Ethylenediamine-<i>N</i>,<i>N</i>′-diacetic acid complexes with divalent manganese, zinc, cadmium, and lead: a thermodynamic study

Gualtieri, Roberto; Powell, H. K. J.

doi:10.1139/v79-018

Cited by 13 publications

(8 citation statements)

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“…The resulting stability constants are presented in Table and serve to correct those originally calculated in ref with the misidentified ligand. The results are compared to literature values for EDDA and demonstrate that DEDA-(PO) follows the expected trend in stability across the series (Ca 2+ < Zn 2+ < Cu 2+ ). ,, Complex formation with Cu 2+ was further examined qualitatively by pH-dependent UV–vis spectrophotometry (Figure ), and the results fully support the corresponding speciation diagram (Figure ). The 1:1 complex [Cu(DEDA-(PO))OH 2 ] − begins to form above approximately pH 1.5, as indicated by an increase in the absorbance of the d–d absorption band to λ max = 670 nm in the UV–vis spectra (Figure a).…”

Section: Resultssupporting

confidence: 62%

“…The results are compared to literature values for EDDA and demonstrate that DEDA-(PO) follows the expected trend in stability across the series (Ca 2+ < Zn 2+ < Cu 2+ ). 14,16,24 Complex formation with Cu 2+ was further examined qualitatively by pHdependent UV−vis spectrophotometry (Figure 4), and the results fully support the corresponding speciation diagram (Figure 5). From the titrations performed thus far (and from the literature) 14−17 pM values at pH 7.4 were calculated for EDDA and DEDA-(PO) with the trivalent lanthanide and divalent metal ions (Table 4).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“… a From ref (25 °C and I = 0.1 M KNO 3 ). b From ref (30 °C and I = 0.1 M KNO 3 ). c From ref (25 °C and I = 0.1 M KNO 3 ). …”

Section: Resultsmentioning

confidence: 99%

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Di- and Trivalent Metal-Ion Solution Studies with the Phosphinate-Containing Heterocycle DEDA-(PO)

et al. 2017

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A 7-membered triprotic heterocycle, DEDA-(PO), was synthesized, characterized, and tested for its solution properties with three trivalent lanthanides (La, Gd, and Lu) and three biologically relevant divalent metal ions (Ca, Zn, and Cu). The ligand synthesis has been reported once before; however, the characterization results were previously misinterpreted to correspond to a larger, 14-membered heterocycle, TETA-(PO). This manuscript serves to correct the original paper. Potentiometric titrations were carried out with each of the metal ions, and the thermodynamic stability values in terms of log β and log K were calculated showing a 1:1 metal-to-ligand ratio preference for the divalent metal ions and a 1:2 ratio for the lanthanides. The stability of the 1:2 complexes decreased across the lanthanide series, presumed to be a steric effect. Further resolution to the potentiometry results was given via pH-dependent NMR spectrometry (with La) and pH-dependent UV-vis spectroscopy (with Cu), and the pM values were calculated for all metal ions. The solid-state structure of the 1:1 Cu-DEDA-(PO) complex was further characterized by X-ray crystallography.

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Section: Resultssupporting

confidence: 62%

Section: ■ Results and Discussionmentioning

confidence: 99%

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Di- and Trivalent Metal-Ion Solution Studies with the Phosphinate-Containing Heterocycle DEDA-(PO)

et al. 2017

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“…Comparison of the stability constants for lysinoalanine and ethylenediaminediacetic acid (EDDA) complexes of divalent metal ions. The data for EDDA are from Martell and Smith (1974,1982), Gualtieri et al (1979), and Ewin and Hill (1983). This plot can be used to predict LAL binding constants for other metal ions from known values for EDDA.…”

Section: Methodsmentioning

confidence: 99%

Binding of copper(II) and other metal ions by lysinoalanine and related compounds and its significance for food safety

