Platinum and palladium complexes of 3-methyl orotic acid: A route toward palladium complexes with good antitumor activity

Castan, Paule; Colacio-Rodríguez, E.; Beauchamp, André L.; Cros, S.; Wimmer, Smita

doi:10.1016/0162-0134(90)84015-h

Cited by 79 publications

(31 citation statements)

References 37 publications

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“…Aside from the Ł Correspondence to: Irena Kostova, Department of Chemistry, Faculty of Pharmacy, Medical University, 2 Dunav St., Sofia 1000, Bulgaria. E-mail: irenakostova@yahoo.com significance of orotic acid and its derivatives in biological systems, 3 these compounds possess a fascinating coordination behavior with potential hydrogen-bonding interactions, such as asymmetric geometry and multiple coordination sites. 4 However, previous studies on the coordination chemistry of orotic acid mainly focused on transition metals 5 -8 or alkali metals; 9 the lanthanides have been neglected.…”

Section: Introductionmentioning

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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Section: Introductionmentioning

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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“…13 In several copper(II) and palladium(II) complexes of orotic acid and its derivatives, mono-, di-and full deprotonation occurred, showing the multiplicity of the binding sites. 14,15 Two groups of workers 16,17 have also reported on the antitumor activity of platinum(II) and palladium(II) orotates and 3-methylorotates.…”

Section: Introductionmentioning

confidence: 99%

Organometallic complexes with biological molecules. X: dialkyltin(IV) and trialkyltin(IV) orotates: spectroscopic andin vivo investigations

Lencioni

Pellerito

Fiore

et al. 1999

Appl. Organometal. Chem.

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Several novel diorgano‐ and triorgano‐tin(IV) derivatives of orotic acid, (2,6‐dihydroxypyrimidine‐4‐carboxylic acid; H3or) have been synthesized. In the diorganotin(IV) derivatives, the orotic acid behaved either as a monoanionic or as a dianionic ligand, yielding R2Sn(H2or)2 and R2SnHor (R = Me, Bu) species, respectively, while in the triorganotin(IV) orotates only monodeprotonation of the orotic acid occurred, giving R3SnH2or (R = Me, Bu) derivatives. Structural hypotheses are proposed and discussed for the solid state based on Mössbauer and IR spectroscopic data, and for solution on 1H and 13C NMR results. Finally, investigations have been carried out in vivo, showing the inhibitor properties of all of the newly synthesized derivatives towards Ciona intestinalis embryos. In particular, in order to test the cytotoxicity in vivo of Me2SnHor, Bu2SnHor, Me3SnH2or and Bu3SnH2or, exposure to these chemicals of C. intestinalis embryos at the 2–4‐blastomere stage has been studied. The compound which exerts the highest cytotoxic effect is Bu3SnH2or at 10−5 M concentration because it blocks embryo development immediately. Me3SnH2or at 10−5 M concentration inhibits cell cleavage in the embryos at the 32‐blastomere stage, while Bu2SnHor at the same concentration gives rise to abnormal embryos. Me2SnHor, is less toxic than the trimethyl, dibutyl and tributyl analogues, since 40% of the total number of treated embryos resulted in normal larvae. The ligand does not affect embryonic development significantly. The results seem to indicate that the chemical species under investigation, especially Bu3SnH2or, interfere with polymerization of tubulin during the process of cell division in early embryo development. Copyright © 1999 John Wiley & Sons, Ltd.

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“…The reaction therefore of rhenium with versatile ligands may lead to interesting and unexpected coordination compounds, and to this end we have focussed on 5-aminoorotic acid (2,6-dioxo-5-amino-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid; H 2 aor) as a possible ligand for rhenium (V). Metal complexes of orotic acid and its derivatives have been found to display anti-tumour activity [2]. Orotate as a ligand may coordinate to metals via its four oxygen and two nitrogen atoms, leading to a total of 12 different coordination modes in mono-and poly-nuclear complexes [3].…”

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confidence: 99%

Decarboxylation of 5-amino-orotic acid and a Schiff base derivative by rhenium(V)

Mukiza

Gerber

Hosten

2015

Inorganic Chemistry Communications

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Platinum and palladium complexes of 3-methyl orotic acid: A route toward palladium complexes with good antitumor activity

Cited by 79 publications

References 37 publications

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

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

Organometallic complexes with biological molecules. X: dialkyltin(IV) and trialkyltin(IV) orotates: spectroscopic andin vivo investigations

Decarboxylation of 5-amino-orotic acid and a Schiff base derivative by rhenium(V)

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