Theoretical and spectroscopic studies of lanthanum (III) complex of 5-aminoorotic acid

Kostova, Irena; Peica, N.; Kiefer, W.

doi:10.1016/j.chemphys.2006.05.029

Cited by 27 publications

(34 citation statements)

References 112 publications

(160 reference statements)

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“…The density-function calculations revealed that the mode of binding was bidentate through the carboxylic oxygen atoms. On the bases of our experimental spectral data and our theoretical investigations [58] we are able to suggest the most probable structural formula of the complex as presented in Fig. 5.…”

Section: Spectral Region 3500 -2000 CM -1mentioning

confidence: 96%

“…The metal-ligand binding mode of 5-aminoorotic acid was recently explained by us through modeling of the La(III)-5-aminoorotic acid structure [58]. It was suggested that 5-aminoorotic acid binds to the La(III) ion through both oxygen atoms of the carboxylic group from all three ligands, and the central ion La(III) is six-coordinated.…”

Section: Spectral Region 3500 -2000 CM -1mentioning

confidence: 98%

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New Lanthanum (III) Complex – Synthesis, Characterization, and Cytotoxic Activity

Kostova¹,

Rastogi

Kiefer

et al. 2006

Archiv der Pharmazie

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The complex of lanthanum (III) was synthesized reacting the respective inorganic salt with 5-aminoorotic acid in amounts equal to the metal:ligand molar ratio of 1:3. The complex was prepared by adding an aqueous solution of lanthanum (III) nitrate to an aqueous solution of the ligand, subsequently raising the pH of the mixture gradually to approx. 5.0 through addition of a dilute solution of sodium hydroxide. The structure of the final complex was determined by means of spectral data (IR, Raman,( 1)H-NMR) and elemental analysis. Significant differences in the IR spectrum of the complex were observed as compared to the spectrum of the ligand. A comparative analysis of the Raman spectrum of the complex with that of the free 5-aminoorotic acid allowed a straightforward assignment of the vibrations of the ligand groups involved in coordination. The ligand and the complex were tested for the cytotoxic activities on the chronic myeloid leukemia derived K-562, overexpressing the BCR-ABL fusion protein and the non-Hodgkin lymphoma derived DOHH-2, characterized by a re-expression of the anti-apoptotic protein bcl-2 cell lines. The results obtained indicate that the tested compounds exerted a considerable cytotoxic activity upon the evaluated cell lines in a concentration-dependent matter, which enabled the construction of dose-response curves and the calculation of the corresponding IC(50 )values. The inorganic salt exerted a very weak cytotoxic effect on these cells, which is in contrast to the lanthanum (III) complex.

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Section: Spectral Region 3500 -2000 CM -1mentioning

confidence: 96%

Section: Spectral Region 3500 -2000 CM -1mentioning

confidence: 98%

New Lanthanum (III) Complex – Synthesis, Characterization, and Cytotoxic Activity

Kostova¹,

Rastogi

Kiefer

et al. 2006

Archiv der Pharmazie

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“…26 This combination is the most effective level of theory available for the analysis of metallic systems; several applications have already been reported. 27 Molecular geometries were fully optimized by Benny's optimization algorithm using redundant internal coordinates. All optimized structures were confirmed to be of the minimum energy conformation.…”

Section: Computational Detailsmentioning

confidence: 99%

FT‐Raman, IR and UV‐visible spectral investigations and ab initio computations of a nonlinear food dye amaranth

