Linear free energy relationships for proton dissociation and metal complexation of pyrimidine acids

Tucci, Edmond R.; Ke, C.H.; Li, N.C.

doi:10.1016/0022-1902(67)80209-4

Cited by 22 publications

(4 citation statements)

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“…Linear free energy relationships for proton dissociation and metal complexation have been evidenced for the pyrimidine-acid systems (35) and have also been reported in the literature for various aromatic or aliphatic systems. In water, the acidity constants of orotic acid are pK 1 = 2.07 and pK 2 = 9.45 with pK 1 corresponding to COOH and pK 2 to NH deprotonations.…”

Section: Solution Studiessupporting

confidence: 60%

“…Relationships between complexation sites of pyrimidine derivatives and UV data have been reported in the past and one may note that the UV spectra predict the sites of deprotonation and then those of coordination (35)(36)(37); this was the case with copper and nickel complexes of orotic acid (38) for which the complexation induced a significant bathochromic shift of the ligand absorption band (λ max = 316 nm versus 285 nm for the free ligand) correlated to complexation at the carboxylic group and adjacent endocyclic nitrogen atom.…”

Section: Solution Studiesmentioning

confidence: 89%

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Crystal structure, spectroscopic and magnetic studies, and antioxidative properties of catena-[diaqua(dihydro-orotato)manganese(II)]

Castan¹,

Viala²,

Fabre³

et al. 1998

Can. J. Chem.

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The polynuclear manganese(II) complex of L-dihydroorotic acid has been synthesized and characterized by X-ray crystallography, UV-visible spectroscopy, and magnetic susceptibility measurements. Crystal data: triclinic, space group P1 _ , a = 4.7239 (5) D, b = 7.902(1) D, c = 10.552(2) D, α = 105.80(1)°, β = 98.864(7)°, γ = 104.69(1)°, V = 355.9(1) D 3 , Z = 1, R = 0.035, Rw = 0.028. This complex consists of polymer chains of manganese atoms that are bound together via carboxylate bridges with a Mn⋅⋅⋅Mn distance in the chain of 4.724 D. The radical scavenging properties of the complex have been evaluated by ESR spectroscopy and cyclic voltammetry methods and compared to those of vitamin E and BHT (2,6-di-tert-butyl-4-methylphenol). Résumé : Le complexe du manganèse(II) et de l'acide L-dihydroorotique a été synthétisé et caractérisé par spectroscopie UV-visible, susceptibilité magnétique et par diffraction des rayons X. Données cristallographiques : triclinique, groupe d'espace P1 _ , a = 4.7239(5) D, b = 7.902(1) D, c = 10.552(2) D, α = 105.80(1)°, β = 98.864(7)°, γ = 104.69(1)°, V = 355.9(1) D 3 , Z = 1, R = 0.035, Rw = 0.028. Ce complexe se présente comme une chaine polymérique d'atomes de manganèse liés entre eux par des ponts carboxylate, la distance Mn⋅⋅⋅Mn étant de 4.724 D. Les propriétés antioxydantes de ce composé ont été évaluées par RPE et voltammétrie cyclique et comparées à celles de la vitamine E et du BHT (2,6-di-tert-butyl-4-methylphenol).Mots clés : acide orotique, acide L-dihydroorotique, complexe du manganèse(II), propriétés antioxydantes.

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Section: Solution Studiessupporting

confidence: 60%

Section: Solution Studiesmentioning

confidence: 89%

Crystal structure, spectroscopic and magnetic studies, and antioxidative properties of catena-[diaqua(dihydro-orotato)manganese(II)]

Castan¹,

Viala²,

Fabre³

et al. 1998

Can. J. Chem.

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“…However, there is no study comparing those organic compounds, although both are approved supplements. Zinc aspartate is less stable than zinc orotate (log 10 K Zn aspartate = 2.9, log 10 K Zn orotate = 6.42) [75,76], and therefore might provide more absorbable zinc ions. Other chemical factors affecting a substance's bioavailability in addition to its stability: there are, for example, its solubility in water, the charge density, its reduction potential, the environmental pH and the formation of complexes.…”

Section: Influences On Zinc Bioavailability and Functions In Experimementioning

confidence: 99%

Parameters Influencing Zinc in Experimental Systems in Vivo and in Vitro

Ollig

Kloubert

Weßels

et al. 2016

Metals

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Abstract:In recent years, the role of zinc in biological systems has been a subject of intense research. Despite wide increase in our knowledge and understanding of zinc homeostasis, numerous questions remain to be answered, encouraging further research. In particular, the quantification of intracellular zinc ions and fluctuation, as well as the function of zinc in signaling processes are being intensely investigated. The determination of free intracellular zinc ions is difficult and error-prone, as concentrations are extremely low (in the pico-to nanomolar range), but techniques exist involving fluorescent probes and sensors. In spite of zinc deficiency being accepted as a global problem, causing death and disease worldwide, to date there are no markers to reliably assess a person's zinc status. This review summarizes the difficulties and major pitfalls when working with zinc in in vitro and in vivo research. Additionally, it specifies important aspects for zinc substitution and supplementation, including the bioavailability of zinc and its intestinal absorption. In particular, it is intended to help researchers with yet minor experience working with zinc efficiently set up experiments and avoid commonly occurring mistakes, starting with the choice and preparation of reagents and instrumentation, and concluding with possibilities for measuring the status of zinc in humans.

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“…Owing to biological interest in orotic acid complexes, several investigators have focused attention on the coordinating properties of the acid. It was found that, in neutral or slightly acidic pH, Cu(II), Zn(II), Co(II), Mn(II), Fe(III), Cr(III), VO(II), Cd(II), Hg(II) and Ag(I) complexes, the acid can coordinate through the carboxylate group, while in Ni(II), Co(II) and Cu(II) complexes it coordinates through the carboxylate and the adjacent N(3) [10][11][12][13][14]. The crystal structure determination of the complexes confirmed the bidentate coordination of orotic acid through N(3) and the carboxylate group [15][16][17][18][19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

Novel Cobalt(II), Nickel(II) and Copper(II) Complexes of Neutral Orotic Acid. Synthesis, Spectroscopic and Thermal Studies

Yeşılel

Ölmez

2005

Transition Met Chem

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The new orotic acid complexes, [MCl 2 (H 2 O) 3 (H 3 Or)], M ¼ Co(II), Ni(II) and [CuCl 2 (H 2 O)(H 3 Or) 3 ] AE H 2 O, were synthesized and characterized by elemental analysis, magnetic susceptibility, spectral (Diffuse reflectance UV-Vis and FTIR) methods, and simultaneous thermal analysis (TG, DTG and DTA) techniques. Physical measurements indicate that the neutral orotic acid ligands are bonded to metal ions through the carbonyl groups. Two thermal processes of the complexes can occur: dehydration and pyrolytic decomposition. On the basis of the DTG max , the thermal stability of the complexes follows the order: Co(II) (122°C) > Cu(II) (77°C) > Ni(II) (66°C).

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Linear free energy relationships for proton dissociation and metal complexation of pyrimidine acids

Cited by 22 publications

References 28 publications

Crystal structure, spectroscopic and magnetic studies, and antioxidative properties of catena-[diaqua(dihydro-orotato)manganese(II)]

Crystal structure, spectroscopic and magnetic studies, and antioxidative properties of catena-[diaqua(dihydro-orotato)manganese(II)]

Parameters Influencing Zinc in Experimental Systems in Vivo and in Vitro

Novel Cobalt(II), Nickel(II) and Copper(II) Complexes of Neutral Orotic Acid. Synthesis, Spectroscopic and Thermal Studies

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