Iron chelators of the pyridoxal isonicotinoyl hydrazone class Part II. Formation constants with iron(III) and iron(II)

Vitolo, Lucia M. Wis; Hefter, Glenn; Clare, Brian W.; Webb, James L. A.

doi:10.1016/s0020-1693(00)80472-7

Cited by 82 publications

(49 citation statements)

References 18 publications

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“…Interestingly, PIH was also found to bind Fe(II) although with lower affinity . The ferrous complex of PIH was found to be sensitive to oxidation, forming ferric complexes in the presence of oxygen (Avramovici-Grisaru et al, 1985;Vitolo et al, 1990). The ability of PIH to bind Fe(II) is believed to be responsible in its role of protecting plasmid pUC-18 DNA against OH ⅐ -mediated strand breaks by scavenging Fe(II) and enhancing its autooxidation rate (Hermes-Lima et al, 1998).…”

Section: Aroylhydrazones: Pyridoxal Isonicotinoyl Hydrazone and Analogsmentioning

confidence: 99%

“…It is interesting to note that the structural alteration involving the change of the pyridoxal group to the salicylaldehyde group resulted in increased Fe(III) binding affinity of SIH over the lead compound PIH . Hence, the electron-withdrawing effects of the pyridoxal nitrogen on the phenolate group of PIH greatly affect the binding affinity of this ligand (Rich- , 1990;Vitolo et al, 1990). As seen with a number of analogs of the 100 series, 86% of SIH remains in its neutral state at physiological pH, enhancing membrane permeability .…”

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confidence: 99%

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The Evolution of Iron Chelators for the Treatment of Iron Overload Disease and Cancer

2005

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Section: Aroylhydrazones: Pyridoxal Isonicotinoyl Hydrazone and Analogsmentioning

confidence: 99%

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confidence: 99%

The Evolution of Iron Chelators for the Treatment of Iron Overload Disease and Cancer

2005

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“…1) have been shown to have very high chelation efficacy [111,112,121] and their Fe-binding site is the same [118,122,123], suggesting similar Fe(III) binding affinity. Despite the structural similarities of these two ligands [118,122,123], they have vastly different profiles of cytotoxicity [101]. Studies using 311 in vitro show its marked antiproliferative activity and ability to inhibit 3 H-thymidine incorporation in a variety of cell types [111,115].…”

Section: Relationship Between Anti-proliferative Activity Of a Chelatmentioning

confidence: 99%

Iron chelators for the treatment of iron overload disease: Relationship between structure, redox activity, and toxicity

Chaston¹,

Richardson²

2003

American J Hematol

153

120

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The success of the iron (Fe) chelator desferrioxamine (DFO) in the treatment of ␤-thalassemia is limited by its lack of bioavailability. The design and characterization of synthetic alternatives to DFO has attracted much scientific interest and has led to the discovery of orally active chelators that can remove pathological Fe deposits. However, chelators that access intracellular Fe pools can be toxic by either inhibiting Fe-containing enzymes or promoting Fe-mediated free radical damage. Interestingly, toxicity does not necessarily correlate with Fe-binding affinity or with chelation efficacy, suggesting that other factors may promote the cytopathic effects of chelators. In this review, we discuss the interactions of chelators and their Fe complexes with biomolecules that can lead to toxicity and tissue damage. Am.

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“…Pyridoxal isonicotinoyl as well as 2-hydroxybenzaldehyde benzoyl hydrazones are tridentate ligands and form monomeric structures upon complexation with iron(III) [3][4][5]. It was demonstrated [6][7][8] that these iron-binding tridentate ligands are also useful for inhibiting the growth of tumors.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and isomerism of hydrazones of 2-(5-thioxo-4,5-dihydro-1,3,4-thiadiazol-2-ylthio)acetohydrazide

Kuodis¹,

Rutavicius²,

Matijoška³

et al. 2007

Open Chemistry

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New hydrazones of 2-(5-thioxo-4,5-dihydro-1,3,4-thiadiazol-2-ylthio)acetohydrazide have been obtained and the percentages of anti/syn -conformers were determined. Based on the analyses of 1 H NMR spectra, it was concluded that for hydrazones obtained from the 2-hydroxybenzaldehydes and 2'-hydroxycetophenones the ratio between the anti-and syn-conformers depends on the strength of intramolecular hydrogen bond (IMHB) between the nitrogen atom of the imino group and the proton of the 2-hydroxy group. It was shown that increase in IMHB strength results in stabilization of the anticonformer in solution.

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Iron chelators of the pyridoxal isonicotinoyl hydrazone class Part II. Formation constants with iron(III) and iron(II)

Cited by 82 publications

References 18 publications

The Evolution of Iron Chelators for the Treatment of Iron Overload Disease and Cancer

The Evolution of Iron Chelators for the Treatment of Iron Overload Disease and Cancer

Iron chelators for the treatment of iron overload disease: Relationship between structure, redox activity, and toxicity

Synthesis and isomerism of hydrazones of 2-(5-thioxo-4,5-dihydro-1,3,4-thiadiazol-2-ylthio)acetohydrazide

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