Aqua (1, 10-phenanthroline)(L-serinato) copper (II) Nitrate (original) (raw)
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Molecules, 2021
Copper is an endogenous metal ion that has been studied to prepare a new antitumoral agent with less side-effects. Copper is involved as a cofactor in several enzymes, in ROS production, in the promotion of tumor progression, metastasis, and angiogenesis, and has been found at high levels in serum and tissues of several types of human cancers. Under these circumstances, two strategies are commonly followed in the development of novel anticancer Copper-based drugs: the sequestration of free Copper ions and the synthesis of Copper complexes that trigger cell death. The latter strategy has been followed in the last 40 years and many reviews have covered the anticancer properties of a broad spectrum of Copper complexes, showing that the activity of these compounds is often multi factored. In this work, we would like to focus on the anticancer properties of mixed Cu(II) complexes bearing substituted or unsubstituted 1,10-phenanthroline based ligands and different classes of inorganic and...
Novel copper(II) complexes as new promising antitumour agents. A crystal structure of Cu(1,10-phenanthroline-5,6-dione)2(OH2)(OClO3)
Journal of Inorganic Biochemistry, 2014
The cytotoxic properties of copper(II) complexes with 1,10-phenanthroline (phen) can be modified by substitution in the phen backbone. For this purpose, Cu(II) complexes with phen, 1,10-phenanthrolin-5,6-dione (phendione) and 1,10-phenanthrolin-5,6-diol (phendiol) have been synthesised and characterised. The crystal structure of [Cu(phendione) 2 (OH 2 )(OClO 3 )](ClO 4 ) is discussed. The complex formation equilibria between Cu(II) and phen or phendione were studied by potentiometric measurements at 25 and 37°C in 0.1 M ionic strength (NaCl). The antitumour activity of the compounds has been tested in vitro against a panel of tumour (DU-145, HEP-G2, SK-MES-1, CCRF-CEM, CCRF-SB) and normal (CRL-7065) human cell lines. The studied compounds generally present an antiproliferative effect greater than that of cisplatin. The phen and phendione ligands present a similar antiproliferative effect against all the tested cells. Phendiol presents an antiproliferative effect 1.3 to 18 times greater than that of phen or phendione for leukemic, lung, prostatic and fibroblast cells, while it presents less activity towards hepatic cells. Complexes with two ligands are more cytotoxic towards all the tested cell lines than complexes with one ligand and are generally more cytotoxic than the ligand alone. Complexes [Cu(phendiol) 2 (OH 2 )](ClO 4 ) 2 and [Cu(phendione) 2 (OH 2 )(OClO 3 )](ClO 4 ) appear to be the most active compounds for the treatment of SK-MES-1 and HEP-G2 cells, respectively, being at least 18 times more cytotoxic than cisplatin. The studied Cu(II) complexes are characterised by a strong DNA affinity and were found to interact with DNA mainly by groove binding or electrostatic interactions. The complexes appear to act on cells with a mechanism different from that of cisplatin. j o u r n a l h o m e p a g e : w w w . e l s e v i e r . c o m / l o c a t e / j i n o r g b i o
Cu(C3H6NOE)(Cz4H 16N2)(H20)]NO2.H20 (I), Mr = 566.1, monoclinic, P21, a = 11.864 (3), b = 7.726 (2), c = 14.832 (3) A, fl = 102.17 (2) °, V = 1329.0 (9) A 3, z = 2, Dx = 1.414 Mg m -3, a(Mo Ka) =0.71069A, / z = 0 . 8 6 8 m m -1 , 0108-2701/93/050890-04506.00 © 1993 International Union of Crystallography X. SOLANS et al. 891 2235 independent reflections (2 < 0 < 30 °) for (I);
Inorganica Chimica Acta, 2006
We present here the synthesis, crystal structure, electrochemical behavior, spectroscopic properties (FT-IR, UV-Vis and EPR), nuclease and in vitro antitumor activities against human myeloid leukemia cell line of the mononuclear copper complex [Cu(HPCl-NOL)(Cl)]Cl AE MeOH (1). The reaction of the tetradentate ligand HPClNOL [1-(bis-pyridin-2-ylmethyl-amino)-3-chloropropan-2-ol] and 1 equiv. of [Cu(OH 2 ) 6 ](Cl) 2 , in methanol, resulted in 1, which crystallizes as blue monoclinic crystals. The complex is pentacoordinated with a distorted square-pyramidal geometry. The activity of complex 1 toward plasmid DNA and THP-1 carcinogenic cells was investigated. Complex 1 promotes the cleavage of supercoiled DNA (pBlueScript KS + DNA) to nicked circular and linear DNA forms. In addition to the three typical KS + DNA forms, the cleavage resulted in a fourth band, which was visualized above of the nicked circular form. The results reveal that the cleavage mechanism is radical-independent. Furthermore, complex 1 is able to promote cell death of THP-1 cells by apoptosis, as confirmed by fluorescent microscopy, cell morphology and DNA degradation.
