Skip to main content
SpringerLink
Log in
Book cover

Concepts in Biochemical Pharmacology pp 584–608Cite as

Mercapturic Acid Conjugation

  • Chapter

Abstract

Baumann and Preusse (1879) and Jaffé (1879) investigated the metabolism of bromobenzene and chlorobenzene and showed that they were excreted as unstable complexes of S-(p-bromophenyl) acetylcysteine (1, X = Br) and S-(p-chlorophenyl) acetylcysteine (1, X = Cl) respectively. The structures of the complexes were not realised at the time, but the derivatives isolated after treatment with acid and other excretion products containing acetylcysteine residues are called mercapturic acids. Iodobenzene (Mills and Wood, 1953), 1:2-dichlorobenzene and 1:3; dichlorobenzene (A3003, Parke and Williams, 1955) are also excreted as the corresponding phenyl mercapturic acid derivatives (1, X = I; 2 and 3) which still contain the halogen atoms. The isomeric 1:4-dichlorbenzene does not appear to

be metabolised to a mercapturic acid. In these benzene derivatives, in which the halogen residues of the original compounds are not reactive, the metabolic route is probably analogous to that of naphthalene described below; the active chemical group which reacts with the sulphydryl derivative (which eventually yields the mercapturic acid) must be introduced by some preliminary metabolic step.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Al-Kassab, S., Boyland, E., Williams, K.: An enzyme from rat liver catalysing conjugations with glutathione. Replacement of nitro groups. Biochem. J. 87, 4–9 (1963).

    PubMed  CAS  Google Scholar 

  • Angielski, S., Rogulski, J.: The influence of kidney homogenate upon the reaction between glutathione and maleic acid. Acta biochim. pol. 8, 89–110 (1961).

    PubMed  CAS  Google Scholar 

  • Azouz, W.M., Parke, D.V., Williams, R.T.: Studies in detoxication. 62. The metabolism of halogenobenzenes. ortho-and para-dichlorobenzenes. Biochem. J. 59, 410–415 (1955).

    PubMed  CAS  Google Scholar 

  • Baer, J.E., Beyer, K.H.: Renal pharmacology. Ann. Rev. Pharmacol. 6, 261 (1966).

    Article  PubMed  CAS  Google Scholar 

  • Barnes, M.M., James, S.P.: Glutathione and formation of mercapturic acid in vivo. Biochem. J. 66, 3P (1957).

    Google Scholar 

  • Barnes, M.M., James, S.P., Wood, P.B.: The formation of mercapturic acids. 1. Formation of mercapturic acid and the levels of glutathione in tissues. Biochem. J. 71, 680–690 (1959).

    PubMed  CAS  Google Scholar 

  • Barnsley, E.A.: The formation of N-acetyl-S-(2-hydroxypropyl)-L-cysteine from 1-bromopropane in the rat. Biochem. J. 93, 15P (1964a).

    Google Scholar 

  • Barnsley, E.A.: The metabolism of S-methyl-L-cysteine in the rat. Biochim. biophys. Acta (Amst.) 90, 24–36 (1964b).

    Article  CAS  Google Scholar 

  • Barnsley, E.A.: The formation of 2-hydroxypropylmercapturic acid from 1-halogenopropanes in the rat. Biochem. J. 100, 362–372 (1966).

    PubMed  CAS  Google Scholar 

  • Barnsley, E.A.: The metabolism of methyl methanesulphonate in the rat. Biochem. J. 106, 18P–19P (1968).

    CAS  Google Scholar 

  • Barnsley, E.A., Grenby, T.H., Young, L.: Biochemical study of toxic agents. The metabolism of 1-and 2-bromopropane in rats. Biochem. J. 100, 282–288 (1966).

    PubMed  CAS  Google Scholar 

  • Barnsley, E.A., Thomson, A.E.R., Young, L.: Biochemical studies of toxic agents. 15. The biosynthesis of ethylmercapturic acid sulphate. Biochem. J. 90, 588–596 (1964).

    PubMed  CAS  Google Scholar 

  • Barnsley, E.A., Young, L.: Biochemical studies of toxic agents. The metabolism of iodomethane. Biochem. J. 77–81 (1965).

    Google Scholar 

  • Baumann, E., Preusse, C.: Über Bromphenylmercaptursäure. Ber. dtsch. Ges. 12, 806–810 (1879).

    Article  Google Scholar 

  • Betts, J.J., Bray, H.G., James, S.P., Thorpe, W.V.: The metabolism of the trichloronitrobenzenes in the rabbit. Biochem. J. 66, 610–621 (1957).

    PubMed  CAS  Google Scholar 

  • Betts, J.J., James, S.P., Thorpe, W.V.: The metabolism of pentachloronitrobenzene and 2:3:4:6-tetrachloronitrobenzene and the formation of mercapturic acids in the rabbit. Biochem. J. 61, 611–617 (1955).

    PubMed  CAS  Google Scholar 

  • Beyer, K.H., Baer, J.E., Michaelson, J.K., Russo, H.E.: Renotropic characteristics of ethacrynic acid: A phenoxyacetic saluretic-diuretic agent. J. Pharmacol. exp. Ther. 147, 1–22 (1965).

    PubMed  CAS  Google Scholar 

  • Binet, L., Wellers, G.: Role du glutathion lors de l’intoxication du rat par le monobromobenzène. Bull. Soc. Chim. biol. (Paris) 33, 279–285 (1951).

    CAS  Google Scholar 

  • Binkley, F.: Formation of mercapturic acids by cystinuric and normal dogs. J. biol. Chem. 178, 811–820 (1949).

