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 liposarcom...a 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.
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 .
