TY  - JOUR
AU  - Kaluđerović, Goran N.
AU  - Pantelić, Nebojša Đ.
AU  - Eichhorn, Thomas
AU  - Bette, Martin
AU  - Wagner, Christoph
AU  - Zmejkovski, Bojana
AU  - Schmidt, Harry
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1424
AB  - Three novel complexes of platinum(II) with R(2)edda bidentate ligands [PtCl2(R(2)edda)] (R = Me, Et, n-Pr; edda = ethylenediamine-N,N'-diacetate; 1-3), are synthesized and characterized by IR and NMR spectroscopy and elemental analysis. All complexes exist in three stereoisomeric forms (R,R), (S,S) and (R,S)(S,R). In addition crystal structure of one platinum(IV) complex [PtCl4((n-Pr)(2)edda)], 4, is presented. Furthermore, in order to assign stereoisomers of 1-3, a reduction of racemic [PtCl4(Et(2)edda)] by ascorbic acid to [PtCl2(Et(2)edda)] (2) was performed and analyzed by H-1 NMR. Time-depending H-1 NMR spectroscopic experiments were implemented to study the stability of ethylenediamine-N,N'-diacetate diesters. Finally, the in vitro cytotoxic activity of complexes 1-3 was studied on 11 tumor cell lines, 518A2 (melanoma), 8505C (human thyroid carcinoma), A253 (head and neck tumor), A431 (cervix), A549 (lung), A2780 (ovarian), MCF-7 (breast) and HT-29, HCT-8, DLD-1, SW1736 (all colon) by the SRB colorimetric assay method. Complex 3 showed the highest action against ovarian (A2780) cells with an IC50 value 51 +/- 1 mu M.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Polyhedron
T1  - Platinum(II) complexes with R(2)edda ligands (R = Me, Et, n-Pr; edda = ethylenediamine-N,N '-diacetate): Synthesis and characterization
VL  - 80
SP  - 53
EP  - 59
DO  - 10.1016/j.poly.2014.01.018
ER  - 

@article{
author = "Kaluđerović, Goran N. and Pantelić, Nebojša Đ. and Eichhorn, Thomas and Bette, Martin and Wagner, Christoph and Zmejkovski, Bojana and Schmidt, Harry",
year = "2014",
abstract = "Three novel complexes of platinum(II) with R(2)edda bidentate ligands [PtCl2(R(2)edda)] (R = Me, Et, n-Pr; edda = ethylenediamine-N,N'-diacetate; 1-3), are synthesized and characterized by IR and NMR spectroscopy and elemental analysis. All complexes exist in three stereoisomeric forms (R,R), (S,S) and (R,S)(S,R). In addition crystal structure of one platinum(IV) complex [PtCl4((n-Pr)(2)edda)], 4, is presented. Furthermore, in order to assign stereoisomers of 1-3, a reduction of racemic [PtCl4(Et(2)edda)] by ascorbic acid to [PtCl2(Et(2)edda)] (2) was performed and analyzed by H-1 NMR. Time-depending H-1 NMR spectroscopic experiments were implemented to study the stability of ethylenediamine-N,N'-diacetate diesters. Finally, the in vitro cytotoxic activity of complexes 1-3 was studied on 11 tumor cell lines, 518A2 (melanoma), 8505C (human thyroid carcinoma), A253 (head and neck tumor), A431 (cervix), A549 (lung), A2780 (ovarian), MCF-7 (breast) and HT-29, HCT-8, DLD-1, SW1736 (all colon) by the SRB colorimetric assay method. Complex 3 showed the highest action against ovarian (A2780) cells with an IC50 value 51 +/- 1 mu M.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Polyhedron",
title = "Platinum(II) complexes with R(2)edda ligands (R = Me, Et, n-Pr; edda = ethylenediamine-N,N '-diacetate): Synthesis and characterization",
volume = "80",
pages = "53-59",
doi = "10.1016/j.poly.2014.01.018"
}

Kaluđerović, G. N., Pantelić, N. Đ., Eichhorn, T., Bette, M., Wagner, C., Zmejkovski, B.,& Schmidt, H.. (2014). Platinum(II) complexes with R(2)edda ligands (R = Me, Et, n-Pr; edda = ethylenediamine-N,N '-diacetate): Synthesis and characterization. in Polyhedron
Oxford : Pergamon-Elsevier Science Ltd., 80, 53-59.
https://doi.org/10.1016/j.poly.2014.01.018

Kaluđerović GN, Pantelić NĐ, Eichhorn T, Bette M, Wagner C, Zmejkovski B, Schmidt H. Platinum(II) complexes with R(2)edda ligands (R = Me, Et, n-Pr; edda = ethylenediamine-N,N '-diacetate): Synthesis and characterization. in Polyhedron. 2014;80:53-59.
doi:10.1016/j.poly.2014.01.018 .