    PubMed  CAS  Google Scholar 

  • Booth, J., Boyland, E., Sato, T., Sims, P.: The reaction of 1:2-dihydronaphthalene and 1:2-epoxy-1:2:3:4-tetrahydronaphthalene with glutathione catalysed by tissue preparations. Biochem. J. 77, 182–186 (1960).

    PubMed  CAS  Google Scholar 

  • Booth, J., Boyland, E., Sims, P.: The conversion of naphthalene into a derivative of glutathione by rat liver slices. Biochem. J. 74, 117–122 (1960).

    PubMed  CAS  Google Scholar 

  • Booth, J., Boyland, E., Sims, P.: An enzyme from rat liver catalysing conjugations with glutathione. Biochem. J. 79, 516–524 (1961).

    PubMed  CAS  Google Scholar 

  • Bourne, M.C., Young, L.: The metabolism of naphthalene in rabbits. Biochem. J. 28, 803–808 (1934).

    PubMed  CAS  Google Scholar 

  • Boyland, E.: Some chemical constituents and biochemical reactions of tumours. Acta Un. int. Cancr. 3, 3–12 (1938).

    CAS  Google Scholar 

  • Boyland, E.: Biological significance of metabolism of hydrocarbons. Biochem. Soc. Symp. 5, 40–54 (1950).

    CAS  Google Scholar 

  • Boyland, E.: Mercapturic Acid Conjugation. In: Proc. 1st International Pharmacological Meeting “Mode of action of drugs”, Vol. 6, pp. 65–74. Oxford: Pergamon Press 1962.

    Google Scholar 

  • Boyland, E.: Polycyclic hydrocarbons. Brit. med. Bull. 20, 121–126 (1964).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Chasseaud, L.F.: An enzyme catalysing the reaction of glutathione with unsaturated compounds. Biochem. J. 99, 13P (1966).

    Google Scholar 

  • Boyland, E., Chasseaud, L.F.: Enzyme-catalysed conjugations of glutathione with unsaturated compounds. Biochem. J. 104, 95–102 (1967).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Chasseaud, L.F.: Enzymes catalysing conjugations of glutathione with αβ-unsaturated carbonyl compounds. Biochem. J. 109, 651–661 (1968).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Chasseaud, L.F.: Glutathione S-aralkyltransferase. Biochem. J. 115, 985–991 (1969).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Grover, P.L.: The relationship between hepatic glutathione conjugation and BSP excretion and the effect of therapeutic agents. Clin. chim. Acta 16, 205–213 (1967).

    Article  PubMed  CAS  Google Scholar 

  • Boyland, E., Kimura, M., Sims, P.: The hydroxylation of some aromatic hydrocarbons by the ascorbic acid model hydroxylating system and by rat-liver microsomes. Biochem. J. 92, 631–638 (1964).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Levi, A.A.: Anthrylmercapturic acid. Biochem. J. 30, 1225–1227 (1936).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Manson, D.: The biochemistry of aromatic amines. The metabolism of 2-naphthylamine and 2-naphthylhydroxylamine derivatives. Biochem. J. 101, 84–102 (1966).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Manson, D., Nery, R.: The biochemistry of aromatic amines. 9. Mercapturic acids as metabolites of aniline and 2-naphthylamine. Biochem. J. 86, 263–271 (1963).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Nery, R.: The metabolism of urethane and related compounds. Biochem. J. 94, 198–208 (1965).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Nery, R.: Mercapturic acid formation during the metabolism of arecoline and arecaidine in the rat. Biochem. J. 113, 123–130 (1969).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Ramsay, G.S., Sims, P.: The secretion of metabolites of naphthalene, 1,2-dihydronaphthalene and 1,2-epoxy-1,2,3,4-tetrahydronaphthalene in rat bile. Biochem. J. 78, 376–384 (1961).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Rhoden, E.: The distribution of urethane in animal tissues, as determined by a microdiffusion method, and the effect of urethane treatment on enzymes. Biochem. J. 44, 528–531 (1949).

    Google Scholar 

  • Boyland, E., Sims, P.: An acid-labile precursor of 1-naphthylmercapturic acid and naphthol: an N-acetyl-S-(1:2-dihydroxynaphthyl)-L-cysteine. Biochem. J. 68, 440–447 (1958).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Sims, P.: The metabolism of 1:2-dihydronaphthalene and 1:2-epoxy-l:2:3:4-tetrahydronaphthalene. Biochem. J. 77, 175–181 (1960).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Sims, P.: The metabolism of phenanthrene in rabbits and rats: mercapturic acids and related compounds. Biochem. J. 84, 564–570 (1962).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Sims, P.: The metabolism of benz[a]anthracene. Biochem. J. 91, 493–506 (1964a).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Sims, P.: The metabolism of pyrene in rats and rabbits. Biochem. J. 90, 391–398 (1964b).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Sims, P.: The metabolism of 9,10-epoxy-9,10-dihydrophenanthrene in rats. Biochem. J. 95, 788–792 (1965a).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Sims, P.: The metabolism of benz[a]anthracene and dibenz[a,h]anthracene and their 5,6-epoxy-5,6-dihydro derivatives by rat-liver homogenates. Biochem. J. 97, 7–16 (1965b).

    PubMed  CAS  Google Scholar 

  • Boyland, E., Williams, K.: A new enzyme, catalysing the conjugations of epoxides. Biochem. J. 94, 190–197 (1965).

    PubMed  CAS  Google Scholar 

  • Brand, E., Harris, M.M.: Some aspects of intermediary protein metabolism. Science 77, 589–590 (1933).

