-MS/MS Method for Quantification of Ethylenediamine-N,N '-di-2-(3-cyclohexyl) Propanoic Acid Derivatives in Mouse Serum" in Acta Chromatographica, 29, no. 2 (2017):235-252,
https://doi.org/10.1556/1326.2017.29.2.7 . .

TY  - JOUR
AU  - Misirlić-Denčić, Sonja
AU  - Poljarević, Jelena
AU  - Isaković, Anđelka M.
AU  - Marković, Ivanka
AU  - Sabo, Tibor
AU  - Grgurić-Šipka, Sanja
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2483
AB  - This study presents the synthesis, characterization, and antitumor action of five new Pt(II) halogenido, chlorido, and iodido complexes with edda type of ligands. (S,S)-Ethylenediamine-N,N-di-2-(3-cyclohexyl)propanoic acid dihydrochloride and its methyl, ethyl, and n-propyl esters were prepared according to the previously reported procedure. All investigated complexes were characterized by IR, ESI-MS (H-1, C-13, and HMBC) NMR spectroscopy, and elemental analysis. Their cytotoxic action was investigated in four human tumor cell lines: promyelocytic (HL-60) and lymphocytic (REH) leukemia, glioma (U251), and lung carcinoma (H460). Cell viability was assessed by acid phosphatase and LDH assay, while oxidative stress and cell death parameters were analyzed by flow cytometry. The results showed that novel Pt(II) complexes exhibited antitumor action superior to precursor ligands, with iodido complexes being more efficient than corresponding chlorido complexes. Human promyelocytic cell line (HL-60) was the most sensitive to antitumor action of all investigated substances and was used for investigation of the underlying mode of antileukemic action. The investigated Pt(II) complexes showed more potent antileukemic action than corresponding Pt(IV) complex, through induction of oxidative stress and apoptosis, evidenced by caspase (8, 9, and 3) activation and phosphatidylserine externalization.
PB  - Wiley, Hoboken
T2  - Chemical Biology and Drug Design
T1  - Antileukemic action of novel diamine Pt(II) halogenido complexes: Comparison of the representative novel Pt(II) with corresponding Pt(IV) complex
VL  - 90
IS  - 2
SP  - 262
EP  - 271
DO  - 10.1111/cbdd.12945
ER  - 

@article{
author = "Misirlić-Denčić, Sonja and Poljarević, Jelena and Isaković, Anđelka M. and Marković, Ivanka and Sabo, Tibor and Grgurić-Šipka, Sanja",
year = "2017",
abstract = "This study presents the synthesis, characterization, and antitumor action of five new Pt(II) halogenido, chlorido, and iodido complexes with edda type of ligands. (S,S)-Ethylenediamine-N,N-di-2-(3-cyclohexyl)propanoic acid dihydrochloride and its methyl, ethyl, and n-propyl esters were prepared according to the previously reported procedure. All investigated complexes were characterized by IR, ESI-MS (H-1, C-13, and HMBC) NMR spectroscopy, and elemental analysis. Their cytotoxic action was investigated in four human tumor cell lines: promyelocytic (HL-60) and lymphocytic (REH) leukemia, glioma (U251), and lung carcinoma (H460). Cell viability was assessed by acid phosphatase and LDH assay, while oxidative stress and cell death parameters were analyzed by flow cytometry. The results showed that novel Pt(II) complexes exhibited antitumor action superior to precursor ligands, with iodido complexes being more efficient than corresponding chlorido complexes. Human promyelocytic cell line (HL-60) was the most sensitive to antitumor action of all investigated substances and was used for investigation of the underlying mode of antileukemic action. The investigated Pt(II) complexes showed more potent antileukemic action than corresponding Pt(IV) complex, through induction of oxidative stress and apoptosis, evidenced by caspase (8, 9, and 3) activation and phosphatidylserine externalization.",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology and Drug Design",
title = "Antileukemic action of novel diamine Pt(II) halogenido complexes: Comparison of the representative novel Pt(II) with corresponding Pt(IV) complex",
volume = "90",
number = "2",
pages = "262-271",
doi = "10.1111/cbdd.12945"
}

Misirlić-Denčić, S., Poljarević, J., Isaković, A. M., Marković, I., Sabo, T.,& Grgurić-Šipka, S.. (2017). Antileukemic action of novel diamine Pt(II) halogenido complexes: Comparison of the representative novel Pt(II) with corresponding Pt(IV) complex. in Chemical Biology and Drug Design
Wiley, Hoboken., 90(2), 262-271.
https://doi.org/10.1111/cbdd.12945

Misirlić-Denčić S, Poljarević J, Isaković AM, Marković I, Sabo T, Grgurić-Šipka S. Antileukemic action of novel diamine Pt(II) halogenido complexes: Comparison of the representative novel Pt(II) with corresponding Pt(IV) complex. in Chemical Biology and Drug Design. 2017;90(2):262-271.
doi:10.1111/cbdd.12945 .

