TY  - JOUR
AU  - Kaluđerović, Goran N.
AU  - Mijatovic, Sanja A.
AU  - Zmejkovski, Bojana B.
AU  - Bulatović, Mirna Z.
AU  - Gomez-Ruiz, Santiago
AU  - Mojic, Marija K.
AU  - Steinborn, Dirk
AU  - Miljkovic, Djordje M.
AU  - Schmidt, Harry
AU  - Stošić-Grujičić, Stanislava D.
AU  - Sabo, Tibor
AU  - Maksimovic-Ivanic, Danijela D.
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1523
AB  - Several new R(2)eddp (R = i-Pr, i-Bu; eddp = ethylenediamine-N,N'-di-3-propionate) esters and corresponding platinum(II) and platinum(IV) complexes of the general formula [PtCln(R(2)edda-type)] (n = 2, 4) were synthesized and characterized by spectroscopic methods (IR, H-1 and C-13 NMR) and elemental analysis. The crystal structure of platinum(IV) complex [PtCl4{(c-Pe)(2)eddip}] (3a) was resolved and is given herein. Ligand precursors, platinum(II), and platinum(IV) complexes were tested against eight tumor cell lines (CT26CL25, HTC116, SW620, PC3, LNCaP, U251, A375, and B16). Selectivity in the action of those compounds between tumor and two normal primary cells (fibroblasts and keratinocytes) are discussed. A structure-activity relationship of these compounds is discussed. Furthermore, cell cycle distribution, induction of necrosis, apoptosis, autophagy, anoikis, caspase activation, ROS, and RNS are presented on the cisplatin-resistant colon carcinoma HCT116 cell line.
PB  - Royal Soc Chemistry, Cambridge
T2  - Metallomics
T1  - Platinum(II/IV) complexes containing ethylenediamine-N,N '-di-2/3-propionate ester ligands induced caspase-dependent apoptosis in cisplatin-resistant colon cancer cells
VL  - 4
IS  - 9
SP  - 979
EP  - 987
DO  - 10.1039/c2mt20058a
ER  - 

@article{
author = "Kaluđerović, Goran N. and Mijatovic, Sanja A. and Zmejkovski, Bojana B. and Bulatović, Mirna Z. and Gomez-Ruiz, Santiago and Mojic, Marija K. and Steinborn, Dirk and Miljkovic, Djordje M. and Schmidt, Harry and Stošić-Grujičić, Stanislava D. and Sabo, Tibor and Maksimovic-Ivanic, Danijela D.",
year = "2012",
abstract = "Several new R(2)eddp (R = i-Pr, i-Bu; eddp = ethylenediamine-N,N'-di-3-propionate) esters and corresponding platinum(II) and platinum(IV) complexes of the general formula [PtCln(R(2)edda-type)] (n = 2, 4) were synthesized and characterized by spectroscopic methods (IR, H-1 and C-13 NMR) and elemental analysis. The crystal structure of platinum(IV) complex [PtCl4{(c-Pe)(2)eddip}] (3a) was resolved and is given herein. Ligand precursors, platinum(II), and platinum(IV) complexes were tested against eight tumor cell lines (CT26CL25, HTC116, SW620, PC3, LNCaP, U251, A375, and B16). Selectivity in the action of those compounds between tumor and two normal primary cells (fibroblasts and keratinocytes) are discussed. A structure-activity relationship of these compounds is discussed. Furthermore, cell cycle distribution, induction of necrosis, apoptosis, autophagy, anoikis, caspase activation, ROS, and RNS are presented on the cisplatin-resistant colon carcinoma HCT116 cell line.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Metallomics",
title = "Platinum(II/IV) complexes containing ethylenediamine-N,N '-di-2/3-propionate ester ligands induced caspase-dependent apoptosis in cisplatin-resistant colon cancer cells",
volume = "4",
number = "9",
pages = "979-987",
doi = "10.1039/c2mt20058a"
}

