Bisamidoximes: Synthesis and Complexation with Iron(III)

Johnson, James E.; Carvallo, Carol; Dolliver, Debra D.; Sánchez, Natalia Montoya; Garza, Vilma; Canseco, Diana C.; Eggleton, Gordon L.; Fronczek, Frank R.

doi:10.1071/ch07157

Cited by 4 publications

(7 citation statements)

References 15 publications

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“…The band at 600 nm became less pronounced, and the absorbance at any other wavelength between 400 and 600 nm increased, with the latter also being observed for the free Fe(III) control, hence indicating the presence of some noncomplexed Fe(III) in the 0.5:1 solution. Overall, this suggests that the P(EtOx 35 - stat -AO-BuOx 21 ) reached its limit to chelate Fe(III) in a ratio of approximately 1:0.5, which is in good agreement with previous reports on small molecules . It is noteworthy that the excess Fe(III) did not precipitate upon pH adjustment, suggesting a stabilization of the metal ions by the complexes. , This qualitative investigation demonstrated that the AO-modified POx can form metal complexes with Fe(III) and that P(EtOx 35 - stat -AO-BuOx 21 ) could have the potential for the treatment of excessive iron levels.…”

Section: Resultssupporting

confidence: 90%

“…AOs have two p K a values, (i) p K a1 ≈ 6 and (ii) p K a2 ≈ 13, which correspond to the protonated oxime nitrogen and oxime hydroxy group, respectively. , Thus, at physiological pH, the AO group exists in its neutral form bearing an oxime and amino group. Studies on AO-containing small molecules have revealed these to act as bidentate ligands in organic solvents. , To determine the complexation potential of the present systems in an aqueous environment, qualitative tests with different ratios of Fe(III) to AO were performed. To allow for an efficient Fe(III) complexation, metal-to-ligand ratios below 0.5:1 were studied under the assumption that two AO moieties will complex one Fe(III) ion .…”

Section: Resultsmentioning

confidence: 99%

“…Studies on AO-containing small molecules have revealed these to act as bidentate ligands in organic solvents. , To determine the complexation potential of the present systems in an aqueous environment, qualitative tests with different ratios of Fe(III) to AO were performed. To allow for an efficient Fe(III) complexation, metal-to-ligand ratios below 0.5:1 were studied under the assumption that two AO moieties will complex one Fe(III) ion . Blue complexes were visually observed after mixing the yellowish Fe(III) and the colorless P(EtOx 35 - stat -AO-BuOx 21 ) solutions (Figure S19), whereas mixtures of Fe(III) and the unmodified nitrile-functionalized precursor P(EtOx 35 - stat -BuNiOx 21 ) remained yellow (Figure ).…”

Section: Resultsmentioning

confidence: 99%

“…Studies on AO-containing small molecules have revealed these to act as bidentate ligands in organic solvents. 65,66 To determine the complexation potential of the present systems in an aqueous environment, qualitative tests with different ratios of Fe(III) to AO were performed. To allow for an efficient Fe(III) complexation, metal-to-ligand ratios below 0.5:1 were studied under the assumption that two AO moieties will complex one Fe(III) ion.…”

Section: T H I S C O N T E N T Imentioning

confidence: 99%

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Nitrile-Functionalized Poly(2-oxazoline)s as a Versatile Platform for the Development of Polymer Therapeutics