Kaluđerović, Goran N., Pantelić, Nebojša Đ., Eichhorn, Thomas, Bette, Martin, Wagner, Christoph, Zmejkovski, Bojana, Schmidt, Harry, "Platinum(II) complexes with R(2)edda ligands (R = Me, Et, n-Pr; edda = ethylenediamine-N,N '-diacetate): Synthesis and characterization" in Polyhedron, 80 (2014):53-59,
https://doi.org/10.1016/j.poly.2014.01.018 . .

TY  - JOUR
AU  - Krajčinović, Bojana B.
AU  - Kaluđerović, Goran N.
AU  - Steinborn, Dirk
AU  - Schmidt, Harry
AU  - Wagner, Christoph
AU  - Žižak, Željko
AU  - Juranić, Zorica
AU  - Trifunović, Srećko R.
AU  - Sabo, Tibor
PY  - 2008
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4330
AB  - Syntheses of two novel ligand precursors O,O′-diisopropyl- (1a) and O,O′-diisobutyl-(S,S)-ethylenediamine-N,N′-di-2-propanoate dihydrochloride monohydrate (1b) and the corresponding dichloroplatinum(II) (2a and 2b) and tetrachloroplatinum(IV) complexes (3a and 3b) are described here. The substances were characterized by IR, 1H and 13C spectroscopy and elemental analysis. Crystal structures were determined for 1a and the corresponding platinum(IV) complex, 3a. In vitro antiproliferative activity was determined against tumor cell lines: human adenocarcinoma HeLa, human myelogenous leukemia K562, human malignant melanoma Fem-x, rested and stimulated normal immunocompetent cells (human peripheral blood mononuclear PBMC cells) using KBR test (Kenacid Blue Dye binding test). The IC50(μM) values for the most active compound 3a were: 30.48 ± 2.54; 12.26 ± 2.60; 13.68 ± 3.22; 80.18 ± 24.07 and 71.30 ± 21.70, respectively.
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Synthesis and in vitro antitumoral activity of novel O,O′-di-2-alkyl-(S,S)-ethylenediamine-N,N′-di-2-propanoate ligands and corresponding platinum(II/IV) complexes
VL  - 102
IS  - 4
SP  - 892
EP  - 900
DO  - 10.1016/j.jinorgbio.2007.12.009
ER  - 

@article{
author = "Krajčinović, Bojana B. and Kaluđerović, Goran N. and Steinborn, Dirk and Schmidt, Harry and Wagner, Christoph and Žižak, Željko and Juranić, Zorica and Trifunović, Srećko R. and Sabo, Tibor",
year = "2008",
abstract = "Syntheses of two novel ligand precursors O,O′-diisopropyl- (1a) and O,O′-diisobutyl-(S,S)-ethylenediamine-N,N′-di-2-propanoate dihydrochloride monohydrate (1b) and the corresponding dichloroplatinum(II) (2a and 2b) and tetrachloroplatinum(IV) complexes (3a and 3b) are described here. The substances were characterized by IR, 1H and 13C spectroscopy and elemental analysis. Crystal structures were determined for 1a and the corresponding platinum(IV) complex, 3a. In vitro antiproliferative activity was determined against tumor cell lines: human adenocarcinoma HeLa, human myelogenous leukemia K562, human malignant melanoma Fem-x, rested and stimulated normal immunocompetent cells (human peripheral blood mononuclear PBMC cells) using KBR test (Kenacid Blue Dye binding test). The IC50(μM) values for the most active compound 3a were: 30.48 ± 2.54; 12.26 ± 2.60; 13.68 ± 3.22; 80.18 ± 24.07 and 71.30 ± 21.70, respectively.",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Synthesis and in vitro antitumoral activity of novel O,O′-di-2-alkyl-(S,S)-ethylenediamine-N,N′-di-2-propanoate ligands and corresponding platinum(II/IV) complexes",
volume = "102",
number = "4",
pages = "892-900",
doi = "10.1016/j.jinorgbio.2007.12.009"
}