Kaluđerović, G. N., Mijatovic, S. A., Zmejkovski, B. B., Bulatović, M. Z., Gomez-Ruiz, S., Mojic, M. K., Steinborn, D., Miljkovic, D. M., Schmidt, H., Stošić-Grujičić, S. D., Sabo, T.,& Maksimovic-Ivanic, D. D.. (2012). Platinum(II/IV) complexes containing ethylenediamine-N,N '-di-2/3-propionate ester ligands induced caspase-dependent apoptosis in cisplatin-resistant colon cancer cells. in Metallomics
Royal Soc Chemistry, Cambridge., 4(9), 979-987.
https://doi.org/10.1039/c2mt20058a

Kaluđerović GN, Mijatovic SA, Zmejkovski BB, Bulatović MZ, Gomez-Ruiz S, Mojic MK, Steinborn D, Miljkovic DM, Schmidt H, Stošić-Grujičić SD, Sabo T, Maksimovic-Ivanic DD. Platinum(II/IV) complexes containing ethylenediamine-N,N '-di-2/3-propionate ester ligands induced caspase-dependent apoptosis in cisplatin-resistant colon cancer cells. in Metallomics. 2012;4(9):979-987.
doi:10.1039/c2mt20058a .

Kaluđerović, Goran N., Mijatovic, Sanja A., Zmejkovski, Bojana B., Bulatović, Mirna Z., Gomez-Ruiz, Santiago, Mojic, Marija K., Steinborn, Dirk, Miljkovic, Djordje M., Schmidt, Harry, Stošić-Grujičić, Stanislava D., Sabo, Tibor, Maksimovic-Ivanic, Danijela D., "Platinum(II/IV) complexes containing ethylenediamine-N,N '-di-2/3-propionate ester ligands induced caspase-dependent apoptosis in cisplatin-resistant colon cancer cells" in Metallomics, 4, no. 9 (2012):979-987,
https://doi.org/10.1039/c2mt20058a . .

TY  - JOUR
AU  - Zmejkovski, Bojana B.
AU  - Kaluđerović, Goran N.
AU  - Gomez-Ruiz, Santiago
AU  - Žižak, Željko S.
AU  - Steinborn, Dirk
AU  - Schmidt, Harry
AU  - Paschke, Reinhard
AU  - Juranić, Zorica D.
AU  - Sabo, Tibor
PY  - 2009
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1005
AB  - New R(2)eddip-type esters (R = cyclopentyl, L3 center dot 2HCl 1.5H(2)O; cyclohexyl, L4 center dot 2HCl center dot H2O) and corresponding palladium(II) complexes, [PdCl(2)L3] (3) and [PdCl2L4]center dot H2O (4), as well as [PdCl2L2] (2: L2 diisobutyl ester of eddip) were synthesized and characterized by IR, H-1 and C-13 NMR spectroscopies and elemental analysis. The crystal structure of L3 center dot 2HCl center dot 2CHCl(3) was resolved and is given herein. The NMR spectroscopy confirmed the presence of two isomers (from three possible) for each palladium(II) complex. DFT calculations support the formation of two diastereoisomers. In addition, antitumoral investigations were performed and these investigations also included the diisopropyl ester of eddip (L1) and corresponding palladium(II) complex, [PdCl(2)L1] (1). In vitro anti proliferative activity was determined against several tumor cell lines HeLa, Fem-x, K562 and rested and stimulated normal immunocompetent cells (human peripheral blood mononuclear cells -PBMCs) using MTT test. (C) 2009 Elsevier Masson SAS. All rights reserved.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Palladium(II) complexes with R(2)edda-derived ligands. Part II. Synthesis, characterization and in vitro antitumoral studies of R(2)eddip esters and palladium(II) complexes
VL  - 44
IS  - 9
SP  - 3452
EP  - 3458
DO  - 10.1016/j.ejmech.2009.02.002
ER  - 

