Penicillamine, its metabolism and therapeutic applications: A review

Jc, Crawhall; Lecavalier, Denis; Ryan, Patricia

doi:10.1002/bdd.2510010205

Cited by 37 publications

(19 citation statements)

References 152 publications

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“…The kinetics of exchange of the cysteamine moiety among CSH, CSSC and GSSC at pD 8. 4 Pseudo-first-order rate constants determined from the 1D EXSY spectra are listed in Table 1. The rate constants were calculated in terms of the populations of the three sites, which for CSSC is twice the concentration.…”

Section: Csh(b)-cssc(b)-gssc(b)mentioning

confidence: 99%

Characterization of symmetrical and unsymmetrical thiol–disulfide interchange reactions by one‐and two‐dimensional magnetization transfer NMR spectroscopy

Keire¹,

Guo²,

Rabenstein³

1992

Magnetic Reson in Chemistry

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One-and two-dimensional magnetization transfer NMR methods were used to characterize symmetrical and unsymmetrical thiol-disulifide interchange reactions in the glutathione-cysteamine system. The chemical system consists of four symmetrical and two unsymmetrical thioklisulfide interchange reactions. In terms of the magnetization transfer experiment, these reactions can be treated as two three-site exchange networks, one for exchange of the cysteamine moiety among cysteamine, cystamine and the cysteamine part of the glutathione-cysteamine mixed disulfide and another for exchange of the glutathione moiety among glutathione, glutathione disulfide and the glutathione part of the mixed disulfide. Two-dimensional 13C-{'H} EXSY NMR spectroscopy was used to identify specific exchange reactions which take place on the time scale of the magnetization transfer experiment at a given pD. The kinetics of the interchange reactions were quantitatively characterized using an overdetermined version of the one-dimensional "C-{ 'H} EXSY experiment and a "C-{ 'H} selective inversion-transfer experiment with a linear-least-squares analysis of the time course data. Second-order rate constants were calculated for all six of the thioklisulfide interchange reactions from the pseudo-first-order rate constants obtained from the selective inversion-transfer experiments.

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Section: Csh(b)-cssc(b)-gssc(b)mentioning

confidence: 99%

Characterization of symmetrical and unsymmetrical thiol–disulfide interchange reactions by one‐and two‐dimensional magnetization transfer NMR spectroscopy

Keire¹,

Guo²,

Rabenstein³

1992

Magnetic Reson in Chemistry

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“…Penicillamine (PenA, 3,3-dimethylcysteine) is a nonprotienogenic amino acid containing thiol group and its D-isomer is widely used in the treatment of Wilson's disease, polyarthritis cystinuria, heavy metal intoxication (Crawhall et al, 1979) and rheumatoid arthritis (Bonta et al, 1980). The pure D (or S) form of the drug is used because L (or R) form and DL (RS) racemates are very toxic and have mutagenicity (Kean et al, 1991).…”

Section: Introductionmentioning

confidence: 99%

Indirect resolution of enantiomers of penicillamine by TLC and HPLC using Marfey's reagent and its variants

Bhushan

Brückner

Kumar

2007

Biomedical Chromatography

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TLC and HPLC methods were developed for indirect chiral separation of penicillamine (3,3-dimethylcysteine) enantiomers after derivatization with Marfey's reagent (FDNP-Ala-NH(2)) and two of its structural variants, FDNP-Phe-NH(2) and FDNP-Val-NH(2). The binary mobile phase of phenol-water (3:1 v/v) and solvent combinations of acetonitrile and triethylamine phosphate buffer were found to give the best separation in normal and reversed-phase TLC, respectively. The diastereomers were also resolved on a reversed-phase C18 HPLC column with gradient elution of acetonitrile and 0.01 m trifluoroacetic acid. The results due to these three reagents were compared. The method was successful for checking the enantiomeric impurity of l-penicillamine in d-penicillamine and to check the enantiomeric purity of pharmaceutical formulations of d-penicillamine. The method was validated for linearity, repeatability, limit of detection and limit of quantification.

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“…For instance, glutathione (GSH), a representative thiol, occupies 90% of non-protein thiols in mammalian cells and plays important roles in the protection of the body from oxidation and in detoxication (Kosower and Kosower, 1978;Orrenius et al, 1983). D-Penicillamine, not being a biological thiol, was found in human urine as a metabolite of pencillin and has been used as an excellent therapeutic agent (Crawhall et al, 1979). Recently it has been reported that D-penicillamine has a potential activity for the AIDS virus (Chandra and Sarin,19S6).…”

Section: Introductionmentioning

confidence: 99%

High‐performance liquid chromatography/chemiluminescence determination of biological thiols with n‐[4‐(6‐dimethylamino‐2‐benzofuranyl)phenyl]maleimide

Nakashima¹,

Umekawa²,

Nakatsuji³

et al. 1989

Biomedical Chromatography

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The peroxyoxalate chemiluminescence detection of biological thiols combined with high-performance liquid chromatography (HPLC) is described. SH groups of the thiol compounds including glutathione (GSH), cysteine, N-acetylcysteine, cysteamine, and D-penicillamine were labelled with N-[4-(6-dimethylamino-2-benzofuranyl)phenyl]maleimide (DBPM), a specific fluorogenic reagent for SH group. The labelling reaction was carried out at 60 degrees C for 30 min and at pH 8.5 and a sample of the resulting reaction mixture was subjected to HPLC. Five kinds of labelled thiols were separated within 12 min on ODS-80 column (150 x 4.6 mm ID; 5 microns) and detected in the ranges from 500 fmol to 2 pmol/100 microL (cysteamine and N-acetylcysteine), to 3 pmol/100 microL (cysteine) and to 5 pmol/100 microL (GSH and D-penicillamine). The lower detection limits were from 7 fmol (cysteamine) to 113 fmol (GSH) per 100 microL (S/N = 2). The method was applied to the determination of thiols in a rat liver. The amounts of glutathione and cysteine were 1.23 +/- 0.15 mumol/g (n = 5) and 0.15 +/- 0.04 mumol/g (n = 5), respectively.

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Penicillamine, its metabolism and therapeutic applications: A review

Cited by 37 publications

References 152 publications

Characterization of symmetrical and unsymmetrical thiol–disulfide interchange reactions by one‐and two‐dimensional magnetization transfer NMR spectroscopy

Characterization of symmetrical and unsymmetrical thiol–disulfide interchange reactions by one‐and two‐dimensional magnetization transfer NMR spectroscopy

Indirect resolution of enantiomers of penicillamine by TLC and HPLC using Marfey's reagent and its variants

High‐performance liquid chromatography/chemiluminescence determination of biological thiols with n‐[4‐(6‐dimethylamino‐2‐benzofuranyl)phenyl]maleimide

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