Neutral water-soluble post-transition-metal chelate complexes of medical interest: aluminum and gallium tris(3-hydroxy-4-pyronates)

Finnegan, M. M.; Lutz, Tammy G.; Nelson, William O.; Smith, Alexis; Orvig, Chris

doi:10.1021/ic00260a033

Cited by 119 publications

(95 citation statements)

References 2 publications

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“…The complex formation is accompanied by significant electronic shielding effects, namely downfield shifts of all the aromatic ring and methyl protons are observed in all cases ( Fig. 5a and Table S1) as it was also found previously in the case of the tris(maltolato) [34] and tris(thiomaltolato) complexes [23].…”

Section: Figsupporting

confidence: 84%

“…It can be concluded that the stability of the Ga(III)-maltolato and -thiomaltolato complexes are comparable to that of Fe(III) [34,35], and both metal ions form more stable complexes with the (O,O) donor maltol. This is in accordance with Pearson's principle [36] i.e.…”

Section: Figs 4 Andmentioning

confidence: 94%

“…The maltolato complex is known to undergo very rapid isomerization in solution [34], however significant line broadening was not observed in the 1 H NMR spectra (Figs. 4, 5a), which may indicate existence of merely one kind if isomer under the applied conditions.…”

Section: Figs 4 Andmentioning

confidence: 99%

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Comparative solution equilibrium studies of anticancer gallium(III) complexes of 8-hydroxyquinoline and hydroxy(thio)pyrone ligands

Enyedy

Dömötör

Varga

et al. 2012

Journal of Inorganic Biochemistry

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Section: Figsupporting

confidence: 84%

Section: Figs 4 Andmentioning

confidence: 94%

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Comparative solution equilibrium studies of anticancer gallium(III) complexes of 8-hydroxyquinoline and hydroxy(thio)pyrone ligands

Enyedy

Dömötör

Varga

et al. 2012

Journal of Inorganic Biochemistry

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“…The materials used were as previously detailed (3,9); maltol (Aldrich) and kojic acid (Sigma) were used as received. 'H NMR spectra were recorded with a Bruker WH-80; infrared spectra were obtained on a Perkin-Elmer PE 783 spectrometer and were referenced to polystyrene.…”

Section: Methodsmentioning

confidence: 99%

“…1. Neither the metal-pyrone complexes nor the product ligands were isolated because the aim of this work is the direct preparation; however, the conditions are completely compatible with those used in their formation (3,4). The accepted mechanism for the preparation of a 4-pyridinone by conversion of an appropriate 4-pyrone is nucleophilic attack by a primary amine, followed by ring opening, 1 elimination of water, and ring closure to give the 4-pyridinone 1 (23).…”

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confidence: 99%

One-pot synthesis of N-substituted-3-hydroxy-4-pyridinone chelate complexes of aluminum, gallium, and indium

Zhang¹,

Hui²,

Orvig³

1989

Can. J. Chem.

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Thispaper is dedicated to Professor Ronald J . Gillespie on the occasiorz of his 65th birthday ZAIHUI ZHANG, T. L. THOMAS HUI, and CHRIS ORVIG. Can. J. Chem. 67, 1708Chem. 67, (1989. A series of tris(3-hydroxy-2-methyl-4-pyridinonato)metal(III) and tris(3-hydroxy-6-hydroxymethyl-4-pyridinonat0)-metal(II1) complexes have been prepared in water by one-pot synthesis directly from maltol and kojic acid, respectively, and the metal ion (M = AI, Ga, In) with an appropriate amine. The pyridinones have substituents at the ring nitrogen atom (CH3, C2H5). The tris(3-hydroxy-4-pyronato)metal(III) complexes are formed in situ and these undergo nucleophilic attack by the primary amine; the appropriate tris(3-hydroxy-4-pyridinonato)metal(III) complexes are obtained. This method bypasses the sequential syntheses of ligand and metal complex, and has improved the yields of the tris(1igand)metal complexes, in particular by making them much more easily accessible. The electronic effects of binding the pyrone to the metal ions and of the substituents on the pyrone ring on the reactivity are discussed.Key words: 3-hydroxy-4 pyridinone complexes, group 13 metal ions, one-pot synthesis.ZAIHUI ZHANG, T. L. THOMAS HUI et CHRIS ORVIG. Can. J. Chem. 67, 1708Chem. 67, (1989. Utilisant des reactions de type <

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Medicinal Inorganic Chemistry: Correcting Essential Metal‐Ion Deficiencies

Thompson

2005

Encyclopedia of Inorganic Chemistry

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Essential metal ions are those for which there is a known requirement for good health in the body. When dietary intake does not, or cannot, maintain adequate tissue stores of an essential trace or ultratrace metal ion, metal‐ion supplementation may be necessary. Simple salts of metal ions are often poorly tolerated, not well absorbed, or too rapidly excreted (or all three of these); therefore, appropriate ligand binding of the particular metal ion can significantly improve the success of supplementation efforts. The most common deficiency disorder, iron‐deficiency anemia, is now treated with a number of iron complexes, e.g., Ferrochel™ and ferrous gluconate, that are superior to simple iron salts such as ferrous sulfate; others, such as ferric maltol, are being proposed as useful substitutes. Marginal deficiencies of trace and ultratrace elements, such as zinc, copper, manganese, and chromium, are purported to have long‐term negative health effects, especially in aging or ill populations. Defining marginal deficiency is difficult, owing to lack of reliable and accurate biomarkers for the determination of trace element status.

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Neutral water-soluble post-transition-metal chelate complexes of medical interest: aluminum and gallium tris(3-hydroxy-4-pyronates)

Cited by 119 publications

References 2 publications

Comparative solution equilibrium studies of anticancer gallium(III) complexes of 8-hydroxyquinoline and hydroxy(thio)pyrone ligands

Comparative solution equilibrium studies of anticancer gallium(III) complexes of 8-hydroxyquinoline and hydroxy(thio)pyrone ligands

One-pot synthesis of N-substituted-3-hydroxy-4-pyridinone chelate complexes of aluminum, gallium, and indium

Medicinal Inorganic Chemistry: Correcting Essential Metal‐Ion Deficiencies

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