Biology and function of the reversible sulfation pathway catalysed by human sulfotransferases and sulfatases

Chemico-Biological Interactions

Volumn 109, Issue 1-3, 1998, Pages 3-27

  Coughtrie, Michael W H ^a   Sharp, Sheila ^a   Maxwell, Kaera ^a   Innes, Nicola P ^a  

^a UNIVERSITY OF DUNDEE   (United Kingdom)

Author keywords

Sulfatases; Sulfation; Sulfotransferases

Indexed keywords

4 NITROPHENOL; ARYLSULFATASE; CAFFEIC ACID; CARCINOGEN; COMPLEMENTARY DNA; DOPAMINE; ESTRONE SULFATE; MUTAGENIC AGENT; PRASTERONE SULFATE; STEROID; SULFATASE; SULFATE; SULFOTRANSFERASE;

AMINO ACID SEQUENCE; ANIMAL CELL; BEVERAGE; CATALYSIS; CHINESE HAMSTER; COFFEE; CONFERENCE PAPER; DETOXIFICATION; ENVIRONMENTAL FACTOR; ENZYME ANALYSIS; ENZYME SUBSTRATE; FRUIT JUICE; GENETICS; HUMAN; HUMAN CELL; LUNG FIBROBLAST; NONHUMAN; NUCLEOTIDE SEQUENCE; PROTEIN EXPRESSION; STEROIDOGENESIS; SULFATION; TEA; THROMBOCYTE;

AMINO ACID SEQUENCE; ANIMALS; HUMANS; MOLECULAR SEQUENCE DATA; SEQUENCE HOMOLOGY, AMINO ACID; SULFATASES; SULFATES; SULFOTRANSFERASES;

EID: 0032549065     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(97)00117-8     Document Type: Conference Paper

References (129)

1. Falany C.N. Molecular enzymology of human liver cytosolic SULTs. Trends Pharmacol. Sci. 12:1991;255-259.
2. Weinshilboum R., Otterness D. Sulfotransferase enzymes. Kauffman F.C. Conjugation-Deconjugation Reactions in Drug Metabolism and Toxicity. 1994;45-78 Springer, Berlin.
3. Coughtrie M.W.H. Sulphation catalysed by the human cytosolic sulphotransferases-chemical defence or molecular terrorism? Hum. Exp. Toxicol. 15:1996;547-555.
4. Jedlitschky G., Leier I., Buchholz U., Barnouin K., Kurz G., Keppler D. Transport of glutathione, glucuronate and sulfate conjugates by the MRP gene-encoded conjugate export pump. Cancer Res. 56:1996;988-994.
5. Hassen A.M., Lam D., Chiba M., Tan E., Geng W., Pang K.S. Uptake of sulfate conjugates by isolated rat hepatocytes. Drug Metab. Dispos. 24:1996;792-798.
6. Oddy E.A., Manchee G.R., Coughtrie M.W.H. Assessment of rat liver slices as a suitable model system for studying the simultaneous sulphation and glucuronidation of phenolic xenobiotics. Xenobiotica. 27:1997;369-377.
7. Lyle S., Stanczak J., Ng K., Schwartz N.B. Rat chondrosarcoma ATP sulfurylase and adensosine 5′-phosphosulfate kinase reside on a single bifunctional protein. Biochemistry. 33:1994;5920-5925.
8. Lyle S., Ozeran D., Stanczak J., Westley J., Schwartz N.B. Intermediate channeling between ATP sulfurylase and adenosine 5′-phosphosulfate kinase from rat chondrosarcoma. Biochemistry. 33:1994;6822-6827.
9. Sugahara K., Schwartz N.B. Defect in PAPS formation in brachymorphic mice. Proc. Natl. Acad. Sci. USA. 76:1979;6615-6618.
10. Lyle S., Stanczak J.D., Westley J., Schwartz N.B. Sulfate-activating enzymes in normal and brachymorphic mice: evidence for a channeling defect. Biochemistry. 34:1995;940-945.
