Triclosan is a potent inhibitor of estradiol and estrone sulfonation in sheep placenta

Environment International

Volumn 36, Issue 8, 2010, Pages 942-949

  James, Margaret O ^a   Li, Wenjun ^a   Summerlot, David P ^a   Rowland Faux, Laura ^a   Wood, Charles E ^b  

^a UNIVERSITY OF FLORIDA HEALTH   (United States)

^b UNIVERSITY OF FLORIDA COLLEGE OF MEDICINE   (United States)

Author keywords

Placental estrogen sulfotransferase inhibition; Polychlorobiphenylol; Triclosan

Indexed keywords

BIOCHEMISTRY; CONSUMER PRODUCTS; POLYCHLORINATED BIPHENYLS; SEWAGE SLUDGE; SUBSTRATES;

FETAL DEVELOPMENT; GLUCURONIDATION; HIGH POTENCY; PERSONAL CARE PRODUCTS; POLYCHLOROBIPHENYLOL; POTENT INHIBITOR; SUBSTRATE INHIBITION; TRICLOSAN;

SULFONATION;

2' HYDROXYTRICLOCARBAN; 4 HYDROXY 3,3',4',4 TETRACHLOROBIPHENYL; ESTRADIOL; ESTROGEN SULFOTRANSFERASE; ESTRONE; TRICLOSAN; UNCLASSIFIED DRUG;

DRUG; ENZYME ACTIVITY; ESTROGENIC COMPOUND; INHIBITOR; PCB; SEX HORMONE; XENOBIOTICS;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; COMPETITIVE INHIBITION; CONCENTRATION PROCESS; CONTROLLED STUDY; CYTOSOL; DETOXIFICATION; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME SUBSTRATE; FEMALE; FETUS; GLUCURONIDATION; HORMONE INHIBITION; IC 50; MICROSOME; NONHUMAN; PLACENTA; PRIORITY JOURNAL; SHEEP; SULFONATION;

OVIS ARIES;

EID: 77955865306     PISSN: 01604120     EISSN: 18736750     Source Type: Journal    
DOI: 10.1016/j.envint.2009.02.004     Document Type: Article

References (49)