@article{
author = "Zmejkovski, Bojana B. and Kaluđerović, Goran N. and Gomez-Ruiz, Santiago and Žižak, Željko S. and Steinborn, Dirk and Schmidt, Harry and Paschke, Reinhard and Juranić, Zorica D. and Sabo, Tibor",
year = "2009",
abstract = "New R(2)eddip-type esters (R = cyclopentyl, L3 center dot 2HCl 1.5H(2)O; cyclohexyl, L4 center dot 2HCl center dot H2O) and corresponding palladium(II) complexes, [PdCl(2)L3] (3) and [PdCl2L4]center dot H2O (4), as well as [PdCl2L2] (2: L2 diisobutyl ester of eddip) were synthesized and characterized by IR, H-1 and C-13 NMR spectroscopies and elemental analysis. The crystal structure of L3 center dot 2HCl center dot 2CHCl(3) was resolved and is given herein. The NMR spectroscopy confirmed the presence of two isomers (from three possible) for each palladium(II) complex. DFT calculations support the formation of two diastereoisomers. In addition, antitumoral investigations were performed and these investigations also included the diisopropyl ester of eddip (L1) and corresponding palladium(II) complex, [PdCl(2)L1] (1). In vitro anti proliferative activity was determined against several tumor cell lines HeLa, Fem-x, K562 and rested and stimulated normal immunocompetent cells (human peripheral blood mononuclear cells -PBMCs) using MTT test. (C) 2009 Elsevier Masson SAS. All rights reserved.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Palladium(II) complexes with R(2)edda-derived ligands. Part II. Synthesis, characterization and in vitro antitumoral studies of R(2)eddip esters and palladium(II) complexes",
volume = "44",
number = "9",
pages = "3452-3458",
doi = "10.1016/j.ejmech.2009.02.002"
}

Zmejkovski, B. B., Kaluđerović, G. N., Gomez-Ruiz, S., Žižak, Ž. S., Steinborn, D., Schmidt, H., Paschke, R., Juranić, Z. D.,& Sabo, T.. (2009). Palladium(II) complexes with R(2)edda-derived ligands. Part II. Synthesis, characterization and in vitro antitumoral studies of R(2)eddip esters and palladium(II) complexes. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 44(9), 3452-3458.
https://doi.org/10.1016/j.ejmech.2009.02.002

Zmejkovski BB, Kaluđerović GN, Gomez-Ruiz S, Žižak ŽS, Steinborn D, Schmidt H, Paschke R, Juranić ZD, Sabo T. Palladium(II) complexes with R(2)edda-derived ligands. Part II. Synthesis, characterization and in vitro antitumoral studies of R(2)eddip esters and palladium(II) complexes. in European Journal of Medicinal Chemistry. 2009;44(9):3452-3458.
doi:10.1016/j.ejmech.2009.02.002 .

Zmejkovski, Bojana B., Kaluđerović, Goran N., Gomez-Ruiz, Santiago, Žižak, Željko S., Steinborn, Dirk, Schmidt, Harry, Paschke, Reinhard, Juranić, Zorica D., Sabo, Tibor, "Palladium(II) complexes with R(2)edda-derived ligands. Part II. Synthesis, characterization and in vitro antitumoral studies of R(2)eddip esters and palladium(II) complexes" in European Journal of Medicinal Chemistry, 44, no. 9 (2009):3452-3458,
https://doi.org/10.1016/j.ejmech.2009.02.002 . .

