- Chemical and biological profiles of novel copper(II) complexes containing S-donor ligands for the treatment of cancer
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In the last years, we have synthesized some new platinum(II), palladium(II), gold(I/III) complexes with dithiocarbamato derivatives as potential anticancer drugs, to obtain compounds with superior chemotherapeutic index in terms of increased bioavailability, higher cytotoxicity, and lower side effects than cisplatin. On the basis of the obtained encouraging results, we have been studying the interaction of CuCl2 with methyl-/ethyl-/tert- butylsarcosine-dithiocarbamato moieties in a 1:2 molar ratio; we also synthesized and studied the N,N-dimethyl- and pyrrolidine-dithiocarbamato copper complexes for comparison purposes. The reported compounds have been successfully isolated, purified, and fully characterized by means of several spectroscopic techniques. Moreover, the electrochemical properties of the designed compounds have been studied through cyclic voltammetry. In addition, the behavior in solution was followed by means of UV - vis technique to check the stability with time in physiological conditions. To evaluate their in vitro cytotoxic properties, preliminary biological assays (MTT test) have been carried out on a panel of human tumor cell lines. The results show that cytotoxicity levels of all of the tested complexes are comparable or even greater than that of the reference drug (cisplatin).
- Giovagnini, Lorena,Sitran, Sergio,Montopoli, Monica,Caparrotta, Laura,Corsini, Maddalena,Rosani, Claudia,Zanello, Piero,Dou, Q. Ping,Fregona, Dolores
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- Ecotoxicity assessment of sodium dimethyldithiocarbamate and its micro-sized metal chelates in Caenorhabditis elegans
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Sodium dimethyldithiocarbamate (SDDC) is a widely used heavy metal chelating agent in harmless treatment of wastewater and hazardous waste, but SDDC and its heavy metal chelates may leak into the environment and bring potential ecological risks. In this study, the model organism Caenorhabditis elegans was used to evaluate the toxic effect of SDDC and its heavy metal Cu, Pb chelates. Multiple endpoints were investigated by subacute exposure to SDDC (0.01–100 mg/L) and micro-sized Cu, Pb chelates of SDDC (1–100 mg/L). Our data indicated that the LC50 value of SDDC was 139.39 mg/L (95% Cl: 111.03, 174.75 mg/L). In addition, SDDC was found that concentration of 1 mg/L is a safe limit value for nematode C. elegans, and concentration above 1 mg/L caused adverse effects on the survival, growth, locomotion behaviors and reactive oxygen species (ROS) production of exposed nematodes. Furthermore, all tested SDDC-Cu and SDDC-Pb chelates had obviously lower toxic effect than untreated Cu, Pb metals. These two chelates also had a lower toxic effect than SDDC agent due to its more stable structure. Moreover, SDDC-Cu had a higher toxic effect than SDDC-Pb at the same concentration. Thus, our results suggest that SDDC as a kind of chelating agent applied in harmless treatment of heavy metals, the safe addition limit should not be exceeded.
- Cai, Lankun,Hu, Yang,Khan, Asim,Liu, Fuwen,Wang, Yitian,Wu, Xiangyu,Xue, Cheng,Zhang, Han
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- The crystal structure, equilibrium and spectroscopic studies of bis(dialkyldithiocarbamate) copper(II) complexes [Cu2(R2dtc)4] (dtc=dithiocarbamate)
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Four copper(II) complexes of bis(dialkyldithiocarbamate) [Cd(R2dtc)2] (R=Me, Et, Pr, i-Pr; dtc=dithiocarbamate) have been prepared and characterized by elemental analysis, IR and ESR spectra studies. Their equilibrium constants (K), determined by a UV-vis spectrometry in EtOH, were influenced by the alkyl groups in the following order: i-Pr>n-Pr≈Et>Me. The single crystal structures of complex [Cu2(R2dtc)4] have been determined using X-ray diffraction methods. The compounds [Cu2(Et2dtc)4] and [Cu2(Pr2dtc)4] are built of centrosymmetric neutral dimeric [Cu2(R2dtc)4] entities. The copper atom lies in a distorted square-pyramidal environment. The four equatorial donors are two bidentate chelate sulfur atoms from two dtc ligands. One of the sulfur atoms from the third dtc ligand acts as a bridging ligand occupying the apical position of the symmetry-related copper atom in the dimer structure, which is viewed as two edge-sharing distorted square-pyramids. The structure of [Cu2(i-Pr2dtc)4] is square planar with an exactly planar CuS4 unit and nearly planar NCS2 moieties. The Cu-S distances shows small decreases along the series n-Pr>Et>i-Pr, the biggest change being for the diisopropyl complex. The alkyl substituents at the nitrogen atom affect their coordination number and CuCu distance. In the solid, [Cu2(n-Pr2dtc)4] has the shortest CuCu distance and [Cu(i-Pr2dtc)2] has the longest one. Elsevier Science Ltd.