11. Ozeran J.D., Westley J., Schwartz N.B. Kinetics of PAPS translocase-evidence for an antiport mechanism. Biochemistry. 35:1996;3685-3694.
12. Ozeran J.D., Westley J., Schwartz N.B. Identification and partial-purification of PAPS translocase. Biochemistry. 35:1996;3695-3703.
13. Hjelle J.J., Hazelton G.A., Klaassen C.D. Acetaminophen decreases adenosine PAPS and uridine diphosphoglucuronic acid in rat liver. Drug Metab. Dispos. 13:1985;35-41.
14. Kim H.J., Cho J.H., Klassen C.D. Depletion of hepatic PAPS and sulfate in rats by xenobiotics that are sulfated. J. Pharmacol. Exp. Ther. 275:1995;654-658.
15. Krijgsheld K.R., Scholtens E., Mulder G.J. An evaluation of methods to decrease the availability of inorganic sulphate for sulphate conjugation in the rat in vivo. Biochem. Pharmacol. 30:1981;1973-1979.
16. Kim H.J., Rozman P., Klaassen C.D. Acetaminophen does not decrease hepatic PAPS in mice. J. Pharmacol. Exp. Ther. 275:1995;1506-1511.
17. Nagata K., Ozawa S., Miyata M., Shimada M., Gong D.-W., Yamazoe Y., Kato R. Isolation and expression of a cDNA encoding a male-specific rat sulfotransferase that catalyzes activation of N-hydroxy-2-acetylaminofluorene. J. Biol. Chem. 268:1993;24720-24725.
18. Sakakibara Y., Takami Y., Zwieb C., Nakayama T., Suiko M., Nakajima H., Liu M.C. Purification, characterization and molecular cloning of a novel rat liver Dopa/tyrosine sulfotransferase. J. Biol. Chem. 270:1995;30470-30478.
19. Her C., Kaur G.P., Athwal R.S., Weinshilboum R.M. Human sulfotransferase SULT1C1: cDNA cloning, tissue-specific expression and chromosomal localization. Genomics. 41:1997;467-470.
20. Bamforth K.J., Jones A.L., Roberts R.C., Coughtrie M.W.H. Common food additives are potent inhibitors of human liver 17-α-ethinylestradiol and dopamine SULTs. Biochem. Pharmacol. 46:1993;1713-1720.
21. Ballabio A., Shapiro L.J. Steroid sulfatase deficiency and X-linked ichthyosis. Scriver C.R., Beaudet A.L., Sly W.S., Valle D. The Metabolic and Molecular Bases of Inherited Disease. 1995;2999-3022 McGraw-Hill, New York.
22. Kolodny E.H., Fluharty A.L. Metachromatic leukodystrophy and multiple sulfatase deficiency: sulfatide lipidosis. Scriver C.R., Beaudet A.L., Sly W.S., Valle D. The Metabolic and Molecular Bases of Inherited Disease. 1995;2693-2741 McGraw-Hill, New York.
23. Neufeld E.F., Muenzer J. The mucopolysaccharidoses. Scriver C.R., Beaudet A.L., Sly W.S., Valle D. The Metabolic and Molecular Bases of Inherited Disease. 1995;2465-2494 McGraw-Hill, New York.
24. Franco B., Meroni G., Parenti G., Levilliers J., Bernard L., Gebbia M., Cox L., Maroteaux P., Sheffield L., Rappold G.A., Andria G., Petit C., Ballabio A. A cluster of sulfatase genes on Xp22.3: mutations in chondrodysplasia punctata (CDPX) and implications for warfarin embryopathy. Cell. 81:1995;15-25.
25. Meroni G., Franco B., Archidiacono N., Messali S., Andolfi G., Rocchi M., Ballabio A. Characterization of a cluster of sulfatase genes on Xp22.3 suggests gene duplications in an ancestral pseudoautosomal region. Hum. Mol. Genet. 5:1996;423-431.
