Iron(II) and iron(III) complexes of penicillamine

Stadtherr, Leon G.; Martin, R. Bruce

doi:10.1021/ic50107a021

Cited by 17 publications

(3 citation statements)

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“…Computer analysis of the difference spectra was carried out to obtain A , , , (nm) and corresponding difference absorbance (hA) values of different absorption bands. All differential molar absorptivities (A€, M-' cm-l) for various iron(II1)-amino acid complexes at different wavelengths were calculated on the basis of total iron content (Stadtherr and Martin, 1972). All experiments were performed at room temperature, 24 f 1 "C.…”

Section: Methodsmentioning

confidence: 99%

Solution Visible Difference Spectral Properties of Fe3+-L-Amino Acid Complexes at pH 6.60

Reddy¹,

Mahoney²

1995

J. Agric. Food Chem.

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Solution visible difference absorption spectral properties of the complexes of Fe3+ with different L-amino acids, N-acetyl-L-amino acids, L-amino acid methyl esters, 0-phospho-L-serine, phosvitin, and conalbumin were studied at pH 6.60 in the range 350-750 nm. There were extensive similarities in the spectral properties of various Fe3+-amino acid complexes but considerable variation in the differential molar absorptivities (A€, M-' cm-l) of the absorption bands ( A, , , , nm) calculated for different Fe3+-amino acid complexes. In general, N-acetyl-L-amino acid derivatives showed much higher affinity to complex with Fe3+ than either L-amino acids or their methyl ester derivatives.The spectral data indicated that coordination of Fe3+ to an oxygen is more strongly favored than that to the nitrogen group of the amino acid. a-Amino nitrogens in amino acids, however, appear to lack an affinity for Fe3+ ions, as do hydroxyl groups of L-serine and L-threonine. The spectra of the complexes of Fe3+ with various amino acids and their derivatives were used to make the following spectral band assignments: The positive peaks at 422-424, 470-472, and 571-575 nm and the positive shoulder at 493-494 nm, as in the case of various L-amino acids (except L-tyrosine) and their N-acetylated derivatives, were assigned to yellow complexes of Fe3+ with carboxyl oxygens, although the €-amino nitrogen of lysine, the guanidino nitrogen of arginine, and the imidazole nitrogen of hisitidine may also be involved in the Fe3+-ligand bonding. The single positive peak at 485-493 nm as in the case of L-tyrosine and N-acetyl-L-tyrosinamide was assigned to reddish brown complexes of Fe3+ with phenolate oxygens. The negative absorption band at 416-420 nm as in the case of 0-phospho-L-serine and phosvitin was assigned to rust colored complexes of Fe3+ with phosphoseryl groups. The complexes of Fe3+ involving both carboxyl and phenolate oxygens as in the case of N-acetyl-L-tyrosine and conalbumin, however, had a characteristic spectrum with positive peaks at 473 and 493 nm and positive shoulders at 430 and 570 nm.

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Section: Methodsmentioning

confidence: 99%

Solution Visible Difference Spectral Properties of Fe3+-L-Amino Acid Complexes at pH 6.60

Reddy¹,

Mahoney²

1995

J. Agric. Food Chem.

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“…In fact, both have been reported to coordinate with high affinity, a wide variety of metal ions, and oxidation states [ 8 ]. For example, DPA coordinates Cu 2+ with log K 1 = 16.5, but also Cu + (log K 1 = 19.5), Zn 2+ (log β 2 = 19.6) [ 8 ], and Fe 2+ , Fe 3+ , Co 2+ and Co 3+ [ 9 ], along with many other non-biological metals [ 8 ]. In addition, the structures of metal complexes of DPA can be diverse, including ternary complexes that involve other amino acids such as histidine or methionine [ 10 , 11 ].…”

Section: Introductionmentioning

confidence: 99%

The Specific Copper(II) Chelator TDMQ20 Is Efficient for the Treatment of Wilson’s Disease in Mice

