Estrogen hydroxylation - The good and the bad

Annals of the New York Academy of Sciences

Volumn 1155, Issue , 2009, Pages 57-67

  Sepkovic, Daniel W ^a   Bradlow, H Leon ^a  

^a HACKENSACK UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

di(2 ethylhexyl) phthalate (DEHP); Cervical interepithelial neoplasia (CIN); Cytochromes; Diindolylmethane (DIM); Estrogen hydroxylation; Genetic polymorphisms; Indole 3 carbinol (I3C); Laryngeal papillomatosis; Soy isoflavones

Indexed keywords

16ALPHA HYDROXYESTRONE; ESTROGEN; PHTHALIC ACID ESTER;

BODY FAT; BREAST CANCER; CANCER RISK; CASE CONTROL STUDY; CONFERENCE PAPER; ESTROGEN METABOLISM; HORMONAL CARCINOGENESIS; HUMAN; HYDROXYLATION; METABOLITE; MOLECULAR INTERACTION; NONHUMAN; PAPILLOMATOSIS; PILOT STUDY; PREDICTION; PROSPECTIVE STUDY; RECURRENT DISEASE; RESPIRATORY TRACT DISEASE; RISK ASSESSMENT; UTERINE CERVIX CANCER; UTERINE CERVIX DYSPLASIA; WART VIRUS;

HUMAN PAPILLOMAVIRUS;

EID: 61649104348     PISSN: 00778923     EISSN: 17496632     Source Type: Book Series    
DOI: 10.1111/j.1749-6632.2008.03675.x     Document Type: Conference Paper

References (56)

