N-diacetic Acid Research Articles

Evaluation of 99mTc-labeled amino acids as radiopharmaceuticals. V. 99mTc complex of ethylenediamine-N,N-diacetic acid as a scintigraphic agent for tumors.

Tumor tissues were clearly visualized in scintigrams of experimental animals bearing tumors a few hours after the administration of 99mTc complex of ethylenediamine-N, N-diacetic acid. The animals used were mice bearing Ehrlich tumor, mice bearing Sarcoma 180, golden hamsters bearing lymphoma, mice bearing fibrosarcoma induced by 3-methylcholanthrene (MC), rats bearing MC-induced fibrosarcoma that had been transplanted at the limb and had spontaneously metastasized to the lung, and mice bearing spontaneous mammary carcinoma. In the mice bearing Ehrlich tumor, the ratios of radioactivity, tumor/blood and tumor/muscle, were 3.32 and 7.96, respectively, at 3 h after the administration.

Technetium-99m chelates as tumor visualizing agents

For scintigraphic visualization of tissues and organs, Tc-99m is an ideal radionuclide because of its optimal half life and good quality scintigrams. There is at present no outstanding Tc-99m radiopharmaceutical for the imaging of various malignant tumors. A need exist for such agents. Hoping to find good radiotracers for tumors, we prepared Tc-99m complexes of substances which were expected to have affinity for tumor tissues such as amino acids, peptides, and porphyrins and studied the scintigraphic behaviors in experimental animals bearing spontaneous or transplanted tumors. In the course of the study, we found that S-containing amino acids and peptides were complexed with Tc-99m in high yield, and the images of tansplanted Ehrlich tumors in mice were visualized with the complexes of cysteine, S-carboxymethylcysteine, and glutathione. Recently the Tc-99m complex of ethylenediamine-N,N-diacetic acid (EDDA) was found to give much more satisfactory scintigrams of Ehrlich tumor in mice. Sequential scintigrams show that the image of the tumor was recognized in 1 hr and visualized very clearly 2–5 hr after the i.v. administration of Tc-99m complex of EDDA. The radioactivity was not accumulated in any specific organ other than the tumor and excreted through kidneys. The Tc-99m EDDA complex was also effective for scintigraphic visualization of other malignant tumors in experimental animals. A number of chelating ligands structurally related to EDDA were examined for Tc-99m labeled radiotracers, those of ethylenediamine-N,N′-diacetic acid, N-hydroxyethyliminodiacetic acid, and propylene-1,3-diamine-N,N-diacetic acid achieved clear visualization of Ehrlich tumors. Studies on the scintigraphic visualization of human tumors and on the mechanism of the concentration in the tumor tissues of the Tc-99m complexes are in progress in our laboratories.

Hydrolytically stable chemically bonded silica supports with metal complexating ligands: Synthesis, characterization and use in high-performance ligand-exchange chromatography (HPLEC)

A silica of 14 nm pore size was reacted according to two procedures with the following silanes: γ-aminopropyltriethoxysilane (1), N-aminoethyl-N′-aminopropyltrimethoxysilane (2), N-aminoethyl-N′-aminoethyl-N″-aminopropyltrimethoxysilane (3), N-(3-triethoxysilanepropyl)-N, N-diacetic dimethylester (4), N-(3-trisodiumsilanolatepropyl)-N, N-diacetic acid disodium salt (5) and N-(3-trisodiumsilanolatepropyl)-ethylenediamine-N, N′, N′-triacetic acid trisodium salt (6). The reaction of silanes 1–4 with the silica was carried out under anhydrous conditions (procedure A). Silanes 1–6 were subjected to surface modification under essentially hydrous conditions applying a two-step procedure (procedure B). Procedure B is much simpler to perform and allows binding of high and definite amounts of silane onto the surface. Complexation of all bonded phases with Cu2+ was examined by measuring the sorption isotherms at constant pH. The pH-dependence of Cu2+ uptake at constant Cu2+ concentration was evaluated. Tests on the chemical and chromatographic stability of the packings showed that only the silicas with bonded iminodiacetate and ethylenediaminetriacetate groups remain hydrolytically stable. Retention of aliphatic and α-amino acids on these two packings was found to be mainly controlled by the pH and the ionic strength of the eluent.