Pearce¹,

Friedman²

1988

J. Agric. Food Chem.

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Acid-base equilibrium constants for the five ionizable groups and metal ion (Ca2+, Mn2+, Fe2+, Co2+, Ni2+, Cu+, Cu2+, Zn2+, Cd2+, Hg2+) binding constants of 7V'-(2-amino-2-carboxyethyl)-L-lysine (lysinoalanine, LAL) have been determined at 25 °C and 0.16 M ionic strength by potentiometric titration.Less extensive data are reported for the related compounds DL-2,3-diaminopropanoic acid (DAPA), 3-[(2-phenylethyl)amino]-DL-alanine (PEAA), and L-lanthionine (LAN), three other unnatural amino acids also formed during food processing. These unnatural amino acids are sufficiently strong chelators to influence copper transport by histidine in vivo at plasma levels of 49 µ LAL, 23 µ DAPA, 243 µ PEAA, and 511 µ LAN. Relatively high concentrations of these compounds are calculated to be necessary for competitive binding of essential zinc ions and inactivation of carboxypeptidase A and other enzymes. Possible mechanisms for kidney damage by these dehydroalanine-derived copper chelators are discussed.

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“…The pK a value is rather low for a -2 charged complex (typical pK a values range between 8 and 10 positively charged complexes and are usually above 10 for neutral or -1 charged complexes). [72][73][74][75] Correlations of Properties in GSSG Analogs. Similarly to the case of protonation equilibria, a deeper understanding of Zn(II)-GSSG complexes can be gained from the analysis of tendencies in the series of Zn(II) complexes of disulfide analogs studied.…”

Section: Discussionmentioning

confidence: 99%

Zn(II) Complexes of Glutathione Disulfide: Structural Basis of Elevated Stabilities

et al. 2010

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Glutathione disulfide (GSSG), a long disregarded redox partner of glutathione (GSH), is thought to participate in intracellular zinc homeostasis. We performed a concerted potentiometric and NMR spectroscopic study of protonation and Zn(II) binding properties of GSSG ((γECG)(2)) and a series of its nine analogs with C-terminal modifications, tripeptide disulfides: (γECS)(2), (γECE)(2), (γECG-NH(2))(2), (γECG-OEt)(2), and (γEcG)(2); dipeptide disulfides, (γEC)(2) and (γEC-OEt)(2); and mixed disulfides, γECG-γEC and γECG-γEC-OEt. The acid-base and Zn(II) complexation properties in this group of compounds are strictly correlated to average C-terminal electrostatic charges. In particular, it was demonstrated that GSSG assumes a bent (head-to-tail) conformation in solution at neutral pH, which is controlled by electrostatic attraction between the protonated γ-amino groups of the Glu residue and the deprotonated C-terminal Gly carboxylates. This interaction modulates the ability of GSSG to coordinate Zn(II), both indirectly, by affecting the basicities of the amino groups, and directly, through the participation of the Gly carboxylates in the outer coordination sphere of the Zn(II) ion. A specific coiled structure of the major [Zn-GSSG](2-) complex is additionally stabilized by the formation of hydrogen bonds between glycinyl carboxylates and two Zn(II)-coordinated water molecules. The elevated stability of Zn(II)-GSSG complexes was demonstrated by competition with FluoZin-3, a fluorescent sensor with high Zn(II) affinity, commonly used in in vitro and in vivo studies. The potential biological functions and reactivity of GSSG complexes of Zn(II) ions are discussed.

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Ethylenediamine-N,N′-diacetic acid complexes with divalent manganese, zinc, cadmium, and lead: a thermodynamic study

Cited by 13 publications

References 1 publication

Di- and Trivalent Metal-Ion Solution Studies with the Phosphinate-Containing Heterocycle DEDA-(PO)

Di- and Trivalent Metal-Ion Solution Studies with the Phosphinate-Containing Heterocycle DEDA-(PO)

Binding of copper(II) and other metal ions by lysinoalanine and related compounds and its significance for food safety

Zn(II) Complexes of Glutathione Disulfide: Structural Basis of Elevated Stabilities

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