26. Schmidt B., Selmer T., Ingendoh A., von Figura K. A novel amino acid modification in sulfatases that is defective in multiple sulfatase deficiency. Cell. 82:1995;271-278.
27. Selmer T., Hallmann A., Schmidt B., Sumper M., von Figura K. The evolutionary conservation of a novel protein modification, the conversion of cysteine to serinesemialdehyde in arylsulfatase from Volvox carteri. Eur. J. Biochem. 238:1996;341-345.
28. Kung M.-P., Spaulding S.W., Roth J.A. Desulfation of 3,5,3′-triiodothyronine sulfate by microsomes from human and rat tissues. Endocrinology. 122:1988;1195-1200.
29. Spaulding S.W., Smith T.J., Hinkle P.M., Davis F.B., Kung M.-P., Roth J.A. Studies on the biological activity of triidothyronine sulfate. J. Clin. Endocrinol. Metab. 74:1992;1062-1067.
30. Falany C.N., Krasnykh V., Falany J.L. Bacterial expression and characterization of a cDNA for human liver estrogen sulfotransferase. J. Steroid Biochem. Mol. Biol. 52:1995;529-539.
31. Falany C.N., Wheeler J., Oh T.S., Falany J.L. Steroid sulfation by expressed human cytosolic SULTs. J. Steroid Biochem. Mol. Biol. 48:1994;369-375.
32. Lewis A.J., Kelly M.M., Walle U.K., Eaton E.A., Falany C.N., Walle T. Improved bacterial expression of the human P form phenolsulfotransferase-applications to drug metabolism. Drug Metab. Dispos. 24:1996;1180-1185.
33. Veronese M.E., Burgess W., Zhu X.Y., Mcmanus M.E. Functional-characterization of two human sulfotransferase cDNAs that encode monoamine-sulfating and phenol-sulfating forms of phenol sulfotransferase-substrate kinetics, thermal-stability and inhibitor-sensitivity studies. Biochem. J. 302:1994;497-502.
34. Zhu X., Veronese M.E., Iocco P., Mcmanus M.E. cDNA cloning and expression of a new form of human aryl sulfotransferase. Int. J. Biochem. Cell. Biol. 28:1996;565-571.
35. Aksoy I.A., Wood T.C., Weinshilboum R. Human liver estogen sulfotransferase: identification by cDNA cloning and expression. Biochem. Biophys. Res. Commun. 200:1994;1621-1629.
36. Wood T.C., Aksoy I.A., Aksoy S., Weinshilboum R.M. Human liver thermolabile phenol sulfotransferase, cDNA cloning, expression and characterization. Biochem. Biophys. Res. Commun. 198:1994;1119-1127.
37. Wilborn T.W., Comer K.A., Dooley T.P., Reardon I.M., Heinrikson R.L., Falany C.N. Sequence analysis and expression of the cDNA for the phenol-sulfating form of human liver phenol sulfotransferase. Mol. Pharmacol. 43:1993;70-77.
38. Comer K.A., Falany J.L., Falany C.N. Cloning and expression of human liver dehydropiandrosterone sulphotransferase. Biochem. J. 289:1993;233-240.
39. Jones A.L., Hagen M., Coughtrie M.W.H., Roberts R.C., Glatt H. Human platelet phenol-SULTs, cDNA cloning, stable expression in V79 cells and identification of a novel allelic variant of the phenol-sulfating form. Biochem. Biophys. Res. Commun. 208:1995;855-862.
40. Forbes K.J., Hagen M., Glatt H., Hume R., Coughtrie M.W.H. Human fetal adrenal hydroxysteroid sulphotransferase: cDNA cloning stable expression in V79 cells and functional characterisation of the expressed enzyme. Mol. Cell. Endocrinol. 112:1995;53-60.
41. Remmel R.P., Burchell B. Validation and use of cloned, expressed human drug-metabolizing enzymes in heterologous cells for analysis of drug metabolism and drug-drug interactions. Biochem. Pharmacol. 46:1993;559-566.
