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  • 1
    Electronic Resource
    Electronic Resource
    Identification ofS-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-3-mercaptopyruvic acid with a metabolic intermediate betweenS-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-l-cysteine andS-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-3-mercaptolactic acid (1997)
    Springer
    Amino acids 13 (1997), S. 163-169 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Imidazole compound ; Mercaptopyruvic acid ; Urocanic acid ; Histidine ; Mass spectrometry ; Paper electrophoresis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary S-[2-Carboxy-1-(1H-imidazol-4-yl)ethyl]-3-mercaptopyruvic acid (I) was chemically synthesized in 15% yield by incubating a reaction mixture oftrans-urocanic acid and 3-fold excess of 3-mercaptopyruvic acid at 45°C for 6 days. The synthesized compound was characterized by fast-atom-bombardment mass spectrometry and high-voltage paper electrophoresis. CompoundI was identified with a product of an enzymatic reaction ofS-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-l-cysteine (II) with rat liver homogenate in a phosphate buffer, pH 7.4. CompoundI was degraded toS-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-3-mercaptolactic acid (III), a compound previously found in human urine [Kinuta et al. (1994) Biochem J 297: 475–478], by incubation with rat liver homogenate. From these results, we suggest that compoundI is a metabolic intermediate for the formation of compoundIII from compoundII. The present pathway follows a formation of compoundII fromS-[2-carboxy-1-(1H-imidazol-4-yl)ethyl] gluthathione [Kinuta et al. (1993) Biochim Biophys Acta 1157: 192–198], a proposed metabolite ofl-histidine.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01373214
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  • 2
    Electronic Resource
    Electronic Resource
    Effect ofN-acetylcysteine administration on cysteine and glutathione contents in liver and kidney and in perfused liver of intact and diethyl maleate-treated rats (1994)
    Springer
    Amino acids 7 (1994), S. 255-266 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; N-Acetylcysteine ; Cysteine ; Glutathione ; Diethyl maleate ; Perfused rat liver
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Effect ofN-acetyl-l-cysteine (NAC) administration on cysteine and glutathione (GSH) contents in rat liver and kidney was studied using intact and diethyl maleate (DEM)-treated rats and perfused rat liver. Cysteine contents increased rapidly, reaching peak at 10 min after intraperitoneal NAC administration. In liver mitochondria it increased slowly, reaching peak at 60 min. GSH content did not change significantly in these tissues. However, in liver and kidney depleted of GSH with DEM, NAC administration restored GSH contents in 60 and 120 min, respectively. Perfusion with 10 mM NAC resulted in 76% increase in liver cysteine content, but not in GSH content. Liver perfusion of DEM-injected rats with 10 mM NAC restored GSH content by 15%. Present findings indicate that NAC is an effective precursor of cysteine in the intact liver and kidney and in the perfused rat liver, and that NAC stimulated GSH synthesis in GSH-depleted tissues.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00807701
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  • 3
    Electronic Resource
    Electronic Resource
    Protective effect of glucose-cysteine adduct on thein situ perfused rat liver (1997)
    Springer
    Amino acids 12 (1997), S. 33-40 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Glucose-cysteine adduct ; Cysteine prodrug ; Liver perfusion ; Glutathione ; Diethyl maleate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Insitu perfusion of rat liver was performed with a medium containing glucose-cysteine adduct [2-(D-gluco-pentahydroxypentyl) thiazolidine-4-carboxylic acid, glc-cys] and its effect on glutathione (GSH) and ATP levels and bile production was examined. The GSH content in the liver was maintained at the original level during perfusion with 1 mM glc-cys for 2h, while it decreased significantly in the absence of glc-cys. After 4h of perfusion without glc-cys, ATP content and bile production decreased significantly besides the decrease in GSH content, but they were maintained at the original levels with glc-cys. When the perfusion was performed with the liver of rats injected with diethyl maleate (DEM), the GSH level, which was decreased to 6.0% of the control by DEM injection, was restored to 22.6% of the original level by perfusion with 2mM glc-cys for 30 min. Data indicate that glccys is a cysteine prodrug with protective action on the liver.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01373424
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  • 4
    Electronic Resource
    Electronic Resource
    l-Cysteine metabolism via 3-mercaptopyruvate pathway and sulfate formation in rat liver mitochondria (1992)
    Springer
    Amino acids 2 (1992), S. 143-155 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Cysteine metabolism ; 3-Mercaptopyruvate pathway ; Sulfate formation ; Mitochondria ; Glutathione
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary We have studied the 3-mercaptopyruvate pathway (transamination pathway) ofl-cysteine metabolism in rat liver mitochondria.l-Cysteine and other substrates at 10 mM concentration were incubated with mitochondrial fraction at pH 8.4, and sulfate and thiosulfate were determined by ion chromatography. Whenl-cysteine alone was incubated, sulfate formed was 0.7µmol per mitochondria from one g of liver per 60 min. Addition of 2-oxoglutarate and GSH resulted in more than 3-fold increase in sulfate formation, and thiosulfate was formed besides sulfate. The sum (A + 2B) of sulfate (A) and thiosulfate (B) formed was approximately 7-times that withl-cysteine alone. Incubation with 3-mercaptopyruvate resulted in sulfate and thiosulfate formation, and sulfate was formed with thiosulfate. These reactions were stimulated with glutathione. Sulfate formation froml-cysteinesulfinate and 2-oxoglutarate was not enhanced by glutathione and thiosulfate was not formed. These findings indicate thatl-cysteine was metabolized and sulfate was formed through 3-mercaptopyruvate pathway in mitochondria.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00806085
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  • 5
    Electronic Resource
    Electronic Resource
    Effect of glucose-cysteine adduct as a cysteine prodrug in rats (1997)
    Springer
    Amino acids 12 (1997), S. 85-94 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Glucose-cysteine adduct ; Cysteine prodrug ; Glutathione ; Cysteine ; Sulfate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Effect of intraperitoneal administration (5 mmol/kg of body weight) of glucose- cysteine adduct (glc-cys) as a cysteine prodrug in rat tissues was studied. Cysteine levels in liver and kidney increased to 1.08 and 1.98μmol per g or ml, respectively, at 2h after the administration. GSH levels did not change substantially. However, when glc-cys was injected to rats treated with diethyl maleate, a GSH-depleting agent, the decreased GSH levels were restored rapidly. The recoveries in liver and kidney were 72% at 1h and 66% at 2h, respectively, after glc-cys administration. Metabolism of glc-cys was assessed by urinary excretion of glc-cys, sulfate and taurine. Average excretion of glc-cys was 2.86mmol/kg/24h after glc-cys administration. Increased excretions of sulfate and taurine were 0.77 and 0.14mmol/kg/24h, respectively. Data show that, although glc-cys excretion was relatively rapid, glc-cys was effectively utilized for GSH synthesis in GSH-depleted tissues.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01373429
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