Redox processes as a route for the formation of an unusual structure of the Co(II)/Zn(II) complex isolated from the system: [Co(0)/Zn(II)-1-hydroxymethyl-3,5-dimethylpyrazole]

Adach, Anna; Daszkiewicz, Marek; Barszcz, Barbara; Cieślak‐Golonka, Maria; Maciejewska, Gabriela

doi:10.1016/j.inoche.2009.12.022

Cited by 20 publications

(16 citation statements)

References 36 publications

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“…The complexes were prepared according to the general procedure [ 13 , 14 , 20 ] with some modifications [ 18 , 19 , 22 ]. Compounds 1 and 2 were isolated from zerovalent cobalt and 1-hydroxymethyl-3,5-dimethylpyrazole (L) as one of the substrates [ 18 , 22 ], whereas 3 was obtained using VOSO 4 .…”

Section: Methodsmentioning

confidence: 99%

“…Complexes with N,N,N-tris(3.5-dimethylpyrazol-1-ylmethyl)amine ligands (L S ) showed high antiproliferative activities against a panel of human cancer cells [6,15,16]. The nature of ligands and their architectures significantly determines the properties of resulting complex species [6,[13][14][15][16][18][19][20][21].We have also previously found that cationic-anionic (Co/Zn and Co/Cd) complexes containing N-scorpionate ligands (such as N,N,N-tris (3.5-dimethylpyrazol-1-ylmethyl)amine (L S )), express substantial antiproliferative potency [6,15]. The cytotoxic evaluation of these complexes also revealed their high selectivity for cancer cells.…”

Section: Introductionmentioning

confidence: 99%

“…The identification of structural properties of metal-based complexes that may augment their antitumour activities is the sole basis of designing novel potent complexes. We have previously reported the one pot synthesis and physicochemical characterizations of complexes containing N,N,N-tris (3.5-dimethylpyrazol-1-ylmethyl)amine ligands (L S ) [ 6 , 13 , 14 , 15 , 16 ], which is an analogue of original poly(pyrazol-1-yl) borates called scorpionates [ 17 ]. Complexes with N,N,N-tris(3.5-dimethylpyrazol-1-ylmethyl)amine ligands (L S ) showed high antiproliferative activities against a panel of human cancer cells [ 6 , 15 , 16 ].…”

Section: Introductionmentioning

confidence: 99%

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Selective Cytotoxicity of Complexes with N,N,N-Donor Dipodal Ligand in Tumor Cells

Tyszka-Czochara

Adach

Grabowski

et al. 2021

IJMS

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The present article demonstrates selective cytotoxicity against cancer cells of the complexes [Co(LD)2]I2∙CH3OH (1), [CoLD(NCS)2] (2) and [VOLD(NCS)2]∙C6H5CH3 (3) containing the dipodal tridentate ligand LD = N,N-bis(3,5-dimethylpyrazol-1-ylmethyl)amine), formed in situ. All tested complexes expressed greater anticancer activities and were less toxic towards noncancerous cells than cisplatin. Cobalt complexes (1 and 2) combined high cytotoxicity with selectivity towards cancer cells and caused massive tumour cell death. The vanadium complex (3) induced apoptosis specifically in cancer cells and targeted proteins, controlling their invasive and metastatic properties. The presented experimental data and computational prediction of drug ability of coordination compounds may be helpful for designing novel and less toxic metal-based anticancer species with high specificities towards tumour cells.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Selective Cytotoxicity of Complexes with N,N,N-Donor Dipodal Ligand in Tumor Cells

Tyszka-Czochara

Adach

Grabowski

et al. 2021

IJMS

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“…We have found synthetic methods of two kinds of multipodal and multidentate Nligands such as N,N,N-tris and N,N-bis(pyrazolylmethyl)amines created in situ from 1-hydroxymethyl-3,5-dimethylpyrazole (L). [10][11][12][13][14][15] N-substituted pyrazole derivatives such as N,N-bis(pyrazolylmethyl)amines are pincer ligands and analogues of poly-(pyrazolyl)borates, called scorpionates. 16,17 Our goal was to investigate the system containing zerovalent chromium.…”

Section: Introductionmentioning

confidence: 99%

New oxovanadium(iv) complexes with pincer ligand obtained in situ: experimental and theoretical studies on the structure, spectroscopic properties and antitumour activity