42. Glatt H., Pauly K., Pieestaffa A., Seidel A., Hornhardt S., Czich A. Activation of promutagens by endogenous and heterologous SULTs expressed in continuous cell-cultures. Toxicol. Lett. 72:1994;13-21.
43. Glatt H., Pauly K., Czich A., Falany J.L., Falany C.N. Activation of benzylic alcohols to mutagens by rat and human SULTs expressed in E. coli. Eur. J. Pharmacol. 293:1995;173-181.
44. Glatt H., Bartsch I., Czich A., Seidel A., Falany C.N. S. typhimurium strains and mammalian cells genetically engineered for expression of sulfotransferases. Toxicol. Lett. 82(3):1995;829-834.
45. Glatt H.R. Bioactivation of mutagens via sulfation. FASEB J. 11:1997;314-321.
46. Stein C., Hille A., Seidel J., Rijnbout S., Waheed A., Schmidt B., von Figura K. Cloning and expression of human steroid sulfatase. Membrane topology glycosylation and subcellular distribution in BHK-21 cells. J. Biol. Chem. 264:1989;13865-13872.
47. Peters C., Schmidt B., Rommerskirch W., Rupp K., Zuhlsdorf M., Vingron M., Meyer H.E., Pohlmann R., von Figura K. Phylogenetic conservation of ARS-cDNA cloning and expression of human arylsulfatase B. J. Biol. Chem. 265:1990;3374-3381.
48. Stein C., Gieselmann V., Kreysing J., Schmidt B., Pohlmann R., Waheed A., Meyer H.E., O'Brien J.S., von Figura K. Cloning and expression of human arylsulfatase A. J. Biol. Chem. 264:1989;1252-1259.
49. Mulder G.J., Jakoby W.B. Sulfation. Mulder G.J. Conjugation Reactions in Drug Metabolism. 1990;107-161 Taylor and Francis, London.
50. Ratge D., Kohse K.P., Steegmuller U., Wisser H. Distribution of free and conjugated catecholamines between plasma, platelets and erythrocytes: different effects of intravenous and oral catecholamine administrations. J. Pharmacol. Exp. Ther. 257:1991;232-238.
51. Ratge D., Knoll E., Wisser H. Plasma free and conjugated catecholamines in clinical disorders. Life Sci. 39:1986;557-564.
52. Rubin G.L., Sharp S., Jones A.L., Glatt H., Mills J.A., Coughtrie M.W.H. Design, production and characterisation of antibodies discriminating between the phenol- and monoamine-sulphating forms of human phenol sulphotransferase. Xenobiotica. 26:1996;1113-1119.
53. Roy A.K. Regulation of steroid hormone action in target cells by specific hormone-inactivating enzymes. Proc. Soc. Exp. Biol. Med. 199:1992;265-272.
54. Buirchell B.J., Hähnel R. Metabolism of estradiol-17β in human endometrium during the menstrual cycle. J. Steroid Biochem. 6:1975;1489-1494.
55. Clarke C.L., Adams J.B., Wren B.G. Induction of estrogen sulfotransferase in the human endometrium by progesterone in organ culture. J. Clin. Endocrinol. Metab. 55:1982;70-75.
56. Falany J.L., Falany C.N. Regulation of estrogen sulfotransferase in human endometrial adenocarcinoma cells by progesterone. Endocrinology. 137:1996;1395-1401.
57. Jones A.L., Hume R., Bamforth K.J., Coughtrie M.W.H. Estrogen and phenol sulfotransferase activities in human fetal lung. Early Hum. Dev. 28:1992;65-77.
58. Barker E.V., Hume R., Hallas A., Coughtrie M.W.H. Dehydroepiandrosterone sulfotransferase in the developing human fetus-quantitative biochemical and immunological characterization of the hepatic, renal and adrenal enzymes. Endocrinology. 134:1994;982-989.
59. Hume R., Barker E.V., Coughtrie M.W.H. Differential expression and immunohistochemical localization of the phenol and hydroxysteroid sulfotransferase enzyme families in the developing lung. Histochem. Cell Biol. 105:1996;147-152.
