Advertisement

Isolation of Conjugates and Identification of the Attached Groups

  • Jelka Tomašić
Part of the Methodological Surveys in Biochemistry and Analysis book series (MSBA, volume 12)

Abstract

Metabolic Phase II reactions convert a wide variety of drugs, endogenous substances and environmental chemicals into conjugates. The application of various isolation and characterization procedures to the analysis of several types of conjugates is considered, including:
  1. (a)

    conjugates with glucuronic acid, special attention being paid to some novel types, to possible formation of isomeric structures in ester-type glucuronides, and to the use of β-glucuronidase in the assay of glucuronides;

     
  2. (b)

    conjugates with amino acids, and particularly glutathione conjugates and mercapturic acids, mention being made of substrate specificity of glutathione S-transferase;

     
  3. (c)

    sulphoconjugates as products of conjugation of steroids and phenols.

     

Keywords

Glucuronic Acid Styrene Oxide Glutathione Conjugate Mercapturic Acid Synthetic Standard 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Williams, R.T. (1959) Detoxication Mechanisms, 2nd edn., Wiley, New York.Google Scholar
  2. 2.
    Fishman, W.H. (1961) Chemistry: of Drug Metabolism, C.C.Thomas, Springfield, Illinois.Google Scholar
  3. 3.
    Tomasic, J. (1978) in Drug Fate and Metabolism, Vol. 2 (Garrett, E. & Hirtz, J.L., eds.) , Dekker, New York, pp. 281–335Google Scholar
  4. 4.
    Wakabayashi, M. (1970) in Metabolic Conjugation and Metabolic Hydrolysis, Vol. 2 (Fishman, W.H., ed.) , Academic Press, New York, pp. 519–602.Google Scholar
  5. 5.
    Hümpel, M., Uli, V., Milius, W., Wendt, H. & Kurowski, M. (1979)Eur. J. Drug Metab. Pharmacokinet. 4, 237–243.CrossRefGoogle Scholar
  6. 6.
    Mayo, B.C., Hawkins, D.R., Hümpel, M., Chasseaud, L.F. & Girkin, R. (1980)Xenobiotica10, 413–420.CrossRefGoogle Scholar
  7. 7.
    Hackett, A.M., Marsh, I., Barrow, A. & Griffiths, L.A. (1979)Xenobiotica9, 491–502.CrossRefGoogle Scholar
  8. 11.
    Bansal, S.K. & Gessner, T. (1980)Anal. Biochem. 109, 321–329CrossRefGoogle Scholar
  9. 12.
    Zumoff, B., Freed, S.Z., Levin, J., Whitmore, W.F., Hellman, L Fishman, J. & Fukushima, D.K. (1980)Eur. J. Cancer16, 219–221.CrossRefGoogle Scholar
  10. 13.
    Parker, R.J., Hirom, P.C. & Millburn, P. (1980)Xenobiotica10, 689–703.Google Scholar
  11. 14.
    Shaw, I.C. & Griffiths, L.A. (1980)Xenobiotica10, 905–911.CrossRefGoogle Scholar
  12. 16.
    Siddik, Z.H., Barnes, R.D., Dring, L.G., Smith, R.L. & Williams, R.T. (1979) Biochem. Pharmacol. 28, 3081–3091. Google Scholar
  13. 17.
    Chipman, J.K., Hirom, P.C. & Millburn, P. (1980) Biochem. Pharmacol. 29, 1299–1301.Google Scholar
  14. 18.
    Frolik, C.A., Swanson, B.N., Dart, L.L. & Sporn, M.B. (1981)Arch. Biochem. Biophys. 208, 344–352.CrossRefGoogle Scholar
  15. 19.