Krajčinović, B. B., Kaluđerović, G. N., Steinborn, D., Schmidt, H., Wagner, C., Žižak, Ž., Juranić, Z., Trifunović, S. R.,& Sabo, T.. (2008). Synthesis and in vitro antitumoral activity of novel O,O′-di-2-alkyl-(S,S)-ethylenediamine-N,N′-di-2-propanoate ligands and corresponding platinum(II/IV) complexes. in Journal of Inorganic Biochemistry
Elsevier., 102(4), 892-900.
https://doi.org/10.1016/j.jinorgbio.2007.12.009

Krajčinović BB, Kaluđerović GN, Steinborn D, Schmidt H, Wagner C, Žižak Ž, Juranić Z, Trifunović SR, Sabo T. Synthesis and in vitro antitumoral activity of novel O,O′-di-2-alkyl-(S,S)-ethylenediamine-N,N′-di-2-propanoate ligands and corresponding platinum(II/IV) complexes. in Journal of Inorganic Biochemistry. 2008;102(4):892-900.
doi:10.1016/j.jinorgbio.2007.12.009 .

Krajčinović, Bojana B., Kaluđerović, Goran N., Steinborn, Dirk, Schmidt, Harry, Wagner, Christoph, Žižak, Željko, Juranić, Zorica, Trifunović, Srećko R., Sabo, Tibor, "Synthesis and in vitro antitumoral activity of novel O,O′-di-2-alkyl-(S,S)-ethylenediamine-N,N′-di-2-propanoate ligands and corresponding platinum(II/IV) complexes" in Journal of Inorganic Biochemistry, 102, no. 4 (2008):892-900,
https://doi.org/10.1016/j.jinorgbio.2007.12.009 . .

TY  - JOUR
AU  - Kaluđerović, Goran N.
AU  - Schmidt, Harry
AU  - Schwieger, Sebastian
AU  - Wagner, Christoph
AU  - Paschke, Reinhard
AU  - Dietrich, Andrea
AU  - Mueller, Thomas
AU  - Steinborn, Dirk
PY  - 2008
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4329
AB  - The novel N,N-type bidentate ligand precursors, diethyl, dipropyl esters of ethylenediamine-N,N′-diacetic acid dihydrochloride (HOOCCH2NHCH2CH2NHCH2COOH • 2HCl, H2edda • 2HCl), and the corresponding tetrachloroplatinum(IV) complexes, [PtCl4(R2edda)] • H2O (ROOCCH2NHCH2CH2NHCH2COOR, R = Me, Et, n-Pr), were synthesized. The esters coordinated as bidentate ligands via both N donor atoms. The esters, as well as the complexes, have been characterized by infrared, 1H and 13C NMR spectroscopy and elemental analysis. Solid state structures of both dimethyl and diethyl ester platinum(IV) complexes have been determined by X-ray crystallography. Quantum chemical calculations were performed in order to investigate diastereoselectivity in the formation of the platinum(IV) complexes. The in vitro cytotoxic evaluation of the investigated complexes in human tumor cell lines 1411HP, H12.1 (both testicular germ cell tumors), DLD-1 (colon carcinoma), 518A2 (melanoma), A549 (lung carcinoma) and liposarcoma showed a dose-dependent antiproliferative effect in all cell lines. Remarkably, the highest cytotoxic activity was observed in the cisplatin-resistant cell line 1411HP. In addition, at higher concentrations the treatment with these complexes led to the induction of apoptosis in all cell lines except for DLD-1.
PB  - Elsevier
T2  - Inorganica Chimica Acta
T1  - Platinum(IV) complexes with ethylenediamine-N,N0-diacetate diester (R2edda) ligands: Synthesis, characterization and in vitro antitumoral activity
VL  - 361
IS  - 5
SP  - 1395
EP  - 1404
DO  - 10.1016/j.ica.2007.09.010
ER  - 