60. Mortola J.F., Yen S.S.C. The effects of oral dehydroepiandrosterone on endocrine-metabolic parameters in postmenopausal women. J. Clin. Endocrinol. Metab. 71:1990;696-704.
61. Orienteich L., Brind J.L., Rizer R.L., Vogelman J.H. Age changes and sex differences in serum DHEAS concentration throughout adulthood. J. Clin. Endocrinol. Metab. 59:1984;551-555.
62. Woods M.N., Gorbach S.L., Longcope C., Goldin B.R., Dwyer J.T., Morrill-LaBrode A. Low-fat, high-fiber diet and serum estrone sulfate in premenopausal women. Am. J. Hum. Nutr. 49:1989;1179-1183.
63. Kuss E. The fetoplacental unit of primates. Exp. Clin. Endocrinol. 102:1994;135-165.
64. Howarth N.M., Purohit A., Reed M.J., Potter B.V.L. Estrone sulfamates-potent inhibitors of estrone sulfatase with therapeutic potential. J. Med. Chem. 37:1994;219-221.
65. Purohit A., Woo L.W.L., Singh A., Winterborn C.J., Potterk B.V.L., Reed M.J. In vivo activity of 4-methylcoumarin-7-O-sulfamate, a nonsteroidal, nonestrogenic steroid sulfatase inhibitor. Cancer Res. 56:1996;4950-4955.
66. Selcer K.W., Jagannathan S., Rhodes M.E., Li P.K. Inhibition of placental estrone sulfatase activity and MCF-7 breast cancer cell proliferation by estrone-3-amino derivatives. J. Steroid Biochem. Mol. Biol. 59:1996;83-91.
67. Woo L.L.W., Purohit A., Reed M.J., Potter B.V.L. Active site directed inhibition of estrone sulfatase by nonsteroidal coumarin sulfamates. J. Med. Chem. 39:1996;1349-1351.
68. Rearick J.I., Albro P.W., Jetten A.M. Increase in cholesterol sulfotransferase activity during in vitro squamous differentiation of rabbit tracheal epithelial cells and its inhibition by retinoic acid. J. Biol. Chem. 262:1987;13069-13074.
69. Jetten A.M., George M.A., Nervi C., Boone L.R., Rearick J.I. Increased cholesterol sulfate and cholesterol sulfotransferase activity in relation to the multi-step process of differentiation in human epidermal keratinocytes. J. Invest. Dermatol. 92:1989;203-209.
70. Meisheri K.D., Johnson G.A., Puddington L. Enzymatic and non-enzymatic sulfation mechanisms in the biological actions of minoxidil. Biochem. Pharmacol. 45:1993;271-279.
71. + permeability. J. Pharmacol. Exp. Ther. 245:1988;751-760.
72. Garay R.P., Rosati C., Fanous K., Allard M., Morin E., Lamiable D., Vistelle R. Evidence for (+)-cicletanine sulfate as an active natriuretic metabolite of cicletanine in the rat. Eur. J. Pharmacol. 274:1995;175-180.
73. Robel P., Baulieu E. Neurosteroids: biosynthesis and function. Trends Endocrinol. Metab. 5:1994;1-8.
74. Lambert J.J., Belelli D., Hill-Venning C., Peters J.A. Neurosteroids and GABAA receptor function. Trends Pharmacol. Sci. 16:1995;295-303.
75. Flood J.F., Morley J.E., Roberts E. Memory-enhancing effects in male mice of pregnenolone and steroids metabolically derived from it. Proc. Natl. Acad. Sci. USA. 89:1989;1567-1571.
76. Li P., Rhodes M.E., Burke A.M., Johnson D.A. Memory enhancement mediated by the steroids sulfatase inhibitor (p-O-sulfamoyl)-N-tetradecanoyl tyramine. Life Sci. 60:1996;PL45-PL51.