1. Adolfsson-Erici M., Pettersson M., Parkkonen J., Sturve J. Triclosan, a commonly used bactericide found in human milk and in the aquatic environment in Sweden. Chemosphere 2002, 46:1485-1489.
2. Allmyr M., Adolfsson-Erici M., McLachlan M.S., Sandborgh-Englund G. Triclosan in plasma and milk from Swedish nursing mothers and their exposure via personal care products. Sci Total Environ 2006, 372:87-93.
3. Allmyr M., McLachlan M.S., Sandborgh-Englund G., Adolfsson-Erici M. Determination of triclosan as its pentafluorobenzoyl ester in human plasma and milk using electron capture negative ionization mass spectrometry. Anal Chem 2006, 78:6542-6546.
4. Allmyr M., Harden F., Toms L.M., Mueller J.F., McLachlan M.S., Adolfsson-Erici M., et al. The influence of age and gender on triclosan concentrations in Australian human blood serum. Sci Total Environ 2008, 393:162-167.
5. Alnouti Y., Klaassen C.D. Tissue distribution and ontogeny of sulfotransferase enzymes in mice. Toxicol Sci 2006, 93:242-255.
6. Buchanan-Smith J.G., Nelson E.C., Tillman A.D. Effect of vitamin E and selenium deficiencies on lysosomal and cytoplasmic enzymes in sheep tissues. J Nutr 1969, 99:387-394.
7. Calafat A.M., Ye X., Wong L.Y., Reidy J.A., Needham L.L. Urinary concentrations of triclosan in the U.S. population: 2003-2004. Environ Health Perspect 2008, 116:303-307.
8. Carnegie J.A., Robertson H.A. Conjugated and unconjugated estrogens in fetal and maternal fluids of the pregnant ewe: a possible role for estrone sulfate during early pregnancy. Biol Reprod 1978, 19:202-211.
9. Challis J.R.G. Mechanism of parturition and preterm labor. Obstet Gynecol Surv 2000, 55:650-660.
10. Cheng Y., Prusoff W.H. Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol 1973, 22:3099-3108.
11. Collier A.C., Ganley N.A., Tingle M.D., Blumenstein M., Marvin K.W., Paxton J.W., et al. UDP-glucuronosyltransferase activity, expression and cellular localization in human placenta at term. Biochem Pharmacol 2002, 63:409-419.
12. Collier A.C., Tingle M.D., Paxton J.W., Mitchell M.D., Keelan J.A. Metabolizing enzyme localization and activities in the first trimester human placenta: the effect of maternal and gestational age, smoking and alcohol consumption. Hum Reprod 2002, 17:2564-2572.
13. Coogan M.A., Edziyie R.E., La Point T.W., Venables B.J. Algal bioaccumulation of triclocarban, triclosan, and methyl-triclosan in a North Texas wastewater treatment plant receiving stream. Chemosphere 2007, 67:1911-1918.
14. Cornish-Bowden A. Fundamentals of enzyme kinetics 2004, Portland Press, London.
15. Falany C.N., Wheeler J., Oh T.S., Falany J.L. Steroid sulfation by expressed human cytosolic sulfotransferases. J Steroid Biochem Mol Biol 1994, 48:369-375.
16. Gamage N., Barnett A., Hempel N., Duggleby R.G., Windmill K.F., Martin J.L., et al. Human sulfotransferases and their role in chemical metabolism. Toxicol Sci 2006, 90:5-22.
17. Gee R.H., Charles A., Taylor N., Darbre P.D. Oestrogenic and androgenic activity of triclosan in breast cancer cells. J Appl Toxicol 2008, 28:78-91.
18. Gniot-Szulzycka J. Arylsulphatase C and sterol sulphatase activities in microsomes from human placenta. Acta Biochim Pol 1982, 29:205-212.
19. Heidler J., Halden R.U. Mass balance assessment of triclosan removal during conventional sewage treatment. Chemosphere 2007, 66:362-369.
20. Hirayama H., Sawai K., Moriyasu S., Hirayama M., Goto Y., Kaneko E., et al. Excess estrogen sulfoconjugation as the possible cause for a poor sign of parturition in pregnant cows carrying somatic cell clone fetuses. Reproduction 2008, 136:639-647.
21. Hoffmann B., Falter K., Vielemeier A., Failing K., Schuler G. Investigations on the activity of bovine placental oestrogen sulfotransferase and -sulfatase from midgestation to parturition. Exp Clin Endocrinol Diabetes 2001, 109:294-301.
22. Hovander L., Malmberg T., Athanasiadou M., Athanassiadis I., Rahm S., Bergman A., et al. Identification of hydroxylated PCB metabolites and other phenolic halogenated pollutants in human blood plasma. Arch Environ Contam Toxicol 2002, 42:105-117.
23. Hua W., Bennett E.R., Letcher R.J. Triclosan in waste and surface waters from the upper Detroit River by liquid chromatography-electrospray-tandem quadrupole mass spectrometry. Environ Int 2005, 31:621-630.
24. James M.O., Little P.J. Modification of benzo(a)pyrene metabolism in hepatic microsomes from untreated and induced rats by imidazole derivatives which inhibit monooxygenase activity and enhance epoxide hydrolase activity. Drug Metab Dispos 1983, 11:350-354.
25. Jurgella G.F., Marwah A., Malison J.A., Peterson R., Barry T.P. Effects of xenobiotics and steroids on renal and hepatic estrogen metabolism in lake trout. Gen Comp Endocrinol 2006, 148:273-281.
