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. 1994 Oct;102(Suppl 6):99–103. doi: 10.1289/ehp.94102s699

Characterization and expression of hepatic sulfotransferase involved in the metabolism of N-substituted aryl compounds.

Y Yamazoe 1, S Ozawa 1, K Nagata 1, D W Gong 1, R Kato 1
PMCID: PMC1566861  PMID: 7889867

Abstract

An aryl sulfotransferase, whose cDNA was isolated from the rat liver library, was found to catalyze bioactivation of minoxidil through N-O-sulfation and N-sulfation of a carcinogenic heterocyclic amine, IQ, by expression in COS-1 cells. cDNA of a human ortholog also was isolated and characterized as a major minoxidil-activating enzyme in human liver. Another group of aryl sulfotransferases catalyzing O-sulfation of carcinogenic N-hydroxyarylamines was separated from livers of rats and humans. These sulfotransferases have been shown to possess similar functional properties and also to relate immunochemically with each other. Current understanding on the primary structure of these sulfotransferases also is discussed.

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Selected References

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  1. Abu-Zeid M., Nagata K., Miyata M., Ozawa S., Fukuhara M., Yamazoe Y., Kato R. An arylamine acetyltransferase (AT-I) from Syrian golden hamster liver: cloning, complete nucleotide sequence, and expression in mammalian cells. Mol Carcinog. 1991;4(1):81–88. doi: 10.1002/mc.2940040112. [DOI] [PubMed] [Google Scholar]
  2. Abu-Zeid M., Yamazoe Y., Kato R. Sulfotransferase-mediated DNA binding of N-hydroxyarylamines(amide) in liver cytosols from human and experimental animals. Carcinogenesis. 1992 Aug;13(8):1307–1314. doi: 10.1093/carcin/13.8.1307. [DOI] [PubMed] [Google Scholar]
  3. Buhl A. E., Waldon D. J., Baker C. A., Johnson G. A. Minoxidil sulfate is the active metabolite that stimulates hair follicles. J Invest Dermatol. 1990 Nov;95(5):553–557. doi: 10.1111/1523-1747.ep12504905. [DOI] [PubMed] [Google Scholar]
  4. DeBaun J. R., Miller E. C., Miller J. A. N-hydroxy-2-acetylaminofluorene sulfotransferase: its probable role in carcinogenesis and in protein-(methion-S-yl) binding in rat liver. Cancer Res. 1970 Mar;30(3):577–595. [PubMed] [Google Scholar]
  5. GRIFFIN A. C., RICHARDSON H. L., ROBERTSON C. H., O'NEAL M. A., SPAIN J. D. The role of hormones in liver carcinogenesis. J Natl Cancer Inst. 1955 Apr;15(5 Suppl):1623–1632. [PubMed] [Google Scholar]
  6. Gong D. W., Murayama N., Yamazoe Y., Kato R. Hepatic triiodothyronine sulfation and its regulation by growth hormone and triiodothyronine in rats. J Biochem. 1992 Jul;112(1):112–116. doi: 10.1093/oxfordjournals.jbchem.a123848. [DOI] [PubMed] [Google Scholar]
  7. Gong D. W., Ozawa S., Yamazoe Y., Kato R. Purification of hepatic N-hydroxyarylamine sulfotransferases and their regulation by growth hormone and thyroid hormone in rats. J Biochem. 1991 Aug;110(2):226–231. doi: 10.1093/oxfordjournals.jbchem.a123561. [DOI] [PubMed] [Google Scholar]
  8. Johnson G. A., Baker C. A. Sulfation of minoxidil by human platelet sulfotransferase. Clin Chim Acta. 1987 Nov 16;169(2-3):217–227. doi: 10.1016/0009-8981(87)90322-6. [DOI] [PubMed] [Google Scholar]
  9. King C. M., Phillips B. Enzyme-catalyzed reactions of the carcinogen N-hydroxy-2-fluorenylacetamide with nucleic acid. Science. 1968 Mar 22;159(3821):1351–1353. doi: 10.1126/science.159.3821.1351. [DOI] [PubMed] [Google Scholar]
  10. Lotlikar P. D. Effects of sex hormones on enzymic esterification of 2-(N-hydroxy-acetamido) fluorene by rat liver cytosol. Biochem J. 1970 Nov;120(2):409–416. doi: 10.1042/bj1200409. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. MILLER E. C., MILLER J. A. Biochemical investigations on hepatic carcinogenesis. J Natl Cancer Inst. 1955 Apr;15(5 Suppl):1571–1590. [PubMed] [Google Scholar]