    Article  PubMed  CAS  Google Scholar 

  • Bray, H.G., Carpanini, F.M.B.: The metabolism of thiophen and benzo[b]thiophen. Biochem. J. 109, IIP (1968).

    Google Scholar 

  • Bray, H.G., Caygill, J.C., James, S.P., Wood, P.B.: Formation of mercapturic acids. 5. Metabolism of some halogenoparaffms and nitroparaffins. Biochem. J. 90, 127–132 (1964).

    PubMed  CAS  Google Scholar 

  • Bray, H.G., Franklin, T.J.: Glutathione and formation of mercapturic acid in vitro. Biochem. J. 66, 3P (1957).

    CAS  Google Scholar 

  • Bray, H.G., Franklin, T.J., James, S.P.: The formation of mercapturic acids. 2. The possible role of glutathione, Biochem. J. 71, 690–696 (1959a).

    PubMed  CAS  Google Scholar 

  • Bray, H.G., Franklin, T.J., James, S.P.: The formation of mercapturic acids. 3. N-acetylation of S-substituted cysteines in the rabbit, rat and guinea pig. Biochem. J. 73, 465–473 (1959b).

    PubMed  CAS  Google Scholar 

  • Bray, H.G., Garrett, A.J.: The metabolism of 1:4-quinones and their reactivity with sulphydryl groups. Biochem. J. 80, 6P (1961).

    Google Scholar 

  • Bray, H.G., Hybs, Z., James, S.P., Thorpe, W.V.: The metabolism of 2:3:5:6-and 2:3:4:5-tetrachloronitrobenzenes in the rabbit and the reduction of aromatic nitro compounds in the intestine. Biochem. J. 53, 266–273 (1953).

    PubMed  CAS  Google Scholar 

  • Bray, H.G., James, S.P., Thorpe, W.V.: The metabolism of 3:4-dichloronitrobenzene in the rabbit with special reference to the formation of mercapturic acids. Biochem. J. 60, 23P–24P (1955a).

    Google Scholar 

  • Bray, H.G., James, S.P., Thorpe, W.V.: The formation of mercapturic acids from aliphatic compounds in vivo. Biochem. J. 69, 24P (1958).

    CAS  Google Scholar 

  • Bray, H.G., James, S.P., Thorpe, W.V.: The metabolism of the trichloronitrobenzenes in the rabbit. Biochem. J. 61, 5P–6P (1955b).

    Google Scholar 

  • Bray, H.G., James, S.P., Thorpe, W.V.: The metabolism of the monochloronitrobenzenes in the rabbit. Biochem. J. 64, 38–44 (1956).

    PubMed  CAS  Google Scholar 

  • Bray, H.G., James, S.P., Thorpe, W.V.: The metabolism of 2:4-dichloronitrobenzene in the rabbit. Biochem. J. 65, 483–490 (1957a).

    PubMed  CAS  Google Scholar 

  • Bray, H.G., James, S.P., Thorpe, W.V.: The metabolism of 2:3-, 2:6-and 3:5-dichloronitrobenzene and the formation of a mercapturic acid from 2:3:4:5-tetrachloronitrobenzene in the rabbit. Biochem. J. 67, 607–616 (1957b).

    PubMed  CAS  Google Scholar 

  • Bray, H.G., James, S.P., Thorpe, W.V.: Metabolism of o-, m-and p-fluoro-, bromo-and iodo-nitrobenzenes in the rabbit. Biochem. J. 68, 561–568 (1958a).

    PubMed  CAS  Google Scholar 

  • Bray, H.G., James, S.P., Thorpe, W.V.: Metabolism of some ω-halogenoalkylbenzenes and related alcohols in the rabbit. Biochem. J. 70, 570–579 (1958b).

    CAS  Google Scholar 

  • Calam, D.H., Waley, S.G.: Acidic peptides of the lens. 8. S-(ββ-dicarboxyethyl)glutathione. Biochem. J. 86, 226–231 (1963).

    PubMed  CAS  Google Scholar 

  • Chasseaud, L.F.: Enzyme-catalysed conjugations of glutathione with unsaturated compounds. Ph.D. Thesis, University of London, 1967.

    Google Scholar 

  • Clapp, J.J.: Biochemical studies on arylalkyl mercapturic acids. Ph.D. Thesis, University of London, 1967.

    Google Scholar 

  • Clapp, J.J., Kaye, C.M., Young, L.: Observations on the metabolism of allyl compounds in the rat. Biochem. J. 114, 6P–7P (1969).

    PubMed  CAS  Google Scholar 

  • Clark, A.G., Darby, F.J., Smith, J.N.: Species differences in the inhibition of glutathione S-aryltransferase by phthaleins and dicarboxylic acids. Biochem. J. 103, 49–54 (1967).

    PubMed  CAS  Google Scholar 

  • Cohen, A.J., Smith, J.N.: Comparative detoxication. 9. The metabolism of some halogenated compounds by conjugation with glutathione in the locust. Biochem. J. 90, 449–456 (1964).

    PubMed  CAS  Google Scholar 

  • Cohen, A.J., Smith, J.N., Turbert, H.: Comparative detoxication. 10. The enzymic conjugation of chloro compounds with glutathione in locusts and other insects. Biochem. J. 90, 457–464 (1964).

    PubMed  CAS  Google Scholar 

  • Colucci, D.F., Buyske, D.A.: The biotransformation of a sulfonamide to a mercaptan and to mercapturic acid and glucuronide conjugates. Biochem. Pharmacol. 14, 457–466 (1965).

