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Platinum(II) complexes with l-methionylglycine and l-methionyl-l-leucine ligands: Synthesis, characterization and in vitro antitumoral activity

Authorized Users Only
2007
Authors
Kaluđerović, Goran N.
Schmidt, Harry
Paschke, Reinhard
Kalinowski, Bernd
Dietrich, Andrea
Mueller, Thomas
Steinborn, Dirk
Article (Published version)
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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-methio...nylglycine 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.

Keywords:
Antiproliferative activity / Dipeptide / Platinum uptake / Platinum(II) complexes
Source:
Journal of Inorganic Biochemistry, 2007, 101, 3, 543-549
Publisher:
  • Elsevier

DOI: 10.1016/j.jinorgbio.2006.11.016

ISSN: 0162-0134

PubMed: 17223197

WoS: 000244773800018

Scopus: 2-s2.0-33846682210
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9
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/4252
Collections
  • Radovi istraživača / Researchers' publications
Institution
IHTM
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",
url = "https://cer.ihtm.bg.ac.rs/handle/123456789/4252",
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 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. Journal of Inorganic Biochemistry. 2007;101(3):543-549
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.
Journal of Inorganic BiochemistryElsevier., 101(3), 543-549.
https://doi.org/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" 101, no. 3 (2007):543-549,
https://doi.org/10.1016/j.jinorgbio.2006.11.016 .

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