    Jeffcoat, A.R., Gibson, W.B., Rodriguez, R. A., Turan, T.S., Hughes, P.F. & Twine, M.E. (1980)Toxicol. Appl. Pharmacol. 56, 141–154.CrossRefGoogle Scholar
  16. 20.
    Wu, W.N., Wearier, L.E., Kalbron, J., O’ Neill, P.J. & Grindel, J.M. (1980) Drug Metab. Dispos. 8, 349–352.Google Scholar
  17. 21.
    Warrander, A., Metealf, R. & Fromson, J.M. (1981) Drug Metab. Dispos. 9, 161–167.Google Scholar
  18. 22.
    Le Van, L.W., Schnoes, H.K. & De Luca, H.F. (1981)Biochemistry20, 222–226.CrossRefGoogle Scholar
  19. 23.
    Hains, A.H. (1976)Adv. Carbohydr. Chem. Biochem. 33, 11–109.CrossRefGoogle Scholar
  20. 24.
    Tsuda, Y. & Yoshimoto, K. (1981)Carbohydr. Res. 87, C1 - C4.CrossRefGoogle Scholar
  21. 25.
    Sinclair, K.A. & Caldwell, J. (1981)Biochem. Soc. Trans. 9, 215.Google Scholar
  22. 26.
    Ljevakovic, D j. & Keglevic, D. (1980)Carbohydr. Res. 86, 43–57CrossRefGoogle Scholar
  23. 27.
    Illing, P.A. & Wilson, I.D. (1981) Biochem. Pharmacol. 30, 3381–3884Google Scholar
  24. 28.
    Eggers, N.J. & Doust, K. (1981)J. Pharm. Pharmacol. 33, 123–124.CrossRefGoogle Scholar
  25. 29.
    Hignite, C.E., Tachanz, C., Lemons, S., Wiese, H., Azarnoff, L. & Huffman, D.H. (1981)Life Sci. 28, 2077–2081.CrossRefGoogle Scholar
  26. 30.
    Nemoto, N. & Gelboin, H. (1975)Arch. Biochem. Biophys. 170, 739–742.CrossRefGoogle Scholar
  27. 31.
    Chasseaud, L.F., Down, W.H., Grover, P.L., Sacharin, R.M. & Sims, P. (1980) Biochem. Pharmacol. 29, 1589–1590.Google Scholar
  28. 32.
    Delbressine, L.P.C., Seutter-Berlage, F. & Seutter, E. (1981)Xenobiotica11, 241–247.CrossRefGoogle Scholar
  29. 33.
    Van Bladeren, P.J., Delbressine, L.P.C., Hoogeterp, J.J., Beaumont, A.H.G.M., Breimer, D.D., Seutter-Berlage, F. & van der Gen, A. (1981) Drug Metab. Dispos. 9, 246–249.Google Scholar
  30. 34.
    van Bladeren, P.J., Breimer, D.D., Seghers, C.J.R., Vermeulen, N.P.E., van der Gen, A. & Cauvet, J. (1981) Drug Metab. Dispos. 9, 207–211.Google Scholar
  31. 35.
    Seutter-Berlage, F., Delbressine, L.P.C., Smeets, F. L. M. & Ketalaars, H.C.J. (1978)Xenobiotica8, 413–418.CrossRefGoogle Scholar
  32. 36.
    Watabe, T., Hiratsuka, A., Ozawa, N. & Isobe, M. (1981) Biochem. Pharmacol. 30, 390–392.Google Scholar
  33. 37.
    Plummer, J.L., Smith, B.R., Ball, L.M. & Bend, J.R. (1980)Drug Metab, Dispos. 8, 68–72.Google Scholar
  34. 38.
    Mangold, J.B. & Abdel-Monem, M.M. (1980)Biochem. Biophys. Res. Comm. 96, 333–340.CrossRefGoogle Scholar
  35. 39.
    van Doorn, R., Bos, R.P., Brouns, R.M.E., Leijdekkers, Ch.-M. & Henderson, P. Th. (1980)Arch. Toxicol. 43, 293–304.CrossRefGoogle Scholar
  36. 40.
    Burstein, S. & Lieberman, S. (1958)J. Biol. Chem. 233, 331–335.Google Scholar
  37. 41.
    Goodall, A.B. & James, V.H.T. (1981)J. Steroid Biochem. 14, 465- 471.Google Scholar
  38. 42.
    Baldwin, M.K. & Hutson, D.H. (1980)Xenobiotica10, 135–144.CrossRefGoogle Scholar
  39. 43.
    Islam, M.A., Raicht, R.F. & Cohen, I.B. (1981)Anal. Biochem. 112, 371–377.CrossRefGoogle Scholar