    Article  PubMed  CAS  Google Scholar 

  • Combes, B.: The biliary excretion of sulfobromophthalein sodium (BSP) in the rat as a conjugate of glycine and glutamic acid. J. clin. Invest. 38, 1426–1433 (1959).

    Article  PubMed  CAS  Google Scholar 

  • Combes, B.: The importance of conjugation with glutathione for sulfobromophthalein sodium (CBSP) transfer from blood to bile. J. clin. Invest. 44, 1214–1224 (1965).

    Article  PubMed  CAS  Google Scholar 

  • Combes, B., Stakelum, G.S.: A liver enzyme that conjugates sulfobromophthalein sodium with glutathione. J. clin. Invest. 40, 981–988 (1961).

    Article  PubMed  CAS  Google Scholar 

  • Cornish, H.H., Block, W.D.: Metabolism of chlorinated naphthalenes. J. biol. Chem. 231, 583–588 (1958).

    PubMed  CAS  Google Scholar 

  • Daniel, J.W., Gage, J.C., Jones, D.I.: The metabolism of 3,5-di-tert.-butyl-4-hydroxytoluene in the rat and in man. Biochem. J. 106, 783–790 (1968).

    PubMed  CAS  Google Scholar 

  • Davison, C., Rozman, R.S., Smith, P.K.: Metabolism of bis-β-chloroethyl sulfide (sulfur mustard gas). Biochem. Pharmacol. 7, 65–74 (1961).

    Article  PubMed  CAS  Google Scholar 

  • Day, E.A.: Role of milk lipids in Flavours of dairy products. Advanc. Amer. Chem. Ser. 56, 94–120 (1966).

    CAS  Google Scholar 

  • Dickens, F.: Carcinogenic lactones and related substances. Brit. med. Bull. 20, 96–101 (1964).

    PubMed  CAS  Google Scholar 

  • Dickens, F., Jones, H.E.H., Waynforth, H.B.: Oral subcutaneous and intratracheal administration of carcinogenic lactones and related substances: the intratracheal administration of cigarette tar in the rat. Brit. J. Cancer 20, 134–144 (1966).

    Article  PubMed  CAS  Google Scholar 

  • Fassett, D.W., Irish, D.D.: Industrial hygiene and toxicology. 2nd rev. ed., Vol. 2. New York: Interscience 1963.

    Google Scholar 

  • Forss, D.A., Dunstone, E. A., Ramshaw, E.H., Stark, W.: The flavor of cucumbers. J. Food Sci. 27, 90–93 (1962).

    Article  CAS  Google Scholar 

  • Foxwell, C.J., Young, L.: The metabolism of S-alkylglutathiones. Biochem. J. 92, 50P (1964).

    Google Scholar 

  • Friedman, M., Cavins, J.F., Wall, J.S.: Relative nucleophilic reactivities of amino groups and mercaptide ions in addition reactions with αβ-unsaturated compounds. J. Amer. chem. Soc. 87, 3672–3682 (1965).

    Article  CAS  Google Scholar 

  • Fukami, J., Shishido, T.: Nature of a soluble glutathione dependent enzyme system active in cleavage of methylparathion to demethyl parathion. J. Econ. Entomol. 59, 1338–1346 (1966).

    PubMed  CAS  Google Scholar 

  • Geiger, W.B., Conn, J.E.: The mechanism of antibiotic action of clavacin and penicillic acid. J. Amer. chem. Soc. 67, 112–116 (1945).

    Article  CAS  Google Scholar 

  • Gillham, B., Young, L.: Isolation of biosynthetic p-bromophenylmercapturic acid. Biochem. J. 103, 24P–25P (1967).

    CAS  Google Scholar 

  • Grodsky, G.M., Carbone, J.V., Fanska, R.: Identification of metabolites of sulfobromophthalein. J. clin. Invest. 38, 1981–1988 (1959).

    Article  PubMed  CAS  Google Scholar 

  • Grover, P.L.: Conjugations with glutathione. Ph.D. Thesis, University of London, 1965.

    Google Scholar 

  • Grover, P.L., Sims, P.: Conjugations with glutathione. I. Distribution of glutathione S-aryltransferase in vertebrate species. Biochem. J. 90, 603–606 (1964).

    PubMed  CAS  Google Scholar 

  • Gutmann, H.R., Wood, J.L.: The effect of bromobenzene and 3,4-benzpyrene on the metabolism of radioactive L-cystine. Cancer Res. 10, 8–12 (1950).

    CAS  Google Scholar 

  • Gutmann, H.R., Wood, J.L.: A note on the acetylation of sulfur amino acids by liver and kidney. J. biol. Chem. 189, 473–477 (1951).

    PubMed  CAS  Google Scholar 

  • Hauschka, T., Toennies, G., Swain, A.P.: The mechanism of growth inhibition by hexenolactone. Science 101, 383–385 (1945).

    Article  PubMed  CAS  Google Scholar 

  • Heppel, L.A., Hilmoe, R.J.: Metabolism of inorganic nitrite and nitrate esters. II The enzymatic reduction of nitro-glycerin and erythritol tetranitrate by glutathione. J. biol. Chem. 183, 129–138 (1950)

    CAS  Google Scholar 

  • Hurd, C.D., Gershbein, L.L.: Reactions of mercaptans with acrylic and methacrylic derivatives. J. Amer. chem. Soc. 69, 2328–2335 (1947).

    Article  CAS  Google Scholar 

  • Hutson, D.H., Akintonwa, D.A.A., Hathway, D.E.: The metabolism of 2-chloro-1-(2′,4′-dichlorophenylvinyl diethyl phosphate (Chlorfenvinphos) in the dog and rat. Biochem. J. 102, 133–142 (1967).