  12. Meerman J. H., van Doorn A. B., Mulder G. J. Inhibition of sulfate conjugation of N-hydroxy-2-acetylaminofluorene in isolated perfused rat liver and in the rat in vivo by pentachlorophenol and low sulfate. Cancer Res. 1980 Oct;40(10):3772–3779. [PubMed] [Google Scholar]
  13. Meisheri K. D., Oleynek J. J., Puddington L. Role of protein sulfation in vasodilation induced by minoxidil sulfate, a K+ channel opener. J Pharmacol Exp Ther. 1991 Sep;258(3):1091–1097. [PubMed] [Google Scholar]
  14. Ogura K., Kajita J., Narihata H., Watabe T., Ozawa S., Nagata K., Yamazoe Y., Kato R. cDNA cloning of the hydroxysteroid sulfotransferase STa sharing a strong homology in amino acid sequence with the senescence marker protein SMP-2 in rat livers. Biochem Biophys Res Commun. 1990 Feb 14;166(3):1494–1500. doi: 10.1016/0006-291x(90)91036-r. [DOI] [PubMed] [Google Scholar]
  15. Ozawa S., Nagata K., Gong D. W., Yamazoe Y., Kato R. Nucleotide sequence of a full-length cDNA (PST-1) for aryl sulfotransferase from rat liver. Nucleic Acids Res. 1990 Jul 11;18(13):4001–4001. doi: 10.1093/nar/18.13.4001. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. RUMSFELD H. W., Jr, MILLER W. L., Jr, BAUMANN C. A. A sex difference in the development of liver tumors in rats fed 3'-methyl-4-dimethylaminoazobenzene or 4'-fluoro-4-dimethylaminoazobenzene. Cancer Res. 1951 Oct;11(10):814–819. [PubMed] [Google Scholar]
  17. Sekura R. D., Jakoby W. B. Aryl sulfotransferase IV from rat liver. Arch Biochem Biophys. 1981 Oct 1;211(1):352–359. doi: 10.1016/0003-9861(81)90464-1. [DOI] [PubMed] [Google Scholar]
  18. Shimada M., Murayama N., Yamazoe Y., Kamataki T., Kato R. Further studies on the persistence of neonatal androgen imprinting on sex-specific cytochrome P-450, testosterone and drug oxidations. Jpn J Pharmacol. 1987 Dec;45(4):467–478. doi: 10.1254/jjp.45.467. [DOI] [PubMed] [Google Scholar]
  19. Sugimura T. New environmental carcinogens in daily life. Trends Pharmacol Sci. 1988 Jun;9(6):205–209. doi: 10.1016/0165-6147(88)90086-7. [DOI] [PubMed] [Google Scholar]
  20. Turesky R. J., Aeschbacher H. U., Würzner H. P., Skipper P. L., Tannenbaum S. R. Major routes of metabolism of the food-borne carcinogen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in the rat. Carcinogenesis. 1988 Jun;9(6):1043–1048. doi: 10.1093/carcin/9.6.1043. [DOI] [PubMed] [Google Scholar]
  21. Turesky R. J., Skipper P. L., Tannenbaum S. R., Coles B., Ketterer B. Sulfamate formation is a major route for detoxification of 2-amino-3-methylimidazo[4,5-f]quinoline in the rat. Carcinogenesis. 1986 Sep;7(9):1483–1485. doi: 10.1093/carcin/7.9.1483. [DOI] [PubMed] [Google Scholar]
  22. Weinshilboum R. Sulfotransferase pharmacogenetics. Pharmacol Ther. 1990;45(1):93–107. doi: 10.1016/0163-7258(90)90010-y. [DOI] [PubMed] [Google Scholar]
  23. Weisburger J. H., Yamamoto R. S., Williams G. M., Grantham P. H., Matsushima T., Weisburger E. K. On the sulfate ester of N-hydroxy-N-2-fluorenylacetamide as a key ultimate hepatocarcinogen in the rat. Cancer Res. 1972 Mar;32(3):491–500. [PubMed] [Google Scholar]
  24. Yamazoe Y., Manabe S., Murayama N., Kato R. Regulation of hepatic sulfotransferase catalyzing the activation of N-hydroxyarylamide and N-hydroxyarylamine by growth hormone. Mol Pharmacol. 1987 Oct;32(4):536–541. [PubMed] [Google Scholar]
  25. Yamazoe Y., Shimada M., Kamataki T., Kato R. Effects of hypophysectomy and growth hormone treatment on sex-specific forms of cytochrome P-450 in relation to drug and steroid metabolisms in rat liver microsomes. Jpn J Pharmacol. 1986 Nov;42(3):371–382. doi: 10.1254/jjp.42.371. [DOI] [PubMed] [Google Scholar]
  26. Yamazoe Y., Shimada M., Murayama N., Kato R. Suppression of levels of phenobarbital-inducible rat liver cytochrome P-450 by pituitary hormone. J Biol Chem. 1987 May 25;262(15):7423–7428. [PubMed] [Google Scholar]

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