- Jian, Fangfang,Wang, Zuoxiang,Bai, Zhiping,You, Xiaozeng,Fun, Hoong-Kun,Chinnakali, Kandasamy,Razak, Ibrahim Abdul
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p. 3401 - 3406
(2008/10/09)
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- Gas-phase electron diffraction study of bis(dimethyldithiocarbamato)copper(II), [Cu(S2CNMe2)2], and bis(dimethyldithiocarbamato)zinc(II), [Zn(S2CNMe2)2]
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The molecular structures of [Cu(S2CNMe2)2] and [Zn(S2CNMe2)2] have been studied by gas-phase electron diffraction. Both compounds are monomeric in the gas phase with the metal atoms being bound to two chelating [S2CNMe2] groups (rg(Cu-S) = 2.284 (9) ?; rg(Zn-S) = 2.348 (8) ?). The major difference between the two structures is in the geometry of the MS4 fragments, that of the copper compounds being pseudo square planar (D2h) while that of the zinc compound is pseudotetrahedral (D2d). The reason for the difference is attributed to the availability in the copper(II) compound of crystal field stabilization energy that is greater than the repulsive energy of the steric interactions imposed by the metal adopting a coordination sphere of D2h symmetry. Selected bond lengths and angles in the [S2CNMe2] groups are as follows (the data for the copper compound are quoted first with those for the zinc species being in brackets): rg(C-S) = 1.716 (10) ? [1.727 (10) ?]; rg(C=N) = 1.334 (18) ? [1.351 (17) ?]; rg(C-N) = 1.476 (18) ? [1.479 (17) ?]; ∠αS-M-S(chelate angle) = 78.78 (69)° [79.68 (59)°]; ∠αC=N-C = 124.9 (1.3)° [122.5 (1.2)°].
- Hagen, Kolbj?rn,Holwill, Catherine J.,Rice, David A.
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p. 3239 - 3242
(2008/10/08)
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- THE DIRECT ELECTROCHEMICAL SYNTHESIS OF DIALKYLDITHIOCARBAMATE AND DIETHYLDITHIOPHOSPHATE COMPLEXES OF MAIN GROUP AND TRANSITION METALS
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Dialkyldithiocarbamate derivatives (R2NCS2)nM of a number of metals (M=Fe, Co, Ni, Cu, Ag, Zn, Cd, In, Tl) have been synthesised in good yield by electrochemical oxidation of appropriate sacrificial anodes in non-aqueous solutions of either the corresponding tetraalkylthiuran disulphide (R2NCS2)2 (R=Me, Et) or a mixture of carbon disulphide plus the secondary amine R2NH (R=Et, i-Pr; R2NH=piperidine).Similar experiments with solutions of (EtO)2P(S)SH (=HL) gave MLn* derivatives (M=Fe, Co, Ni, Cu, Ag, Au, Zn, Cd, Hg, Ga, In, Tl) while in the presence of HL+1,10-phenanthroline, MLn.phen derivatives were obtained for M=V, Mn, Fe, Co, Zn, and Ga.
- Geloso, Corrado,Kumar, Rajesh,Lopez-Grado, Jaime Romero,Tuck, Dennis G.
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p. 928 - 932
(2007/10/02)
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- Magnetic and Structural Studies on Copper(II) Dialkyldithiocarbamates
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The magnetic susceptibilities of a series of copper(II) dialkyldithiocarbamates have been measured over the range 4-290 K, the alkyl groups being methyl, ethyl, isopropyl, and n-butyl.Contrary to a previous report of strong ferromagnetic interaction in the diethyl derivative, we find no evidence of any significant exchange interaction in this compound.The dimethyl and di-isopropyl analogues show weak antiferromagnetic interactions.Only the di-n-butyl derivative in the dialkyl series shows evidence of strong magnetic exchange interaction but of an antiferromagnetic nature; this effect is peculiar to the phase recrystallized from chloroform-light petroleum (α), the phase obtained from chloroform-ethanol (β) showing no such interaction.To seek the origin of the exchange interaction in the α derivative, its crystal structure has been determined by single-crystal X-ray diffraction methods at 295 K and refined by least squares to a residual 0.032 for 1976 'observed' reflections.Crystals are triclinic, P1, a=15.29(1), b=9.963(7), c=9.243(7) Angstroem, α=67.94(7), β=82.92(7), γ=71.55(7) deg, and Z=2.The copper environment is the usual pseudo-square-planar array of four sulphur atoms from two bidentate ligands (, 2.31 Angstroem), but there is a long fifth interaction S, 2.899(4) Angstroem> through the inversion centre leading to pseudo-dimer formation.Although similar to the diethyl analogue in this respect, differences are observed in regard to (a) the bridging geometry in the 'dimer' and (b) the proximity to the 'dimer' sulphur ligands of sulphur atoms from neighbouring dimers at ca. 3.8 Angstroem.The likely relative importance of these two features in determining the origin of the antiferromagnetic coupling is discussed.The structure of the β phase has also been determined, the final residual being 0.036 for 1324 'observed' reflections.Crystals are monoclinic, P21/n, a= 14.593(5), b= 7.840(2), c= 10.822(5) Angstroem, β= 101.55(3) deg, and Z= 2.The molecules are located with the copper atoms on crystallographic centres of symmetry, and the only significant intermolecular interactions observed are SH contacts.The CuS4 entity is planar with 2.30 Angstroem.
- Boyd, Peter D. W.,Mitra, Samaresh,Raston, Colin L.,Rowbottom, Graham L.,White, Allan H.
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