    PubMed  CAS  Google Scholar 

  • Hutson, D.H., Pickering, B.A., Donninger, C.: Phosphoric acid triester: glutathione alkyltransferase. Biochem. J. 106, 20P (1968).

    Google Scholar 

  • Hyde, C.W., Young, L.: Biosynthesis of 1-and 2-menaphthylmercapturic acid. Biochem. J. 94, 34P (1965).

    Google Scholar 

  • Hyde, C.W., Young, L.: Biochemical studies of toxic agents. The metabolic formation of 1-and 2-menaphthylmercapturic acid. Biochem. J. 107, 519–522 (1968).

    PubMed  CAS  Google Scholar 

  • Jaffé, M.: Über die nach Einführung von Bromobenzol und Chlorbenzol in Organismus entstehenden schwefelhaltigen Sauren. Ber. dtsch. chem. Ges. 12, 1092–1098 (1879).

    Article  Google Scholar 

  • Jagenburg, O.R., Toczko, K.: The metabolism of acetophenetidine. Isolation and characterization of S-(1-acetamido-4-hydroxyphenyl)-cysteine, a metabolite of acetophenetidine. Biochem. J. 92, 639–643 (1964).

    PubMed  CAS  Google Scholar 

  • James, S.P.; The metabolism of some bromo paraffins. Biochem. J. 80, 4P (1961)

    CAS  Google Scholar 

  • James, S.P., Jeffery, D.J.: The biosynthesis of N-acetyl-S-hydroxyalkylcysteines. Biochem. J. 93, 16P (1964).

    Google Scholar 

  • Waring, R.H., Wood, P.B.: Some metabolites of 1-bromobutane in the rabbit and the rat. Biochem. J. 109, 727–736 (1968).

    PubMed  Google Scholar 

  • Waring, R.H., Waring, R.H., White, D.A.: Some metabolites of bromocyclopentane, bromocyclohexane and bromocycloheptane. Biochem. J. 103, 25P (1967).

    Google Scholar 

  • Waring, R.H., White, D.A.: The metabolism of phenethyl bromide, styrene and styrene oxide in the rabbit and rat. Biochem. J. 104, 914–921 (1967).

    Google Scholar 

  • Jerina, D.M., Daly, J.W., Witkop, B., Zaltzman-Nirenberg, P., Udenfriend, S.: The role of arene oxide-oxepin systems in the metabolism of aromatic substrates. III. Formation of 1,2-naphthalene oxide from naphthalene by liver microsomes. J. Amer. chem. Soc. 90, 6525–6527 (1968).

    Article  CAS  Google Scholar 

  • Johnson, M.K.: A distinct enzyme of rat liver and kidney coupling glutathione with some aliphatic halogen compounds. Biochem. J. 87, 9P–10P (1963).

    CAS  Google Scholar 

  • Johnson, M.K.: The influence of some aliphatic compounds on rat liver glutathione levels. Biochem. Pharmacol. 14, 1383–1385 (1965).

    Article  PubMed  CAS  Google Scholar 

  • Johnson, M.K.: Metabolism of iodomethane in the rat. Biochem. J. 98, 38–43 (1966a).

    PubMed  CAS  Google Scholar 

  • Johnson, M.K.: Studies on glutathione S-alkyltransferase of the rat. Biochem. J. 98, 44–56 (1966b).

    PubMed  CAS  Google Scholar 

  • Jondorf, W.R., Parke, D.V., Williams, R.T.: Studies in detoxication. 66. The metabolism of halogenobenzenes. 1:2:3-, 1:2:4-and 1:3:5-trichlorobenzenes. Biochem. J. 61, 512–521 (1955).

    PubMed  CAS  Google Scholar 

  • Klaassen, C.D., Plaa, G.L.: Species variation in metabolism storage and excretion of sulfobromophthalein. Amer. J. Physiol. 213, 1322–1326 (1967).

    PubMed  CAS  Google Scholar 

  • Knight, R.H., Young, L.: Biochemical studies of toxic agents. 11. The occurrence of premercapturic acids. Biochem. J. 70, 111–119 (1958).

    PubMed  CAS  Google Scholar 

  • Knuth, C., Bavley, A., Lazier, W.A.: Reaction of thiols with unsaturated compounds. J. Org. Chem. 19, 845–850 (1954).

    Article  CAS  Google Scholar 

  • Kuwaki, T.: Enzymatic cleavage of S-(isopropylcarboxymethyl) glutathione into isovalthine. J. Biochem. (Tokyo) 57, 125–130 (1965).

    CAS  Google Scholar 

  • Kuwaki, T., Mizuhara, S.: S-(1-2-dicarboxyethyl)cysteine in urine and kidney. Biochim. biophys. Acta (Amst.) 115, 491–493 (1966).

    Article  CAS  Google Scholar 

  • Kuwaki, T., Ohmori, S., Mizuhara, S.: Biosynthesis of isovalthine precursor in liver homogenates. Biochim. biophys. Acta (Amst.) 78, 553–555 (1963).

    Article  CAS  Google Scholar 

  • Marsden, C.M., Young, L.: Biochemical studies of toxic agents. 10. Observations of the metabolism of 35S-labelled mercapturic acids. Biochem. J. 69, 257–265 (1958).

    PubMed  CAS  Google Scholar 

  • Mayo, F.R., Walling, C.: The peroxide effect in the addition of reagents on saturated compounds and in rearrangement reactions. Chem. Rev. 27, 351–412 (1940).