Misirlić-Denčić, Sonja, Poljarević, Jelena, Isaković, Anđelka M., Marković, Ivanka, Sabo, Tibor, Grgurić-Šipka, Sanja, "Antileukemic action of novel diamine Pt(II) halogenido complexes: Comparison of the representative novel Pt(II) with corresponding Pt(IV) complex" in Chemical Biology and Drug Design, 90, no. 2 (2017):262-271,
https://doi.org/10.1111/cbdd.12945 . .

TY  - JOUR
AU  - Tubić, Biljana K.
AU  - Marković, Bojan D.
AU  - Vladimirov, S.
AU  - Savic, S.
AU  - Poljarević, Jelena
AU  - Sabo, Tibor
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2499
AB  - Fourteen compounds representing ester derivatives of (S,S)-1,2-ethanediamine-N,N'-di-2-(3-cyclohexyl) propanoic and (S,S)-1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acids, expressing antiproliferative activity in vitro were examined. The objective of this study was to determinate their lipophilicity data, and also to ensure a mathematical model for prediction lipophilicity data of potential in vivo metabolites and new derivatives of (S,S)-1,2-ethanediannine-N,N'-di-2-(3-cyclohexyl)propanoic acid, based on chromatographic parameters. Experimentally, lipophilicity data were obtained by a traditional shake flask procedure and an ultra-high performance liquid chromatographic tandem mass spectrometry (UHPLC-MS) method. A correlation between the partition coefficient n-octanol/water (logD(7,4)) and chromatographic data (CHI, phi(0)), and also, between logD(7,4) and retention time was investigated. A very good correlation (r(2)=0.8969) was found between lipophilicity parameters phi(0) and logD(7,4) obtained using UHPLC-MS and shake flask methods: logD(7,4) = (0.11 +/- 0.01)x phi(0) + (1.25 +/- 0.20)xN(c) - (9.19 +/- 1.18); statistical parameter F=47.84; significance of F = 3.74x10(-6), N-c=number of C atoms between two amino groups (N-c=2 for 1,2-ethanediamine derivatives and N-c=3 for 1,3-propanediamine derivatives).The model predictivity power was determined by cross validation leave one out (LOO) technique, and expressed by the term Q(2), was 0.89. The developed model has good predictivity power for prediction lipophilicity data of potential in vivo metabolites of the investigated compounds, such as novel 1,2-ethanediamine and 1,3-propanediamine N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives. Also, the lipophilicity data obtained in the present study correlated with the antiproliferative activity of the investigated substances shown previously in in vitro studies.
PB  - Govi-Verlag  Pharmazeutischer Verlag Gmbh, Eschborn
T2  - Pharmazie
T1  - A new model to determine lipophilicity of 1,2-ethanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives with antiproliferative activity by combining shake flask procedure and UHPLC-MS me
VL  - 72
IS  - 6
SP  - 317
EP  - 323
DO  - 10.1619/ph.2017.6208
ER  - 

@article{
author = "Tubić, Biljana K. and Marković, Bojan D. and Vladimirov, S. and Savic, S. and Poljarević, Jelena and Sabo, Tibor",
year = "2017",
abstract = "Fourteen compounds representing ester derivatives of (S,S)-1,2-ethanediamine-N,N'-di-2-(3-cyclohexyl) propanoic and (S,S)-1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acids, expressing antiproliferative activity in vitro were examined. The objective of this study was to determinate their lipophilicity data, and also to ensure a mathematical model for prediction lipophilicity data of potential in vivo metabolites and new derivatives of (S,S)-1,2-ethanediannine-N,N'-di-2-(3-cyclohexyl)propanoic acid, based on chromatographic parameters. Experimentally, lipophilicity data were obtained by a traditional shake flask procedure and an ultra-high performance liquid chromatographic tandem mass spectrometry (UHPLC-MS) method. A correlation between the partition coefficient n-octanol/water (logD(7,4)) and chromatographic data (CHI, phi(0)), and also, between logD(7,4) and retention time was investigated. A very good correlation (r(2)=0.8969) was found between lipophilicity parameters phi(0) and logD(7,4) obtained using UHPLC-MS and shake flask methods: logD(7,4) = (0.11 +/- 0.01)x phi(0) + (1.25 +/- 0.20)xN(c) - (9.19 +/- 1.18); statistical parameter F=47.84; significance of F = 3.74x10(-6), N-c=number of C atoms between two amino groups (N-c=2 for 1,2-ethanediamine derivatives and N-c=3 for 1,3-propanediamine derivatives).The model predictivity power was determined by cross validation leave one out (LOO) technique, and expressed by the term Q(2), was 0.89. The developed model has good predictivity power for prediction lipophilicity data of potential in vivo metabolites of the investigated compounds, such as novel 1,2-ethanediamine and 1,3-propanediamine N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives. Also, the lipophilicity data obtained in the present study correlated with the antiproliferative activity of the investigated substances shown previously in in vitro studies.",
publisher = "Govi-Verlag  Pharmazeutischer Verlag Gmbh, Eschborn",
journal = "Pharmazie",
title = "A new model to determine lipophilicity of 1,2-ethanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives with antiproliferative activity by combining shake flask procedure and UHPLC-MS me",
volume = "72",
number = "6",
pages = "317-323",
doi = "10.1619/ph.2017.6208"
}

