S-(1,2-Dicarboxyethyl)glutathione and S-(1,2-Dicarboxyethyl)L-cysteine in Lens

Tsuboi, Seiji; Uda, Naoto; Ikeda, Mikiko; Hirota, Kazuhiro; Ohmori, Shinji

doi:10.1515/cclm.1984.22.4.285

Cited by 6 publications

(7 citation statements)

References 5 publications

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“…In conclusion, these findings indicate that the changes in concentration of S-(l,2-dicarboxyethyl)GSH and GSH in the lens of naphthalene-treated rabbits are similar to those reported during cataract formation after galactose administration (5). The findings also indicate that the ratio of the synthesis and the degradation of GSH in rabbit lenses during cataract formation after naphthalene administration may be the same as that of S-(l ,2-dicarboxyethyl)GSH.…”

Section: Normalsupporting

confidence: 83%

“…All other chemicals used were of analytical More recently, S-(l,2-dicarboxyethyl)GSH was deter-&a e ' mined by using high performance liquid chromatogra-Tissue preparation phy (HPLC) after pre-column reaction with 2,4-dinitro-Male and female albino rabbits> weighing approximately 2 kg were fluorobenzene, and a decrease of S-(l,2-dicarboxy-used. Rabbits were killed by injecting air into an ear vein., and lens ethyl)GSH in rat lens during galactose cataract forma-and liver were then Amoved, blotted, weighed, and used immedition has been reported (5).…”

Section: Introductionmentioning

confidence: 99%

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S-(1,2-Dicarboxyethyl)glutathione and Glutathione in Lens and Liver of Naphthalene-Treated Rabbits

Takemura¹,

Ueno²,

Kodama³

1996

CCLM

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Summary:The determination of S-(l,2-dicarboxyethyl)glutathione and reduced glutathione (GSH) in the rabbit lens and liver was developed using an isotachophoretic analyser.The recovery of S-(l,2-dicarboxyethyl)GSH from the rabbit liver after ion-exchange treatment was 96.8 ± 11.3% (n = 3). The contents of S-(l,2-dicarboxyethyl)GSH in the rabbit lens and liver were 219.9 ± 29.1 (n = 5) and 44.0 ± 13.5 (n = 8) nmol/g, respectively.The contents of S-(l,2-dicarboxyethyl)GSH in the lens and GSH in the lens and liver of naphthalene-treated rabbits was also determined by this method 24 hours after naphthalene administration, at which time the axial opacity "spichen" was observed at the equatorial region of the lens. The content of S-(l,2-dicarboxyethyl)GSH in the lens decreased in proportion to the content of GSH.During the further development of true lens opacity after naphthalene administration, the S-(l,2-dicarboxyethyl)GSH content further compared with that in the spichen stage, but the S-(l,2-dicarboxyethyl)GSH content of the lens that did not develop true opacity after naphthalene administration returned to the normal level. The change of S-(l,2-dicarboxyethyl)GSH content of the lens in the spichen and true opacity stages coincided with that of GSH content.On the other hand, the content of GSH of the liver decreased markedly until 24 hours after naphthalene administration, then returned to normal, irrespective of whether true opacity did or did not subsequently develop.

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Section: Normalsupporting

confidence: 83%

Section: Introductionmentioning

confidence: 99%

S-(1,2-Dicarboxyethyl)glutathione and Glutathione in Lens and Liver of Naphthalene-Treated Rabbits

Takemura¹,

Ueno²,

Kodama³

1996

CCLM

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“…1). These addition products have been found in the lenses of different vertebrates [13,14], in human urine [15] and in the liver and kidney of the ox [16].…”

Section: Introductionmentioning

confidence: 99%

Stereochemical Considerations on Concomitant Allergic Contact Dermatitis to Ester of the <i>cis-trans</i> Isomeric Compounds Maleic Acid and Fumaric Acid

Hansson

Thörneby‐Andersson²

2003

Skin Pharmacol Physiol

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Allergic contact dermatitis from esters of fumaric acid or esters of maleic acid is rare. The case of a chemist with allergic reactions to esters both of fumaric acid and of maleic acid is presented. Extremely high sensitivity of the patient to diethyl fumarate was noted. The formation of identical complete antigens from esters of these two cis-trans isomeric acids may be an explanation of the patient’s double allergy. This is discussed from a stereochemical point of view. These stereochemical considerations point to a general mechanism where cis-trans isomeric α,β-unsaturated carbonyl compounds are converted into the same complete antigen.