    Article  CAS  Google Scholar 

  • McGowan, J.C., Brian, P.W., Hemming, H.G.: Fungistatic activity of ethylenic and acetylenic compounds. Effect of the affinity of the substituents for electrons upon the biological activity of ethylenic compounds. Aim. appl. Biol. 35, 25–36 (1948).

    Article  CAS  Google Scholar 

  • Mills, G.C., Wood, J.L.: Metabolism of iodobenzene. J. biol. Chem. 204, 547–552 (1953).

    CAS  Google Scholar 

  • Mills, G.C., Wood, J.L.: Mercapturic acid precursors. J. biol. Chem. 219, 1–8 (1956).

    PubMed  CAS  Google Scholar 

  • Morello, A., Vardanis, A., Spencer, E.Y.: Differential glutathione-dependent detoxication of two geometrical vinyl organophosphorus (mevinphos) isomers. Biochem. biophys. Res. Commun. 29, 241–245 (1967).

    Article  PubMed  CAS  Google Scholar 

  • Morris, J.E.: The carcinogenic activity in the rat of some derivatives of 5-nitrofuran. Dissertation Abstr. 28, 1594–1595 (1967).

    Google Scholar 

  • Nakahara, W., Fukuoka, F.: Study of carcinogenic mechanisms based on experiments with 4-nitroquinoline N-oxide. Gann 50, 1–15 (1959).

    CAS  Google Scholar 

  • Nakashima, T.: Chemical studies on the origin of naphthalene cataracts. J. Biochem. (Tokyo) 19, 281–314 (1934).

    CAS  Google Scholar 

  • Needleman, P. Hunter, F.E.: The transformation of glyceryl trinitrate and other nitrates by glutathioneorganic nitrate reductase. Molec. Pharmacol. 1, 77–86 (1965).

    CAS  Google Scholar 

  • Nickerson, W.J., Falcone, G., Strauss, G.: Studies on quinone-thioethers. I. Mechanism of formation and properties of thiodione. Biochemistry 2, 537–543 (1963).

    Article  PubMed  CAS  Google Scholar 

  • Nursten, H.E., Williams, A.A.: Fruit aromas: a survey of components identified. Chem. Ind. (Lond.) 486–497 (1967).

    Google Scholar 

  • Ohmori, S., Mizuhara, S.: Structure of a new sulfur-containing amino acid. Arch. Biochem. Biophys. 96, 179–185 (1962).

    Article  Google Scholar 

  • Ohmori, S., Shimomura, T., Azumi, T., Mizuhara, S.: S-(β-carboxy-n-propyl)-L-cysteine and S-(β-carboxyethyl)-L-cysteine in urine. Biochem. Z. 343, 9–15 (1965).

    PubMed  CAS  Google Scholar 

  • Parke, D.V., Williams, R.T.: Studies in detoxication. 63. The metabolism of halogenobenzenes. (a) Meta-dichlorobenzene. (b) Further observations on the metabolism of chlorobenzene. Biochem. J. 59, 415–422 (1955).

    PubMed  CAS  Google Scholar 

  • Patai, S., Rappoport, Z.: Nucleophilic attacks on carbon-carbon double bonds. In: The chemistry of alkenes, pp. 469–584. S. Patai, ed. New York and London: Interscience 1964.

    Google Scholar 

  • Pillinger, D.J., Craig, A.W., Jackson, H.: Tracer studies of the metabolism of methyl methanesulphonate. Biochem. J. 90, 43P (1964).

    Google Scholar 

  • Porter, C.C.: Cited in Baer, J.E., and Beyer, K.H.: Renal Pharmacology. Ann. Rev. Pharmacol. 6, 261–292 (1966).

    Article  Google Scholar 

  • Revel, J.P., Ball, E.G.: The reaction of glutathione with amino acids and related compounds as catalyzed by γ-glutamyl transpeptidase. J. biol. Chem. 234, 577–582 (1959).

    PubMed  CAS  Google Scholar 

  • Rhode, H.: The excretion of ethereal sulfates by rabbits after feeding phenol, bromophenol and bromobenzene. Hoppe-Seylers Z. physiol. Chem. 124, 15–36 (1922).

    Article  CAS  Google Scholar 

  • Roberts, J.J., Warwick, G.P.: Studies on the mode of action of tumour-growth-inhibiting alkylating agents. I. The fate of ethyl methanesulphonate (“half Myleran”) in the rat. Biochem. Pharmacol. 1, 60–75 (1958a).

    Article  Google Scholar 

  • Roberts, J.J., Warwick, G.P.: The metabolism of alkyl alkanesulphonates and related compounds. A.R. Brit. Emp. Cancer Campgn. 36, 53–54 (1958b).

    Google Scholar 

  • Roberts, J.J., Warwick, G.P.: Metabolic and chemical studies of ‘Myleran’: formation of 3-hydroxy-tetrahydrothiophene-1,1-dioxide in vivo and reactions with thiols in vitro. Nature (Lond.) 184, 1288–1289 (1959).

    Article  CAS  Google Scholar 

  • Rosenthal, S.M., White, E.C.: Hepatic function. VI. The pharmacological behavior of certain phthalein dyes. The value of selected phthalein compounds in the estimation of hepatic function. J. Pharmacol. 24, 265–288 (1924).

    CAS  Google Scholar 

  • Schales, O., Graefe, H.A.: Arylnitroalkenes. A new group of antibacterial agents. J. Amer. chem. Soc. 74, 4486–4490 (1952).

    Article  CAS  Google Scholar 

  • Searle, C.E.: Tumour initiatory activity of chloromononitrobenzenes. Cancer Res. 26, 12–17 (1966).