Tubić, B. K., Marković, B. D., Vladimirov, S., Savic, S., Poljarević, J.,& Sabo, T.. (2017). A new model to determine lipophilicity of 1,2-ethanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives with antiproliferative activity by combining shake flask procedure and UHPLC-MS me. in Pharmazie
Govi-Verlag  Pharmazeutischer Verlag Gmbh, Eschborn., 72(6), 317-323.
https://doi.org/10.1619/ph.2017.6208

Tubić BK, Marković BD, Vladimirov S, Savic S, Poljarević J, Sabo T. A new model to determine lipophilicity of 1,2-ethanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives with antiproliferative activity by combining shake flask procedure and UHPLC-MS me. in Pharmazie. 2017;72(6):317-323.
doi:10.1619/ph.2017.6208 .

Tubić, Biljana K., Marković, Bojan D., Vladimirov, S., Savic, S., Poljarević, Jelena, Sabo, Tibor, "A new model to determine lipophilicity of 1,2-ethanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives with antiproliferative activity by combining shake flask procedure and UHPLC-MS me" in Pharmazie, 72, no. 6 (2017):317-323,
https://doi.org/10.1619/ph.2017.6208 . .

TY  - CONF
AU  - Jeremić, J.
AU  - Stojić, I.
AU  - Nikolic, T.
AU  - Šmigić, Jelena
AU  - Živković, Vladimir
AU  - Srejović, Ivan
AU  - Sabo, Tibor
AU  - Jakovljević, Vladimir
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2519
PB  - Wiley, Hoboken
C3  - Acta Physiologica
T1  - The Effects of Chronic Administration of Cisplatin on Oxidative Stress in Isolated Rat Heart
VL  - 221
SP  - 166
EP  - 166
UR  - https://hdl.handle.net/21.15107/rcub_cherry_2519
ER  - 

@conference{
author = "Jeremić, J. and Stojić, I. and Nikolic, T. and Šmigić, Jelena and Živković, Vladimir and Srejović, Ivan and Sabo, Tibor and Jakovljević, Vladimir",
year = "2017",
publisher = "Wiley, Hoboken",
journal = "Acta Physiologica",
title = "The Effects of Chronic Administration of Cisplatin on Oxidative Stress in Isolated Rat Heart",
volume = "221",
pages = "166-166",
url = "https://hdl.handle.net/21.15107/rcub_cherry_2519"
}

Jeremić, J., Stojić, I., Nikolic, T., Šmigić, J., Živković, V., Srejović, I., Sabo, T.,& Jakovljević, V.. (2017). The Effects of Chronic Administration of Cisplatin on Oxidative Stress in Isolated Rat Heart. in Acta Physiologica
Wiley, Hoboken., 221, 166-166.
https://hdl.handle.net/21.15107/rcub_cherry_2519

Jeremić J, Stojić I, Nikolic T, Šmigić J, Živković V, Srejović I, Sabo T, Jakovljević V. The Effects of Chronic Administration of Cisplatin on Oxidative Stress in Isolated Rat Heart. in Acta Physiologica. 2017;221:166-166.
https://hdl.handle.net/21.15107/rcub_cherry_2519 .

Jeremić, J., Stojić, I., Nikolic, T., Šmigić, Jelena, Živković, Vladimir, Srejović, Ivan, Sabo, Tibor, Jakovljević, Vladimir, "The Effects of Chronic Administration of Cisplatin on Oxidative Stress in Isolated Rat Heart" in Acta Physiologica, 221 (2017):166-166,
https://hdl.handle.net/21.15107/rcub_cherry_2519 .