Labeling of amine ligands with 99mTc in aqueous solutions by ligand exchange

Cyclam, ethylenediamine (EN) and a linear tetraamine (TA) form structurally similar complexes in high yields when pertechnetate is reduced with Sn(II) in aqueous alkaline solutions. Efficient labeling of these amine ligands is also accomplished by transfer of 99 m Tc from its complexes with diethylenetriaminepentaacetate (DTPA) and citrate. The labeling yields of cyclam, TA and EN using [ 99 m Tc]DTPA are greater than 95% after standing for 30 min at room temperature in 0.03 M solutions of the amine ligands at pH above 11, but less than 10% at pH below 9. Yields of greater than 90% are obtained using [ 99 m Tc]citrate under similar conditions at pH 7 or greater. Ethylenediamine- N, N-diacetic acid (ENDA) also forms a complex with 99 m Tc that exhibits pH dependent stability characteristics that are the same as those of [ 99 m Tc]EN. The labeling efficiency of ENDA with 99 m Tc as a function of pH is nearly identical to that of the other amine ligands.

Synthesis and study of platinum(II) and palladium(II) hydrazine-N,N-diacetates

1. Complexes of platinum(II) and palladium(II) with hydrazine-N,N-diacetic acid have been synthesized. 2. The results of potentiometric titration of the compounds with acid and alkali have been used to calculate acidic dissociation pK for these substances. The effect of concentration of the complexonate, the nature of the central ion, and the background electrolyte on the acidic properties of the coordinated complexon have been considered. 3. An IR spectroscopic study has been made of platinum(II) and palladium(II) hydrazine-N,N-diacetates. The compounds that were synthesized were found to have a trans structure.

Evaluation of 99mTc-labeled amino acids as radiopharmaceuticals. III. 99mTc complexes of ligands related to ethylenediamine-N,N-diacetic acid for tumor visualization.

Seventeen 99mTc-labeled ligands were evaluated as tumor scanning agents by preparing sequential scintigrams of mice bearing intramuscularly transplanted Ehrlich tumor. The ligands were labeled by the SnCl2 method and were administered intravenously to the mice. The ligands studied were ethylenediamine-N, N-diacetic acid (u-EDDA) and structurally related compounds. 99mTc complexes of u-EDDA, ethylenediamine-N, N'-diacetic acid, N-hydroxyethyliminodiacetic acid, and propylene-1, 3-diamine-N, N-diacetic acid achieved clear visualization of Ehrlich tumors. The image of the tumor was less clearly visualized with the complexes of iminodiacetic acid, N-methyliminodiacetic acid, nitrilotriacetic acid, ethylenediamine-N, N, N, ', N'-tetraacetic acid, N-hydroxyethylethylenediamine-N, N, ', N'-triacetic acid, hydrazine-N, N-diacetic acid, and 3-oxopiperazine-1-acetic acid.

Tumor visualization by 99mTc-labeled ethylenediamine-N,N-diacetic acid.

Tumor tissues were clearly visualized in scintigrams of mice bearing Ehrlich ascites tumor a few hours after the administration of ethylenediamine-N, N-diacetic acid labeled with 99mTc.

Contribution to the solution chemistry and polarographic behaviour of anthrapurpurin complexan

The reduction of the 1,2,7-trihydroxyanthraquinone-3-methylamino-N,N-diacetic acid at dropping mercury electrode has been investigated. The reduction involves two electrons as well as either one or two hydrogen ions depending on the pH. Two alternative reaction mechanisms are proposed. Five acid-dissociation constants have been determined by potentiometric and spectrophotometric methods. A sequence for the dissociation of the protons is proposed. Thermal gravimetric and differential analysis of the anhydrous and dihydrated reagent are reported.