Snehalatha¹,

Ravikumar²,

Sekar

et al. 2008

J Raman Spectroscopy

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Amaranth (E123, Food Red 9, FD & C Red 2) is a sulfonated azo dye used as a color additive in foodstuffs, pharmaceuticals and cosmetics. FT-IR and FT-Raman spectra of amaranth were recorded and analyzed. Density functional theory (DFT) calculations were performed to derive the equilibrium geometry, vibrational wavenumbers, intensities and first hyperpolarizability. The results of the optimized molecular structure gave clear evidence for the intramolecular charge transfer (ICT) and intramolecular hydrogen bonding in the molecule. Azo stretching wavenumbers are lowered owing to conjugation and p-electron delocalization. Time-dependent density functional theory (TD-DFT) calculations of the electronic spectra were performed on the optimized structure and compared with the experimental UV-visible spectrum. Vibrational spectra, natural bonding orbitals (NBO) analysis and optimized geometry indicate C-H· · ·N hydrogen bonding in the molecule. The first hyperpolarizability of the molecule was calculated. The optical nonlinearity of the dye is due to the donation of the electron density from the hydroxyl group of the conjugated system via naphthalene (2) ring into p * -orbital of the azo moiety.

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“…We recently discussed the geometry optimization of La(III) complex of H 4 L in terms of the nature of the bonding and the possible structural types. 91 Through our DFT calculations with different bases, H 4 L is seen to coordinate to the lanthanum ion as a dianion and the complex contains three 5-aminoorotic ligands. 91 -93 H 4 L, as a derivative of orotic acid, usually can act as a bidentate dianionic ligand chelating to one metal ion through the deprotonated carboxylic group and the adjacent nitrogen atom.…”

Section: Vibrational Spectroscopymentioning

confidence: 99%

“…92,93,96 The La(III) ion is quite symmetrically sixcoordinated, with bonds to each of the two oxygen atoms from the carboxylate groups of the 5-aminoorotate ligands. 91 We suppose that the coordination polyhedron of the central atom in the Ce(III) and Nd(III) complexes of H 4 L is a distorted octahedron in the same way as for the La(III) complex of H 4 L, because of the similar properties of Ln(III). 91 The carboxylate groups exhibit bidentate coordination; the Ce(III) and Nd(III) complexes of H 4 L formed in this way are mononuclear and each local coordination unit around the metal ion contains one 5-aminoorotate ligand.…”

Section: Vibrational Spectroscopymentioning

confidence: 99%

Theoretical and spectroscopic studies of 5‐aminoorotic acid and its new lanthanide(III) complexes

Kostova

Peica

Kiefer

2006

J Raman Spectroscopy

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The complexes of cerium(III) and neodymium(III) were synthesized by reaction of the respective inorganic salts with 5-aminoorotic acid (H 4 L) in amounts equal to the metal : ligand molar ratio of 1 : 3. The structures of the final complexes were determined by means of spectral (IR, Raman, 1 H NMR and 13 C NMR) and elemental analysis. Significant differences in the IR spectra of the complexes were observed as compared to the spectrum of the ligand. A comparative analysis of the Raman spectra of the complexes with that of the free H 4 L allowed a straightforward assignment of the vibrations of the ligand groups involved in coordination. The geometry of H 4 L was computed and optimized for the first time with the Gaussian03 program using the B3PW91/6-311++G * * , B3PW91/LANL2DZ, B3LYP/6-311++G * * and B3LYP/LANL2DZ methods. The experimental IR and Raman bands of the ligand were assigned to normal modes on the basis of DFT calculations. The vibrational analysis performed for the studied species, H 4 L and its complexes, helped to explain the vibrational behavior of the ligand vibrational modes sensitive to interaction with the lanthanides. The vibrational study gave evidence for the coordination mode of the ligand to lanthanide ions and was in agreement with the other theoretical prediction.

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Theoretical and spectroscopic studies of lanthanum (III) complex of 5-aminoorotic acid

Cited by 27 publications

References 112 publications

New Lanthanum (III) Complex – Synthesis, Characterization, and Cytotoxic Activity

New Lanthanum (III) Complex – Synthesis, Characterization, and Cytotoxic Activity

FT‐Raman, IR and UV‐visible spectral investigations and ab initio computations of a nonlinear food dye amaranth

Theoretical and spectroscopic studies of 5‐aminoorotic acid and its new lanthanide(III) complexes

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