1. Martucci, C. & J. Fishman. 1977. Direction of estradiol metabolism as a control of its hormonal action: Uterotropic activity of estradiol metabolites. Endocrinology 101 : 1709 1715.
2. Fishman, J. et al. 1984. Increased estrogen 16 alpha-hydroxylase activity in women with breast and endometrial cancer. J. Steroid Biochem. Mol. Biol. 20 : 1077 1081.
3. Schneider, J. et al. 1982. Abnormal oxidative metabolism of estradiol in women with breast cancer. Proc. Soc. Acad. Sci. 79 : 3047 3051.
4. Swaneck, G.E. & J. Fishman. 1988. Covalent binding of the endogenous estrogen 16α -hydroxyestrone to estradiol receptor in human breast cancer cells: Characterization and intranuclear localization. Proc. Natl. Acad. Sci. 85 : 7831 7835.
5. Lustig, R.H. et al. 1989. Differential effects of estradiol and 16α-hydroxyestrone on pituitary and preoptic estrogen receptor regulation. Endocrinology 125 : 2701 2709.
6. Cavalieri, E. & E.G. Rogan. 2004. A unifying mechanism in the initiation of cancer and other diseases by catechol quinones. In Signal Transduction and Communication in Cancer Cells, Vol. 1028. H.L. Bradlow, L. Castagnetta, L. Massimo & K. Zaenker, Eds 247 257. New York Academy of Sciences. New York, NY.
7. Unpublished observations from this laboratory.
8. Jellinck, P.H., E.F. Hahn & J. Fishman. 1986. Absence of reactive intermediates in the formation of catechol estrogens by rat liver microsomes. J. Biol. Chem. 261 : 7729 7732.
9. Jellinck, P.H. & J. Fishman. 1988. P-450-catalyzed oxidations. Biochemistry 27 : 6111 6116.
10. 2O from labeled estrogens by mushroom tyrosinase. J. Steroid Biochem. 21 : 361 365.
11. Klug, T.L., H.L. Bradlow & D.W. Sepkovic. 1994. Monoclonal antibody based enzyme immunoassay for simultaneous quantitation of 2- and 16α-hydroxyestrone in urine. Steroids 59 : 648 655.
12. Ziegler, R.G. et al. 1997. Quantifying estrogen metabolism: An evaluation of the reproducibility and validity of enzyme immunoassays for 2-hydroxyestrone and 16α-hydroxyestrone in urine. Environ. Health Perspect. 105 : 607 614.
13. Bradlow, H.L. et al. 1998. Application of an improved ELISA assay to the analysis of urinary estrogen metabolites. Steroids 63 : 406 413.
14. Sepkovic, D.W. et al. 1994. Catechol estrogen production in rat microsomes after treatment with indole carbinol, ascorbigen, or B-napthaflavone: A comparison of stable isotope dilution gas chromatography-mass spectrometry and radiometric methods. Steroids 59 : 318 323.
15. Raju, U. et al. 2000. Estrone and estradiol metabolism in vivo in human breast cysts. Steroids 65 : 883 888.
16. Jellnick, P.H. et al. 1993. Influence of indol carbinols and growth hormone on the metabolism of 4-androstenedione by rat liver microsomes. J. Steroid Biochem. Molec. Biol. 46 : 791 798.
17. Adlercreutz, H. et al. 1975. Mass spectrometric and mass fragmentographic determination of natural and synthetic steroids in biological fluids. J. Steroid Biochem. 6 : 247 259.
18. Xu, X. et al. 2006. Analysis of fifteen estrogen metabolites using packed column supercritical fluid chromatography-mass spectrometry. Anal. Chem. 78 : 1553 1558.
19. Nelson, R.E. et al. 2004. Liquid chromatography-tandem mass spectrometry assay for simultaneous measurement of estradiol and estrone in human plasma. Clin. Chem. 50 : 373 384.
20. Guo, T. et al. 2008. Rapid measurements of estrogens and their metabolites in human serum by liquid chromatography-tandem mass spectrometry without derivitization. Clin. Biochem. 41 : 734 741.
21. Xu, X. et al. 2007. A liquid chromatography-mass spectrometry method for the quantitative analysis of urinary endogenous estrogen metabolites. Nat. Protocols 2 : 1350 1355.
22. Meilahn, E. et al. 1998. Do urinary estrogen metabolites predict breast cancer? Follow up of the Guernsey III cohort. Br. Cancer J. 78 : 1250 1255.
23. Muti, P. et al. 2000. Estrogen metabolism and risk of breast cancer: A prospective analysis of 2/16α-hydroxyestrone ratio in premenopausal and in postmenopausal women. Epidemiology 11 : 635 640.
24. Ho, G.H. et al. 1998. Using 2/16 alpha-hydroxyestrone ratio: Correlation with serum insulin-like growth factor binding protein-3 and a potential biomarker of breast cancer risk. Ann. Acad. Med. Singapore 27 : 294 299.
25. Kabat, G.C. et al. 1997. Urinary estrogen metabolites and breast cancer. A case-control study. Cancer Epidemiol. Biomarkers Prev. 6 : 505 509.
26. Kabat, G.C. et al. 2006. Estrogen metabolism and breast cancer on Long Island. Epidemiology 17 : 80 88.
27. Crane, M.M. et al. 1996. Association of estrogen urinary metabolites and breast cancer: Pilot study. Breast Cancer Res. Treat. 37 : 68.
28. Ursin, G.S. et al. 1997. A pilot study of urinary estrogen metabolites (16alpha-OHE1 and 2-OHE1) in postmenopausal women with and without breast cancer. Environ. Health Perspect. 105 : 601 605.