TY  - JOUR
AU  - Krajcinovic, Bojana B.
AU  - Kaluđerović, Goran N.
AU  - Steinborn, Dirk
AU  - Schmidt, Harry
AU  - Wagner, Christoph
AU  - Merzweiler, Kurt
AU  - Trifunović, Srećko R.
AU  - Sabo, Tibor
PY  - 2009
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/989
AB  - The reaction of K-2[PdCl4] with (S,S)-(i-Pr)(2)eddip diester (diisopropyl (S,S)-2,2'-(1,2-ethanediyldiimino)dipropanoate) resulted in {PdCl2[(S,S)-(i-Pr)-Pr)(2)eddip-kappa N-2,N']} (1) and {PdCl[(S,S)-(i-Pr)eddip-kappa N-2,N',kappa O]} (2) with one hydrolyzed ester group. The compounds were characterized by spectroscopic methods and it was proved that the reaction is diastereoselective (H-1- and C-13-NMR) in the case of 2 (one diastereoisomer of four possible). The structure of 2 was determined by X-ray diffraction analysis, indicating that the product is the (R,R)-N,N' configured isomer. In contrast, the reaction yielding 1 produced two of three possible diastereoisomers. DFT calculations support the formation of two diastereoisomers of I and of one diastereoisomer of 2.
AB  - U reakciji K2[PdCl4] sa (S,S)-(i-Pr)2eddip diestrom [diizopropil-(S,S)-2,2'-(1,2-etandi-ildiimino)dipropanoat] dobijaju se {PdCl2[(S,S)-(i-Pr)2eddip-κ2N,N']} (1) i {PdCl[(S,S)-(i-Pr)eddip-κ2N,N',κO]} (2) sa jednom hidrolizovanom estarskom grupom. Jedinjenja su okarakterisana spektroskopskim metodama i dokazano je da je ova reakcija dijastereoselektivna (1H- i 13C-NMR) u slučaju 2 (jedan dijastereoizomer od moguća četiri). Struktura jedinjenja 2 je određena rendgenskom strukturnom analizom i nađeno je da je dobijeni proizvod (R,R)-N,N' izomer. Suprotno tome, u slučaju jedinjenja 1 dobijeni proizvod je smeša dva od tri moguća dijastereoizomera. DFT proračuni potvrđuju formiranje dva dijastereoizomera jedinjenja 1 i jednog dijastereoizomera jedinjenja 2.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Palladium(II) complexes with R(2)edda derived ligands. Part I. Reaction of diisopropyl (S,S)-2,2 '-(1,2-ethanediyldiimino)-dipropanoate with K-2[PdCl4]
T1  - Kompleksi paladijuma(II) sa ligandima R2edda tipa, deo I - reakcija diizopropil-(S,S)-2,2'-(1,2-etandiildiimino)dipropanoata sa K2[PdCl4]
VL  - 74
IS  - 4
SP  - 389
EP  - 400
DO  - 10.2298/JSC0904389K
ER  - 

@article{
author = "Krajcinovic, Bojana B. and Kaluđerović, Goran N. and Steinborn, Dirk and Schmidt, Harry and Wagner, Christoph and Merzweiler, Kurt and Trifunović, Srećko R. and Sabo, Tibor",
year = "2009",
abstract = "The reaction of K-2[PdCl4] with (S,S)-(i-Pr)(2)eddip diester (diisopropyl (S,S)-2,2'-(1,2-ethanediyldiimino)dipropanoate) resulted in {PdCl2[(S,S)-(i-Pr)-Pr)(2)eddip-kappa N-2,N']} (1) and {PdCl[(S,S)-(i-Pr)eddip-kappa N-2,N',kappa O]} (2) with one hydrolyzed ester group. The compounds were characterized by spectroscopic methods and it was proved that the reaction is diastereoselective (H-1- and C-13-NMR) in the case of 2 (one diastereoisomer of four possible). The structure of 2 was determined by X-ray diffraction analysis, indicating that the product is the (R,R)-N,N' configured isomer. In contrast, the reaction yielding 1 produced two of three possible diastereoisomers. DFT calculations support the formation of two diastereoisomers of I and of one diastereoisomer of 2., U reakciji K2[PdCl4] sa (S,S)-(i-Pr)2eddip diestrom [diizopropil-(S,S)-2,2'-(1,2-etandi-ildiimino)dipropanoat] dobijaju se {PdCl2[(S,S)-(i-Pr)2eddip-κ2N,N']} (1) i {PdCl[(S,S)-(i-Pr)eddip-κ2N,N',κO]} (2) sa jednom hidrolizovanom estarskom grupom. Jedinjenja su okarakterisana spektroskopskim metodama i dokazano je da je ova reakcija dijastereoselektivna (1H- i 13C-NMR) u slučaju 2 (jedan dijastereoizomer od moguća četiri). Struktura jedinjenja 2 je određena rendgenskom strukturnom analizom i nađeno je da je dobijeni proizvod (R,R)-N,N' izomer. Suprotno tome, u slučaju jedinjenja 1 dobijeni proizvod je smeša dva od tri moguća dijastereoizomera. DFT proračuni potvrđuju formiranje dva dijastereoizomera jedinjenja 1 i jednog dijastereoizomera jedinjenja 2.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Palladium(II) complexes with R(2)edda derived ligands. Part I. Reaction of diisopropyl (S,S)-2,2 '-(1,2-ethanediyldiimino)-dipropanoate with K-2[PdCl4], Kompleksi paladijuma(II) sa ligandima R2edda tipa, deo I - reakcija diizopropil-(S,S)-2,2'-(1,2-etandiildiimino)dipropanoata sa K2[PdCl4]",
volume = "74",
number = "4",
pages = "389-400",
doi = "10.2298/JSC0904389K"
}

