The urinary partition of sulphur in rats treated with aromatic hydrocarbons, with special reference to growth retardation

Elson, L. A.; Goulden, F.; Warren, F. L.

doi:10.1042/bj0390301

Cited by 23 publications

(5 citation statements)

References 7 publications

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“…They did not identify it but its solvent and chromatographic behaviour indicated an acidic nature. Elson, Goulden and Warren (1945), investigating the urine after the intraperitoneal injection of large doses of a number of hydrocarbons in the rat, reported relatively large increases in the levels of ethereal sulphate, neutral sulphur and glucuronic acid together with a fall in inorganic sulphate after the injection of pyrene.…”

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The Metabolism of Pyrene

Kh¹

1957

Br J Cancer

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THE biological effects induced by the polycycic hydrocarbons have been extensively studied in many species and attempts have been made to correlate these effects with the metabolism of the hydrocarbon. To this end investigations of a number of them have been made and from existing data summarised by Young (1950) and Boyland (1950) it would appear that several rather broad conclusions can be drawn.1. The non-carcinogenic hydrocarbons as represented by naphthalene, anthracene and phenanthrene are metabolised to a variety of water soluble products which are excreted in the urine. These metabolic end products consist of phenols and the allied dihydroxy-dihydro compounds both free and conjugated.In addition the urine contains a substance which regenerates the parent hydrocarbon on heating the urine with acid and in the case of naphthalene this precursor has been identified as the glucuronide of 1: 2-dihydro-1-naphthol (Boyland and Solomons, 1955). 2. The carcinogenic hydrocarbons as represented by 1: 2-benzanthracene and chrysene (weak carcinogens), and 1: 2: 5: 6-dibenzanthracene, 3: 4-benzpyrene and 9: 10-dimethyl-1: 2-benzanthracene are metabolised to a variety of excretion products which appear mainly in the faeces, but to a certain extent in the urine, as the free phenols and quinones. Further degradation products have been identified for 1: 2:5: 6-dibenzanthracene (Heidelberger and Wiest, 1951;Bhargava, Hadler and Heidelberger, 1955) and in the case of 3: 4-benzpyrene tissue intermediates have been isolated but not identified (Weigert and Mottram, 1943 and1946). These intermediates readily revert to the fully aromatic benzpyrenoid state and by analogy with the non-carcinogenic hydrocarbons a dihydroxy-dihydro structure has been postulated for them.The essential differences therefore between the metabolic end products of the non-carcinogenic and the carcinogenic hydrocarbons would appear to be:(1) The preponderance of free phenols and quinones as major excretion products of the carcinogenic members. This could possibly be explained on the basis of unstable dihydroxy-dihydro intermediates. The theoretical chemist Pullman (1954) has indeed calculated from resonance energy considerations that the diols of the carcinogenic hydrocarbons should be more susceptible to dehydration than the diols of the non-carcinogenic members.(2) The apparent absence of conjugation amongst the carcinogenic members and (3) the formation of an acid-labile hydrocarbon precursor from the noncarcinogenic members.These conclusions, however, are based upon the behaviour of a relatively small cross-section of the polycyclic hydrocarbons and it was with the idea of extending this field that this investigation was started.

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confidence: 99%

The Metabolism of Pyrene

Kh¹

1957

Br J Cancer

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“…This raises the interesting possibility that there may be some premercapturic acids which on acidification yield mainly hydroxy compounds and little or no mercapturic acid. For example, although studies of the influence of phenanthrene on sulphur metabolism (Elson, Goulden & Warren, 1945;Crabtree, 1945Crabtree, , 1946 have yielded results consistent with the formation of an acetylcysteine conjugate of this hydrocarbon, there have been no reports of the isolation of such a compound from the urine of the dosed animals. Although mercapturic acids have not been isolated from the urine of animals dosed with carcinogenic hydrocarbons, the isolation of hydroxy derivatives has been reported.…”

Section: Nh-co-ch3 H S-ch2-ch H C02hmentioning

confidence: 99%

Biochemical studies of toxic agents. 11. The occurrence of premercapturic acids

Knight

Young

1958

Biochemical Journal

176

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Baumann & Preusse (1879) and Jaff6 (1879) showed that the mercapturic acids which they isolated from the urine of dogs dosed with bromobenzene or chlorobenzene were formed by the decomposition of acid-labile compounds in the urine, and they believed that these precursors were derivatives of glucuronic acid. This work has recently been revised and extended as a result of the findings of Boyland, Sims & Solomon (1957) and Knight & Young (1957). From the urine of rabbits dosed with naphthalene, Boyland et al. (1957) and Boyland & Sims (1958) isolated a compound which on acidification yielded 1-and 2naphthol as well as 1-naphthylmercapturic acid, and they suggested that the compound is N-acetyl-S-(2-hydroxy-1:2-dihydro-1-naphthyl)-L-cysteine.

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“…(Received 5 March 1962) Investigations on rats dosed with phenanthrene (Elson, Goulden & Warren, 1945;Crabtree, 1946) showed that there was an increase in the neutralsulphur output in tihe urines, and Gutmann & Wood (1950) found an increase in the radioactivity in the urines when animals were fed with phenanthrene and L-[35S]cysteine. Stekol (1935Stekol ( , 1939 had noticed that the growth of dogs and rats was retarded when the animals, maintained on a casein-free diet, were given phenanthrene.…”

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