    PubMed  CAS  Google Scholar 

  • Sherwin, C.P.: The fate of foreign organic compounds in the animal body. Physiol. Rev. 2, 238–276 (1922).

    CAS  Google Scholar 

  • Sims, P.: The metabolism of 3-methylcholanthrene and some related compounds by rat-liver homogenates. Biochem. J. 98, 215–228 (1966).

    PubMed  CAS  Google Scholar 

  • Sims, P.: The metabolism of 7-and 12-methylbenz[a]anthracene and their derivatives. Biochem. J. 105, 591–598 (1967).

    PubMed  CAS  Google Scholar 

  • Sims, P.: The metabolism of some aromatic hydrocarbons by mouse embryo cell cultures. Biochem. Pharmacol. (in press) (1969).

    Google Scholar 

  • Sims, P., Grover, P.L.: Conjugations with glutathione. The enzymic conjugation of some chlorocyclohexenes. Biochem. J. 95, 156–160 (1965).

    PubMed  CAS  Google Scholar 

  • Sklan, N.M., Barnsley, E.A.: The metabolism of S-methyl-L-cysteine. Biochem. J. 107, 217–223 (1968).

    PubMed  CAS  Google Scholar 

  • Smith, J.N., Spencer, B., Williams, R.T.: Studies in detoxication. 34. The metabolism of chlorobenzene in the rabbit. Isolation of dihydrodihydroxychlorobenzene, p-chlorophenylglucuronide, 4-chlorocatechol glucuronide and p-chlorophenylmercapturic acid. Biochem. J. 47, 284–293 (1950).

    PubMed  CAS  Google Scholar 

  • Spencer, B., Williams, R.T.: Studies in detoxication. 33. The metabolism of halogenobenzenes. A comparison of the glucuronic acid, ethereal sulphate and mercapturic acid conjugations of chloro-, bromo-and iodo-benzenes and of the o-, m-and p-chlorophenols. Biosynthesis of o-, m-and p-chlorophenylglucuronides. Biochem. J. 47, 279–284 (1950).

    PubMed  CAS  Google Scholar 

  • Stekol, J.A.: Studies on the mercapturic acid synthesis in animals. I. The extent of the synthesis of p-bromophenylmercapturic acid in dogs as affected by diets of varying sulfur content. J. biol. Chem. 117, 147–159 (1937a).

    CAS  Google Scholar 

  • Stekol, J.A.: Studies on the mercapturic acid synthesis in animals. III. The extent of the synthesis of pbromophenylmercapturic acid in dogs as related to the time of administration of food and bromobenzene. J. biol. Chem. 118, 155–160 (1937b).

    CAS  Google Scholar 

  • Stekol, J.A.: Studies on the mercapturic acid synthesis in animals. VI. The dependence of the extent of the synthesis of p-bromophenylmercapturic acid in dogs on the body weight. J. biol. Chem. 121, 93–98 (1937c).

    CAS  Google Scholar 

  • Stekol, J.A.: Studies on the mercapturic acid synthesis in animals. V. The effect of naphthalene on the growth of rats as related to diets of varying sulfur content. J. biol. Chem. 121, 87–91 (1937d).

    CAS  Google Scholar 

  • Stekol, J.A.: Studies on the mercapturic acid synthesis in animals. VIII. 1-cystine dl-methionine, glutathione and taurine in relation to the synthesis of mercapturic acids in the rat. J. biol. Chem. 122, 333–342 (1937e).

    Google Scholar 

  • Stekol, J.A.: Studies on the mercapturic acid synthesis in animals. IX. The conversion of benzyl chloride and S-benzylcysteine into benzylmercapturic acid in the organism of the dog, rabbit and rat. J. biol. Chem. 124, 129–132 (1938).

    CAS  Google Scholar 

  • Stekol, J.A.: Studies on the mercapturic acid synthesis in animals. X. Glutathione in relation to growth of rats on a low casein diet which contained bromobenzene and naphthalene. J. biol. Chem. 127 131–136 (1939a).

    CAS  Google Scholar 

  • Stekol, J.A.: Studies on the mercapturic acid synthesis in animals. XI. The detoxication of benzyl chloride, benzyl alcohol, benzaldehyde and S-benzylhomocysteine in the rabbit and rat. J. biol. Chem. 128, 199–205 (1939b).

    CAS  Google Scholar 

  • Stekol, J.A.: Conversion of S-benzylglutathione to benzylmercapturic acid. Proc. Soc. exp. Biol. (N.Y.) 43, 108–110 (1940).

    CAS  Google Scholar 

  • Stekol, J.A.: Studies on the mercapturic acid synthesis in animals. XII. The synthesis of N-acetyl-S-p-bromobenzyl-1-cysteine in the rat from p-bromobenzyl bromide, S-p-bromobenzyl-1-cysteine, and S-p-bromobenzylglutathione. J. biol. Chem. 138, 225–229 (1941).

    CAS  Google Scholar 

  • Stekol, J.A.: Studies on the mercapturic acid synthesis in animals. XIV. On the synthesis of mercapturic acids in man. J. biol. Chem. 164, 651–656 (1946).

    PubMed  CAS  Google Scholar 

  • Suga, T., Kumaoka, H., Akagi, M.: Studies on mercapturic acids. Participation of glutathionase in the conversion of glutathione derivatives to cysteine derivatives. J. Biochem. (Tokyo) 60, 133–139 (1966a).

    CAS  Google Scholar 

  • Suga, T., Ohata, I., Akagi, M.: Studies on mercapturic acids. Effect of some aromatic compounds on the level of glutathione and the activity of glutathionase in the rat. J. Biochem. (Tokyo) 59, 209, 215 (1966b).

