Copper coordination compounds based on bis-quinolylhydrazone of 2,6-diacetylpyridine: Synthesis, structure and cytotoxic activity

[Display omitted] Bis-hetarylhydrazone H2L (1), a condensation product of 2,6-diacetylpyridine with 2-hydrazinoquinoline, has been synthesized. By reaction of 1 with Cu(II) nitrate and perchlorate binuclear mixed-valence coordination compounds [CuICuII(H2L)2](NO3)3⋅2H2O (2) and [CuICuII(H2L)2](ClO4)...

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Bibliographic Details
Published in:	Polyhedron Vol. 233; p. 116292
Main Authors:	Tupolova, Yuliya P., Shcherbakov, Igor N., Popov, Leonid D., Vlasenko, Valery G., Gishko, Konstantin B., Kapustina, Anna A., Berezhnaya, Aleksandra G., Golubeva, Yuliya A., Klyushova, Lyubov S., Lider, Elizaveta V., Lazarenko, Vladimir A., Minin, Vadim V., Knyazev, Pavel A.
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 15-03-2023
Subjects:	Copper complexes Cytotoxicity Hep-2 and HepG2 Hydrazone MEP and ALIE surfaces Hep-2 and HepG2 Cytotoxicity Hydrazone MEP and ALIE surfaces Copper complexes
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Summary:	[Display omitted] Bis-hetarylhydrazone H2L (1), a condensation product of 2,6-diacetylpyridine with 2-hydrazinoquinoline, has been synthesized. By reaction of 1 with Cu(II) nitrate and perchlorate binuclear mixed-valence coordination compounds [CuICuII(H2L)2](NO3)3⋅2H2O (2) and [CuICuII(H2L)2](ClO4)3 (3) were obtained. Cu(I) Ion in the compounds 2, 3 is in the distorted tetrahedral N-donor environment, while Cu(II) center is in the distorted octahedral one. Cu(II) Chloride and bromide form with 1 asymmetric mononuclear compounds with composition [Cu(H2L)Cl]Cl (4) and [Cu(H2L)Br]Br (5) with tetragonal–pyramidal coordination polyhedron. The structures of the compounds were studied by means of NMR, IR, ESR, UV–vis, X-ray absorption spectroscopy and X-ray single crystal diffraction methods. The effect of compounds on viability of the Hep-2 and HepG2 cell lines was investigated in vitro. The study showed that 1 is non-toxic at tested concentrations (1–100 μM), while all the complexes exhibit significant dose-dependent cytotoxic effect. It is shown that compounds 2–5 demonstrate higher cytotoxicity towards considered cancer cell cultures than widely used commercial anticancer pharmaceuticals – cisplatin and carboplatin. Quantum-chemical modeling of the structure of the ligand 1 and its complexes was performed using density functional theory at B3LYP/6-311G(d) level of theory. Molecular electrostatic potential (MEP) and average local ionization energy (ALIE) surfaces were calculated to rationalize the reactive properties of the compounds.
ISSN:	0277-5387
DOI:	10.1016/j.poly.2023.116292