An investigation into copper catalyzed D-penicillamine oxidation and subsequent hydrogen peroxide generation

Gupte, Anshul; Mumper, Russell J.

doi:10.1016/j.jinorgbio.2006.12.007

Cited by 41 publications

(51 citation statements)

References 56 publications

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“…The complex of copper and D-pen is polymeric with various formations in aqueous solution depending on chloric ion, oxygen, time and copper/D-pen ratio [37,56,57]. D-pen reduces Cu 2+ to Cu 1+ in the process of chelation while simultaneously being oxidized to D-pen disulfide [57][58][59]. The reaction process of copper ions, D-pen and glutathione under anaerobic and aerobic conditions was monitored by means of 1 H nuclear magnetic resonance spectroscopy [57].…”

Section: D-penicillamine Chelatormentioning

confidence: 99%

“…Both changes are less favorable for protein binding, so that D-pen, remarkably reducing Cu 2+ to Cu 1+ and chelating both Cu 1+ and Cu 2+ simultaneously, is presented with the ability to decrease excess copper levels in Wilson's disease [58]. In addition, hydrogen peroxide is generated during the process of copper-D-pen complex formation [59] and contributes to the cytotoxicity to cancer cells, suggesting a molecular mechanism of D-pen in cancer therapy [60,61].…”

Section: D-penicillamine Chelatormentioning

confidence: 99%

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The significance of copper chelators in clinical and experimental application

Ding

Xie

Kang

2011

The Journal of Nutritional Biochemistry

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Section: D-penicillamine Chelatormentioning

confidence: 99%

Section: D-penicillamine Chelatormentioning

confidence: 99%

The significance of copper chelators in clinical and experimental application

Ding

Xie

Kang

2011

The Journal of Nutritional Biochemistry

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“…Since this drug chelates Cu ions, its positive action may be partly ascribed to Cu complexation. Yet, as has been claimed, under aerobic conditions, the d-PN -copper complex can generate H 2 O 2 [7]. On the other hand, d-PN has been assigned to the scavengers of H 2 O 2 .…”

mentioning

confidence: 93%

Degradation of High‐Molar‐Mass Hyaluronan by Ascorbate plus Cupric Ions: Effects of D‐Penicillamine Addition

Valachová

Rapta

Kogan

et al. 2009

Chemistry & Biodiversity

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Pro- and anti-oxidative effects of an anti-rheumatoid drug, D-penicillamine (D-PN), on the kinetics of high-molar-mass hyaluronan (HA) degradation were monitored using the method of rotational viscometry. The degradation of the dissolved HA macromolecules was attained by applying the Weissberger's system comprising ascorbic acid plus cupric ions. Electron paramagnetic resonance (EPR) spectroscopy was used to identify the generated free radicals. The results obtained indicate that the initial anti-oxidative action of D-PN is followed by induction of pro-oxidative conditions due to the generation of reactive free radicals. It is speculated, however, that the latter situation may be considered as an advantageous property of D-PN. Hydroxyl radicals formed in this way may participate in decomposition of proteinases, which are believed to be responsible for the destruction of joint cartilage under rheumatoid arthritic conditions.

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“…It exhibits a dual behavior producing and scavenging H 2 O 2 . This fact might partially explain its pro-and antioxidative properties observed in vitro [6] [7]. Reduced l-glutathione (l-g-glutamyl-l-cysteinyl-glycine; GSH; Fig.…”

mentioning

confidence: 99%

“…DTE, widely accepted and used as an effective antioxidant in the field of enzyme and protein oxidation, is a new potential antioxidant standard exhibiting very good solubility in a variety of solvents. [7]; b) reduced l-glutathione: À 8.75 [7]/8.83…”

mentioning

confidence: 99%

An Alternative Standard forTrolox‐Equivalent Antioxidant‐Capacity Estimation Based on Thiol Antioxidants. Comparative 2,2′‐Azinobis[3‐ethylbenzothiazoline‐6‐sulfonic Acid] Decolorization and Rotational Viscometry Study Regarding Hyaluronan Degradation

Hrabárová

Valachová

Rapta

et al. 2010

Chemistry & Biodiversity

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Comparison of the effectiveness of antioxidant activity of three thiol compounds, D-penicillamine, reduced L-glutathione, and 1,4-dithioerythritol, expressed as a radical-scavenging capacity based on the two independent methods, namely a decolorization 2,2'-azinobis[3-ethylbenzothiazoline-6-sulfonic acid] assay and a rotational viscometry, is reported. Particular concern was focused on the testing of potential free-radical scavenging effects of thiols against hyaluronan degradation, induced by hydroxyl radicals. A promising, solvent-independent, antioxidative function of 1,4-dithioerythritol, comparable to that of a standard compound, Trolox(®), was confirmed by the 2,2'-azinobis[3-ethylbenzothiazoline-6-sulfonic acid] assay. The new potential antioxidant 1,4-dithioerythritol exhibited very good solubility in a variety of solvents (e.g., H(2)O, EtOH, and DMSO) and could be widely accepted and used as an effective antioxidant standard instead of a routinely used Trolox(®) on 2,2'-azinobis[3-ethylbenzothiazoline-6-sulfonic acid] assay.

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An investigation into copper catalyzed D-penicillamine oxidation and subsequent hydrogen peroxide generation

Cited by 41 publications

References 56 publications

The significance of copper chelators in clinical and experimental application

The significance of copper chelators in clinical and experimental application

Degradation of High‐Molar‐Mass Hyaluronan by Ascorbate plus Cupric Ions: Effects of D‐Penicillamine Addition

An Alternative Standard forTrolox‐Equivalent Antioxidant‐Capacity Estimation Based on Thiol Antioxidants. Comparative 2,2′‐Azinobis[3‐ethylbenzothiazoline‐6‐sulfonic Acid] Decolorization and Rotational Viscometry Study Regarding Hyaluronan Degradation

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