A comparison between the chelating properties of some dihydroxamic acids, desferrioxamine B and acetohydroxamic acid

Farkas, Etelka; Enyedy, Éva A.; Csóka, Hajnalka

doi:10.1016/s0277-5387(99)00144-8

Cited by 123 publications

(128 citation statements)

References 14 publications

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“…The pK a values measured in these three titrations were not discernibly different from those measured in the other six, showing as expected that the presence of MSA − , in itself, had no effect on the pH of the solution. The 9 titrations together yield an average value of pK a = 9.257 ± 0.008 (Table 5), in beautiful agreement with published measurements of 9.35 in 0.1 M NaNO 3 (Anderegg et al, 1963) and 9.27 ± 0.01 in 0.2 M KCl (Farkas et al, 1999). Unlike the large, linear DFOB molecule (Christenson and Schijf, 2011), equilibrium constants for the small HAH molecule should display Debije-Hückel-like behavior and the value of pK a does indeed seem to decrease with increasing ionic strength.…”

Section: Stability Constants Of Mg−msa and Ca−msa Complexessupporting

confidence: 87%

“…For Ca, only the Ca(AH) + complex was needed to produce good fits (WSOS/DF < 1.2). Values of log AH β 1 were determined to be 2.30 ± 0.03 and 2.25 ± 0.01 in the absence and presence of MSA − , respectively (Table 5), comparing favorably with literature values of 2.4 at I = 0.1 (Anderegg et al, 1963) and 2.45 ± 0.01 at I = 0.2 (Farkas et al, 1999). The value of log MSA β 1 , calculated from these averages with Equation (6), is equal to −0.005 (Table 5), but could be as high as 0.2 or as low as -0.4 within the uncertainty of the measurements.…”

Section: Stability Constants Of Mg−msa and Ca−msa Complexessupporting

confidence: 79%

“…Stability constants, log SO4 β 1 , of the Mg-sulfate and Casulfate complex are 1.01 and 1.03, respectively, at I = 0.7 (Millero and Schreiber, 1982), whereas previous estimates of the stability constant, log L β 3 of the hexadentate Mg-DFOB and Ca-DFOB complex are about 3-4 (Farkas et al, 1999). In this case, DFOB may be a no more than three orders of magnitude stronger ligand than MSA − (Tables 5, 8).…”

Section: Stability Constants Of Mg−msa and Ca−msa Complexesmentioning

confidence: 61%

“…While the authors provide no details of the calculation, their SRC is ostensibly expressed in terms of fully deprotonated DFOB, a species that is virtually nonexistent in seawater and does not form any complex with most metals. They moreover used data of Farkas et al (1999), whose regression model does incorporate a spurious complex with the fully deprotonated ligand, probably accounting for the fact that no stability constants were reported for the bidentate Mg-DFOB and Ca-DFOB complex (see the discussion in Schijf et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

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Determination of the Side-Reaction Coefficient of Desferrioxamine B in Trace-Metal-Free Seawater

Schijf

Burns

2016

Front. Mar. Sci.

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Electrochemical techniques like adsorptive cathodic stripping voltammetry with competitive ligand equilibration (ACSV-CLE) can determine total concentrations of marine organic ligands and their conditional binding constants for specific metals, but cannot identify them. Individual organic ligands, isolated from microbial cultures or biosynthesized through genomics, can be structurally characterized via NMR and tandem MS analysis, but this is tedious and time-consuming. A complementary approach is to compare known properties of natural ligands, particularly their conditional binding constants, with those of model organic ligands, measured under suitable conditions. Such comparisons cannot be meaningfully interpreted unless the side-reaction coefficient (SRC) of the model ligand in seawater is thoroughly evaluated. We conducted series of potentiometric titrations, in non-coordinating medium at seawater ionic strength (0.7 M NaClO 4 ) over a range of metal:ligand molar ratios, to study complexation of the siderophore desferrioxamine B (DFOB) with Mg and Ca, for which it has the highest affinity among the major seasalt cations. From similar titrations of acetohydroxamic acid in the absence and presence of methanesulfonate (mesylate), it was determined that Mg and Ca binding to this common DFOB counter-ion is not strong enough to interfere with the DFOB titrations. Stability constants were measured for all DFOB complexes with Mg and Ca including, for the first time, the bidentate complexes. No evidence was found for Mg and Ca coordination with the DFOB terminal amine. From the improved DFOB speciation, we calculated five SRCs for each of the five (de)protonated forms of DFOB in trace-metal-free seawater, yet we also present a more convenient definition of a single SRC that allows adjustment of all DFOB stability constants to seawater conditions, no matter which of these forms is selected as the "component" (reference species). An example of Cd speciation in seawater containing DFOB illustrates the non-trivial use of different SRCs for polyprotic, polydentate organic ligands.