77. Robel P., Young J., Corpechot C., Mayo W., Perche F., Haug M., Simon H., Baulieu E.E. Biosynthesis and assay of neurosteroids in rats and mice: functional correlates. J. Steroid Biochem. Mol. Biol. 53:1995;355-360.
78. Miller J.A. Sulfonation in chemical carcinogenesis, history and present status. Chem.-Biol. Interact. 92:1994;329-341.
79. Miller J.A. Recent studies on the metabolic-activation of chemical carcinogens. Cancer Res. 54:1994;S1879-S1881.
80. Boberg E.W., Miller E.C., Miller J.A., Poland A., Liem A. Strong evidence from studies with brachymorphic mice and pentachlorophenol that 1′-sulfooxysafrole is the major ultimate electrophilic and carcinogenic metabolite of 1′-hydroxysafrole in mouse liver. Cancer Res. 43:1983;5163-5173.
81. Sugahara K., Schwartz N.R. Defect in PAPS synthesis in brachymorphic mice. I. Characterization of the defect. Arch. Biochem. Biophys. 214:1982;589-601.
82. Sugahara K., Schwartz N.B. Defect in PAPS synthesis in brachymorphic mice. II. Tissue distribution of the defect. Arch. Biochem. Biophys. 214:1982;602-609.
83. Gilissen R.A.H.J., Bamforth K.J., Stavenuiter J.F.C., Coughtrie M.W.H., Meerman J.H.N. Sulfation of aromatic hydroxamic acids and hydroxylamines by multiple forms of human liver sulfotransferases. Carcinogenesis. 15:1994;39-45.
84. Ozawa S., Chou H.C., Kadlubar F.F., Yamazoe Y., Kato R. Activation of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine by cDNA-expressed human and rat aryl sulfotransferases. Jpn. J. Cancer Res. 85:1994;1220-1228.
85. Chou H.-C., Lang N.P., Kadlubar F.F. Metabolic activation of N-hydroxy arylamines and N-hydroxy heterocyclic amines by human sulfotransferase(s). Cancer Res. 55:1995;525-529.
86. Rein G., Glover V., Sandler M. Mutiple forms of phenolsulphotransferase in human tissues. Selective inhibition by dichloronitrophenol. Biochem. Pharmacol. 31:1982;1893-1897.
87. Baranczyk-Kuzma A., Ciszewska-Pilczynska A. Human ileum phenol sulfotransferase. Biochem. Pharmacol. 38:1989;2927-2930.
88. Cappiello M., Giuliani L., Pacifici G.M. Differential distribution of phenol and catechol sulphotransferases in human liver and intestinal mucosa. Drug Metab. Dispos. 17:1990;255-264.
89. Her C., Szumlanski C., Aksoy I.A., Weinshilboum R.M. Human jejunal estrogen sulfotransferase and dehydroepiandrosterone sulfotransferase, immunochemical characterization of individual variation. Drug Metab. Dispos. 24:1996;1328-1335.
90. Apostolides Z., Balentine D.A., Harbowy M.E., Hara Y., Weisburger J.H. Inhibition of PhlP mutagenicity by catechins and by theaflavins and gallate esters. Mutat. Res. 389:1997;167-172.
91. Stavric B. Quercetin in our diet, from potent mutagen to probable anticarcinogen. Clin. Biochem. 27:1994;245-248.
92. Xu M., Bailey A.C., Hernaez J.F., Taoka C.R., Schut H.A.J., Dashwood R.H. Protection by green tea, black tea and indole-3-carbinol against 2-amino-3-methylimidazo[4,5-f]quinoline-induced DNA adducts and colonic aberrant crypts in the F344 rat. Carcinogenesis. 17:1996;1429-1434.
93. Weisburger J.H., Hara Y., Dolan L., Luo F.Q., Pittman B., Zang E. Tea polyphenols as inhibitors of mutagenicity of major classes of carcinogens. Mutat. Res. 371:1996;57-63.