Journal of …, 2011
The triphenyltin(IV) complexes of 4-[((E)-1-{2-hydroxy-5-[(E)-2-(2-carboxyphenyl)-1-diazenyl]phenyl}methylidene)amino]aryls (aryls = 4-CH 3 , 4-Br, 4-Cl, 4-OCH 3 ) have been synthesized and characterized by 1 H-, 13 C-, 119 Sn-NMR, ESI mass spectrometry, IR and 119m Sn Mö ssbauer spectroscopic techniques in combination with elemental analysis. The crystal structures of a representative carboxylate ligand (aryl = 4-CH 3 ) and three Sn complexes, viz., polymeric (Ph 3 Sn[O 2 CC 6 H 4 {N@N(C 6 H 3 -4-OH(C(H)@ NC 6 H 4 X-4))}-o]) n (X = Me (1) and Br (2)) and dimeric (Ph 3 Sn[O 2 CC 6 H 4 {N@N(C 6 H 3 -4-OH(C(H)@NC 6 H 4 X-4))}-o]) 2 (X = OMe (4)) complexes are reported. The coordination environment in each complex is trigonal bipyramidal trans-Ph 3 SnO 2 . A single zwitterionic carboxylate ligand bridges adjacent Sn atoms via the carboxylate and phenoxide O atoms.
Journal of Structural Chemistry, 2016
A new copper(II) complex of 1,10-phenanthroline (C 12 H 8 N 2) and the meta-aminobenzoate ion (m-amb; 7 6 2 C H NO −), having the formula Cu(C 12 H 8 N 2)(C 7 H 6 NO 2)Cl⋅0.5H 2 O, is prepared and characterized by elemental analysis, IR spectroscopy, and single crystal X-ray diffraction. The structure is built up from monomeric units in which the coordination environment around the metal ion is a square plane arising from a bidentate 1,10-phenanthroline molecule, a monodentate m-amb anion, and a chloride ion. A very long (Cu-N = 2.856(5) Å) bond to the nitrogen atom of an adjacent m-amb ion generates [101] polymeric chains in the crystal. The crystal structure is consolidated by N-H⋯O and O-H⋯O hydrogen bonds and
2005 Copper(II) complexes of 1,10-phenanthroline-derived ligands
A series of copper(II) complexes of the type [Cu(L)] 2+ , where L = N,N 0 -dialkyl-1,10-phenanthroline-2,9-dimethanamine and R = methyl (L1), n-propyl (L2), isopropyl (L3), sec-butyl (L4), or tert-butyl (L5) group, have been synthesized. The interaction of the complexes with DNA has been studied by DNA fiber electron paramagnetic resonance (EPR) spectroscopy, emission, viscosity and electrochemical measurements and agarose gel electrophoresis. In the X-ray crystal structure of [Cu(HL2)Cl 2 ]NO 3 , copper(II) is coordinated to two ring nitrogens and one of the two secondary amine nitrogens of the side chains and two chloride ions as well and the coordination geometry is best described as trigonal bipyramidal distorted square based pyramidal (TBDSBP). Electronic and EPR spectral studies reveal that all the complexes in aqueous solution around pH 7 possess CuN 3 O 2 rather than CuN 4 O chromophore with one of the alkylamino side chain not involved in coordination. The structures of the complexes in aqueous solution around pH 7 change from distorted tetragonal to trigonal bipyramidal as the size of the alkyl group is increased. The observed changes in the physicochemical features of the complexes on binding to DNA suggest that the complexes, except [Cu(L5)] 2+ , bind to DNA with partial intercalation of the derivatised phen ring in between the DNA base pairs. Electrochemical studies reveal that the complexes prefer to bind to DNA in Cu(II) rather than Cu(I) oxidation state. Interestingly, [Cu(L5)] 2+ shows the highest DNA cleavage activity among all the present copper(II) complexes suggesting that the bulky N-tert-butyl group plays an important role in modifying the coordination environment around the copper(II) center, the Cu(II)/Cu(I) redox potential and hence the formation of activated oxidant responsible for the cleavage. These results were compared with those for bis(1,10-phenanthroline)copper(II), [Cu(phen) 2 ] 2+ .
Copper(II) N,N,OChelating Complexes as Potential Anticancer Agents
Three novel dinuclear Cu(II) complexes based on a N,N,O-chelating salphen-like ligand scaffold and bearing varying aromatic substituents (−H, −Cl, and −Br) have been synthesized and characterized. The experimental and computational data obtained suggest that all three complexes exist in the dimeric form in the solid state and adopt the same conformation. The mass spectrometry and electron paramagnetic resonance results indicate that the dimeric structure coexists with the monomeric form in solution upon solvent (dimethyl sulfoxide and water) coordination. The three synthesized Cu(II) complexes exhibit high potentiality as ROS generators, with the Cu(II)/Cu(I) redox potential inside the biological redox window, and thus being able to biologically undergo Cu(II)/Cu(I) redox cycling. The formation of ROS is one of the most promising reported cell death mechanisms for metal complexes to offer an inherent selectivity to cancer cells. In vitro cytotoxic studies in two different cancer cell lines (HeLa and MCF7) and in a normal fibroblast cell line show promising selective cytotoxicity for cancer cells (IC 50 about 25 μM in HeLa cells, which is in the range of cisplatin and improved with respect to carboplatin), hence placing this N,N,O-chelating salphen-like metallic core as a promising scaffold to be explored in the design of future tailor-made Cu(II) cytotoxic compounds.