et al. 2015

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Experimental and theoretical studies on the structure and spectroscopic properties of two complexes: [VOL 1 (NCS) 2 ] (1) and [VOL 1 (NCS) 2 ]·C 6 H 5 CH 3 (2) where L 1 -bis(3,5dimethylpyrazol-1-ylmethyl)amine have been reported.The products, isolated in one-pot synthesis, contain multipodal pincer ligand L 1 obtained in situ from the system containing 1-hydroxymethyl-3,5-dimethylpyrazole (L) as one of the substrates. The crystal structure, electronic (UV-VIS) and infrared (IR) spectra of the complexes have been analyzed. The combined use of experiments and computations allowed a firm assignment of the majority of the observed electronic and vibrational transitions.Theoretical (DFT) calculations have been carried out at the B3LYP/LanL2DZ level to investigate the geometry of 1 and 2. They were found to be in a good agreement with the experimental results. Additionally biological activity of complex 2 was investigated. The complex 2 exhibited anti-proliferative activity towards panel of human cancer cells (hepatocellular carcinoma Hep G2, lung carcinoma A549, colorectal adenocarcinomas SW 480 and SW 620). The anti-proliferative potency of complex 2 and its higher selectivity towards cancer cells than those of the vanadium salt tested, makes it an interesting candidate for further investigation of its anti-cancer properties. * AbstractExperimental and theoretical studies on the structure and spectroscopic properties of two complexes: [VOL 1 (NCS) 2 ] (1) and [VOL 1 (NCS) 2 ]·C 6 H 5 CH 3 (2) where L 1 -bis(3,5dimethylpyrazol-1-ylmethyl)amine have been reported.The products, isolated in one-pot synthesis, contain multipodal princer ligand L 1 obtained in situ from the system containing 1-hydroxymethyl-3,5-dimethylpyrazole (L) as one of the substrates. The crystal structure, electronic (UV-VIS) and infrared (IR) spectra of the complexes have been analyzed. The combined use of experiments and computations allowed a firm assignment of the majority of the observed electronic and vibrational transitions.Theoretical (DFT) calculations have been carried out at the B3LYP/LanL2DZ level to investigate the geometry of 1 and 2. They were found to be in a good agreement with the experimental results. Additionally biological activity of complex 2 was investigated. The complex 2 exhibited anti-proliferative activity towards panel of human cancer cells (hepatocellular carcinoma Hep G2, lung carcinoma A549, colorectal adenocarcinomas SW 480 and SW 620). The anti-proliferative potency of complex 2 and its higher selectivity towards cancer cells than those of the vanadium salt tested, makes it an interesting candidate for further investigation of its anti-cancer properties. Fig.2. Normalized Hirshfeld surface around the [VOL 1 (NCS) 2 ] molecules (a) in 1 and (b) in 2. Chain patterns created (c) by hydrogen bonds in 1 and (d) by C-H···π interactions in 2.

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“…The zinc atom can accommodate different coordination geometries including tetrahedral (fourcoordinate) [9][10][11][12][13][14][15][16][17][18][19], square-pyramidal (five coordinate) [20] and octahedral geometry (sixcoordinate) [21,22]. Zinc is involved in catalytic and structural functions of proteins; it is an essential element for all living organisms and it is the second most abundant metal in the human body [23][24][25][26][27]. Hexamethylenetetramine (HMTA; IUPAC name: 1,3,5,7-tetraazatricyclo[3.3.1.1]decane) is an important product obtained by condensation of formaldehyde and ammonia at room temperature and atmospheric pressure in aqueous acidic conditions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure, infrared spectroscopy, thermal analysis and Hirshfeld surface analysis of a new hemihydrate of [Zn (H2O) 6][{(CH2)6N4}ZnCl3]2·0.5H2O

Basdouri

Trojette

Falvello

et al. 2019

Journal of Molecular Structure

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Synthesis, crystal structure, infrared spectroscopy, thermal analysis and Hirshfeld surface analysis of a new hemihydrate of [Zn (H2O) 6][{(CH2)6N4}ZnCl3]2·0.5H2O. AbstractThe new organic-inorganic hybrid material [Zn(H2O)6][{(CH2)6N4}ZnCl3]2·0.5 H2O, is the second hydrate in this system, the first having been the hexahydrate. The new solid was prepared by slow evaporation of a solution of the reactants at room temperature and was structurally characterized by X-ray crystallography. This compound crystallizes in the trigonal system, space group P-3c1 with a = 9.8303(2)Å, c = 17.5460(2)Å, V = 1468.38(4)Å 3 and with Z = 2. The complex was characterized by FT-IR, thermogravimetric analysis (TGA), differential thermal analysis (DTA) and with a detailed analysis of Hirshfeld surfaces and fingerprint plots. The structural unit of the title compound consists of a [Zn II (H2O)6] 2+ cation, two [Zn II Cl3(hmt)]anions and half of a water molecule, partially occupied and disordered [hmt is hexamethylenetetramine, (CH2)6N4]. Crystal packing is mediated by O-H…N and O-H…Cl hydrogen bonds between the anions and cations, and to a lesser extent by O-H…O contacts, which are present only part of the time as a consequence of the partial occupancy of the isolated water molecules. The relationship between the packing in the new structure and that of the previous hexahydrate is described.

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Redox processes as a route for the formation of an unusual structure of the Co(II)/Zn(II) complex isolated from the system: [Co(0)/Zn(II)-1-hydroxymethyl-3,5-dimethylpyrazole]

Cited by 20 publications

References 36 publications

Selective Cytotoxicity of Complexes with N,N,N-Donor Dipodal Ligand in Tumor Cells

Selective Cytotoxicity of Complexes with N,N,N-Donor Dipodal Ligand in Tumor Cells

New oxovanadium(iv) complexes with pincer ligand obtained in situ: experimental and theoretical studies on the structure, spectroscopic properties and antitumour activity

Synthesis, crystal structure, infrared spectroscopy, thermal analysis and Hirshfeld surface analysis of a new hemihydrate of [Zn (H2O) 6][{(CH2)6N4}ZnCl3]2·0.5H2O

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