    Google Scholar 

  • Suga, T., Ohata, I., Kumaoka, H., Akagi, M.: Studies on mercapturic acids. Investigation of glutathione-conjugating enzyme by the method of thin-layer chromatography. Chem. Pharmacol. Bull. 15, 1059–1064 (1967).

    Article  CAS  Google Scholar 

  • Taggart, J.V., Angielski, S., Morell, H.: Complete oxidation of maleic acid via D(+) malate in the kidney. Biochim. biophys. Acta (Amst.) 58, 141–144 (1962).

    Article  CAS  Google Scholar 

  • Thomson, A.E.R., Barnsley, E.A., Young, L.: Biochemical studies of toxic agents. 14. The biosynthesis of ethylmercapturic acid. Biochem. J. 86, 145–152 (1963).

    PubMed  CAS  Google Scholar 

  • Thomson, A.E.R., Maw, G.A., Young, L.: Ethylmercapturic acid and its formation in vivo. Biochem. J. 69, 23P (1958).

    CAS  Google Scholar 

  • Ubuka, T., Kodama, H., Mizuhara, S.: Isolation of S-(carboxymethyl)-cysteine from urine. Biochim. biophys. Acta (Amst.) 141, 266–269 (1967).

    Article  CAS  Google Scholar 

  • Vest, M.F., Rossier, R.: Detoxification in the newborn: the ability of the newborn infant to form conjugates with glucuronic acid, glycine, acetate and glutathione. Ann. N.Y. Acad. Sci. 111, 183–198 (1963–1964).

    Article  PubMed  CAS  Google Scholar 

  • Virtanen, A.I.: Some organic sulfur compounds in vegetables and fodder plants and their significance in human nutrition. Angew. Chem. Internat. Ed. 1, 299–306 (1962).

    Article  Google Scholar 

  • Vogel, E., Klärner, F.G.: 1,2-Naphthalene oxide. Angew. Chem. Internat. Ed. 7, 374–375 (1968).

    Article  CAS  Google Scholar 

  • Waelsch, H.: Detoxication in the animal organism. Arch. exp. Pathol. Pharmakol. 156, 356–369 (1930).

    Article  CAS  Google Scholar 

  • Wainer, A., Lorincz, A.E.: Studies on mercapturic acid synthesis by humans. Life Sci. 7, 504–508 (1963).

    Article  PubMed  CAS  Google Scholar 

  • Watanabe, T.: Substances in mulberry leaves which attract silkworm larvae (Bombyx mori). Nature (Lond.) 182, 325–326 (1958).

    Article  CAS  Google Scholar 

  • West, H.D., Lawson, J.R., Miller, I.H., Mathura, G.B.: The fate of diphenyl in the rat. Arch. Biochem. Biophys. 60, 14–20 (1956).

    Article  PubMed  CAS  Google Scholar 

  • West, H.D., Mathura, G.R.: Synthesis of some aryl-substituted L-cysteines and their fate in the animal body. J. biol. Chem. 208, 315–318 (1954).

    PubMed  CAS  Google Scholar 

  • West, H.D., Mathura, G.R., Black, L.A.: Laboratory synthesis of p-chlorophenyl-L-cysteine and its acetylation by the rat. J. biol. Chem. 193, 133–135 (1951).

    PubMed  CAS  Google Scholar 

  • West, H.D., Miller, I.H.: The fate of mercapturic acids in the animal body. J. nat. med. Ass. (N.Y.) 54, 17–21 (1962).

    CAS  Google Scholar 

  • Wishner, L.A., Keeney, M.: Comparative study of monocarbonyl compounds formed during deep frying in different fats. J. Amer. Oil. Chem. Soc. 42, 776–778 (1965).

    Article  CAS  Google Scholar 

  • Wit, J.G., Van Genderen, H.: Metabolism of the herbicide 2,6-dichlorobenzonitrile in rabbits and rats. Biochem. J. 101, 698–706 (1966).

    PubMed  CAS  Google Scholar 

  • Wit, J.G., Leeuwangh, P.: Mercapturic acid formation and enzyme-catalyzed conjugations with glutathione in pigeons. Biochim. biophys. Acta (Amst.) 177, 329–335 (1969).

    Article  CAS  Google Scholar 

  • Wit, J.G., Snel, J.: Enzymatic glutathione conjugations with 2,3-epoxyphenylpropylether and diethylmaleate by wild bird liver supernatant. European J. Pharmacol. 3, 370–373 (1968).

    Article  CAS  Google Scholar 

  • Zbarsky, S.H., Young, L.: Mercapturic acids. II. The formation of 1-phenylmercapturic acid from phenyl-1-cysteine in vivo. J. biol. Chem. 151, 217–219 (1943).

    CAS  Google Scholar 

Download references

Authors
  1. E. Boyland
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Department of Health, Education and Welfare, National Institutes of Health, Bethesda, MD, 20014, USA

    Bernard B. Brodie  & James R. Gillette  & 

Rights and permissions

Reprints and permissions

Copyright information

© 1971 Springer-Verlag Berlin · Heidelberg

About this chapter

Cite this chapter

Boyland, E. (1971). Mercapturic Acid Conjugation. In: Brodie, B.B., Gillette, J.R., Ackerman, H.S. (eds) Concepts in Biochemical Pharmacology. Handbook of Experimental Pharmacology / Handbuch der experimentellen Pharmakologie, vol 28 / 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-65177-9_34

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-65177-9_34

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-65179-3

  • Online ISBN: 978-3-642-65177-9

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation