Abstract
Conjugation of many endogenous and exogenous chemicals with glucuronic acid, catalyzed by UDP-glucuronyltransferases (EC 2.4.1.17), is an important step in their detoxification and elimination from the body. We have previously reported on the purification of three different UDP-glucuronyltransferases (UDPGTs) from hepatic microsomes of female Sprague-Dawley rats1. A 17β-hydroxysteroid UDPGT catalyzes the glucuronidation of the 17β-hydroxy position of steroids, such as testosterone and 17β-estradiol, and xenobiotics such as p-nitrophenol and 1-naphthol. A 3α-hydroxysteroid UDPGT has been purified which is specific for the glucuronidation of the 3α-position of steroids and bile acids2,3. A 3-methylcholanthreneinducible form of p-nitrophenol UDPGT catalyzes the conjugation of various xenobiotic substrates, such as p-nitrophenol, 4-methylumbelliferone and 1-naphthol, with glucuronic acid1.
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C. N. Falany and T. R. Tephly, Separation, purification and characterization of three isoenzymes of UDP-glucuronyltransferase from rat liver microsomes, Arch.Biochem.Biophys. 227: 248 (1983).
R. B. Kirkpatrick, C. N. Falany and T. R. Tephly, Glucuronidation of bile acids by rat liver 3–0H androgen UDP-glucuronyltransferase, J. Biol. Chem. 259: 6176 (1984).
C. N. Falany, R. B. Kirkpatrick and T. R. Tephly, Comparison of rat and rabbit liver UDP-glucuronyltransferase activities, in: “Advances in Glucuronide Conjugation,” S. Matern, K. W. Bock and W. Gerok, eds., MTP Press, Lancaster (1985).
E. Boyland, D. Manson and S. F. D. Orr, The biochemistry of aromatic amines. 2. The conversion of arylamines into arylsulphamic acids and arylamine-N-glucosiduronic acids, Biochem. J. 65: 417 (1957).
I. M. Arias, Ethereal and N-linked glucuronide formation by normal and Gunn rats in vitro and in vivo, Biochem. Biophys. Res. Commun. 6: 81 (1961).
F. F. Kadlubar, L. E. Unruh, T. J. Flammang, D. Sparks, R. K. Mitchum and G. J. Mulder, Alteration of urinary levels of the carcinogen, N-hydroxy-2-naphthylamine, and its N-glucuronide in the rat by control of urinary pH, inhibition of metabolic sulfation and changes in biliary excretion, Chem.. - Biol. Interact. 33: 129 (1981).
R. H. Tukey, R. E. Billings and T. R. Tephly, Separation of oestrone UDP-glucuronyltransferase and p-nitrophenol UDP-glucuronyltransferase activities, Biochem. J. 171: 659 (1978).
W. Lilienblum and K. W. Bock, N-Glucuronide formation of carcinogenic aromatic amines in rat and human liver microsomes, Biochem. Pharmacol. 33:2041 (1984).
R. H. Tukey and T. R. Tephly, Purification and properties of rabbit liver estrone and p-nitrophenol UDP-glucuronyltransferases, Arch. Biochem. Biophys. 209: 565 (1981).
C. Y. Wang, K. Zukowski and M. S. Lee, Glucuronidation of carcinogenic arylamine metabolites by rat liver microsomes, Biochem. Pharmacol. 34: 837 (1985).
M. Matsui, F. Nagai and S. Aoyagi, Strain differences in rat liver UDP-glucuronyltransferase activity towards androsterone, Biochem. J. 179: 483 (1979).
M. Matsui and M. Hakozaki, Discontinuous variation in hepatic uridine diphosphate glucuronyltransferase toward androsterone in Wistar rats. A regulatory factor for in vivo metabolism of androsterone, Biochem. Pharmacol. 28: 411 (1979).
M. D. Green, C. N. Falany, R. B. Kirkpatrick and T. R. Tephly, Strain differences in purified rat hepatic 3α-hydroxysteroid UDP-glucuronosyltransferase, Biochem. J. In press (1985).
G. M. Bonser, D. B. Clayson, J. W. Jull and L. N. Pyrah, The carcinogenic properties of 2-amino-l-naphthol hydrochloride and its parent amine 2-naphthylamine, Br. J. Cancer 6: 412 (1952).
D. B. Clayson and R. C. Garner, in: “Chemical Carcinogens,” C.E. Searle, ed., American Chemical Society, Washington, D.C. (1976).
R. M. Hicks, R. Wright and J. St. J. Wakefield, The induction of rat bladder cancer by 2-naphthylamine, Br. J. Cancer 46: 646 (1982).
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© 1986 Plenum Press, New York
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Green, M.D., Irshaid, Y., Tephly, T.R. (1986). The Formation of N-Glucuronides Catalyzed by Purified Hepatic 17β-Hydroxysteroid and 3α-Hydroxysteroid UDP-Glucuronyltransferases. In: Kocsis, J.J., Jollow, D.J., Witmer, C.M., Nelson, J.O., Snyder, R. (eds) Biological Reactive Intermediates III. Advances in Experimental Medicine and Biology, vol 197. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-5134-4_38
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DOI: https://doi.org/10.1007/978-1-4684-5134-4_38
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