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Section: Stability Constants Of Mg−msa and Ca−msa Complexessupporting

confidence: 87%

Section: Stability Constants Of Mg−msa and Ca−msa Complexessupporting

confidence: 79%

Section: Stability Constants Of Mg−msa and Ca−msa Complexesmentioning

confidence: 61%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Determination of the Side-Reaction Coefficient of Desferrioxamine B in Trace-Metal-Free Seawater

Schijf

Burns

2016

Front. Mar. Sci.

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“…Some hydroxamic acids and their derivatives with biological activities, such as anti-inflammatory and anti-asthmatic, are used as pesticides and plant growth promoters [22]. In addition, hydroxamic acids could chelate with metal ions to form complexes [23,24]. Thus, hydroxamic acid derivatives have already been reported as effective corrosion inhibitors for carbon steel and copper corrosion [25][26][27].…”

Section: Introductionmentioning

confidence: 99%

Acetohydroxamic acid adsorbed at copper surface: electrochemical, Raman and theoretical observations

Guo

et al. 2017

Int J Ind Chem

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Corrosion inhibition effect of AHA film formed on the copper surface by self-assembled monolayers technique was estimated in 3 wt% NaCl solution by electrochemical impedance spectroscopy and polarization methods. Polarization data indicated that AHA was an anodic inhibitor. The maximum inhibition efficiency reached 93.5% in the case of assembly 3 h in 10 mM AHA solution. The adsorption of AHA on the copper surface fits Langmuir adsorption isotherm. Surface-enhanced Raman scattering together with quantum chemical studies demonstrated that N-O and C=O groups were attached to the copper surface, predicting the feasible adsorption centers and confirming the relationship between the molecular structures of AHA and its inhibition property.

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⁸⁹Zr Labeled Fe₃O₄@TiO₂ Nanoparticles: In Vitro Afffinities with Breast and Prostate Cancer Cells

Ünak

Tekin

Guldu

et al. 2020

Applied Organom Chemis

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In this study, Fe3O4@TiO2 nanoparticles were synthesized as a new Positron Emission Tomography/Magnetic Resonance Imaging (PET/MRI) hybrid imaging agent and radiolabeled with 89Zr. In addition, Fe3O4 nanoparticles were synthesized and radiolabeled with 89Zr. Df‐Bz‐NCS was used as bifunctional ligand. The nanoconjugates were characterized with transmission electron microscopy, scanning electron microscopy, and dynamic light scattering. Radiolabeling yields were 100%. Breast and prostate cancer cell affinities and cytotoxicity were determined using in vitro cell culture assays. The results demonstrated that Fe3O4@TiO2 nanoparticles are promising for PET/MR imaging. Finally, unlike Fe3O4 nanoparticles, Fe3O4@TiO2 nanoparticles showed a fluorescence spectrum at an excitation wavelength of 250 nm and an emission wavelength of 314 nm. Therefore, in addition to bearing the magnetic properties of Fe3O4 nanoparticles, Fe3O4@TiO2 nanoparticles display fluorescence emission. This provides them with photodynamic therapy potential. Therefore multimodal treatment was performed with the combination of PDT and RT by using human prostate cancer cell line (PC3). The development of 89Zr‐Df‐Bz‐NCS‐Fe3O4@TiO2 nanoparticles as a new multifunctional PET/MRI agent with photodynamic therapy and hyperthermia therapeutic ability would be very useful.

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A comparison between the chelating properties of some dihydroxamic acids, desferrioxamine B and acetohydroxamic acid

Cited by 123 publications

References 14 publications

Determination of the Side-Reaction Coefficient of Desferrioxamine B in Trace-Metal-Free Seawater

Determination of the Side-Reaction Coefficient of Desferrioxamine B in Trace-Metal-Free Seawater

Acetohydroxamic acid adsorbed at copper surface: electrochemical, Raman and theoretical observations

⁸⁹Zr Labeled Fe₃O₄@TiO₂ Nanoparticles: In Vitro Afffinities with Breast and Prostate Cancer Cells

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A comparison between the chelating properties of some dihydroxamic acids, desferrioxamine B and acetohydroxamic acid

Cited by 123 publications

References 14 publications

Determination of the Side-Reaction Coefficient of Desferrioxamine B in Trace-Metal-Free Seawater

Determination of the Side-Reaction Coefficient of Desferrioxamine B in Trace-Metal-Free Seawater

Acetohydroxamic acid adsorbed at copper surface: electrochemical, Raman and theoretical observations

89Zr Labeled Fe3O4@TiO2 Nanoparticles: In Vitro Afffinities with Breast and Prostate Cancer Cells

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Product

Resources

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⁸⁹Zr Labeled Fe₃O₄@TiO₂ Nanoparticles: In Vitro Afffinities with Breast and Prostate Cancer Cells