Adsorbing Colloid Flotation of Cu(II) with a Chelating Surfactant

Abstract Cu(II) is effectively removed from synthetic mixtures by dodecylamine-N,N-diacetic acid with Fe(OH)3 and a carrier foam. The effects of pH and ionic strength on the separation are ascertained. Cu(II) is effectively floated at much higher ionic strengths with dodecylamine-N,N-diacetic acid than with nonchelating surfactants such as sodium lauryl sulfate.

Cobalt complexes of ethylenediamine-N,N'-diacetic acid and ethylenediamine-N,N-diacetic acid. Two-nitrogen oxygen carriers

Mittels Elektronenspektroskopie und Potentiometrie wird die Reaktion von Athylendiamin-N,N′- und -N,N-diacetato-Co(II) mit molekularem Sauerstoff untersucht.

New multidentate ligands. XV. Chelating tendencies of diglycine-N,N-diacetic acid, triglycine-N,N-diacetic acid, and tetraglycine-N,N-diacetic acid

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNew multidentate ligands. XV. Chelating tendencies of diglycine-N,N-diacetic acid, triglycine-N,N-diacetic acid, and tetraglycine-N,N-diacetic acidR. J. Motekaitis and A. E. MartellCite this: Inorg. Chem. 1974, 13, 3, 550–559Publication Date (Print):March 1, 1974Publication History Published online1 May 2002Published inissue 1 March 1974https://doi.org/10.1021/ic50133a011RIGHTS & PERMISSIONSArticle Views69Altmetric-Citations7LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (1 MB) Get e-Alerts Get e-Alerts

Photometric determination of aluminium with alizarin fluorine blue

In order to decide whether Alizarin Fluorine Blue (alizarin complexan, 3-amino-methylalizarin- N, N-diacetic acid) is a suitable reagent for the spectrophotometric determination of aluminium, values of the stability constants for some reactions of this reagent with aluminium(III) and iron(III) have been determined spectrophotometrically in a medium containing 20 % dioxan and 80 % water at ionic strength 0·1. The values of the constants that were determined are log K Al AlHL = 14·3, log K 2Al Al2L = 25·3 and log K Fe FeHL = 19·6. These results were employed in the design of a method for the spectrophotometric determination of aluminium in the presence of iron and titanium. The Sandell sensitivity is 0·01 μg/cm 2 and the coefficient of variation for 34 determinations was 0·9 %.

Preparation and some properties of N,N′-diethylethylenediamine-N,N′-diacetic acid and N′,N′-diethylethylenediamine-N,N-diacetic acid, including ability of the former to associate with lanthanons and yttrium

N,N′-diethylethylenediamine-N,N′-diacetic acid and N′,N′-diethylethylenediamine-N,N-diacetic acid were prepared via a classical cyanomethylation process and subsequently isolated by displacement cation-exchange chromatography. N,N′-diethylethylenediamine-N,N′-diacetic acid melted with decomposition at 205–208° and N′,N′-diethylethylenediamine-N,N-diacetic acid at 175–177°. Successive p K 1 and p K 2 values measured at 25° and μ = 0.10 (KNO a) for N,N′-diethylethylenediamine-N,N′-diacetic acid and N′,N′-diethylethylenediamine-N,N-diacetic acid were, respectively, 6.31, 10.42 and 4.71, 11.65. Log K LnCh + values of 7.1, 6.9, 7.0, 7.0, 6.9, 7.0, 7.1, 7.1, 7.1 and 6.8 were determined by a potentiometric method for Ch = (anion of N,N′-diethylethylenediamine-N,N′-diacetic acid) 2- and Ln = Eu 3+, Gd 3+, Tb 3+, Dy 3+, Ho 3+, Er 3+, Tm 3+, Yb 3+, Lu 3+ and Y 3+, respectively. Because the p K 2 value of N′,N′-diethylethylenediamine-N,N-diacetic acid was so high (11.65), the formation constants of its LnCh + species could not be ascertained below pH 7. The high p K 2 value of unsymmetrical N′,N′-diethylethylenediamine-N,N-diacetic acid has been rationalized by classical arguments.