@article{
author = "Kaluđerović, Goran N. and Schmidt, Harry and Schwieger, Sebastian and Wagner, Christoph and Paschke, Reinhard and Dietrich, Andrea and Mueller, Thomas and Steinborn, Dirk",
year = "2008",
abstract = "The novel N,N-type bidentate ligand precursors, diethyl, dipropyl esters of ethylenediamine-N,N′-diacetic acid dihydrochloride (HOOCCH2NHCH2CH2NHCH2COOH • 2HCl, H2edda • 2HCl), and the corresponding tetrachloroplatinum(IV) complexes, [PtCl4(R2edda)] • H2O (ROOCCH2NHCH2CH2NHCH2COOR, R = Me, Et, n-Pr), were synthesized. The esters coordinated as bidentate ligands via both N donor atoms. The esters, as well as the complexes, have been characterized by infrared, 1H and 13C NMR spectroscopy and elemental analysis. Solid state structures of both dimethyl and diethyl ester platinum(IV) complexes have been determined by X-ray crystallography. Quantum chemical calculations were performed in order to investigate diastereoselectivity in the formation of the platinum(IV) complexes. The in vitro cytotoxic evaluation of the investigated complexes in human tumor cell lines 1411HP, H12.1 (both testicular germ cell tumors), DLD-1 (colon carcinoma), 518A2 (melanoma), A549 (lung carcinoma) and liposarcoma showed a dose-dependent antiproliferative effect in all cell lines. Remarkably, the highest cytotoxic activity was observed in the cisplatin-resistant cell line 1411HP. In addition, at higher concentrations the treatment with these complexes led to the induction of apoptosis in all cell lines except for DLD-1.",
publisher = "Elsevier",
journal = "Inorganica Chimica Acta",
title = "Platinum(IV) complexes with ethylenediamine-N,N0-diacetate diester (R2edda) ligands: Synthesis, characterization and in vitro antitumoral activity",
volume = "361",
number = "5",
pages = "1395-1404",
doi = "10.1016/j.ica.2007.09.010"
}

Kaluđerović, G. N., Schmidt, H., Schwieger, S., Wagner, C., Paschke, R., Dietrich, A., Mueller, T.,& Steinborn, D.. (2008). Platinum(IV) complexes with ethylenediamine-N,N0-diacetate diester (R2edda) ligands: Synthesis, characterization and in vitro antitumoral activity. in Inorganica Chimica Acta
Elsevier., 361(5), 1395-1404.
https://doi.org/10.1016/j.ica.2007.09.010

Kaluđerović GN, Schmidt H, Schwieger S, Wagner C, Paschke R, Dietrich A, Mueller T, Steinborn D. Platinum(IV) complexes with ethylenediamine-N,N0-diacetate diester (R2edda) ligands: Synthesis, characterization and in vitro antitumoral activity. in Inorganica Chimica Acta. 2008;361(5):1395-1404.
doi:10.1016/j.ica.2007.09.010 .

Kaluđerović, Goran N., Schmidt, Harry, Schwieger, Sebastian, Wagner, Christoph, Paschke, Reinhard, Dietrich, Andrea, Mueller, Thomas, Steinborn, Dirk, "Platinum(IV) complexes with ethylenediamine-N,N0-diacetate diester (R2edda) ligands: Synthesis, characterization and in vitro antitumoral activity" in Inorganica Chimica Acta, 361, no. 5 (2008):1395-1404,
https://doi.org/10.1016/j.ica.2007.09.010 . .

TY  - JOUR
AU  - Kaluđerović, Goran N.
AU  - Schmidt, Harry
AU  - Wagner, Christoph
AU  - Steinborn, Dirk
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4336
AB  - The title complex, [PtBr2(CH3)2(C10H20N2O4)], has a slightly distorted octahedral coordination geometry as reflected in the bond lengths and angles around the PtIV atom. A crystallographic C2 rotation axis bisects the C - C bond of the central ethylene group and passes through the Pt atom.
PB  - England : International Union of Crystallography
T2  - Acta Crystallographica Section E: Structure Reports Online
T1  - Trans,cis-Dibromido[diethyl (ethane-1,2-diyldiimino)diacetate-k2 N,N′]dimethylplatinum(IV)
VL  - 63
IS  - 7
SP  - m1985
DO  - 10.1107/S1600536807029534
ER  - 

@article{
author = "Kaluđerović, Goran N. and Schmidt, Harry and Wagner, Christoph and Steinborn, Dirk",
year = "2007",
abstract = "The title complex, [PtBr2(CH3)2(C10H20N2O4)], has a slightly distorted octahedral coordination geometry as reflected in the bond lengths and angles around the PtIV atom. A crystallographic C2 rotation axis bisects the C - C bond of the central ethylene group and passes through the Pt atom.",
publisher = "England : International Union of Crystallography",
journal = "Acta Crystallographica Section E: Structure Reports Online",
title = "Trans,cis-Dibromido[diethyl (ethane-1,2-diyldiimino)diacetate-k2 N,N′]dimethylplatinum(IV)",
volume = "63",
number = "7",
pages = "m1985",
doi = "10.1107/S1600536807029534"
}

