N,N′-bis-(3,4,5-trimethoxybenzyl) ethylenediamine N,N′-diacetic acid as a new iron chelator with potential medicinal applications against oxidative stress

Galey, Jean‐Baptiste; Dumats, Jacqueline; Genard, Sylvie; Destrée, Odile; Pichaud, Patrick; Cctroux, Philippe; Marrot, Laurent; Beck, I.; Fernandez, Bona; Barre, G.; Seité, Michel; Hussler, G.; Hocquaux, M.

doi:10.1016/0006-2952(95)02109-4

Cited by 12 publications

(18 citation statements)

References 42 publications

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“…However, it should be kept in mind that such a consideration refers to equilibrium conditions, which is generally not the case in biological systems, and these results agree with previous data showing that the L3 iron complex is not a catalyst of reductant-driven Fenton reactions. [7] In addition, both the formation and dissociation kinetics of the ferric complex with L3 were measured and were found to give consistent data. It should be emphasized that an interesting feature of L3 is the fast uptake of Fe III and its fast release under acidic conditions.…”

Section: Resultsmentioning

confidence: 93%

“…However, the small difference between the E 1/2 values of NADPH and the L3 ferric chelate could explain the fact that L3Ϫiron is not a catalyst of reductant-driven Fenton reaction under physiological conditions. [7] In addition, a small proportion of the complex remains in the FeL3 form, which could be reduced by physiological reductants. This process would allow potential redox cycling of iron, especially during acidosis, which is generally associated with cell oxidative stress.…”

Section: Electrochemistrymentioning

confidence: 99%

“…We therefore explored the possibility of generating pro-drugs that can be oxidatively activated into species with strong iron-binding capacity. [7] Of particular interest in such a strategy is the degree of control exercised by the oxidative stress conditions, whereby a dormant relatively inactive compound is transformed to an active species by the very conditions prevailing at sites where it is most needed.…”

Section: Introductionmentioning

confidence: 99%

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Iron(III) Complexation by New Aminocarboxylate Chelators − Thermodynamic and Kinetic Studies

Serratrice

Galey

Aman

et al. 2001

Eur. J. Inorg. Chem.

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The complexation of FeIII by new tetradentate and pentadentate aminocarboxylate chelators, designed to protect cells against iron‐catalysed oxidative damage, was investigated. Ferric iron complexes of N,N′‐bis(3,4,5‐trimethoxybenzyl)ethylenediamine‐N,N′‐diacetic acid (L1), N,N′‐dibenzylethylenediamine‐N,N′‐diacetic acid (L2) and [N‐(2‐hydroxybenzyl)‐N′‐benzylethylenediamine‐N,N′‐diacetic acid] (L3) have been characterized in aqueous solution by potentiometric, UV/Vis spectrophotometric and cyclic voltammetric measurements. The parent ligand, ethylenediamine‐N,N′‐diacetic acid (L4), has also been studied. As expected, the presence of a hard phenolate donor group in L3 significantly enhances the affinity for iron while decreasing the potential of the FeIII/FeII redox couple compared to L1 or L2. Kinetics studies have provided the kinetic rate constants related to the formation and the dissociation of the ferric complex with L3. The results reveal a fast FeIII uptake, which is a favorable feature for a biological use of this type of ligand. Overall, these results demonstrate the pertinence of the use of such ligands to protect biological tissues against oxidative stress.

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Section: Resultsmentioning

confidence: 93%

Section: Electrochemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Iron(III) Complexation by New Aminocarboxylate Chelators − Thermodynamic and Kinetic Studies

Serratrice

Galey

Aman

et al. 2001

Eur. J. Inorg. Chem.

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“…10. The compounds contain aromatic rings that are readily attacked by hydroxyl radicals generated at the iron center to produce phenolates that are well positioned to coordinate iron 54-57. Thus under pro-oxidant conditions, i.e.…”

Section: Prochelators For Triggered Activation Against Oxidative Stressmentioning

confidence: 99%

Minding metals: Tailoring multifunctional chelating agents for neurodegenerative disease

2010

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Neurodegenerative diseases like Alzheimer's and Parkinson's disease are associated with elevated levels of iron, copper, and zinc and consequentially high levels of oxidative stress. Given the multifactorial nature of these diseases, it is becoming evident that the next generation of therapies must have multiple functions to combat multiple mechanisms of disease progression. Metalchelating agents provide one such function as an intervention for ameliorating metal-associated damage in degenerative diseases. Targeting chelators to adjust localized metal imbalances in the brain, however, presents significant challenges. In this perspective, we focus on some noteworthy advances in the area of multifunctional metal chelators as potential therapeutic agents for neurodegenerative diseases. In addition to metal chelating ability, these agents also contain features designed to improve their uptake across the blood-brain barrier, increase their selectivity for metals in damage-prone environments, increase antioxidant capabilities, lower Aβ peptide aggregation, or inhibit disease-associated enzymes such as monoamine oxidase and acetylcholinesterase.

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“…Iron chelator N , N ′‐bis(3,4,5‐trimethoxybenzyl)ethylenediamine N , N ′‐diacetic acid (OR10141) was prepared as already described (19). A 10 mM OR10141 stock solution (pH 7.4) was prepared in Tyrode buffer, filtered with 0.22 μm filters and used to prepare daughter solutions at 0.5, 1 and 5 mM final concentration.…”

Section: Methodsmentioning

confidence: 99%

Iron chelation can modulate UVA‐induced lipid peroxidation and ferritin expression in human reconstructed epidermis

Seité

Popovic

Verdier

et al. 2004

Photoderm Photoimm Photomed

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N,N′-bis-(3,4,5-trimethoxybenzyl) ethylenediamine N,N′-diacetic acid as a new iron chelator with potential medicinal applications against oxidative stress

Cited by 12 publications

References 42 publications

Iron(III) Complexation by New Aminocarboxylate Chelators − Thermodynamic and Kinetic Studies

Iron(III) Complexation by New Aminocarboxylate Chelators − Thermodynamic and Kinetic Studies

Minding metals: Tailoring multifunctional chelating agents for neurodegenerative disease

Iron chelation can modulate UVA‐induced lipid peroxidation and ferritin expression in human reconstructed epidermis

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