94. Barch D.H., Rundhaugen L.M., Thomas P.E., Kardos P. Dietary ellagic acid inhibits the enzymatic activity of CYP1A1 without altering hepatic concentrations of CYP1A1 or CYP1A1 messenger RNA. Biochem. Biophys. Res. Commun. 201:1994;1477-1482.
95. Barch D.H., Rundhaugen L.M. Ellagic acid induces NAD(P)H-quinone reductase through activation of the antioxidant responsive element of the rat NAD(P)H-quinone reductase gene. Carcinogenesis. 15:1994;2065-2068.
96. Barch D.H., Rundhaugen L.M., Pillay N.S. Ellagic acid induces transcription of the rat glutathione S-transferase Ya gene. Carcinogenesis. 16:1995;665-668.
97. Nijhoff W.A., Bosboom M.A., Smidt M.H., Peters W.H.M. Enhancement of rat hepatic and gastrointestinal glutathione and glutathione S-transferases by α-angelicalactone and flavone. Carcinogenesis. 16:1995;607-612.
98. Talalay P., Fahey J.W., Holtzclaw W.D., Prestera T., Zhang Y.S. Chemoprotection against cancer by phase-2 enzyme induction. Toxicol. Lett. 82(3):1995;173-179.
99. Gibb C., Glover V., Sandler M. In vitro inhibition of phenolsulphotransferae by food and drink constituents. Biochem. Pharmacol. 36:1987;2325-2330.
100. Littlewood J.T., Glover V., Sandler M. Red wine contains a potent inhibitor of phenolsulfotransferase. Br. J. Clin. Pharmacol. 19:1985;275-278.
101. Jones A.L., Roberts R.C., Colvin D.W., Rubin G.L., Coughtrie M.W.H. Reduced platelet phenolsulphotransferase acitvity towards dopamine and 5-hydroxytryptamine in migraine. Eur. J. Clin. Pharmacol. 49:1995;109-114.
102. Walle T., Eaton E.A., Walle U.K. Quercetin, a potent and specific inhibitor of the human P-form phenolsulfotransferase. Biochem. Pharmacol. 50:1995;731-734.
103. Hollman P.C.H., vanTrijp J.M.P., Mengelers M.J.B., deVries J.H.M., Katan M.B. Bioavailability of the dietary antioxidant flavonol quercetin in man. Cancer Lett. 114:1997;139-140.
104. Katiyar S.K., Mukhtar H. Tea in chemoprevention of cancer, epidemiologic and experimental studies. Int. J. Oncol. 8:1996;221-238.
105. Kohlmeier L., Weterings K.G.C., Steck S., Kok F.J. Tea and cancer prevention, an evaluation of the epidemiologic literature. Nutr. Cancer. 27:1997;1-13.
106. Ji B.T., Chow W.H., Hsing A.W., McLaughlin J.K., Dai Q., Gao Y.T., Blot W.J., Fraumeni J.F. Green tea consumption and the risk of pancreatic and colorectal cancers. Int. J. Cancer. 70:1997;255-258.
107. Wargovich M.J. Experimental evidence for cancer preventive elements in foods. Cancer Lett. 114:1997;11-17.
108. Lowis E.I., Oakey R.E. Steroid sulphatases deficiency: identification of heterozygotes using hydrolysis of dehydroepiandrosterone sulphate by peripheral leucocytes. Ann. Clin. Biochem. 33:1996;219-226.
109. Rizk D.E.E., Johansen K.A. Maternal steroid sulfatase deficiency, cause of high-risk pregnancy? Am. J. Obstet. Gynecol. 171:1994;566-567.
110. Keren D.F., Canick J.A., Johnson M.Z., Schaldenbrand J.D., Haning R.V., Hackett R. Low maternal serum unconjugated estriol during prenatal screening as an indication of placental steroid sulfatase deficiency and X-linked ichthyosis. Am. J. Clin. Pathol. 103:1995;400-403.
111. Taylor N.F. Review: placental sulphatase deficiency. J. Inherit. Metab. Dis. 5:1982;164-176.
112. Traupe H., Happle R. Clinical spectrum of steroid sulfatase deficiency: X-linked recessive ichthyosis, birth complications and cryptorchidsm. Eur. J. Pediatr. 140:1983;19-21.