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“…1) was isolated from calf lenses and its chemical structure was determined by comparison with the synthetic compound.2) By HPLC after reaction with 2,4-dinitrofluorobenzene we previously determined the content of this peptide in the lenses of various vertebrates, 3) in various tissues of rat, and in the subcellular fraction of rat liver. 4) We also reported that DCE-GS was enzymatically synthesized using glutathione (GSH) and L-malate, and that the enzyme catalyzing this reaction was purified from the rat liver cytosolic fraction.…”

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confidence: 99%

Mechanism of Protection by S-(1,2-Dicarboxyethyl) glutathione Triester against Acetaminophen-Induced Hepatotoxicity in Rat Hepatocytes.

Yasuda

Matsumoto

Matsushima

et al. 2001

Biological & Pharmaceutical Bulletin

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2-dicarboxyethyl)glutathione (DCE-GS, Fig. 1) was isolated from calf lenses and its chemical structure was determined by comparison with the synthetic compound.2) By HPLC after reaction with 2,4-dinitrofluorobenzene we previously determined the content of this peptide in the lenses of various vertebrates, 3) in various tissues of rat, and in the subcellular fraction of rat liver. 4) We also reported that DCE-GS was enzymatically synthesized using glutathione (GSH) and L-malate, and that the enzyme catalyzing this reaction was purified from the rat liver cytosolic fraction.4) Successively, we found that DCE-GS had potent inhibitory effects on blood coagulation and platelet aggregation, 5,6) and an enhancing effect on epidermal growth factorstimulated DNA synthesis in primary cultures of rat hepatocytes. 7) We also determined the levels of GSH and DCE-GS in rat liver during the regeneration of rat liver with time after partial hepatectomy. The GSH and DCE-GS levels increased to a great extent in regenerating rat liver.8) Recently we showed that oral administration of DCE-GS triester, S-(1,2-diethoxycarbonyl)glutathione isopropyl ester, to rats inhibited the acetaminophen (APAP)-induced hepatotoxicity via an increased hepatic GSH content. 9)However, it remains unclear how DCE-GS triester is transported into hepatocytes and how DCE-GS triester transported into hepatocytes increases the hepatic GSH content. Therefore, in order to clarify the mechanism of protection by DCE-GS triester against APAP-induced hepatotoxicity, we examined the mechanism as to the enhancement of the hepatocellular GSH level on DCE-GS triester treatment using isolated rat hepatocytes. MATERIALS AND METHODS AnimalsMale Wistar rats aged 6 weeks (150-180 g) were used in this study. The animals were obtained from Shizuoka Laboratory Animal (Shizuoka, Japan). Water and food (MF; Oriental Yeast) were provided ad libitum for at least 1 week before use. ChemicalsThe structures of DCE-GS and its esters are shown in Fig. 1, and S-(1,2-diethoxycarbonylethyl)glutathione isopropyl ester (triester) were supplied by Senju Pharmaceutical Co., Ltd. (Osaka, Japan). Cell culture reagents were purchased from Dainippon Pharmaceutical Co., Ltd. (Osaka, Japan). Other compounds were from Wako Pure Chemical Ind., Ltd. (Osaka, Japan).Preparation and Primary Culture of Isolated Hepatocytes Hepatocytes, exhibiting more than 85% initial viability, as measured as trypan blue exclusion, were isolated from rats by means of the in situ perfusion technique with collagenase.10) The isolated hepatocytes were suspended in William's medium E supplemented with 5% fetal bovine serum, 1 mg/ml insulin, 1 mM dexamethasone and 100 mg/ml kanamycine, inoculated at a cell density of 1ϫ10 5 cells/0.2 ml/cm 2 onto 16-or 35-mm diameter Corning plastic dishes, which had been coated with rat tail collagen, and then cultured under a humidified atmosphere of 5% CO 2 : 95% air at 37°C. After an attachment period of 2 h, the medium was replaced by a serum-free medium containing 100 mg/ml kanamycin...

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S-(1,2-Dicarboxyethyl)glutathione and S-(1,2-Dicarboxyethyl)L-cysteine in Lens

Cited by 6 publications

References 5 publications

S-(1,2-Dicarboxyethyl)glutathione and Glutathione in Lens and Liver of Naphthalene-Treated Rabbits

S-(1,2-Dicarboxyethyl)glutathione and Glutathione in Lens and Liver of Naphthalene-Treated Rabbits

Stereochemical Considerations on Concomitant Allergic Contact Dermatitis to Ester of the <i>cis-trans</i> Isomeric Compounds Maleic Acid and Fumaric Acid

Mechanism of Protection by S-(1,2-Dicarboxyethyl) glutathione Triester against Acetaminophen-Induced Hepatotoxicity in Rat Hepatocytes.

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