Complex formation of lanthanum(III) or cerium(III) with 3-aminomethylalizarin-n.n-diacetic acid and fluoride

The complex formation in aqueous solution of lanthanum(III) or cerium(III) with 3-aminomethylalizarin-N,N-diacetic acid (alizarin complexan, L) and fluoride (F) was studied by spectrophotometry. At pH 4.50 the metals react with alizarin complexan to form the compounds LaL or CeL; the conditional constant of LaL is 3.6·10 4. At pH 5.50 and 6.50 both systems contained a mixture of the 1:1 species with complexes containing two or more metal ions per ligand molecule. The ternary metal-alizarin complexan-fluoride systems were studied by recording absorption and continuous variations curves, and plotting theoretical curves of continuous variations for various ML-fluoride complexes. The results showed that the ternary complexes have the composition (ML) 2F 2, the conditional constant at pH 4.50 being 6.3·10 13 for the lanthanum complex. It is shown theoretically that ternary complexes of the form (ML) 2F 2 and (ML)F are characterized by having continuous variations curves with maxima displaced to higher mole fractions of the binary reactant. The differences between the curves for the two types are discussed. The ternary complex probably consists of a ring-formed dimer La 2L 2 with one fluorine atom attached to each of the two metal atoms.

Preparation of Chromium(III) and Cobalt(III) Complexes with d,l-α-Phenylalanine-N,N-diacetic Acid

Abstract The following chromium(III) and cobalt(III) complexes with PADA (d,l-α-phenylalanine-N,N-diacetic acid) were prepared: K[Cr(OH)pada(H2O)]·5H2O (violet) (I), K[Cr(OH)pada(H2O)2]·3H2O (green)(II), (enH2)1⁄2[Cr(OH)pada(H2O)2] (green) (III), [Cr pada(o-phen)]·H2O (brown) (IV), K2[Cr(ox)pada]·2H2O (violet) (V), K[Co(OH)pada(H2O)]·5H2O (blue-violet) (VI), and K2[Co2(OH)2(pada)2] (brown-pink) (VII). On the basis of electronic spectra in both aqueous solution and solid state, it was found that PADA behaves toward central metal as a quadridentate ligand in complexes I, IV, V, VI, and VII; in other words, unlike the case of nitrilotriacetic acid (NTA), nitriloisopropionicdiacetic acid (NIPDA) and l-leucine-N,N-diacetic acid (LDA), PADA did not give different coordinating structures to the respective complexes in solid state and aqueous solution. From thermal analysis with derivatograph in the reaction processes of complex VI, it was found that the complex liberates one mole of coordinating water at about 170–180°C, resulting in the formation of the diol complex VII.

Chelating Polymers. III. Chelating Monomers and Polymers from s-Triazinyl Substituted Hydrazinoacetic Acids

Abstract The model chelating compounds β-[2,4-bis(dimethylamino)-s-triazin-6-yl] hydrazinoacetic acid, β-[2,4-bis(dimethylaniino)-s-triazind-yl] hydrazino-N, N-diacetic acid, 2,4-bis(dimethylamino)-s-triazin-6-yl-aminoacetic acid, and 2,4-bis(dimethylamino)-s-triazin-6-yl-iminodiacetic acid have been synthesized and characterized by composition analysis, infrared spectroscopy, and potentiometric titration data. The copper(II), nickel(II), cobalt(II), zinc(II), magnesium(II), and palladium(II) complexes of the first two model compounds, and the copper, nickel, cobalt, and zinc complexes of the third and fourth model compounds have been prepared. The infrared absorption spectra of the model compounds and their complexes were recorded for the range 3800 to 600 cm−1, and the assignment of pertinent bands was made by comparison with reported infrared correlations. In those cases where applicable, shifts in the NH stretching vibration and carboxylate stretching vibration frequencies of the metal complexes were ...