29. Taioli, E.J. et al. 1996. Correlation of estradiol 2-hydroxylation and breast cancer risk in patients carrying the MSP-1 polymorphism of CyP4501A1. Proc. Amer. Soc. Cancer. Res. 37 : Abstract 1697, 249.
30. Xu, X. et al. 1998. Effects of soy isoflavones on estrogen and phytoestrogen metabolism in premenopausal women. Cancer Epidemiol. Biomarkers Prev. 7 : 1101 1108.
31. Anderson, K.E. et al. 1984. The influence of dietary protein and carbohydrate on the principal oxidative biotransformations of estradiol in normal subjects. J. Clin. Endocrinol. Metab. 59 : 103 107.
32. Osborne, M.P. et al. 1988. Omega-3 fatty acids: Modulation of estrogen metabolism and potential for breast cancer prevention. Cancer Invest. 8 : 629 631.
33. Fishman, J., H.L. Bradlow & T.F. Gallagher. 1960. Oxidative metabolism of estradiol. J. Biolog. Chem. 235 : 8104 8107.
34. Bradfield, C.A. & L.F. Bjeldanes. 1991. Modification of carcinogen metabolism by indolylic autolysis products of Brassica oleraceae. Adv. Exp. Med. Biol. 289 : 153 163.
35. Sepkovic, D.W., H.L. Bradlow & M. Bell. 2002. Quantitative determination of 3,3′-diindolylmethane in the urine of individuals receiving indole-3-carbinol. Nutr. Cancer 41 : 57 63.
36. Fowke, J.H., C. Longcope & J.R. Hebert. 2000. Brassica vegetable consumption shifts estrogen metabolite ratios in healthy postmenopausal women. Cancer Epidemiol. Biomarkers Prev. 9 : 773 779.
37. Bradlow, H.L. et al. 1996. 2-hydroxyestrone: The "good" estrogen. J. Endocrinol. 150 : S259 S265.
38. Bradlow, H.L. 2008. A review of whether indole-3-carbinol can play a direct and safe role as a chemoprotective agent in breast and prostate cancer. In Vivo 22 : 441 445.
39. Auborn, K. et al. 1998. Estrogen metabolism and respiratory papillomatosis: A pilot study on dietary prevention. Anti-cancer Res. 18 : 4569 4574.
40. Cover, C.M. et al. 1998. Indole-3-carbinol inhibits the expression of cyclin-dependent kinase-6 and induces G1 cell cycle arrest of human breast cancer cells independent of estrogen receptor signaling. J. Biol. Chem. 273 : 3838 3847.
41. Newfield, L. et al. 1998. Estrogen metabolism and malignant potential of human papillomavirus immortalized keratinocytes. Proc. Soc. Exp. Med. Biol. 217 : 322 326.
42. Rosen, C.A. et al. 1998. Preliminary results of the use of indole-3-carbinol for recurrent respiratory papillomatosis. Otolaryngol. 118 : 810 815.
43. Coll, D.A. et al. 1997. Treatment of recurrent respiratory papillomatosis with indole 3-carbinol. Am. J. Otolaryngol. 18 : 283 285.
44. Sepkovic, D.W. et al. 1995. Estrogen metabolite ratios and risk assessment of hormone-related cancers: Assay validation and prediction of cervical cancer risk. In Cancer Prevention: From the Laboratory to the Clinic - Implications of Genetic, Molecular, and Preventive Research, Vol. 768. H. Leon Bradlow & Michael P. Osborne Umberto Veronesi, Eds 312 316. New York Academy of Sciences. New York, NY.
45. Yuan, F. et al. 1999. Anti-estrogen effect of indole-3-carbinol in cervical cancer cells: Implication for prevention of cervical cancer. Anti-cancer Res. 19 : 1673 1680.
46. Bell, M.C. et al. 2000. Placebo controlled trial of indole-3-carbinol in the treatment of cervical dysplasia. Gynecol. Oncol. 78 : 123 129.
47. Fishman, J. & H.L. Bradlow. 1976. Effect of malnutrition on the metabolism of sex hormones in man. Clin. Pharmacol. Ther. 22 : 721 728.
48. Snow, R.C., R.L. Barbieri & R.E. Frisch. 1989. Estrogen 2-hydroxylase oxidation and menstrual function among elite oarswomen. J. Clin. Endo. Metab. 69 : 369 376.
49. Colon, I. et al. 2000. Identification of phthalate esters in the serum of young Puerto Rican girls with premature breast development. Environ. Health Persp. 108 : 895 899.
50. Vang, O. et al. 1993. Cytochrome P450-mediated metabolism of tumor promoters modifies the inhibition of intercellular communication: A model assay for tumor promotion. Carcinogenesis 14 : 2365 2371.
51. Ibanez, L., N. Potau & F. De Zegher. 1999. Endocrinology and metabolism of premature pubarche in young girls. Acta Paediar. Suppl. 88 : 73 77.
52. Ibanez, L. et al. 2000. Adrenal hyperandrogenism in adolescent girls with a history of low birth weight and precocious pubarche. Clin. Endocrinol. 53 : 523 527.
53. Hazelton, W.I. 1992b. A subchronic (4 week) dietary oral toxicity study of di-(2-ethylhexyl) phthalate in B6FC3F1 mice. 8D submission, microfiche no. OTS0535433. Washington, DC : Submitted to the U.S. EPA, Office of Toxic Substances. Prepared for Eastman Kodak Company.
54. Lovekamp, T.N. & B.J. Davis. 2001. Mono-(2-ethylhexyl) phthalate suppresses aromatase transcript levels and estradiol production in cultures rat granulosa cells. Toxicol. Applied Pharmacol. 172 : 217 224.
55. 9k. J. Reprod. Dev. 51 : 253 263.
56. Hwang, D.Y. et al. 2005. An in vivo bioassay for detecting anti-androgens using humanized transgenic mice co-expressing the tetracycline-controlled transactivator and human CYP1B1 gene. Int. J. Toxicol. 24 : 157 164.