Zhu,

Tang,

Huang

et al. 2023

Pharmaceutics

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(1) Background: In patients with Wilson’s disease, the deficiency of the copper carrier ATP7B causes the accumulation of copper in the liver, brain and various other organs. Lifelong treatment is therefore mandatory, using copper chelators to increase the excretion of copper and to avoid life-threatening damage. The clinically used reference drug, D-penicillamine, exhibit numerous adverse effects, especially a frequent severe and irreversible neurological worsening, mainly due to its lack of metal selectivity; (2) Methods: A new tetradentate ligand based on an 8-aminoquinoline entity, named TDMQ20, which is highly selective for copper compared with other metal ions, is evaluated in “toxic milk” TX mice as an oral treatment of this Wilson’s disease murine model; (3) Results: The concentration of copper in the liver of “toxic milk” TX mice decreased and the fecal excretion of copper increased upon oral treatment with TDMQ20. Both effects are dose-dependent, and more pronounced than those of D-penicillamine; (4) Conclusions: The TDMQ20 copper chelator is more efficient than the reference drug D-penicillamine for the treatment of a Wilson’s disease murine model. Pharmacological data obtained with TDMQ20 on the TX mouse model strongly support the selection of this ligand as a drug candidate for this genetic disease.

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“…A survey of literature reveals that no HPLC-UV or UPLC-UV method has been reported for simultaneous determination of D-PEN and DFX after complexation with metal ions. However, information on the complexes of DFX and D-PEN with Cu + , Cu 2+ , Fe 2+ and Fe 3+ are well documented in the literature [25][26][27][28]. Therefore, the present study was undertaken to develop a rapid HPLC-UV method that can be applied for determination of mixtures of D-PEN and DFX using pre-injection complex formation with suitable metal ions such Cu 2+ or Fe 2+ .…”

Section: Introductionmentioning

confidence: 99%

A fast and validated chromatographic method for simultaneous determination of deferoxamine and Dpenicillamine via chelate formation with metal ions in bulk and dosage forms

Alhazmi¹,

Rehman²

2019

Trop. J. Pharm Res

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Purpose: To develop a chromatographic method for the determination of deferoxamine (DFX) and Dpenicillamine (D-PEN) by improving ultra violet (UV)-absorption via complex formation with Fe 2+ and Cu 2+ metal ions. Methods: Chromatographic analysis was performed by Waters RP-HPLC system using a Symmetry® C (18) column with a mobile phase comprising 0.1 % formic acid and methanol (95:5 v/v). For complexation process, drug and metal ion solution were mixed in a ratio of 1:5 and the resulting complex directly analyzed. Validation and system suitability parameters (including chromatographic parameters) were determined. Results: DFX-Fe 2+ and D-PEN-Cu 2+ complexes showed good UV absorption at 260 nm and were easily determined by the newly developed HPLC method. The developed method showed linearity over the concentration range of 8-96 µgmL-1 (R 2 > 0.999 for DFX and > 0.99 for D-PEN). Precision and accuracy were also within acceptable limits (100.0 ± 2.0 %). Conclusion: The developed method is robust and validated, and satisfies all the system suitability requirements as per ICH guidelines. DFX injection and D-PEN capsule dosage forms can be successfully analysed with the proposed method. The method is simple, fast and cost-effective for the analysis of D-PEN and DFX individually, or simultaneously in bulk drugs as well as in capsule and parenteral formulations, using UV-detector.

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Iron(II) and iron(III) complexes of penicillamine

Cited by 17 publications

References 0 publications

Solution Visible Difference Spectral Properties of Fe3+-L-Amino Acid Complexes at pH 6.60

Solution Visible Difference Spectral Properties of Fe3+-L-Amino Acid Complexes at pH 6.60

The Specific Copper(II) Chelator TDMQ20 Is Efficient for the Treatment of Wilson’s Disease in Mice

A fast and validated chromatographic method for simultaneous determination of deferoxamine and Dpenicillamine via chelate formation with metal ions in bulk and dosage forms

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