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Synthesis, Antiproliferative Activity, and DNA Binding Studies of Nucleoamino Acid-Containing Pt(II) Complexes
Article

Synthesis of Platinum(II) Complexes with Some 1-Methylnitropyrazoles and In Vitro Research on Their Cytotoxic Activity

1
Department of Organic Chemistry, Faculty of Pharmacy, Wrocław Medical University, 211A Borowska Street, 50-556 Wrocław, Poland
2
Faculty of Chemistry, The University of Wrocław, 14F Joliot-Curie Street, 50-383 Wrocław, Poland
3
Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, 12 Rudolf Weigl Street, 53-114 Wrocław, Poland
*
Author to whom correspondence should be addressed.
Pharmaceuticals 2020, 13(12), 433; https://0-doi-org.brum.beds.ac.uk/10.3390/ph13120433
Received: 6 October 2020 / Revised: 24 November 2020 / Accepted: 25 November 2020 / Published: 28 November 2020
(This article belongs to the Special Issue Metal-Based Drugs: Updates and Perspectives)
A series of eight novel platinum(II) complexes were synthesized by the reaction of the appropriate 1-methylnitropyrazole derivatives with K2PtCl4 and characterized by elemental analysis, ESI MS spectrometry, 1H NMR, 195Pt NMR, IR and far IR spectroscopy. Thermal isomerization of cis-dichloridobis(1-methyl-4-nitropyrazole)platinum(II) 1 to trans-dichloridobis(1-methyl-4-nitropyrazole)platinum(II) 2 has been presented, and the structure of the compound 2 has been confirmed by X-ray diffraction method. Cytotoxicity of the investigated compounds was examined in vitro on three human cancer cell lines (MCF-7 breast, ES-2 ovarian and A-549 lung adenocarcinomas) and their logP was measured using a shake-flask method. The trans complex 2 showed better antiproliferative activity than cisplatin for all the tested cancer cell lines. Additionally, trans-dichloridobis(1-methyl-5-nitropyrazole)platinum(II) 4 has featured a lower IC50 value than reference cisplatin against MCF-7 cell line. To gain additional information that may facilitate the explanation of the mode of action of tested compounds cellular platinum uptake, stability in L-glutathione solution, influence on cell cycle progression of HL-60 cells and ability to apoptosis induction were determined for compounds 1 and 2. View Full-Text
Keywords: nitropyrazoles-Pt(II)complexes; synthesis; structural analysis; LogP; cellular platinum uptake; antiproliferative activity; normoxia-hypoxia; L-glutathione (GSH); cell cycle; X-ray crystallography nitropyrazoles-Pt(II)complexes; synthesis; structural analysis; LogP; cellular platinum uptake; antiproliferative activity; normoxia-hypoxia; L-glutathione (GSH); cell cycle; X-ray crystallography
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MDPI and ACS Style

Mastalarz, H.; Mastalarz, A.; Wietrzyk, J.; Milczarek, M.; Kochel, A.; Regiec, A. Synthesis of Platinum(II) Complexes with Some 1-Methylnitropyrazoles and In Vitro Research on Their Cytotoxic Activity. Pharmaceuticals 2020, 13, 433. https://0-doi-org.brum.beds.ac.uk/10.3390/ph13120433

AMA Style

Mastalarz H, Mastalarz A, Wietrzyk J, Milczarek M, Kochel A, Regiec A. Synthesis of Platinum(II) Complexes with Some 1-Methylnitropyrazoles and In Vitro Research on Their Cytotoxic Activity. Pharmaceuticals. 2020; 13(12):433. https://0-doi-org.brum.beds.ac.uk/10.3390/ph13120433

Chicago/Turabian Style

Mastalarz, Henryk, Agnieszka Mastalarz, Joanna Wietrzyk, Magdalena Milczarek, Andrzej Kochel, and Andrzej Regiec. 2020. "Synthesis of Platinum(II) Complexes with Some 1-Methylnitropyrazoles and In Vitro Research on Their Cytotoxic Activity" Pharmaceuticals 13, no. 12: 433. https://0-doi-org.brum.beds.ac.uk/10.3390/ph13120433

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