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  - Paschke, Reinhard
AU  - Kalinowski, Bernd
AU  - Dietrich, Andrea
AU  - Mueller, Thomas
AU  - Steinborn, Dirk
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4252
AB  - Four dipeptide complexes of the type [PtX2(dipeptide)] · H2O (X = Cl, I, dipeptide = l-methionylglycine, l-methionyl-l-leucine) were prepared. The complexes were characterized by 1H, 13C, 195Pt NMR and infrared spectroscopy, DTG and elemental analysis. From the infrared, 1H and 13C NMR spectroscopy it was concluded that dipeptides coordinate bidentately via sulfur and amine nitrogen donor atoms. Confirmed with 13C and 195Pt NMR spectroscopy, each of the complexes exists in two diastereoisomeric forms, which are related by inversion of configuration at the sulfur atom. The 1H NMR spectrum for the platinum(II) complex with l-methionylglycine and chloro ligands exhibited reversible, intramolecular inversion of configuration at the S atom; ΔG≠ = 72 kJ mol−1 at coalescence temperature 349 K was calculated. In vitro cytotoxicity studies using the human tumor cell lines liposarcoma, lung carcinoma A549 and melanoma 518A2 revealed considerable activity of the platinum(II) complex with l-methionylglycine and chloro ligands. Further in vitro cytotoxic evaluation using human testicular germ cell tumor cell lines 1411HP and H12.1 and colon carcinoma cell line DLD-1 showed moderate cytotoxic activity for all platinum(II) complexes only in the cisplatin-sensitive cell line H12.1. Platinum uptake studies using atomic absorption spectroscopy indicated no relationship between uptake and activity. Potential antitumoral activity of this class of platinum(II) complexes is dependent on the kind of ligands as well as on tumor cell type.
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - Platinum(II) complexes with l-methionylglycine and l-methionyl-l-leucine ligands: Synthesis, characterization and in vitro antitumoral activity
VL  - 101
IS  - 3
SP  - 543
EP  - 549
DO  - 10.1016/j.jinorgbio.2006.11.016
ER  - 

@article{
author = "Kaluđerović, Goran N. and Schmidt, Harry and Paschke, Reinhard and Kalinowski, Bernd and Dietrich, Andrea and Mueller, Thomas and Steinborn, Dirk",
year = "2007",
abstract = "Four dipeptide complexes of the type [PtX2(dipeptide)] · H2O (X = Cl, I, dipeptide = l-methionylglycine, l-methionyl-l-leucine) were prepared. The complexes were characterized by 1H, 13C, 195Pt NMR and infrared spectroscopy, DTG and elemental analysis. From the infrared, 1H and 13C NMR spectroscopy it was concluded that dipeptides coordinate bidentately via sulfur and amine nitrogen donor atoms. Confirmed with 13C and 195Pt NMR spectroscopy, each of the complexes exists in two diastereoisomeric forms, which are related by inversion of configuration at the sulfur atom. The 1H NMR spectrum for the platinum(II) complex with l-methionylglycine and chloro ligands exhibited reversible, intramolecular inversion of configuration at the S atom; ΔG≠ = 72 kJ mol−1 at coalescence temperature 349 K was calculated. In vitro cytotoxicity studies using the human tumor cell lines liposarcoma, lung carcinoma A549 and melanoma 518A2 revealed considerable activity of the platinum(II) complex with l-methionylglycine and chloro ligands. Further in vitro cytotoxic evaluation using human testicular germ cell tumor cell lines 1411HP and H12.1 and colon carcinoma cell line DLD-1 showed moderate cytotoxic activity for all platinum(II) complexes only in the cisplatin-sensitive cell line H12.1. Platinum uptake studies using atomic absorption spectroscopy indicated no relationship between uptake and activity. Potential antitumoral activity of this class of platinum(II) complexes is dependent on the kind of ligands as well as on tumor cell type.",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "Platinum(II) complexes with l-methionylglycine and l-methionyl-l-leucine ligands: Synthesis, characterization and in vitro antitumoral activity",
volume = "101",
number = "3",
pages = "543-549",
doi = "10.1016/j.jinorgbio.2006.11.016"
}

Kaluđerović, G. N., Schmidt, H., Paschke, R., Kalinowski, B., Dietrich, A., Mueller, T.,& Steinborn, D.. (2007). Platinum(II) complexes with l-methionylglycine and l-methionyl-l-leucine ligands: Synthesis, characterization and in vitro antitumoral activity. in Journal of Inorganic Biochemistry
Elsevier., 101(3), 543-549.
https://doi.org/10.1016/j.jinorgbio.2006.11.016

Kaluđerović GN, Schmidt H, Paschke R, Kalinowski B, Dietrich A, Mueller T, Steinborn D. Platinum(II) complexes with l-methionylglycine and l-methionyl-l-leucine ligands: Synthesis, characterization and in vitro antitumoral activity. in Journal of Inorganic Biochemistry. 2007;101(3):543-549.
doi:10.1016/j.jinorgbio.2006.11.016 .

Kaluđerović, Goran N., Schmidt, Harry, Paschke, Reinhard, Kalinowski, Bernd, Dietrich, Andrea, Mueller, Thomas, Steinborn, Dirk, "Platinum(II) complexes with l-methionylglycine and l-methionyl-l-leucine ligands: Synthesis, characterization and in vitro antitumoral activity" in Journal of Inorganic Biochemistry, 101, no. 3 (2007):543-549,
https://doi.org/10.1016/j.jinorgbio.2006.11.016 . .