Bis-Type Cobalt(III) and Chromium(III) Complexes with Related Compounds of Nitrilotriacetic Acid

Abstract β-Amino-n-butyric-N,N-diacetic acid (β-ABDA) and γ-amino-n-butyric-N,N-diacetic acid (γ-ABDA) were prepared as compounds related to nitrilotriacetic acid (NTA). Bis-type cobalt(III) and chromium(III) complexes with these ligands, viz., K3[Co(β-abda)2] (I), K[Co(H-γ-abda)2]·2H2O (II) and K[Cr(H-γ-abda)2]·2H2O (III), and the same type cobalt(III) complex with β-aminoethylsulfonic-N,N-diacetic acid (AEDA), viz., K3[Co(aeda)2]·4H2O (IV), were also synthesized. Chemical properties of the above complexes were compared with those of the chromium (III) complex corresponding to IV and of the cobalt(III) and chromium(III) complexes with NTA and NPDA. From the analysis of electronic spectra, it was found that the new complexes, I, II, III and IV have the trans form with respect to the nitrogn atoms in the ligands. A spectrochemical series of these ligands, containing iminodiacetic acid (IDA), methylimino-diacetic acid (MDA) and ethyliminodiacetic acid (EDA), was determined to be: IDA>MDA>NPDA>β-ABDA>EDA>AEDA>NTA>γ-ABDA.

The dissociation constants of alizarin fluorine blue

Dissociation constants for the analytical reagent alizarin fluorine blue (3-aminomethylalizarin- N N-diacetic acid) have been determined by potentiometric titration at ionic strength 0.1, and are k 1 = 1·28 ± 0·30 × 10 −5; k 2 = 2·82 ± 0·24 × 10 −8; k 3 = 3·72 ± 0.19 × 10 −11; k 4 = 6·39 ± 0·12 × 10 −12.

The Chromium(III) Complexes with β-Aminoethylsulfonic-N,N-diacetic Acid and Aspartic-N,N-diacetic Acid

Abstract The following chromium (III) complexes with the β-aminoethylsulfonic-N,N-diacetic acid (AEDA) and aspartic-N,N-diacetic acid (ASDA) were newly prepared; K3[Cr(aeda)2]·4H2O (pale red) (I), [Cr(OH)(Haeda)(o-phen)]·2H2O (orange) (II) and [Cr(Hasda)(H2O)2]·H2O (reddish purple) (III). From the results of spectral measurments, it was found that AEDA acts as a quadridentate ligand as well as a terdentate one in an aqueous solution, but only as a terdentate ligand in a crystal state, and that the coordinating ability of the oxygen atom of sulfonic radical in AEDA is weaker than that of carboxylic radical in ammoniapropionicdiacetic acid (APDA). In Complex III, ASDA behaved as a quadridentate ligand rather than as a quinquedentate. Complexes II and III showed some interesting thermal decomposition processes. The former lost one mole of water at 110°C from the hydrogen atom in free sulfonic acid radical and the coordinated OH group, accompanied with the increase of coordination number of AEDA from 3 to 4. In the latter, one mole of crystalline water was lost first, and then the carboxylic acid bound to the methylene group at β-position in the ligand was decomposed to liberate carbon dioxide, and the coordinated asda was changed into apda.

Analytical utility of bimetallic ternary complexes of alizarin fluorine blue: Spectrophotometric determination of nickel

Mixtures of La 3+ and Ni 2+ ions form with Alizarin Fluorine Blue (1,2-dihydroxyanthraquinon-3-ylmethylamine- N, N-diacetic acid; AFB) the ternary complex (AFB) 2La. Ni n− which has maximum light absorption at 550 nm (ϵ = 1.13 × 10 4); K cond = 1.9 × 10 5 lṁole −1 at pH 4.5 and 25°, ionic strength = 0.1. The use of this complex for the photometric determination of nickel has been investigated.