113. Paige D.G., Emilion G.G., Bouloux P.M.G., Harper J.I. A clinical and genetic study of X-linked recessive ichthyosis and contiguous gene defects. Br. J. Dermatol. 131:1994;622-629.
114. Lykkesfeldt G., Bennett P., Lykkesfeldt A.E., Micic S., Rorth M., Skakkebaek N.E., Svenstrup B. Testis cancer, ichthyosis constitutes a significant risk factor. Cancer. 67:1991;730-734.
115. Yamamoto T., Yokota K., Urabe M., Kitawaki J., Honjo H. The inhibitory effect of medroxyprogesterone acetate on steroid sulfatase in human uterine endometrial cancer cells. Endocrine-Rel. Cancer. 3:1996;337-340.
116. Li X.M., Alperin E.S., Salido E., Gong Y., Yen P., Shapiro L.J. Characterization of the promoter region of human steroid sulfatase, a gene which escapes X-inactivation. Somatic Cell Mol. Genet. 22:1996;105-117.
117. Weinshilboum R. Sulfotransferase pharmacogenetics. Pharmacol. Ther. 45:1990;93-107.
118. Weinshilboum R., Aksoy I. Sulfation pharmacogenetics in humans. Chem.-Biol. Interact. 92:1994;233-246.
119. Wood T.C., Her C., Aksoy I., Otterness D.M., Weinshilboum R.M. Human dehydroepiandrosterone sulfotransferase pharmacogenetics: quantitative western analysis and gene sequence polymorphisms. J. Steroid Biochem. Mol. Biol. 59:1996;467-478.
120. Zhu X., Veronese M.E., Sansom L.N., Mcmanus M.E. Molecular characterisation of a human aryl sulfotransferase cDNA. Biochem. Biophys. Res. Commun. 192:1993;671-676.
121. Zhu X., Veronese M.E., Bernard C.C.A., Sansom L.N., Mcmanus M.E. Identification of two human brain aryl sulfotransferase cDNAs. Biochem. Biophys. Res. Commun. 195:1993;120-127.
122. Hwang S.-R., Kohn A.B., Hook V.Y.H. Molecular cloning of an isoform of phenol sulfotransferase from human brain hippocampus. Biochem. Biophys. Res. Commun. 207:1995;707.
123. Ozawa S., Nagata K., Shimada M., Ueda M., Tsuzuki T., Yamazoe Y., Kato R. Primary structures and properties of two related forms of aryl sulfotransferases in human liver. Pharmacogenetics. 5:1995;S135-S140.
124. Aksoy I.A., Sochorová V., Weinshilboum R.M. Human liver dehydroepiandrosterone sulfotransferase, nature and extent of individual variation. Clin. Pharmacol. Ther. 54:1993;498-506.
125. Adams J.B. Enzymatic regulation of estradiol-17β concentrations in human breast-cancer cells. Breast Cancer Res. Treat. 20:1992;145-154.
126. Sharp S., Anderson J.M., Coughtrie M.W.H. Immunohistochemical localization of hydroxysteroid sulfotransferase in human breast-carcinoma tissue, a preliminary-study. Eur. J. Cancer. 30A:1994;1654-1659.
127. Foldes A., Meek J.L. Rat brain phenolsulfotransferase, partial purification and some properties. Biochim. Biophys. Acta. 327:1973;365-374.
128. van der Pal R.H.M., Klein W., van Golde L.M.G., Lopes-Cardozo M. Developmental profiles of arylsulfatase A and B in rat cerebral cortex and spinal cord. Biochim. Biophys. Acta. 1081:1991;315-320.
129. Iwamori M., Moser H.W., Kishimoto Y. Steroid sulfatase in brain: comparison of sulfohydrolase activities for various steroid sulfates in normal and pathological brains, including the various forms of metachromatic leukodystrophy. J. Neurochem. 27:1976;1389-1395.