26. Kester M.H., Bulduk S., Tibboel D., Meinl W., Glatt H., Falany C.N., et al. Potent inhibition of estrogen sulfotransferase by hydroxylated PCB metabolites: a novel pathway explaining the estrogenic activity of PCBs. Endocrinology 2000, 141:1897-1900.
27. Kinney C.A., Furlong E.T., Kolpin D.W., Burkhardt M.R., Zaugg S.D., Werner S.L., et al. Bioaccumulation of pharmaceuticals and other anthropogenic waste indicators in earthworms from agricultural soil amended with biosolid or swine manure. Environ Sci Technol 2008, 42:1863-1870.
28. Magness R.R., Parker C.R., Rosenfeld C.R. Systemic and uterine responses to chronic infusion of estradiol-17 beta. Am J Physiol 1993, 265:E690-E698.
29. Magness R.R., Phernetton T.M., Gibson T.C., Chen D.B. Uterine blood flow responses to ICI 182 780 in ovariectomized oestradiol-17beta-treated, intact follicular and pregnant sheep. J Physiol 2005, 565:71-83.
30. Mason J.I., France J.T., Magness R.R., Murry B.A., Rosenfeld C.R. Ovine placental steroid 17 alpha-hydroxylase/C-17,20-lyase, aromatase and sulphatase in dexamethasone-induced and natural parturition. J Endocrinol 1989, 122:351-359.
31. Purinton S.C., Wood C.E. Estrogen sulfatase and sulfotransferase are found in brain regions important for hypothalamus-pituitary-adrenal axis control. J Soc Gynecol Investig 1998, 5:153A. [Supplement].
32. Sandborgh-Englund G., Adolfsson-Erici M., Odham G., Ekstrand J. Pharmacokinetics of triclosan following oral ingestion in humans. J Toxicol Environ Health A 2006, 69:1861-1873.
33. Saoud C.J., Wood C.E. Modulation of ovine fetal adrenocorticotropin secretion by androstenedione and 17beta-estradiol. Am J Physiol 1997, 272:R1128-R1134.
34. Shevtsov S., Petrotchenko E.V., Pedersen L.C., Negishi M. Crystallographic analysis of a hydroxylated polychlorinated biphenyl (OH-PCB) bound to the catalytic estrogen binding site of human estrogen sulfotransferase. Environ Health Perspect 2003, 111:884-888.
35. Stanley E.L., Hume R., Visser T.J., Coughtrie M.W. Differential expression of sulfotransferase enzymes involved in thyroid hormone metabolism during human placental development. J Clin Endocrinol Metab 2001, 86:5944-5955.
36. Tong M.H., Jiang H., Liu P., Lawson J.A., Brass L.F., Song W.C. Spontaneous fetal loss caused by placental thrombosis in estrogen sulfotransferase-deficient mice. Nat Med 2005, 11:153-159.
37. Tsang C.P. Changes in plasma levels of estrone sulfate and estrone in the pregnant ewe around parturition. Steroids 1974, 23:855-868.
38. Ushizawa K., Takahashi T., Hosoe M., Ishiwata H., Kaneyama K., Kizaki K., et al. Global gene expression analysis and regulation of the principal genes expressed in bovine placenta in relation to the transcription factor AP-2 family. Reprod Biol Endocrinol 2007, 5:17.
39. Vagnoni K.E., Shaw C.E., Phernetton T.M., Meglin B.M., Bird I.M., Magness R.R. Endothelial vasodilator production by uterine and systemic arteries. III. Ovarian and estrogen effects on NO synthase. Am J Physiol 1998, 275:H1845-H1856.
40. Wang L.Q., James M.O. Sulfotransferase 2A1 forms estradiol-17-sulfate and celecoxib switches the dominant product from estradiol-3-sulfate to estradiol-17-sulfate. J Steroid Biochem Mol Biol 2005, 96:367-374.
41. Wang L.Q., James M.O. Sulfonation of 17beta-estradiol and inhibition of sulfotransferase activity by polychlorobiphenylols and celecoxib in channel catfish, Ictalurus punctatus. Aquat Toxicol 2007, 81:286-292.
42. Wang L.H., Rudolph A.M., Benet L.Z. Pharmacokinetic studies of the disposition of acetaminophen in the sheep maternal-placental-fetal unit. J Pharmacol Exp Ther 1986, 238:198-205.
43. Wang L.Q., Falany C.N., James M.O. Triclosan as a substrate and inhibitor of 3'-phosphoadenosine 5'-phosphosulfate-sulfotransferase and UDP-glucuronosyl transferase in human liver fractions. Drug Metab Dispos 2004, 32:1162-1169.
44. Wood C.E. Estrogen/hypothalamus-pituitary-adrenal axis interactions in the fetus: the interplay between placenta and fetal brain. J Soc Gynecol Investig 2005, 12:67-76.
45. Wood C.E., Saoud C.J. Influence of estradiol and androstenedione on ACTH and cortisol secretion in the ovine fetus. J Soc Gynecol Investig 1997, 4:279-283.
46. Wood C.E., Gridley K.E., Keller-Wood M. Biological activity of 17beta-estradiol-3-sulfate in ovine fetal plasma and uptake in fetal brain. Endocrinology 2003, 144:599-604.
47. Ying G.G., Kookana R.S. Triclosan in wastewaters and biosolids from Australian wastewater treatment plants. Environ Int 2007, 33:199-205.
48. Zhang H., Varlamova O., Vargas F.M., Falany C.N., Leyh T.S. Sulfuryl transfer: the catalytic mechanism of human estrogen sulfotransferase. J Biol Chem 1998, 273:10888-10892.
49. Zorrilla L.M., Gibson E.K., Jeffay S.C., Crofton K.M., Setzer W.R., Cooper R.L., et al. The effects of triclosan on puberty and thyroid hormones in male Wistar rats. Toxicol Sci 2008.