Krajcinovic, B. B., Kaluđerović, G. N., Steinborn, D., Schmidt, H., Wagner, C., Merzweiler, K., Trifunović, S. R.,& Sabo, T.. (2009). Palladium(II) complexes with R(2)edda derived ligands. Part I. Reaction of diisopropyl (S,S)-2,2 '-(1,2-ethanediyldiimino)-dipropanoate with K-2[PdCl4]. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 74(4), 389-400.
https://doi.org/10.2298/JSC0904389K

Krajcinovic BB, Kaluđerović GN, Steinborn D, Schmidt H, Wagner C, Merzweiler K, Trifunović SR, Sabo T. Palladium(II) complexes with R(2)edda derived ligands. Part I. Reaction of diisopropyl (S,S)-2,2 '-(1,2-ethanediyldiimino)-dipropanoate with K-2[PdCl4]. in Journal of the Serbian Chemical Society. 2009;74(4):389-400.
doi:10.2298/JSC0904389K .

Krajcinovic, Bojana B., Kaluđerović, Goran N., Steinborn, Dirk, Schmidt, Harry, Wagner, Christoph, Merzweiler, Kurt, Trifunović, Srećko R., Sabo, Tibor, "Palladium(II) complexes with R(2)edda derived ligands. Part I. Reaction of diisopropyl (S,S)-2,2 '-(1,2-ethanediyldiimino)-dipropanoate with K-2[PdCl4]" in Journal of the Serbian Chemical Society, 74, no. 4 (2009):389-400,
https://doi.org/10.2298/JSC0904389K . .

TY  - JOUR
AU  - Krajcinovic, Bojana B.
AU  - Kaluđerović, Goran N.
AU  - Steinborn, Dirk
AU  - Schmidt, Harry
AU  - Wagner, Christoph
AU  - Žižak, Željko S.
AU  - Juranić, Zorica D.
AU  - Trifunović, Srećko R.
AU  - Sabo, Tibor
PY  - 2008
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/932
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, H-1 and C-13 spectroscopy and elemental analysis. Crystal structures were determined for la 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(mu M) 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. (C) 2008 Elsevier Inc. All rights reserved.
PB  - Elsevier Science Inc, New York
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 = "Krajcinovic, Bojana B. and Kaluđerović, Goran N. and Steinborn, Dirk and Schmidt, Harry and Wagner, Christoph and Žižak, Željko S. and Juranić, Zorica D. 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, H-1 and C-13 spectroscopy and elemental analysis. Crystal structures were determined for la 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(mu M) 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. (C) 2008 Elsevier Inc. All rights reserved.",
publisher = "Elsevier Science Inc, New York",
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"
}

Krajcinovic, B. B., Kaluđerović, G. N., Steinborn, D., Schmidt, H., Wagner, C., Žižak, Ž. S., Juranić, Z. D., 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 Science Inc, New York., 102(4), 892-900.
https://doi.org/10.1016/j.jinorgbio.2007.12.009

Krajcinovic BB, Kaluđerović GN, Steinborn D, Schmidt H, Wagner C, Žižak ŽS, Juranić ZD, 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 .

Krajcinovic, Bojana B., Kaluđerović, Goran N., Steinborn, Dirk, Schmidt, Harry, Wagner, Christoph, Žižak, Željko S., Juranić, Zorica D., 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 . .