Platinum(II) complexes with R(2)edda ligands (R = Me, Et, n-Pr; edda = ethylenediamine-N,N '-diacetate): Synthesis and characterization
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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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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 activitySource:
Polyhedron, 2014, 80, 53-59Publisher:
- 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
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IHTMTY - 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 . .