Gallium(III) and Iron(III) Complexes of α-N-Heterocyclic Thiosemicarbazones: Synthesis, Characterization, Cytotoxicity, and Interaction with Ribonucleotide Reductase
Christian R. Kowol
1
,
Roland Berger
1
,
Rene Eichinger
1
,
Alexander Roller
1
,
Peter P Schmidt
1
,
1
Institute of Inorganic Chemistry, Faculty of Chemistry, University of Vienna, Waehringer Strasse 42, A-1090 Vienna, Austria, and Max-Planck Institute for Bioinorganic Chemistry, Stiftstrasse 34-38, Mülheim an der Ruhr, D-45470 Germany
|
Publication type: Journal Article
Publication date: 2007-02-22
scimago Q1
wos Q1
SJR: 1.801
CiteScore: 11.5
Impact factor: 6.8
ISSN: 00222623, 15204804
PubMed ID:
17315858
Drug Discovery
Molecular Medicine
Abstract
A series of gallium(III) and iron(III) complexes with five different 4N-substituted alpha-N-heterocyclic thiosemicarbazones, viz., 2-acetylpyridine N,N-dimethylthiosemicarbazone (1), 2-acetylpyridine N-pyrrolidinylthiosemicarbazone (2), acetylpyrazine N,N-dimethylthiosemicarbazone (3), acetylpyrazine N-pyrrolidinylthiosemicarbazone (4), and acetylpyrazine N-piperidinylthiosemicarbazone (5), with the general formula [GaLCl2] (HL = 1 and 2) and [ML2][Y] (M = Ga, HL = 1-5, Y = PF6; M = Fe, HL = 1-5, Y = FeCl4 and PF6) were synthesized and characterized by elemental analysis, a number of spectroscopic methods (NMR, IR, UV-vis), mass spectrometry, and X-ray crystallography. The in vitro antitumor potency was studied in two human cancer cell lines (41M and SK-BR-3). The central metal ions exert pronounced effects in a divergent manner: gallium(III) enhances, whereas iron(III) weakens the cytotoxicity of the ligands. The capacity of ligand 1 and its Ga(III) and Fe(III) complexes to destroy the tyrosyl radical of the presumed target ribonucleotide reductase is reported.
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Total citations:
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(2.17%)
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Kowol C. R. et al. Gallium(III) and Iron(III) Complexes of α-N-Heterocyclic Thiosemicarbazones: Synthesis, Characterization, Cytotoxicity, and Interaction with Ribonucleotide Reductase // Journal of Medicinal Chemistry. 2007. Vol. 50. No. 6. pp. 1254-1265.
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Kowol C. R., Berger R., Eichinger R., Roller A., Jakupec M. A., Schmidt P. P., Arion V. B., Keppler B. Gallium(III) and Iron(III) Complexes of α-N-Heterocyclic Thiosemicarbazones: Synthesis, Characterization, Cytotoxicity, and Interaction with Ribonucleotide Reductase // Journal of Medicinal Chemistry. 2007. Vol. 50. No. 6. pp. 1254-1265.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jm0612618
UR - https://doi.org/10.1021/jm0612618
TI - Gallium(III) and Iron(III) Complexes of α-N-Heterocyclic Thiosemicarbazones: Synthesis, Characterization, Cytotoxicity, and Interaction with Ribonucleotide Reductase
T2 - Journal of Medicinal Chemistry
AU - Kowol, Christian R.
AU - Berger, Roland
AU - Eichinger, Rene
AU - Roller, Alexander
AU - Jakupec, Michael A.
AU - Schmidt, Peter P
AU - Arion, Vladimir B.
AU - Keppler, Bernhard
PY - 2007
DA - 2007/02/22
PB - American Chemical Society (ACS)
SP - 1254-1265
IS - 6
VL - 50
PMID - 17315858
SN - 0022-2623
SN - 1520-4804
ER -
Cite this
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@article{2007_Kowol,
author = {Christian R. Kowol and Roland Berger and Rene Eichinger and Alexander Roller and Michael A. Jakupec and Peter P Schmidt and Vladimir B. Arion and Bernhard Keppler},
title = {Gallium(III) and Iron(III) Complexes of α-N-Heterocyclic Thiosemicarbazones: Synthesis, Characterization, Cytotoxicity, and Interaction with Ribonucleotide Reductase},
journal = {Journal of Medicinal Chemistry},
year = {2007},
volume = {50},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/jm0612618},
number = {6},
pages = {1254--1265},
doi = {10.1021/jm0612618}
}
Cite this
MLA
Copy
Kowol, Christian R., et al. “Gallium(III) and Iron(III) Complexes of α-N-Heterocyclic Thiosemicarbazones: Synthesis, Characterization, Cytotoxicity, and Interaction with Ribonucleotide Reductase.” Journal of Medicinal Chemistry, vol. 50, no. 6, Feb. 2007, pp. 1254-1265. https://doi.org/10.1021/jm0612618.