85650-01-7Relevant academic research and scientific papers
Cobalt(II) and copper(II) covalently and non-covalently dichlorido-bridged complexes of an unsymmetrical tripodal pyrazolyl-pyridyl amine ligand: Structures, magnetism and cytotoxicity
Herchel, Radovan,Dvo?ák, Zdeněk,Trávní?ek, Zdeněk,Mikuriya, Masahiro,Louka, Febee R.,Mautner, Franz A.,Massoud, Salah S.
, p. 102 - 110 (2016)
The reaction of a methanolic solution containing MIICl2(M = Co or Cu) with bis(3,5-dimethyl-1H-pyrazol-1-yl-1-ethyl)(2-pyridylmethyl)amine (bedmpzp) in the presence of NH4PF6afforded the dinuclear doubly bridged-dichlorido complex [Co2(bedmpzp)2(μ-Cl)2](PF6)2(1) and the mononuclear [Cu(bedmpzp)Cl]PF6(2) one. The complexes were structurally and magnetically characterized. The weak ferromagnetic exchange and the axial type of magnetic anisotropy found in 1 is associated with slow relaxation of magnetization as revealed by AC susceptibility measurements. This finding puts 1 into a class of polynuclear single-molecule magnets based on 3d metals. X-ray structure of 2 revealed mononuclear nature of the complex, forming supramolecular dimers in the solid state. The non-covalent interactions of the Cu???Cl type present in its crystal structure induced a weak antiferromagnetic exchange. The results of magnetic analysis were also supported by DFT and CASSCF/NEVPT2 calculations. The in vitro cytotoxicity of the complexes against MCF7 and HeLa human cancer cell lines were also tested. The best cytotoxicity was achieved for complex 2 on HeLa, with IC50= 2.5(0.9) μM.
Identification of potent anticancer copper(ii) complexes containing tripodal bis[2-ethyl-di(3,5-dialkyl-1H-pyrazol-1-yl)]amine moiety
Dial, Madison T.,Dvo?ák, Zdeněk,Fischer, Roland C.,Louka, Febee R.,Malek, Andrew J.,Malina, Tomá?,Massoud, Salah S.,Mautner, Franz A.,Trávní?ek, Zdeněk,Van?o, Ján
, p. 11521 - 11534 (2021/08/30)
A series of heteroleptic copper(ii) complexes of the composition [Cu(L1-5)Cl]X, where X = ClO4 and/or PF6 and [bis(2-ethyl-di(3,5-dimethyl-1H-pyrazol-1-yl))-(6-methyl-(2-pyridylmethyl))]amine (L1), [bis(2-ethyl-di(3,5-dimethyl-1H-pyrazol-1-yl))-(3,4-dimethoxy-(2-pyridylmethyl))]amine (L2), [bis(2-ethyl-di(3,5-dimethyl-1H-pyrazol-1-yl)-(2-quinolymethyl)]amine (L3), [bis(2-ethyl-di(3,5-dimethyl-1H-pyrazolyl)-(di(3,5-dimethyl-1H-pyrazol-1-yl-methyl))]amine (L4) and [bis(2-ethyl-di(3,5-dimethyl-1H-pyrazol-1-yl)-(5-methyl-3-phenyl-1H-pyrazol-1-yl-methyl)]amine (L5), were prepared and thoroughly characterized including single-crystal X-ray diffraction technique. The in vitro cytotoxicity of complexes against A2780, A2780R, HOS and MCF-7 human cancer cell lines was evaluated using the MTT test. The results revealed that complexes [Cu(L1)Cl]PF6 (1-PF6), [Cu(L2)Cl]ClO4 (2-ClO4) and [Cu(L3)Cl]PF6 (3-PF6) are the most effective, with IC50 values ranging from 1.4 to 6.3 μM, thus exceeding the cytotoxic potential of metallodrug cisplatin (IC50 values ranging from 29.9 to 82.0 μM). The complexes [Cu(L4)Cl]PF6 (4-PF6) and [Cu(L5)Cl]PF6 (5-PF6) showed only moderate cytotoxicity against A2780, with IC50 = 53.6 μM, and 33.8 μM, respectively. The cell cycle profile, time-resolved cellular uptake, interactions with small sulfur-containing biomolecules (cysteine and glutathione), intracellular ROS production, induction of apoptosis and activation of caspases 3/7 were also evaluated in the case of the selected complexes. It has been found that the best performing complexes 1 and 2 cause cell arrest in the G2/M phase and induce apoptosis via the increase in production of ROS, dominantly due to the overproduction of superoxide.
