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Platinum(II) complexes with R(2)edda ligands (R = Me, Et, n-Pr; edda = ethylenediamine-N,N '-diacetate): Synthesis and characterization

Authorized Users Only
2014
Authors
Kaluđerović, Goran N.
Pantelić, Nebojša Đ.
Eichhorn, Thomas
Bette, Martin
Wagner, Christoph
Zmejkovski, Bojana
Schmidt, Harry
Article (Published version)
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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 colo...n) by the SRB colorimetric assay method. Complex 3 showed the highest action against ovarian (A2780) cells with an IC50 value 51 +/- 1 mu M.

Keywords:
Platinum(II) complexes / Platinum(IV) complexes / R(2)edda-type ligands / Diastereoisomers / Crystal structure / cytotoxic activity
Source:
Polyhedron, 2014, 80, 53-59
Publisher:
  • Oxford : Pergamon-Elsevier Science Ltd
Funding / projects:
  • Alexander von Humboldt Foundation (Germany)
  • Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)

DOI: 10.1016/j.poly.2014.01.018

ISSN: 0277-5387

WoS: 000341348300008

Scopus: 2-s2.0-84905502683
[ Google Scholar ]
9
8
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/1424
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
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 . .

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