Electrochemical properties of copper complexes with unsubstituted and substituted 1,10-o-phenanthrolines in N,N-dimethylformamide solvent

Pilo, Maria Itria; Manca, G; Zoroddu, M. A.; Seeber, Renato

doi:10.1016/s0020-1693(00)84936-1

Cited by 23 publications

(9 citation statements)

References 10 publications

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“…The oxidation potentials of copper(I) systems are sensitive to the steric crowding about the metal center. It has been found that substituents at the α-carbon positions in 1,10-phenanthroline ligands tend to stabilize the copper(I) state increasing the oxidation potential for [Cu(L) 2 ] + complexes …”

Section: Discussionmentioning

confidence: 99%

Spectroelectrochemical Studies of Copper(I) Complexes with Binaphthyridine and Biquinoline Ligands. Crystal Structure Determination of Bis(6,7-dihydrodipyrido[2,3-b:3‘,2‘-j][1,10]phenanthroline)copper(I) Tetrafluoroborate

1996

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The electrochemical and spectral properties of some copper(I) polypyridyl complexes based on 6,7-dihydrodibenzo[b,j][1,10]phenanthroline, dmbiq, and 6,7-dihydrodipyrido[2,3-b:3',2'-j][1,10]phenanthroline, dmbinap, are reported. These complexes are [Cu(dmbiq)(2)](+), 1; [Cu(dmbiq)(PPh(3))(2)](+), 2; [Cu(dmbinap)(2)](+), 3; and [Cu(dmbinap)(PPh(3))(2)](+), 4. 3 and 4 may be reduced to form ligand-based radical anion species. The resonance Raman spectra of 3(*)()(-)() and 4(*)()(-)() are almost identical and correspond closely to the spectrum of dmbinap(*)()(-)() and the reported spectra of complexes containing 2,2'-biquinoline radical anion moieties. Reduction processes for 1 and 2 are irreversible. For 1 the electronic spectral changes arising from reduction suggest demetallation of the complex. The structure of [Cu(C(18)H(12)N(4))(2)][BF(4)].CH(2)Cl(2) (3[BF(4)].CH(2)Cl(2)) was determined by single-crystal X-ray diffraction. It crystallized in the monoclinic space group P2(1)/c with cell dimensions a = 14.059(7) Å, b = 15.058(6) Å, c = 16.834(9) Å, beta = 111.56(5) degrees, Z = 4, rho(calcd) = 1.611 g/cm(3), and R(F(o)) = 0.0497.

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Section: Discussionmentioning

confidence: 99%

Spectroelectrochemical Studies of Copper(I) Complexes with Binaphthyridine and Biquinoline Ligands. Crystal Structure Determination of Bis(6,7-dihydrodipyrido[2,3-b:3‘,2‘-j][1,10]phenanthroline)copper(I) Tetrafluoroborate

1996

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“…In general, the c.v.s are typical of an-N 4 macrocyclic copper complex (x 5, 16). Salient features of the data obtained in acetonitrile are discussed first.…”

Section: Electronic Absorption Spectramentioning

confidence: 91%

Cyclic voltammetric and e.s.r. studies of a tetraaza 14-membered macrocyclic copper(II) complex derived from 3-salicylideneacetylacetone ando-phenylenediamine: stabilization and activation of unusual oxidation states

Jeyasubramanian

Samath

Thambidurai

et al. 1995

Transition Met Chem

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A 14-membered macrocyclic Schiff base derived from 3-salicylideneacetylacetone and o-phenylenediamine acts as a tctradentate and strongly conjugated ligand to form a cationic solid complex with CuC12. U.v.-vis. and e.s.r. spectral data reveal a strong ligand to metal 7z-interaction in the square planar complex. C.v. data reveal that the title ligand is able to stabilize the copper(III) oxidation state more cffectivcly than comparable saturated or partially unsaturated macrocyclic ligands and confers a weaker tendency for reduction of copper(II) to copper(I) and copper(0). While the inclusion of a PPh 3 ligand suppresses the Cu ~ -, Cu j -, Cu u oxidation, imidazole and pyridinc strongly enhance the Cu ~I ~ Cu ~II oxidation ofthc complex.

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“…The complexes were prepared according to literature procedures used for Cu-phen complexes: ,− Details are given in the Supporting Information section.…”

Section: Methods and Determination Of Binding Constantsmentioning

confidence: 99%

“…Complexes containing phen have been reported to bind DNA by intercalative and nonintercalative interactions, either as free ligands or included in metal complexes. ,,, Overall, they have been mostly proposed as agents for binding, cleavage, and oxidative modification of DNA ,,− and many of them depict cytotoxic activity against several cancer and noncancer cells. ,− DNA has often been suggested as one of the main targets for this class of Cu complexes, and several mechanisms have been suggested. ,, The activities of phen, [Cu(phen) 2 ] 2+ , and CuC1 2 on Ehrlich ascites tumor cells, their membrane permeability, and DNA cleavage activity were compared in a relevant work by Byrnes and co-workers . Both DNA damage and cytotoxicity were observed with cells treated with [Cu(phen) 2 ] 2+ , possibly due to multiple mechanisms of oxidative damage.…”

Section: Introductionmentioning

confidence: 99%

Copper Complexes with 1,10-Phenanthroline Derivatives: Underlying Factors Affecting Their Cytotoxicity

et al. 2020

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The interpretation of in vitro cytotoxicity data of Cu(II)-1,10-phenanthroline (phen) complexes normally does not take into account the speciation that complexes undergo in cell incubation media and its implications in cellular uptake and mechanisms of action. We synthesize and test the activity of several distinct Cu(II)-phen compounds; up to 24 h of incubation, the cytotoxic activity differs for the Cu complexes and the corresponding free ligands, but for longer incubation times (e.g., 72 h), all compounds display similar activity. Combining the use of several spectroscopic, spectrometric, and electrochemical techniques, the speciation of Cuphen compounds in cell incubation media is evaluated, indicating that the originally added complex almost totally decomposed and that Cu(II) and phen are mainly bound to bovine serum albumin. Several methods are used to disclose relationships between structure, activity, speciation in incubation media, cellular uptake, distribution of Cu in cells, and cytotoxicity. Contrary to what is reported in most studies, we conclude that interaction with cell components and cell death involves the separate action of Cu ions and phen molecules, not [Cu(phen) n ] species. This conclusion should similarly apply to many other Cu-ligand systems reported to date.

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Electrochemical properties of copper complexes with unsubstituted and substituted 1,10-o-phenanthrolines in N,N-dimethylformamide solvent

Cited by 23 publications

References 10 publications

Spectroelectrochemical Studies of Copper(I) Complexes with Binaphthyridine and Biquinoline Ligands. Crystal Structure Determination of Bis(6,7-dihydrodipyrido[2,3-b:3‘,2‘-j][1,10]phenanthroline)copper(I) Tetrafluoroborate

Spectroelectrochemical Studies of Copper(I) Complexes with Binaphthyridine and Biquinoline Ligands. Crystal Structure Determination of Bis(6,7-dihydrodipyrido[2,3-b:3‘,2‘-j][1,10]phenanthroline)copper(I) Tetrafluoroborate

Cyclic voltammetric and e.s.r. studies of a tetraaza 14-membered macrocyclic copper(II) complex derived from 3-salicylideneacetylacetone ando-phenylenediamine: stabilization and activation of unusual oxidation states

Copper Complexes with 1,10-Phenanthroline Derivatives: Underlying Factors Affecting Their Cytotoxicity

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