The interaction of sulphate esters and glutathione <i>in vivo</i>

Gillham, Brian; Clapp, J J; Morrison, Adam; Young, L.

doi:10.1042/bj1180024pb

Cited by 12 publications

(5 citation statements)

References 7 publications

(4 reference statements)

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“…These observations raise the possibility that liberation of the alcohol is a necessary step in the formation of mercapturic acids from aralkyl esters in vivo. Some light has been thrown on this question by the study of the catalysis of the reaction of sodium 1-menaphthyl sulphate and glutathione by an enzymic preparation obtained from a rat liver supernatant fraction (Gillham, Clapp, Morrison & Young, 1970). The amount ofS-(1-menaphthyl)glutathione formed from glutathione and sodium 1-menaphthyl sulphate in the presence of the enzyme corresponded to the sulphate ions released and there was no significant liberation of sulphate ions when glutathione was omitted from the system.…”

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confidence: 99%

Formation of mercapturic acids in rats after the administration of aralkyl esters

Clapp

Young

1970

Biochemical Journal

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1. Benzylmercapturic acid and hippuric acid were isolated from the urine of rats that had been injected subcutaneously with benzyl acetate. 2. 1-Menaphthylmercapturic acid and 1-naphthoic acid were isolated from the urine of rats after the subcutaneous injection of each of the following compounds: 1-menaphthyl alcohol and its acetate, propionate, butyrate and benzoate esters. 3. A quantitative method for determining 1-menaphthylmercapturic acid in urine was developed and used to measure the excretion of this compound in the urine of rats in the 4-day period after the subcutaneous injection of 1-menaphthyl alcohol and its acetate, propionate, butyrate and benzoate esters. 4. Chromatographic evidence was obtained for the presence of S-(1-menaphthyl)glutathione and S-(1-menaphthyl)-l-cysteine in bile collected from rats with cannulated bile ducts after the animals had been injected subcutaneously with each of the following compounds: S-(1-menaphthyl)glutathione, 1-menaphthyl acetate, propionate and butyrate. 5. Benzylmercapturic acid and 1-menaphthylmercapturic acid were isolated from the urine of rats that had been injected with sodium benzyl sulphate and sodium 1-menaphthyl sulphate respectively.

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Formation of mercapturic acids in rats after the administration of aralkyl esters

Clapp

Young

1970

Biochemical Journal

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“…Here we must consider the analogy with methylbenzenes once more. Gillham and coworkers (12) showed that benzyl and menapthyl sulphates were substrates for glutathione-S-transferases, while the corresponding alcohols were not. This prompted van Doorn et al (11) to suggest sulphate esters as intermediates in the glutathione conjugation of xylenes.…”

Section: Discussionmentioning

confidence: 99%

Metabolism of detomidine in the rat II. Characterisation of metabolites in urine

Salonen¹,

Vuorilehto²,

Eloranta³

et al. 1988

European Journal of Drug Metabolism and Pharmacokinetics

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In order to investigate the biotransformation of a new alpha 2-adrenoceptor agonist, detomidine, metabolites were isolated from rat urine by solid phase extraction and purified by TLC. The isolated compounds were structurally analysed by 1H-NMR, MS and GC-MS as such or as their methyl and/or silyl derivatives. In addition to detomidine, which was found in trace amounts, four major metabolites were identified: hydroxymethyldetomidine, the corresponding O-glucuronide, detomidine carboxylic acid, and detomidine mercapturate. Together the identified components make up about 80% of urinary detomidine derived compounds. On the basis of these findings a major biotransformation pathway could be suggested. The reaction sequence is initiated by a hydroxylation. Subsequent glucuronidation, glutathione conjugation or secondary oxidation divide the route into three branches each producing one of the other three identified metabolites.

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“…The nature of the proximal aralkylating agent was not clear from the experiments of Hyde & Young (1968) and because both the ester and the parent aralkyl alcohol were converted into mercapturic acid when administered to the rat. The finding by Gillham et al (1970) that rat liver contains an enzyme that catalyses the interaction of 1-menaphthyl sulphate with GSH helped to throw light on this subject. It has been shown in the present work that this enzyme, when purified, catalyses the conversion of 1-menaphthyl sulphate, but not that of the alcohol, into a GSH derivative.…”

Section: Discussionmentioning

confidence: 99%

“…1-menaphthyl acetate) with GSH the rate of reaction was very low. Gillham, Clapp, Morrison & Young (1970) have since shown that the acid sulphate esters of benzyl alcohol and 1 -menaphthyl alcohol are converted by the rat, in relatively high yield, into the corresponding aralkylmercapturic acids. These workers also demonstrated that rat liver contains an enzyme that catalyses the interaction of l-menaphthyl sulphate and GSH.…”

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The reaction of aralkyl sulphate esters with glutathione catalysed by rat liver preparations

Gillham

1971

Biochemical Journal

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1. Rat liver supernatant preparations catalyse the reactions of some aralkyl sulphate esters with GSH to yield S-aralkylglutathione derivatives. 2. A glutathione S-transferase that catalyses these reactions has been purified 16-fold. 3. The purified enzyme preparation catalyses the release of sulphate ions from benzyl sulphate, 1-menaphthyl (naphth-1-ylmethyl) sulphate and phenanthr-9-ylmethyl sulphate only in the presence of GSH. It does not cause the release of sulphate ions from prop-1-yl sulphate, l-serine O-sulphate, phenyl sulphate or oestrone 3-sulphate even when GSH is added. 4. The stability and specificity of the enzyme and its response to inhibitors and to changes of pH were studied. 5. The activity of the preparation was compared with the activities of glutathione S-transferases described previously.

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The interaction of sulphate esters and glutathione in vivo

Abstract: PROCEEDINGS OF THE BIOCHEMICAL SOCIETY mimic the phosphoryl group by permitting the formation of a stable, quasi-transition-state complex.

Cited by 12 publications

References 7 publications

Formation of mercapturic acids in rats after the administration of aralkyl esters

Formation of mercapturic acids in rats after the administration of aralkyl esters

Metabolism of detomidine in the rat II. Characterisation of metabolites in urine

The reaction of aralkyl sulphate esters with glutathione catalysed by rat liver preparations

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