Kaluđerović, G. N., Schmidt, H., Wagner, C.,& Steinborn, D.. (2007). Trans,cis-Dibromido[diethyl (ethane-1,2-diyldiimino)diacetate-k2 N,N′]dimethylplatinum(IV). in Acta Crystallographica Section E: Structure Reports Online
England : International Union of Crystallography., 63(7), m1985.
https://doi.org/10.1107/S1600536807029534

Kaluđerović GN, Schmidt H, Wagner C, Steinborn D. Trans,cis-Dibromido[diethyl (ethane-1,2-diyldiimino)diacetate-k2 N,N′]dimethylplatinum(IV). in Acta Crystallographica Section E: Structure Reports Online. 2007;63(7):m1985.
doi:10.1107/S1600536807029534 .

Kaluđerović, Goran N., Schmidt, Harry, Wagner, Christoph, Steinborn, Dirk, "Trans,cis-Dibromido[diethyl (ethane-1,2-diyldiimino)diacetate-k2 N,N′]dimethylplatinum(IV)" in Acta Crystallographica Section E: Structure Reports Online, 63, no. 7 (2007):m1985,
https://doi.org/10.1107/S1600536807029534 . .

TY  - JOUR
AU  - Kaluđerović, Goran N.
AU  - Schmidt, Harry
AU  - Wagner, Christoph
AU  - Merzweiler, Kurt
AU  - Steinborn, Dirk
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4304
AB  - The reaction of solutions of tetraalkyl ethylenediamine-N,N,N′, N′-tetraacetate esters (alkyl = Me, 1a; Et, 1b) with H 2[PdCl4] led to the complexes [PdCl2(R 4EDTA)] (R = Me, 2a; Et, 2b). The coordination of R4EDTA ligands to palladium(II) ions occurs through the two nitrogen donor atoms, as confirmed by IR, 1H and 13C NMR spectroscopies and X-ray crystallography.
PB  - Ceska Republika : Akademie Ved Ceske Republiky
T2  - Collection of Czechoslovak Chemical Communications
T1  - Synthesis, characterization and crystal structure of palladium(II) complexes containing edta tetraalkyl ester ligands
VL  - 72
IS  - 4
SP  - 560
EP  - 568
DO  - 10.1135/cccc20070560
ER  - 

@article{
author = "Kaluđerović, Goran N. and Schmidt, Harry and Wagner, Christoph and Merzweiler, Kurt and Steinborn, Dirk",
year = "2007",
abstract = "The reaction of solutions of tetraalkyl ethylenediamine-N,N,N′, N′-tetraacetate esters (alkyl = Me, 1a; Et, 1b) with H 2[PdCl4] led to the complexes [PdCl2(R 4EDTA)] (R = Me, 2a; Et, 2b). The coordination of R4EDTA ligands to palladium(II) ions occurs through the two nitrogen donor atoms, as confirmed by IR, 1H and 13C NMR spectroscopies and X-ray crystallography.",
publisher = "Ceska Republika : Akademie Ved Ceske Republiky",
journal = "Collection of Czechoslovak Chemical Communications",
title = "Synthesis, characterization and crystal structure of palladium(II) complexes containing edta tetraalkyl ester ligands",
volume = "72",
number = "4",
pages = "560-568",
doi = "10.1135/cccc20070560"
}

Kaluđerović, G. N., Schmidt, H., Wagner, C., Merzweiler, K.,& Steinborn, D.. (2007). Synthesis, characterization and crystal structure of palladium(II) complexes containing edta tetraalkyl ester ligands. in Collection of Czechoslovak Chemical Communications
Ceska Republika : Akademie Ved Ceske Republiky., 72(4), 560-568.
https://doi.org/10.1135/cccc20070560

Kaluđerović GN, Schmidt H, Wagner C, Merzweiler K, Steinborn D. Synthesis, characterization and crystal structure of palladium(II) complexes containing edta tetraalkyl ester ligands. in Collection of Czechoslovak Chemical Communications. 2007;72(4):560-568.
doi:10.1135/cccc20070560 .

Kaluđerović, Goran N., Schmidt, Harry, Wagner, Christoph, Merzweiler, Kurt, Steinborn, Dirk, "Synthesis, characterization and crystal structure of palladium(II) complexes containing edta tetraalkyl ester ligands" in Collection of Czechoslovak Chemical Communications, 72, no. 4 (2007):560-568,
https://doi.org/10.1135/cccc20070560 . .