  40. 44.
    Bell, J.A., Bradbury, A., Martin, L.E. & Tanner, R.J.N. (1981)Xenobiotica11, 841–847CrossRefGoogle Scholar
  41. 45.
    Crayford, J.V. & Hutson, D.H. (1980)Xenobiotica10, 355–364.CrossRefGoogle Scholar
  42. 48.
    Krstulovic, A.M., Bertani-Dziedzic, L., Dziedzic, S.W. & Gitlow, S.E. (1981)J. Chromatog. 223, 305–314.CrossRefGoogle Scholar
  43. 49.
    von Loffler, S. & Bolt, H.M. (1980)Arzneim. -Forsch. 30, 810–813.Google Scholar
  44. 50.
    Barford, P.A., Olavesen, A.H., Curtis, C.G. & Powell, G.M. (1977)Biochem. J. 168, 373–377.Google Scholar
  45. 51.
    Samarajeewa, P., Leepipatpaiboon, S. & Coulson, V. F. (1980)Steroids36, 611–618.CrossRefGoogle Scholar
  46. 52.
    Gottschlich,R. & Meitzer, M. (1980)Xenobiotica10, 317–327.CrossRefGoogle Scholar
  47. 53.
    Alme, B. & Sjövall, J. (1980)J. Steroid Biochem. 13, 907–916.CrossRefGoogle Scholar
  48. 54.
    Mattox, V.R. & Litwiller, R.D. (1980)J. Chromatog. 189, 33–42.CrossRefGoogle Scholar
  49. 55.
    Matsui, M. & Aoyagi, S. (1979)Biochem. Pharmacol. 28, 1023–1028.Google Scholar
  50. 56.
    Slikker, W., Jr., Lipe, G.W. & Newport, G.D. (1981)J. Chromatog. 224, 205–219.CrossRefGoogle Scholar
  51. 57.
    Weitering, J.G., Krugsheld, K.R. & Mulder, G.J. (1979) Biochem. Pharmacol. 28, 757–762.Google Scholar
  52. 58.
    Chen, K.-C. & Dorough, H.W. (1979)Drug Chem. Toxicol. 2, 331–354.CrossRefGoogle Scholar
  53. 59.
    Pang, K.S. & Terrell, J.A. (1981) Biochem. Pharmacol. 30, 1959–1965.Google Scholar
  54. 60.
    Filer, C.W., Humphrey, H.J., Jeffery, D.J., Jones, K.H. & Langley, P.F. (1980)Xenobiotica10, 761–769.CrossRefGoogle Scholar
  55. 61.
    Shirkey, R.J., Kao, J., Fry, J. R. & Bridges, J. W. (1979)Biochem. Pharmacol. 28, 1461–1466,Google Scholar
  56. 62.
    Hall, B.E. & James, S.P. (1980)Xenobiotica10, 421–434CrossRefGoogle Scholar
  57. 63.
    Autrup, H. (1979) Biochem. Pharmacol. 28, 1727–1730Google Scholar
  58. 64.
    Schenk, J.& Neuman, H.-G. (1980)Xenobiotica10, 675–688.CrossRefGoogle Scholar
  59. 65.
    Szinicz, L.L. & Weger, N. (1980)Xenobiotica10, 611–620.CrossRefGoogle Scholar
  60. 66.
    Elbers, R., Kampffmeyer, H.G. & Rabes, H. (1980)Xenobiotica10, 621–632.CrossRefGoogle Scholar
  61. 67.
    Son, O.S., Everett, D.W. & Fiala, E.S. (1980)Xenobiotica10, 457–468.CrossRefGoogle Scholar
  62. 68.
    Jones, D.P., Sundby, G.-B., Ormstad, K. & Orrenius, S. (1979) Biochem. Pharmacol. 28, 929–935Google Scholar
  63. 69.
    Grafstror., Ormstad, K., Moldeus, P. & Orrenius, S. (1979) Biochem. Pharmacol. 28, 3573–3579Google Scholar
  64. 70.
    von Siegers, C.-P., Younes, M. & Oltmanns, D. (I98O) Arzneim.- Forsch. J. Drug Res. 30, 804–807.Google Scholar
  65. 71.
    Sanborn, H.R. & Malins, D.C. (1980)Xenobiotica10, 193–200.CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1983

Authors and Affiliations

  • Jelka Tomašić
    • 1
  1. 1.“Ruder Bošković” InstituteZagrebYugoslavia

Personalised recommendations