et al. 2021

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In recent years, polymers bearing reactive groups have received significant interest for biomedical applications. Numerous functional polymer platforms have been introduced, which allow for the preparation of materials with tailored properties via post-polymerization modifications. However, because of their reactivity, many functional groups are not compatible with the initial polymerization. The nitrile group is a highly interesting and relatively inert functionality that has mainly received attention in radical polymerizations. In this Article, a nitrile-functionalized 2-oxazoline monomer (2-(4-nitrile-butyl)-2-oxazoline, BuNiOx) is introduced, and its compatibility with the cationic ring-opening polymerization is demonstrated. Subsequently, the versatility of nitrile-functionalized poly(2-oxazoline)s (POx) is presented. To this end, diverse (co)polymers are synthesized and characterized by nuclear resonance spectroscopy, size-exclusion chromatography, and mass spectrometry. Amphiphilic block copolymers are shown to efficiently encapsulate the hydrophobic drug curcumin (CUR) in aqueous solution, and the anti-inflammatory effect of the CUR-containing nanostructures is presented in BV-2 microglia. Furthermore, the availability of the BuNiOx repeating units for post-polymerization modifications with hydroxylamine to yield amidoxime (AO)-functionalized POx is demonstrated. These AO-containing POx were successfully applied for the complexation of Fe(III) in a quantitative manner. In addition, AO-functionalized POx were shown to release nitric oxide intracellularly in BV-2 microglia. Thus nitrile-functionalized POx represent a promising and robust platform for the design of polymer therapeutics for a wide range of applications.

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Section: Resultssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: T H I S C O N T E N T Imentioning

confidence: 99%

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Nitrile-Functionalized Poly(2-oxazoline)s as a Versatile Platform for the Development of Polymer Therapeutics

et al. 2021

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“…Instead, different results on the Z/E configuration were obtained for the amidoxime fragment. In particular, it was found that in the case of compound 2, the calculated data are in agreement with the experimental results of the study of the Z,Zisomerism of bisamidoxime derivatives [40]. At the same time, according to the calculated DG values, the E-isomer of the amidoxime residue is predominated for compounds 3, 7-9, which is consistent with a stabilization of the amidoxime fragment in the aprotic solvent DMSO [36].…”

Section: Scheme 2 a Plausible Mechanism For The Formation Of Minor Psupporting

confidence: 84%

Amidoxime-Functionalized (9,10-Dioxoantracen-1-yl)hydrazones

Stasevych¹,

Zvarych²,

Novikov³

et al. 2019

ChChT

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New (9,10-dioxoanthracen-1-yl)hydrazones containing amidoxime fragments were synthesized by the interaction of corresponding hydrazones of malonodinitrile, ethyl cyanacetate, ethyl acetoacetate, and acetylacetone with hydroxylamine in boiling dioxane in the presence of sodium acetate. It was established that the reaction of N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)carbonohydrazonoyldicyanide 1 with NH 2 OH leads to the formation of 2-(2-(9,10-dioxo-9,10-dihydroanthracen-1yl)hydrazinylidene)-N' 1 ,N' 3-dihydroxymalonimidamide 2 as the major product, and 3-amino-2-(2-(9,10-dioxo-9,10dihydroanthracen-1-yl)hydrazinylidene)-3-(hydroxyimino)propanamide 3 as a minor product. The 1 H, 13 C NMR and LC-MS data showed that the interaction of 9,10dioxoanthracenylhydrazone of acetylacetone 5 by hydroxylamine is accompanied with the elimination of the acetyl fragment formed 1-[2-(2-(hydroxyimino) propylidene)hydrazinyl]anthracene-9,10-dione 9. Possible mechanisms for the formation of amidoximes 3 and 9 are proposed. Quantum-chemical DFT calculations of the Gibbs free energy (D G) to determine conformational advantage of Z-or E-isomers for the amidoxime form of the derivatives 2,3,7-9 were carried out using the M06-2X hybrid method with 6-311++G(d, p) basis set and the SMD solvation model in DMSO.

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Synthesis, Chemical and Biological Properties of Aziridine-1-carbaldehyde Oximes* (Minireview)

Nikitjuka

Jirgensons

2014

Chem Heterocycl Comp

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Bisamidoximes: Synthesis and Complexation with Iron(III)

Cited by 4 publications

References 15 publications

Nitrile-Functionalized Poly(2-oxazoline)s as a Versatile Platform for the Development of Polymer Therapeutics

Nitrile-Functionalized Poly(2-oxazoline)s as a Versatile Platform for the Development of Polymer Therapeutics

Amidoxime-Functionalized (9,10-Dioxoantracen-1-yl)hydrazones

Synthesis, Chemical and Biological Properties of Aziridine-1-carbaldehyde Oximes* (Minireview)

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